It was a year in which I showed up fully as myself, unable to hide because I had spent 220 pages boldly outlining how I intended to live. It was a year in which I found new friends in Austin who invested in Angie and me and actively supported us, encouraged us, invited us into their homes, and never laughed a single time when we shared our silly and crazy dreams for life. 

It was also a year of unexpected financial success, making about 2.5x what I did in 2021. I’m still processing what that means and how to think about a path in which past success certainly does not mean future success but might indicate hidden opportunities I had not considered.

It’s a year of generational shifts in which we were able to share with my grandmother that Angie was 5 weeks pregnant a few weeks before she passed.  Michelle, our daughter, would have been her 17th great-grandchild.

2022 was a year of leaning into “ambition” and realizing that my related fears were tied to the compromises I would have had to make on a previous path, not my current one. I am no longer in danger of ending up stuck and cynical on a path I don’t like. I have more than five years of carving my path with more self-awareness of how to design a life around the things I like doing.  Ultimately, I realized that the “ambition” that many of us were steered toward has been corrupted by the default path. Each of us has an inherent ambition to do things that matter to us and that won’t always come with a paycheck, promotion, or title. 

In 2022, I discovered that there was nothing to be afraid of in putting myself out there. Hiding a bit in the first couple of years on my path probably made a lot of sense. I had to “leave the world” to re-enter the world in the Joseph Campbell sense.  I said to Angie many times this year, “Wow, I’m okay, I really love everything I’m doing, I am not going to wind up trapped on a silly career path again!”

The review that 

• Countries Lived In: US, Portugal
• Places Visited: Johnson City, Seattle, San Francisco, California and Oregon Coast, Portland, Connecticut, New York City, Boston, Lisbon, San Antonio, Porto
• # Of Books Launched: 1
• # of Estimated weekday “days off”: 60-70
• # of Copies Sold (Audio + Print + ebook): ~$10,000
• # of Scheduled Work Hours I’d Skip If I Could: A bit higher this year, probably 200-300 or so
• Revenue in 2022: ~$230,000-250,000
• # of Expected Children for the Wang/Millerd Family in 2023: 1

Learning To Celebrate

Last year, inspired by my friend Chris, I tried to embrace “celebration” a little more in my life. It emerged out of a conversation about my book and with me mentioning that I had no plans for a book launch or any sort of celebration.

Celebrating myself, especially on this path has always seemed silly. I’ve never been overly attached to external achievements and genuinely enjoy most of the things I like doing. What did I want to do after I published my book? Keep writing. Keep living my life.

But it felt like something worth exploring. Over the past year I’ve realized that I like celebrating in two ways:

1. Generally celebrating life with friends
2. Leisure & reflection

On the first, I hosted a party inspired by Nick Gray’s amazing book, I hosted a gathering of internet friends. I sort of made this a celebration of my book launch but not really. I gave out some books and that was pretty much the only book-related event I did for the year. However, I ended up hosting tons of small meetups, writing sessions, pool parties, and small dinners throughout the year and it’s something Angie and I realized that we both want to be part of our life.

In terms of celebrating achievements, I finally realized I had already been doing it. My friend Sky gave me the idea that reflection and leisure could be a way to celebrate. This is something I’ve been doing for several years. and even more purposefully with my “every seventh week off” approach.

2022 Lesson: Celebrations take many forms. It doesn’t need to look like a party. It can be a slow, quiet walk by myself where I have enough space and time to smile and laugh a little at this crazy little thing called life.

In addition to walks, bike rides, and taking time away from active work, one form of leisure for me is writing. This is great because it’s been the source of almost all the success I’ve had with working on my own and it rarely feels like “work” in the way that my old office job did.

So here are ten things worth celebrating!

1. Getting to spend time with my grandmother and let her know that we were expecting a daughter before she passed
2. Expecting our daughter, Michelle, and that Angie’s pregnancy has been healthy and smooth to date
3. Publishing a book and selling far more than I ever could have projected
4. Finding an amazing group of friends in Austin and after several years of being nomadic feeling like we found a “home” of people that support us and want to be part of our lives
5. Angie finding her groove with her work, feeling comfortable in the US, and finding a good group of friends (especially girlfriends) in Austin
6. Reprioritizing my health and joining a gym and going most days I’ve been in Austin
7. Becoming much faster at turning ideas in my head into actions in the real world
8. Being a little more ambitious (which was scary!) while not losing touch with who I want to show up as in the world
9. Hosting a few meetups throughout the year inspired by Nick Gray’s book
10. Meeting some amazing men in Austin that want to live lives built around vulnerability, healthy ambition, and friendship

Revisiting Questions From Last Year

#1 How do I use my happiness, optimism & energy to support others?

In asking this question last year, I was defending against my biggest fear: falling back into cynicism I had my final couple of years of full-time work. I associated moving back to the US with that experience and the reality that the US culture values full-time work and steady (and climbing) incomes. I was scared that I would need to hide from that pressure much like I did the first couple of years on my path.

My conclusion: I’m fine. Moving to Austin has been huge for finding a group of people that are not only supportive but root for me to succeed. This was something I was missing in my life previously and I realize the effect was that I always tried to hide or “play small” and not really believe in myself. Finding people that support me has been the path to reclaiming my optimism from when I was younger.

#2 How do I level up the ambition in ways that are exciting and sustainable?

I was more ambitious over the last year and I was able to do it on my terms which surprised me. Ambition took the form of leaning into things I already cared about like reaching out to popular podcasts and relaunching my own podcast. I made a list before re-launching the podcast of the top people I want to interview. When I did it I assumed it would take a couple of years to build up the courage to ask but I’ve already had a number of them on and I just confirmed a date with the #1 person on that list. Stay tuned

Ambition is something I want to write a bit more about this year. I sense that the word has been poisoned by our modern obsession with full-time jobs and money. Ambition is independent of employment status which is hard to see because so many people pair it with legible monetary success. The kind of ambition I care about is something we might label “alt-ambition” (thanks @vgr) or illegible ambition. An internal drive that we all have and that far too many seem willing to extinguish for the sake of comfort or the appearance of security.

#3 How do I help Angie succeed?

This was a big year for Angie and something I thought about a lot throughout the year. When we first got to the US in October of 2021, she spent a lot of time trying to apply for jobs in Tech and the corporate world. I was a bit saddened by the lack of imagination of recruiters. She has an amazingly diverse mix of interests and never quite fit into anyone’s box.

Luckily after taking Write of Passage in March she made some friends in Austin, started sharing her story in English, and started to believe in following her own “pathless path” on the work front. Over the last six months of 2022 she not only landed multiple freelance projects, but she had to turn down multiple projects because she became too in demand.

It’s really hard as someone’s partner to see them struggle and many times I just wanted to help her fast track through the challenges she was facing. But that’s not how life works. The cool thing is that every time she faces a challenge she persists and doesn’t give up. It’s been inspiring to see her overcome so many challenges so quickly.

#4 What are the business or personal things I’m not thinking about (yet)?

Probably a question I’ll keep asking for the rest of my life. One of the hardest things about this kind of path is figuring out where you are headed and what to focus on in the present. This is true for any human but the potential options and potential randomness relative to paycheck life is an order of magnitude higher.

One random thing I didn’t expect was for my book to succeed at the scale it did. I treated some of the initial success as a cue from the universe to keep writing and talking about these ideas. This led to me relaunching and renaming my podcast The Pathless Path podcast and continuing to write on the newsletter.

#5 What are the experiments I can do to continue to grow?

Over the last year, I did a bunch of stuff and feel like I’ve expanded my own imagination a ton. Some experiments include:

• Took DJ lessons in a studio and did a couple of “gigs” for my family
• I hosted several events and was able to decrease the time from thinking of doing something to sending the first invite substantially
• I did a 6-week experiment with YouTube with a coach that was way more fun than I expected and turned YouTube from a chore to another fun outlet to create and share ideas
• I got a little more ambitious with my podcast, re-launching it as The Pathless Path podcast
• I took sponsors on both my newsletter and podcast and while it’s probably still a bit early to lean into these opportunities fully, it unlocked another “income stream” that I know I can potentially count on in the future.

Some Favorite Places of the Year

Creator Cabins: This is where we spent our first week in Austin and it’s also where I finished my book. This will always be a special place for that reason.

Austin: I find Austin delightful. It’s sunny, filled with happy people, and a place that many fellow creators have decided to call home. I wrote more about Austin here.

Lisbon: This was our “last hurrah” of nomad life for a while. We spent the whole summer traveling around the US, Connecticut, and then Lisbon.

Lisbon is simply a world-class wandering city.

After living in so many places for the past several years, I enjoyed this opportunity to really cherish the joys of adapting to a new place in a month. At the same time, it was interesting to see how eager Angie and I were to return to Austin.

The Pathless Path – Wow!

I sense that publishing The Pathless Path will become an important inflection point in my life. The book seems to have taken on a life of its own, one which seems out of my hands at this point.

In December, Ali Abdaal published a top 15 books of 2022 video and it drove about 2000 sales of my book in a couple of weeks and will likely help me reach about 10,000 copies sold in one year.

People are reading it too because a couple of weeks later I’m receiving 5-6 messages a day thanking me for writing the book.

Writing the book was transformational and I think it’s because in a book there is no point in hedging. If someone is going to spend several hours with you, they want to know what you think. So much of life is filled with people bullshitting, hedging, and half-assed takes.

I really give a damn about helping people thrive on unconventional paths and I’m going to build my life around continuing to make that happen.

(This doesn’t feel scary to type, which definitely would have a couple of years ago.)

Self-publishing a book was also very profitable. The first year will likely end up generating about $50,000 in revenue and 10,000 in book sales. More on this in a future post!

StrategyU Also Had A Record Year

Everything did better this year which is equally terrifying and exciting.

Can it last? What do I do next?

Constant companions on the pathless path!

One of the best things I did was hire Nate Kadlac to help me redesign my brand for StrategyU. I was surprised at how powerful a color palette and brand theme could be for unleashing my creative impulses.

The slides on the right just feel better, right?

Nate radically shifted how I see design in many aspects of my work and I think one of the biggest mistakes I made was not working with Nate earlier!

2022 Lesson: Design inspires creation

Hacked-together PowerPoint graphics are fine for speed but over time there’s probably a slight cost to the hanging desire of always knowing it could be better.

After redesigning everything, I started to see new patterns in the ideas and ended up spending a couple of hundred hours this past summer rebuilding my Think Like A Strategy Consultant course.

This also made me realize the returns of playing long games. Because I have worked with so many students and also so many companies, I have been A/B testing phrases, terms, and ways of presenting ideas that help me figure out what works. Also inspired by people like David Perell and Tiago Forte, I looked for ways to ramp up the performance factor that most other people offering training in the corporate space simply aren’t doing.

After re-launching, sales improved and I ended the year making about $100,000 in revenue (probably $80k in profit) from the course in 2022 and another $50,000 from workshops and multi-week and consulting with companies.

The workshops were a big surprise. After packaging the workshops and selling them as a clear offer (I do these starting at $6,000 for one-off trainings and now $25,000 for a four-week offering), I got a lot more interest. I was able to raise prices and position myself as a unique provider in the space.

The crazy thing is that I rely 100% on inbound requests from clients via YouTube and SEO and send everyone the same standardized offer. This runs as a pretty efficient thing right now and there’s no reason I couldn’t scale this up 2-3x with minimal effort. My biggest roadblock is that given free time, I tend to bike around, sit in the sauna, or write about our relationship to work, and in March, I’ll likely want to nap with my daughter.

This is something I need to explore in 2023. Can I find someone that is wired similarly that would want to help me run this? So far I haven’t really found people excited about building something, most people want a job. Unfortunately, I’m not a very good manager.

Will be cautiously making bets here in 2023 but there’s no reason the course and some coaching won’t continue to be opportunities.

Coming Alive Over Getting Ahead – Podcast & Community

My biggest problem is that StrategyU feels like “getting ahead” mode and I can only last in that mode so long which is why I’ve built the business to run on less than 30-40 hours or attention per month.

This is also why I’ve leaned in the direction of some of the things that don’t really generate any money at all, like my podcast. 

With the success of my book early in the year, I felt called to re-launch my podcast. Much of my book emerged from conversations and the urge to share interesting stories and be able to channel my curiosity into interesting questions was too exciting. 

I sat on the new name “The Pathless Path Podcast” for two months before finally taking action. I’ve been trying to get better at turning ideas into action as soon as possible and launching my podcast was a turning point for this. One day I got fed up with the idea sitting in my head and I ordered a CamLink HD, Better Microphone, and created a new podcast cover, and renamed it. I also created some sponsorship packages and was able to land an initial sponsor that inspired me to hire an editor. I now have a great editor in Poland who I just gave a raise and am planning some bigger things in 2023.

Lesson from 2023: Given that I’ll never be a hyper-optimizing type, getting ideas into a testable action as soon as possible doesn’t have much downside. I’ve “failed” at many of the things I’ve done on this path and I shouldn’t think that should change moving forward.  

This past week I also finally launched a community on top of my newsletter, Find The Others. This came from paying attention to the conversations and requests from people who were reading my book. They saw that I was able to “find the others” through my writing but didn’t have platforms of their own to do the same. I hope the community can emerge as a gathering spot of generous, kind, unconventional path-ers who want to help each other succeed.  

I am not sure where these two bets will lead but they feel true to my principles for this whole journey I am on. 

Coming alive over getting ahead. 

Thanking People Who Shared My Ideas

There are many people with large audiences who thought my work was good enough to share with their audiences and many people behind the scenes who have supported me.

As a creator one of the most important things to think about with an audience is trust and I am appreciative of many people who took a chance on me.

Special shoutouts to:

My “Unpaid Marketing Intern” Ali Abdaal: Ali mentioned me about five or six times on his main YouTube channel (which has 3.7M subscribers), interviewed me on his podcast and shouted out my book so many times in his newsletter that I lost count. Ali is inspiring for his love of learning and ability to move fast. He just also happens to have a massive YouTube channel. I’m most excited about his book too. I sense based on Ali’s interest in my book and his other work rabbit holes that his book is going to be a banger.

Venkatesh Rao: Venkatesh has given many shoutouts to my writing and wrote a nice thread on my book this past year that lead to a ton of sales. A lot of my writing is ribbonfarm / Venkat inspired. It was fun to return the favor by reviewing his excellent book Art of Gig over the past couple of months.

Chris Williamson: I’m inspired by Chris’ incredible focus on Modern Wisdom and his impressive curiosity across a wide range of domains. I messaged Chris when I launched my book not knowing he had moved to Austin and then found myself in a conversation with him a couple of weeks later. It’s been cool to see how energized and alive Chris is with his podcast and I also appreciate him giving me a chance with his massive audience.

Jim O’Shaughnessy: I like to ask a question on my podcast, “who is your path role model?” If I had to pick someone it would likely be Jim. Why? Mostly because of his infectious curiosity and optimism. At his age and experience, he is an outlier in his stance toward life. In addition, he loves finding, connecting, and investing in hidden talent. I’ve gotten to know several people around the world who Jim has discovered and already hired. I got to meet him in New York over the holidays and I sense we could have talked for hours. Which is also what makes his podcast so great. Despite audio difficulties, we had a fun conversation.

Rolf Potts: Probably my biggest fanboy moment this year. I cold emailed Rolf telling him I quoted his podcast in my book. He asked me to send him a copy and he liked it enough to ask me on his podcast. Rolf’s Vagabonding was such a powerful book to read before going nomadic in 2017 and again before I left Taiwan with Angie in 2020.

There are so many others to thank but I want sincerely thank anyone who shared thoughts on my book this year.

Other conversations I enjoyed (but not limited to) include Jonny Miller (Curious Humans) Marshall Kosloff (The Realignment and Deep Dive), Bhav Sharma (Creators Campfire), and Justin Murphy (Other Life).

Questions For 2023

This next year feels wildly uncertain but not in a way that stresses me out. In fact, I am feeling more secure and confident about my path than at any time in my adult life.

I feel like I’m living out something that is true and aligned and it’s still kind of hard to explain how different that feels from my previous path. People look at me and proclaim “you still work!” 

I definitely wanted to escape work after I quit my job but that faded as I found work I enjoyed and enabled me to connect with myself in a deep way. My lived experience of this path feels like I am cheating. I went from only having nights and weekends and a few vacation weeks to myself prior to 2017 to now having what feels like every single day of my life at my disposal.  I guaranteed that being able to scale down some of my work this year for meaningful time with my daughter will make this feel even better.

Given the large increase in financial outcomes in 2022, I am seeing the unexpected income as “excess income” that I can invest in the ability to continue to live this life and do this kind of work. The money has been a little distracting at times this year and I’ve definitely conjured up grandiose plans of even more success. Yet I remind myself that this is almost definitely a trap and the only thing that will lead me in a “successful” direction that I actually want is staying true to myself and doing the things that fire me up in the moment. 

Generally, I am having a hard time thinking about anything beyond the end of February when my daughter is expected to arrive. I am incredibly excited about becoming a dad and can only imagine how much I will have to learn. 

I sense this will be a massive shift in my perspective in life but one that I feel ready for. Quitting my job in 2017 was terrible for my bank account but great for my soul and I am glad my daughter will get to see the version of me that has grown so much and is fully ready for this. 

Here are some themes and questions I’m thinking about for 2023: 

Parenthood & Perspective: I am heading into this new chapter of my life open-minded and humble. I don’t know what to expect but fully expect that there will be changes.  I am excited to see what unfolds.

Life Perspective & Scripts: I don’t know how having a child will change my behavior and priorities around work.  Many people build their lives around the assumption that most workdays are for working and then schedule childcare and support around that.  That is not my base assumption for life and I am interested to see what sort of hidden scripts are at play in parenthood (from my initial conversations with people it seems parenting scripts are even more rigid than work ones!).

Scale StrategyU Or Just Keep Going?: I’ve steadily grown this over four years through constant tinkering into a business that generated about $150,000 in revenue essentially as a side gig.  I like doing the trainings with companies and coaching and consulting work with executives but don’t love the maintenance and content generation.  I have a 10k subscriber mailing list that I could likely monetize and the YouTube could probably grow quite a bit too. How can I get leverage here? Is it targeted freelancers with specific skills? Could I find a young former consultant that might want to use this as a platform to follow a similar path to me? 

Invest Like A Business: I’ve struggled a lot with investing money in things I’m doing. I’ve had a lot of luck hiring freelancers to help with specific tasks and that works well with my inability to manage someone that wants a job.  However, I still find it hard to spend money so with some help from the coaches in Malcolm Ocean’s Goal Crafting Intensive, I decided it would be best to make a fixed commitment of “R&D” spending for the year. So for 2023, I am going to commit to spending $20,000 on freelancers, support, part-time work, and other investments that might help me grow and add some serendipity to my path. 

What Are Some Fun Book Bets I Can Make?: My book seems to have a bigger market than I thought. What are some bets that could 10x the sales in 2023?  100x by 2025?

Leaning Into an Emergent “Pathless Path” Movement:  I love writing my newsletter and suspect I’ll keep doing it for a while. I am going to continue to follow my curiosity and am excited that I’m now pairing it with a Circle community for paid subscribers. I had a lot of experiment ideas around courses and mini-challenges that I wanted to run but didn’t want to launch something. “Find the Others” feels like a fun playground for the next year.

How Do I Write More?: In 2018 I adopted a mantra, “write, most days” and that has led to most of the things that emerged in 2022. I was probably spread a little too thin in 2022 but not in the overworked sense. More in the “I’ll do a Twitter thread” instead of doing deeper thinking, reading, and writing longer pieces.  One of my goals is to write more in 2023 and I’ll be spending some time trying to be more intentional about the ideas I want to write about this year.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Leaning Into Ambition & Deeper Commitments: (Still) Enjoying The Journey in 2022 appeared first on Boundless by Paul Millerd.

This is the first time I’ve sat down to write an in-depth review of my year.  In the past, I’ve only done a quick scan of questions and a surface-level review of my business.  

However, inspired by other people who have shared their reviews, I thought I’d do my own.

In this review I’ll cover a few things:

• Three things to celebrate
• Three lifestyle experiments & lessons
• My five favorite places
• Overall Financial Results from 2021
• Business experiments & learnings from 2021
• Pivoting from freelance to “creator” – five year reflection
• Questions and themes I’m thinking about 2022

Before we dive in, some stats:

• Countries Lived In: US, Taiwan, & Mexico
• # Of Accomodations >1 Week: 14 places Puerto Escondido, Mexico City, Taichung, Taipei, Hualien x3, Taitung, Green Island, Orchid Island, Kenting, Taichung, Connecticut, New York City
• Total Accommodation Expenses For 2021: ~$8,500
• Total Estimated Rent for 2022: Much Higher
• # Of Hours Spent on The Book: ~1,500
• # of Vaccines Gotten In Taiwan: 1
• # of vaccines in the US: 1 (15 weeks after the one in Taiwan)
• Published words in a book: 57,500
• # of Green Cards Acquired for the Wang/Millerd Family: 1

Three Things Worth Celebrating

Inspired by Chris Spark’s own beautiful reflection where he details “five celebrations” I decided it would make sense to do the same.  With the recent release of my book, I realized that I don’t spend much time celebrating myself.  This is partly a good thing – I’ve created a path that isn’t tied to outcomes, status, identities, or things like promotions.  

However, as I’ve become comfortable detaching what I’m doing from any sort of extrinsic reward, I think I’ve become a bit too shy about being excited when good things do happen or even stopping to celebrate just because it’s something worth doing.

So here are three things that I’m really happy about with 2021:

1. Angie getting the green card!
2. Moving to the US and being able to do it with an optimistic and excited attitude
3. Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable

#1 Angie getting the green card!

Although we haven’t got the physical card yet, we went through a 13-month process of endless paperwork and Angie was given a green card to be a permanent resident of the US. It’s so great to see this journey through her eyes. She said something a couple of months ago: “I don’t think you know how lucky I am to have this opportunity.” Despite many people being negative about this country, many people abroad still want the chance to live and work here.

I’m excited to see the US through her eyes as we continue to spend more time with my family, make new friends, and travel the country.

#2 Moving to the US and being able to do it with an optimistic and excited attitude

When I left the US in 2018, I was searching for a new way forward in life.  I was also a bit lost – I had become disconnected from myself and didn’t know who I wanted to be.

A few years later I can say with a lot of confidence that I’ve found myself – as cliche as it sounds.  I’m married to an incredible woman, spend almost every day doing things I am 10/10 excited about and have a great foundation of friends and family across the world to support me.

Yet I was really scared about moving back to the US for most of the year.  Angie and I applied for her green card in late 2020 and our plan was to spend most of 2021 in Taiwan waiting for the completion of the process.  Due to the incredibly slow speed of the immigration process, this meant I had a year to prepare.  

I decided to “practice” optimism.

The first step was remembering.  Remembering who I was when I was younger and figuring out how to inject the joy, enthusiasm, and humor that were once such vital and natural parts of how I showed up in the world back into my life.  This was hard.  I did a number of things like talking to some of my optimistic friends more, writing about my fears and doing things I loved as a kid like Tennis, Basketball, Yo-Yoing.  Through all these things, I realized how rigid I had become as an adult and it made it even more clear how important it is to continue to look for ways to inject a playful attitude into my life.

In our first couple of months back in the US we lived with my cousin Brian in New York.  This was a great decision because he’s someone that I’d describe as fully alive and engaged with the world.  Loves his job, has plenty of things he’s excited about and is constantly getting pumped about what other people are doing.  In only a couple of months, I realized that I really had changed a lot in a few years abroad and was able to channel completely different energy than in the past.

Another thing was concerns about money.  I realized early on in the year that worries about the skyrocketing cost of living in the US were beside the point.  I knew how to make money if I needed it and we have some savings to let us still invest in our life without needing to earn a lot in the next six months.  So I decided to commit to not complaining about money whatsoever and instead start with the life, locations, and things we want to do and then worry about making the money for it later.

Put more simply, I found out who I am and now I have a lot of confidence I can show up in the world as I want to, less impacted by the criticism and pessimism of others than I have been in the past.

Feels awesome!

#3 Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable

In my book, I write about the “real work of your life” as finding the things worth doing and then committing to them.  The book was the biggest project I’ve committed to on the pathless path and it has been by far and away the most rewarding.  

In addition to pushing me well beyond what I thought I was capable of in terms of writing, it also was a learning experience.  I had worked on complex projects, but nothing like a book.  At almost every stage of the process, I overestimated how quickly things would take and underestimated how much work I would have to do.

I had complete confidence the entire year that I’d be able to write the book I wanted to but I didn’t know how I’d get to the finish line.  This is where my experience in consulting, to trust the process amid ambiguity, really helped.  I would write for an extended period, take a step back (time off), then restructure and write again. I went through this process four or five times and each time I felt like I was getting a little closer.

It wasn’t until a couple of weeks before leaving Taiwan that I figured out what the book was about. It came to me after being frustrated with writing and Angie suggested I go for a scooter ride around the town.  Less than 30 seconds into the ride, everything came to me and I started crying.  

A voice in my head was telling me: “these ideas matter and you don’t need to be scared to say that.”

I knew that in order to write a book I needed to unleash the bold side of me that I had kept back in my writing and in my life. 

These ideas fucking matter.

I also was able to connect it to seeing my parents struggle and knowing how much more capable they were than what the world was telling them they were allowed to do because they didn’t have degrees.

It was a book for them and the hundreds of people I’ve talked to over the past few years but also the world.  And from there, the rest of the book seemed to pour out of me like it had been there the entire time.  By mid-December I knew I had the book I was proud of and from there it was just editing and getting the details right.  

If you haven’t bought it yet, check it out here.

Lifestyle Experiments & Learnings

I’m living a life far beyond what I thought possible five years ago.  Most days I wake up and work on whatever I want to do and have the freedom to go wander, exercise, meet up with friends, or go for a bike ride most days if the opportunity presents itself.  At the same time, I’ve found work I love doing – writing, curiosity conversations, mentoring, creating digital products & teaching online.

Despite this optimal existence, I am still fascinated with how motivation shifts based on where I’m living, who I’m surrounded by, and what I’m curious about.  This means I’ve continued to experiment and learn about how I like working.  

Three key themes stand out from 2021:

#1 Improving my Chinese skills during an intensive class that also aligned with a three-month period of living my “ideal life”

In March, I took an on-campus class in Taipei studying Chinese.  I found it incredibly enjoyable.  In addition to the 30+ hours of in-class instruction and studying, I was also spending time biking around in the afternoons, writing my book, and still running my StrategyU business.

It made me remember how much I loved learning and that if I can build in similar blocks of intensive learning throughout my life, I will likely be a very happy and engaged person. 

Each day, I had class from 9:00-12:00 and then would ride my bike around campus and the city.  From there, I might grab lunch with a friend, wander a bit, or do some writing.  During this time, I also hosted my first corporate workshop, which helped me develop a corporate offering for my course, which already has its first client in 2022.

I was “working” a lot and there was no clear separation between night, morning, weekday, or weekend, but it was a period of absolute perfection. Everything I was working on was by my own creation and on my own terms.  I couldn’t have been happier.

This was also when I started to realize that this is why people struggle to talk about work.  They tend to only be talking about “jobs” rather than the work they want to be doing.  Most people want to work, we just accept that some or a lot of it are supposed to be a grind.  Most of my path has been about running away from that and along the way, I essentially realized what I was doing was “designing for liking work” (h/t Venkatesh Rao for pointing this out to me.)

#2 Inspired by Sean McCabe, I tested, implemented and have committed to a “every 7th week off, no matter what” model for at least 2022. 

Inspired by a conversation on our podcast and looking for better ways to structure my work, I implemented Sean’s “take every seventh week off” sabbatical approach.

In our conversation, we both had opposing reasons for doing the experiment.  Sean originally did it because of overwork and I wanted to try it because I felt like I had a lovely life, but wasn’t quite going all-in on the projects I was excited about.  

Now in each six-week block, I plan on picking one or two priorities work-wise and trying to focus on those.  During the past year, it was vital in helping me power through different phases of the book before taking a week off to wander and reflect.

#3 People over work

Coming back to the US I was excited to see some of my friends again!  In New York, I decided that I would prioritize meeting up with anyone who asked over any work I might be doing.

This was great at first but I was a bit too ambitious in terms of how much socializing I wanted to be doing after a year of relative solitude in Taiwan.

In Austin, I’m finding a good balance again and am also excited to have a home base for at least five months where I can get back into a solid routine.

Five Favorite Places of the Year

Mirador de Tortugas: An amazing sunset spot Angie and I found in our last month in Puerto Escondido.  After finding it, we proceeded to design our day around making it there for sunset each night

Dulan in Taitung, Taiwan: If there is any place that has more of a hippie nomad energy in Taiwan, this is it.  Situated right on the cliffs on the southeastern shore of Taiwan, this is a much quieter place in Taiwan that attracts a lot of young and international people.

Fuli District In Hualien, Taiwan: Between an epic bike ride through the greenest rice fields I’ve ever seen and the beautiful golden needle flowers, this place was magical

Green Island and Orchid Island, Taiwan: We spent a week on each of these islands in September and both were unique experiences.  Orchid island feels like a completely different country than Taiwan while on Green Island, I found another place filled with beautiful views.

Austin, Texas: I’ve only been here for three weeks but I am blown away by how much we’ve enjoyed the energy of the city, how relaxed and friendly everyone seems to be, and how nice the weather is (half of each week at least)

Business Results, Experiments & Learnings

Overall this was my best year since becoming self-employed.  I say this from a completely holistic perspective.  It was both my best year financially and my best year personally.  In addition, the amount of work I did that was based on me needing to join specific meetings or be available at certain times of the day was less than 20 hours for the entire year.  

A win for async work!

Overall Financial Results

Overall here’s where I ended up according to my accounting software

• Revenue: $102, 567
• Net Profit: $72,257
• Self-Employed Taxes: $16,195
• Net Income after Self-Employed Taxes: $56,062

Of course, these are only estimates – actual US taxes paid and potential rebates are yet to be determined.  

Here are breakdowns of earnings and costs by source (costs are assigned on a % basis according to revenue).  All earnings are after transaction fees.

Results By Business Focus

StrategyU: $87,510

Developed a clear advertising strategy. Created, piloted, and won first client for $15k corporate virtual workshop program. Ran for BFCM deal using Brennan Dunn’s playbook => $13k in Black Friday sales

• Think Like a Strategy Consultant: $74,531
• Corporate Workshops / Training: $10,897
• Digital Products: $2,082

Costs: ~$24,209 (majority contract labor + advertising spend)

Profit Margin (pre-tax): 72%

Boundless: $8,905

Focused on writing consistently (newsletter & book) – 72 subs for Boundless.  Launched Freelance Skills Course (~3k in Sales) – an opportunity for marketing in 2022. Does not include $5k investment in Book

• Newsletter: $3,906
• Courses + Digital Products: $3,787
• Book Pre-Sales: $1,212

Profit Margin (pre-tax): 90-93% (estimated)

“Passive” Income: $8,905:

 YouTube revenue saw some decline throughout the year, but peaks in Aug-Sep

• YouTube: $2,148
• Other: $2,713 (includes bounties from AppSumo, affiliate deals from Teachable, Podia, Convertkit, courses and payments from Skillshare, Amazon, and Medium)

Profit Margin (pre-tax): 90-93% (estimated)

Coaching: $4,025

This is from 1-on-1 coaching earlier in the year and group coaching kicking off in December.

Profit Margin (pre-tax): 90-93% (estimated)

Five Biggest Experiments & Lessons

#1 – Think Like a Strategy Consultant had its best year – Traffic continued to increase on my website and Youtube with very little effort to add additional content.  I hired two ads people in Croatia who have helped me implement an effective advertising program.  It hasn’t gone as well as I would have hoped, but I definitely see more potent

#2 – Prototyping, launching & selling a Corporate Virtual Workshop – Last spring, a data analytics company in the US wanted to train their team with my self-paced online course.  I decided I would develop a corporate workshop for them and sold it to them at a discount to help me prototype it.  It went far better than I expected and I ended up developing a clear “signature offer” for my course to pitch to companies.

#3 Productizing other stuff on StrategyU  – Inspired by this post on Austin Church’s site, I decided I needed to take some of my own advice and develop “packages” for some of the work I liked doing.  One reason was to make it simpler for the increasing number of corporate types who were stumbling upon my page and also to create easy on-ramps to working with me.  

Here’s an example on the coaching front.  I make it cheap and easy (but still have a cost) to talk with me but also signal that I do higher-end work (with high price signaling).  Using this I’m already working with two senior executives in 2022 to help them with Board presentations (which I love doing!)

Here’s an example of the corporate workshop.  It clearly signals that I am only working with serious companies that are willing to pay my fee.  If they aren’t they can self-select out and I save the time I might spend on a phone call.

#4 Shipped my freelance course – In June after being locked down in Taiwan after a local outbreak, I decided to create a freelance course that had been existing in my head as a future potential creation for more than a year.  

I think it’s a pretty badass course on helping people become strategic partners to senior-level business leaders.  It walks through the nitty-gritty of everything from proposals, to documents, to pricing, to what to say in conversations.  I am still not sure if I should integrate this with StrategyU or keep it separate but I’m guessing the answer will emerge this year as I plan to put a bit more effort behind this in 2022.

#5 Group Coaching – Throughout 2022, I had more people asking questions about finding other people following similar paths.  Inspired by Tim Ferriss’ question, “what if this were easy?” I decided to create a survey gauging interest in group coaching.  I got 30 responses and from this, I created a landing page, some stripe payment links, and sent out an announcement about doing cohorts starting in December.  I’m currently running an “early career” one and a “mid-career” one and both are going really well!  I think group settings are much better for the work stuff than 1-on-1 because I only have so much experience.  I’m not sure what I’ll do next with these but I’ll likely scale up to something more interesting 

Reflecting on the past five years

On the business front, I seem to be nearing successful completion of a pivot I originally made about 9 months into self-employment when I realized I didn’t want to spend the rest of my life as a freelancer.  At that time, I was also realizing I wanted to optimize for non-work time over almost everything else.  This led to a dramatic decrease in earnings (2017 was only 7 months!) and a shift to a different way of thinking about work.  You can see the transformation here in these two charts:

In this first one, we see that for 2018 and 2019 I wasn’t making much money (which was fine at the time, I wasn’t too focused on making money)

What I was focused on instead was developing skills, experimenting with creating online (which I found I really loved), and finding new income streams beyond freelancing. For most of 2021, I had >10 income streams with 3-5 earning me more than $200 a month:

The biggest driver behind this shift was the slow but steady growth of my course Think Like a Strategy Consultant.  The course has generated more than $172,000 in revenue over the last three years, far exceeding anything I could have ever imagined.  

Through the course, I’ve had a ton of inbound requests to work with me and because I only wanted to work on things I liked doing, I’ve purposely only accepted things I want to test and then potentially turn into an offering.

Over the past two years, I’ve now developed a pretty robust corporate offering, a coaching offering and am even turning this experience into freelance strategy work with corporate strategy groups and boutique consulting firms.  I’m pretty excited about most of this because it’s work I like doing, am good at, and it doesn’t take too much time.

You can see this shift in the following chart:

Luckily, this has given me a lot of time and space to continue to write and explore my curiosity around work.  While the course has provided most of the income, most of my time has been devoted to writing for more than three years.

For 2022, here are five questions and themes themes I’m thinking about for both work and life:

#1 How do I use my happiness, optimism & energy to support others?

I’ve found my footing as a self-employed creator/solopreneur/whatever you want to call me.  I’ve also reclaimed some of my childhood excitement towards life.  The question I’m asking this year: how do I broaden the sphere and support others with this energy?

#2 How do I level up the ambition in ways that are exciting and sustainable?

My fear five years ago: creating a job for myself.  I now am quite confident that’s not going to happen.  I know what drives me, how to fire up my curiosity, and I know when to say no.  With this, I’m thinking about ways to be a little more ambitious with what I’m doing.  I’ve been comfortable tweaking and making 1% improvements over time.  I don’t have any interest in 10x-ing anything but am interested in potentially doubling the scale of the things I’m doing and looking for other ways to help people beyond my comfort zone.

#3 How do I help Angie succeed?

My wife is amazing – smart, curious, and creative.  How do I continue to make sure she is able to do the things that bring her alive while also having the resources to take chances and risks in order to grow.  I think about this a lot but it’s worth writing down here as a gentle reminder.

#4 What are the business or personal things I’m not thinking about (yet)?

Angie and I are always asking some form of this question.  It’s an easy way to keep dreaming and imagining new possibilities.  It’s very easy to know what the default next steps are, especially in the US.  Everyone in my age cohort seems obsessed with owning a home.  It all seems a bit too frenzied for me right now not to mention it’s just not my goal.  However, that means we often need something to aim for.  Right now seems incredibly open after finishing my book.  I don’t need to have an answer but I’m listening for clues.

#5 What are the experiments I can do to continue to grow?

This year is all about play, experimenting, having fun, joy, and trying to remain optimistic.  To do this I plan to continue to do things like play sports, Yo-Yo, hosting events, and then try new things.  Some things on my list: tap dancing, DJ lessons, and hosting a party using Nick Gray’s new book.  In addition, I want to write more essays, create more YouTube videos, do some deeper writing for StrategyU, potentially do a meditation retreat, and much more. 

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Paul’s 2021 Annual Review – From Mexico to Taiwan to the US appeared first on Boundless by Paul Millerd.

A Bit About Me & A Warning About Online Courses

As you read this you may be a bit surprised at how obvious some of my failures or are why I seem to shy away from pushing things further or doubling down on trying to make more money.

Throughout this entire journey I was on a broader exploration of how one might design a life not centered around work. While I’ve seen clear opportunities to make more money at several points along the journey, I almost always optimized for a simpler life and more time to write and do the things that bring me alive.

The creation of courses and coaching were downstream of many years of intense coaching and consulting work as well as hundreds of conversations and thousands of hours of writing about these topics. For the most case, I created these courses after I had some validation that people were struggling with these things and that I had some sense that my way of thinking about these issues was helpful for people.

I see many people aiming at creating courses without first finding the things that they enjoy doing or directly helping people first. The following journey is a five year journey and knowing what I know now I’m a bit embarrassed by how poor some of my thinking and decisions were at the beginning of this journey.

I am sharing my journey below of creating digital content and several online courses and meeting mixed success along the way. I am not the most successful or the flashiest online course creator but I am in it for the long-term, really care about doing these things in a lasting way and want to see others find ways to create their own work.

I write this with the intention of saving you some time on your own journey.

Chapter 1: Idea For A Resume Course

It was 2015. I had decided to dabble in my first side gig as a career coach. Careers with Paul was born and I started writing and sharing what I knew publicly. 

When you decide to call yourself a “career coach” everyone wants help with their resumes. After helping 100 people I decided I couldn’t do 101.

Inspired by the Massive Online Open Course movement and learning about things like Udemy, I thought I might dabble with creating an online course. 

My background in consulting blessed me with the ability to create content quickly and to be able to have a good sense for how to sequence and structure that knowledge. Over the course of a few weeks I created a bunch of slide:

Lesson #1: Creating content with the intention of teaching others enables you to learn something in a much deeper way than simply “knowing” how to do something. I had helped many people with resumes but never approached it by thinking about how to clearly explain what I was doing and why. Creating the resume course forced me to sharpen my thinking, develop an easy to understand framework, and actually helped me get better at what I wanted to teach

I bought my first microphone, a Blue Snowball ICE and set out to record voiceovers with the slides. Given that I was still employed and working with my work computer, I didn’t do any video. For me, I just wanted to ship this thing and get it out there.

I had all sorts of roadblocks and issues with recording voiceovers as well as audio and video editing. When you are first starting never discount how much time you will spend tinkering and fixing really minor things.

Chapter 2: Getting Rich!

Just kidding. 

I posted the course on Udemy in May 2016 and I ended up making $30–$40 in that first year.

While I didn’t expect to make a lot of money, I was surprised at how little you could make on a platform like Udemy. Udemy controls a lot of the pricing and even if you priced something at $20, they might sell it at a discount of $0.99. Not really the kind of platform that’s going to support your life.

I did make my first paycheck from selling things online which was a huge confidence boost as I was thinking about potentially leaving my job.

Overall I was still pretty proud that I was able to create and launch something on my own after having my work tightly controlled by overzealous managers for the previous decade in my consulting jobs. 

I ended up using this as something I could send to anyone who asked for resume help too, which felt pretty good. 

At this point I was still thinking a lot about the depth of materials, the quality of video and audio and the “features” of a course. This led me to want to upgrade the content and make it a little more visually appealing and also to upgrade the audio voiceovers. I have a lot of fun messing with content so I thought this was a fun use of time. 

Lesson #2: It doesn’t matter how good your slides or course are if you are competing on a massive platform where there are 25 other resume courses who are priced at $0.99. Udemy was a great place for some early adopters but probably wasn’t a great place long term if I wanted to make money.

At this point I was still thinking of a course as something that could be consumed asynchronously and as a potential passive income product. I was aiming at helping someone make a change but had still not thought about a LIVE cohort-based course until I stumbled upon Seth Godin’s altMBA.

Chapter 3: “Digital Course Experience”

I’m not sure when I first heard about the altMBA but I remember thinking that this was definitely something that needed to exist. 

I was in my first year of self-employment and discovering that although I had worked in some of the best companies in the world, the skills I had developed were inadequate to creating my own work. I had always written or created things to please others and now I was figuring out how to channel my curiosity into something different.

I talked to alums like Cody Royle who credited the program with enabling him to write his own book. He found the support of others and the focus on creating your own work transformation and for only $2,000 at the time it felt like this might be more promising than the two years and $100,000 I spent on business school.

In 2018 I had started creating and was inspired by Godin’s general advice to focus on finding the people who want your help and to do it with generosity. I took this approach and announced to my newsletter that I was going to launch a “LIVE” course called “Solopreneur Shift” and let people sign up using a pay-what-feels right approach. This felt right in terms of balancing generosity and dealing the the terrifying fear of charging people money for the first time. Here is the announcement from my newsletter:

I paired this with a landing page which mapped out my vision of the course. 

To my surprise I ended up getting eight people to signup up at a mix of different price points. A few people paid the full tuition price (>$300!) which felt both amazing and terrifying. “These people really believe in me, wow!” and “Holy crap, can I do this?”

Here’s a secret you should know: I only built about 20% of the content before “launching”

I don’t recommend this for everyone. My superpowers are creating content and figuring out how to fit different ideas together. I knew that getting signups would be rocket fuel to motivate me to build the course, which turned out to be true.

Instead I focused on getting the sequence and structure of the course right and making sure it made sense to others:

Lesson #3: The biggest motivator for me is helping other people and getting people to pay me up front for a course was the biggest motivation in the world to not let them down. It was also terrifying and there’s probably not a good way to fast-track this step. It’s just something you’ll need to figure out how to power through.

A side note: Traditional vs. Online Courses

In this same summer At this time I was also a Teacher’s Assistant for a class at MIT for the MBA program, helping out a professor I knew. I found it striking to compare this kind of Professor-at-the-front type of “school” with my digital course which was interactive, collaborative, enthusiastic and part of an ongoing conversation on Slack. Many of the MIT students were interested in figuring out what they had to do to barely pass the class while the participants in my digital course were craving a transformation and really wanted to improve their live.

Chapter 4: Dreaming Bigger

Coming off this successful course experiment I was excited. I had made about $2,000 and was convinced that I was on to something. The online course felt alive whereas the class I was helping out with at MIT felt like it was from another era.

While I had given up on making money from my resume course, I made it free and kept it on Udemy and forgot about it. Out of the blue, I received the following graphic in an e-mail that made my brain explode. People from 94 countries had taken the course, what?!

This is when I started to realize that the opportunity of online education might be a lot bigger than simply training Americans in my backyard. 

Online courses shifted from something that I saw as a fun experiment to something that I wanted to place a bigger bet on for the future.

Chapter 5: “Strategy Toolkit”

My background before I quit my job was working in the strategy consulting industry for nine years from 2008 to 2017. One of the things I loved while working in the industry was taking extra time to participate in developing content and leading trainings for new hires and colleagues, teaching them the “consulting process.” 

In addition to this, I had started advising an undergraduate consulting group and over a few years had figured out how to backwards engineer a lot of the things I had learned and explain and train them in a way that was making a real different in their skills.

So when I went solo I thought that one thing I might do was to lead internal company trainings and I did exactly that as one of my gigs in the first year. I helped to design and lead a training for first year analysts at a software consulting firm. This was a month before I ran “Solopreneur Shift,” however, and I had never imagined that I might do this online. 

After Solopreneur Shift, I changed my mind about consulting trainings and quickly adapted some of the ideas for a virtual setting. I ended up moving to Taiwan in the fall of that year and when my consulting work evaporated and I was rested after an extended period of non-doing mode, I decided that I would embark on what I was then calling The Strategy Toolkit.

The first thing I did was to purchase a year subscription to Teachable (affiliate) which felt quite bold at the time for someone that had made less than $1,000 in three months. However, what it was was a bet on myself and a way of raising the stakes to guarantee that I would follow through.

I’m a bit embarrassed by the first iteration of the course but not about the Ninja.

I launched this after a steady month of creating and shipping and I got rich!

Just kidding, again.

I sold a few copies of the course to friends that believed in me and then considered it a failure. I stopped thinking about it for a bit and assumed that it might be time to move on from this dream of being involved in online courses. 

Chapter 6: Re-Branding As StrategyU + Think Like A Strategy Consultant

A month before I left my job a company flew me out to Los Angeles to have a conversation about leading an Academy that would help train consultants. I told them that I thought we should go virtual and call it “StrategyU.” They wanted me to merely be a salesperson for the course. They already had the materials and they thought people don’t want virtual trainings. I said no and left to self-employment a month later.

Fast forward 18 months later and I had created my own consulting course but I had launched it under “BoundlessU” which was the home of my main blog. As I mentioned, I had figured this might earn me some money here and there but that it was a lost cause. I was hoping merely to recover the $39 a month teachable fee. 

I moved to Bali after my failed launch and luckily I was joined by Jay a freelance digital marketer who quickly made me realize I was a marketing moron (he’s since moved on to launch a woodworking business in Colorado). He was really impressed with the course and believed in what I had. Simply seeing him excited about it was encouraging. It made me want to pick it up and give it another go. Together we brainstormed four things I would do immediately:

#1 Video: Shoot high quality videos introducing myself and giving more of a personal explanation why this course mattered to me and how the pieces fit together along the way

#2 New Brand and Course Name: Move the consulting articles I had written off my main blog and on quora to a separate site, which I planned to call StrategyU and change the course to “Think Like A Strategy Consultant” to more clearly communicate the shift I was selling. I had the advantage of already having SEO traffic of many of these already as well as many other “validated” posts I had written on Quora that received a lot of attention, including a post upvoted by Ramit Sethi which gave me another confidence boost.

#3 Give away high-quality content: Create a lot of valuable content for people to get an understanding of what kind of skills I was teaching in my course

#4 Free e-mail course: Create an e-mail signup and create a multi-day free e-mail course previewing content in the course.

Excited by this second chance, I started writing like a maniac and had rebuilt the course and site within a few weeks.

By the end of April 2019, I landed my first sale of the course from a stranger on the internet and the excitement of having something that might work motivated me to keep working to improve the course. 

In that first month I ended up selling 10 copies of the course (which I was still pricing at $99) and was kind of shocked that my strategy had worked. Throughout the rest of the year I had a steady stream of sales.

It’s hard to understate how shocking this was to me and how much it shifted my attention away from working as a freelancer and towards the creator economy. I was equally excited to see that less than half of the course sales were from the US and the rest spanned across 23 other countries:

Australia, Austria, Canada, China, Denmark, France, Germany, Hong Kong, India, Indonesia, Kenya, Malaysia, Netherlands, Norway, Peru, Saudi Arabia, Singapore, South Africa, Spain, Thailand, Turkey, UK, USA, Vietnam

Lesson #4: Digital products need some form of distribution. For me, SEO worked really well because this was an in-demand topic via google but other strategies like e-mail marketing, audience building on platforms like Twitter, and partnerships all seem to be viable strategies.

Chapter 7: My First Live Cohorts Of Think Like A Strategy Consultant

Although I was finding success with my course as an evergreen course, I wanted to run it as a cohort-based course to work directly with the students and use it as a way to keep improving and upgrading the course. 

In July 2019 I ran my first cohort to launch my first cohort and used this as an excuse to upgrade the course including adding challenging assignments and structuring it around a four-week cadence. This four-week schedule would pay bigger dividends down the road when I shifted it back to an evergreen course. 

I ran two cohorts and used a discord chat and also added a discourse forum. I enrolled about 10–15 people in each sessions and it went pretty well yet the entire time it felt like something was missing.

The biggest challenge about the cohorts was that almost everyone was a beginner in terms of the skills and they all wanted direct access to me and my feedback. It’s not easy for a novice to identify clear opportunities for improvement as easily as a novice might be able to point out opportunities in something like writing or speaking. 

After running two cohorts, I decided to shift the course back to an evergreen format with the new assignments and four-week structure. I created two clear options. One that was self-paced and another where they could work directly with me to get feedback.

• $429 “Consultant” — Self paced and minor feedback
• $699 “Partner” — Coaching Call + Feedback On Weekly Assignments

With this pricing and structure, I was in a great place when my target audience was forced to work remotely. This lead to a sustained spike in sales from April onward and for 2020, the course was able to fully support me and my wife’s life off, with more than $50,000 in revenue.

While I had made a decent amount of money in 2019 it was nothing like what happened in 2020 and for the first time I started to think that running online courses was something I could really lean into to support my life for the next several years.

Lesson #5: Just because “cohort-based courses” are all the buzz right now does not mean other models won’t work well for your course. I’ve been fascinated by the cohort-based course movement but I think there is room for a number of models to work with online courses.

Chapter 8: Re-launching “Solopreneur Shift” as “Reinvent”

While it was amazing to be gaining traction with my consulting course in 2019, I knew that the course I needed to put into the world was the updated version of solopreneur shift. Since I quit my job in 2017 I have been increasingly drawn to helping people navigate and make sense of this new world of work.

As someone that loves the act of creation, creating a course has the added benefit of forcing me to simplify, synthesize, and communicate my ideas for other people. While the course has only had minor success since I launched it, it has had an incredible downstream impact on my writing and the quality of my ideas, helping me reach many more people through my ideas in 2020.

I had learned my lesson of not validating my course before launching so this time I decided to build it in public, inspired by the approaches of people like Nat Eliason and Ryan Kulp who both took similar approaches with course.

For me this was a great strategy because it channeled my motivation for helping individuals as a push to “keep going.” By tweeting and sharing my progress, asking people for feedback and sharing my progress, I was able to passively sell 10–15 spots in the course before I had built most of the materials.

To raise the stakes for myself I also decided to invest in a $100 light and also signed up for Podia as a way to make another financial commitment. These small purchases seem to have the effect of committing me to following through and once I spend the money I am thinking about running the course as a micro-business where I need to earn back the initial investment. Your mileage may vary. .

The course was designed around a five-week structure and the biggest component was an “action challenge” that would require students to publishing something in week three. 

Several people launched things that they are still working on to this day which is pretty much all I could ask for.

(Side note: I have a much more detailed writeup of the process of creating this course on Podia’s site)

In October of 2019 I finished the course in time to spend a relaxing few days in Japan before I launched the cohort with 35 people from around the globe. I ran two different sessions for the different time zones, had a co-facilitator join me, more actively encouraged sharing in a Discord group and overall it is the best experience I’ve had running an online course. 

Creating and running this cohort of Reinvent was one of the most rewarding things I’ve ever done and although I haven’t run a proper cohort again (mostly due to health issues), I’m excited to potentially run it again in 2021 or 2022 or whenever I find someone that might be interested in re-launching it with me.

Lesson #6: Not every course has to be a monetary success. The biggest benefits for me in creating reinvent have been going much deeper in a number of topics I plan to keep writing about for many years in the future. In many ways creating this course helped me improve my thinking and writing and helped me build the courage to pursue writing a book in 2021.

Chapter 9: Gift Economy Approach

With all the material I’ve created I’ve always tried to integrate a gift economy approach. I’m not going to go in-depth here but my goal in creating is usually for my own selfish reasons of making sense of the world, joy of creation, and then if I’m lucky, helping others. I want as many people as possible to benefit regardless of how much money they have.

It’s taken a few iterations to get right but I have landed on an approach that seems to deter most people from taking advantage of the system and encourages people with less to apply.

Here is the current language I have on my site

This directs people to a small exercise where they can share their motivation and offer a “gift” that feels right. I nudge people to offer something because in previous iterations where I offered it for free no one finished the course!

Here is an example of some of the amazing applications I receive:

Nothing inspires me more than people with the motivation to learn from all parts of the world. I find over and over again that the people with the least are often the most hungry to learn and this makes me incredibly optimistic for the future.

Chapter 10: Ongoing Tweaks and Opportunities

The success of my consulting skills course has continued. At the end of 2020 I was offered a chance to take part in an accelerator program to re-launch the consulting course as a cohort-based course. While it was increasingly clear to me that I had a lot of upside potential, I decided against it and doubled down on making my course even stronger. I invested in experimenting with ads, learned how to upgrade my landing page (h/t to Julian’s guide here) and have continued to slowly upgrade videos and content based on student requests. 

At the beginning of 2020 I crossed $100k in total sales which would have been unbelievable two years earlier when I had all but given up on my course and also reached 300+ students in 36 countries

The money I’m making from this course is more than I need and for now I am spending time writing, learning Chinese, and writing a book. I might decide to take my courses to the next level at some point, but I’m not in a rush. 

That doesn’t mean I’ve ignored all opportunities. I recently kicked off the first cohort-version of my course with a small data consulting firm in the US and am hoping this turns into something I can run with more organizations in the years to come. My hunch is that running it within a single organization solves a lot of the challenges I had with running it with random people across the globe. Time will tell. 

With Reinvent, I’ve turned it into a self-paced course as well but there has not been much interest. I’ve more or less broken even on this experiment which I’m happy with because this is the material I enjoy the most. I’ve recently launched a high-end coaching version of the course which I’ve having a lot of fun doing with someone in Mexico right now.

I’ve had a ton of fun doing all of this and if I never made another dollar from online courses I would have zero regrets from any of this. I feel incredibly lucky that I’ve been able to to build a life and work doing things I enjoy doing and get paid for it. 

Lesson #7: While it can seem like there is a lot of pressure to capitalize on the zeitgeist immediately there is probably also a benefit in playing the long-game and building things in a way that are sustainable and in a way that integrate with how you want to live and work. It seems after five years of doing this that I’m down to keep exploring for another five and I’m excited to see where things go!

Hopefully this guide will help you do the same.

To Learn More & Some Links

If you’re interested in learning more about my courses you can check them out. I’m always open to hearing ideas, or suggestions and definitely open to hearing about ways we might be able to partner on something:

• StrategyU and Think Like A Strategy Consultant
• Reinvent Course

If you are interested in supporting my journey or launching your own course, you can check out my affiliate links for Podia, or Teachable. Here is more I’ve written on creating courses

• Launching a course in 30 days
• My review of Ali Abdaal’s course & online learning in general
• “Are online courses the future?”
• Gift economy thread
• Reinvent launch thread
• Online course journey thread

Some must-read links:

• Tiago Forte’s article on STEVEs and The Future of Online Education

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post My Five-Year Journey Creating, Launching, Failing & Succeeding With Online Courses appeared first on Boundless by Paul Millerd.

There are certainly big chunks of the world where the way to win is to hack the test.

Graham talks about “bad tests” – ones that incentivize people to re-orient their entire attention towards doing well on the test as the primary goal.

In a guest post here on Boundless, Ranjit shared how he stumbled upon the easy-to-follow “test” of breaking into BigLaw:

The great thing about choosing a career like law is that the steps are laid out for you. Life’s existential fears are traded for certainty. Even the uncertainty of winning a training contract was off-set by how formulaic a process it was to land one: attend work experience, attend a summer scheme, talk-up made up extra-curricular activities etc. 

Graham argues that many people follow these paths because they accept “this is the way things work.”

I suspect many people implicitly assume that working in a field with bad tests is the price of making lots of money. But that, I can tell you, is false. It used to be true. In the mid-twentieth century, when the economy was composed of oligopolies, the only way to the top was by playing their game. But it’s not true now.

This certainly resonates with my own perspective as I graduated college and early in my career. It wasn’t until about 2014 when I started to see new possibilities emerge.

You Still Need To Know How To Hack Tests, But Its Not The Only Game

Most college students ask me one type of question:

“What can I do to get accepted by ___________?”

They want to know the answers to the test.

I’m no better than any of these people and this is why I’m interested in writing about it. For the first ten years of my career, I became highly skilled at determining the rules to “bad tests,” and molding myself to gain entry to jobs and universities.

Graham describes my former worldview well:

You might actually like to win by hacking bad tests. Presumably some people do. But I bet most people who find themselves doing this kind of work don’t like it. They just take it for granted that this is how the world works, unless you want to drop out and be some kind of hippie artisan.

I kept playing the game, but increasingly grew to be frustrated with the fact that there was no end to the game. Playing the game seemed to matter more than what you actually did and especially so the higher you got within a company.

When I “dropped out” I was driven by a hunch that there might be more ways to play the “game of work” than ever before.

Turns out I was on to something..

In the first year I discovered that starting from scratch and really focusing on trying to do great work was pretty hard. I felt pretty insecure about what I was doing and found that I was pretty bad at a number of skills that I never really had to test with “skin in the game”: negotiation, end-to-end consulting projects, coaching, listening, business development, design, writing, web development and so on.

Over time, I started to gain a little confidence that there was some payoff in continuing to learn and get better at a number of these things.

I’ve become optimistic because of this and think that there are more ways than ever to make a living through work and to find ways to be rewarded for trying to do great work. This sentiment is shared by Graham:

The more I think about this question, the more optimistic I get. This seems one of those situations where we don’t realize how much something was holding us back until it’s eliminated. And I can foresee the whole bogus edifice crumbling. Imagine what happens as more and more people start to ask themselves if they want to win by hacking bad tests, and decide that they don’t. The kinds of work where you win by hacking bad tests will be starved of talent, and the kinds where you win by doing good work will see an influx of the most ambitious people. And as hacking bad tests shrinks in importance, education will evolve to stop training us to do it. Imagine what the world could look like if that happened.

Don’t Become The Game

I always give one piece of advice to the students I talk to:

“understand the game…don’t become the game”

In my last job I worked with companies to help them assess internal candidates for CEO succession. In one company the eventual successor told us in an interview why he should be the one they pick. He laid out his twenty year career path of working in every function, business unit and region of the company. Exactly the impossible mix of experience that most companies look for when trying to promote someone to CEO.

Was he lucky or did he hack the test? Turns out this was all by design. Early in his career he told us that he “decided” he wanted to be CEO and set out to make it happen.

He became the game.

The reason I’m concerned about this is I see more and more people doing the same thing as the CEO. They come up with a certain goal, identify people who have what they want and then try to reverse engineer how those people got there.

The most striking example of this is when I hear many of my friends starting to talk about college already even though their kids haven’t even left the home. They seem to be embracing beliefs I didn’t really know existed until I entered elite circles myself:

there’s the implicit belief that a premier prekindergarten program guarantees an early leg up in a nearly 14-year battle to gain admission to the country’s most competitive colleges.

Growing up I was lucky to not really have a lot of pressure on what I was meant to do when I grew up. I didn’t even think too deeply about college until I was a junior in high school. Even then I only applied to one school.

I started teaching myself the rules of the game when I was in college trying to break into strategy consulting. Perhaps this enabled me to abandon the game in shifting to my current path. It never really felt natural and I suspect for many of you, you hate how much you have to play the game.

Unlearning this mode of being was hard, but also worth it. Even though I haven’t fully unlocked “permanently successful solopreneur mode” yet, I feel more alive with learning, curiosity and optimism than ever before and seem to be playing a game that I can live with.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Learn the game, don’t become the game appeared first on Boundless by Paul Millerd.

Like many young people, he had an inflated sense of his capabilities. He thought he was capable of more, yet his boss demanded that he put in his time and wait his turn. His boss could be cruel, even abusive. Ben could think of nothing more than overthrowing his boss and replacing him.

He got a small taste of this when his boss was forced to take a leave of absence and for a short period of time, Ben had autonomy and loved the freedom. This gave him a sense that it was something he needed to have in the future.

As soon as his boss returned, the old ways resumed. Resentful, Ben took matters into his own hand. He first tried to secretly obtain work with competitors in the city, but most people knew his boss and didn’t want to get on the wrong side of him. Even though they saw Ben’s talent, they didn’t dare make an enemy in the process.

Ben realized that he would have to leave the city he lived his whole life and start fresh. At the age of 17 years old and after six years working for his brother as an apprentice, Benjamin Franklin set out for Philadelphia.

The urge for freedom, adventure and to carve our own path is timeless. Most college students tell me that one day they “hope to run their own business.” Most people in the corporate world harbor some fantasy to do something more entrepreneurial even if they are afraid. Even those inching towards the end of their careers are not immune. I talk to baby boomers who see retirement as a way to engage in those things they always wished to pursue when younger.

In Franklin’s time, a journey from Boston to Philadelphia was not an easy drive down Interstate 95. He had to take a boat. Here is how he describes his journey in his autobiography

In the evening I found myself very feverish, and went in to bed; but, having read somewhere that cold water drank plentifully was good for a fever, I follow’d the prescription, sweat plentifully most of the night, my fever left me, and in the morning, crossing the ferry, I proceeded on my journey on foot, having fifty miles to Burlington, where I was told I should find boats that would carry me the rest of the way to Philadelphia.

It rained very hard all the day; I was thoroughly soak’d, and by noon a good deal tired; so I stopt at a poor inn, where I staid all night, beginning now to wish that I had never left home

Most people’s capacity for discomfort is less than Franklin’s. Yet we still have the same urge to carve our paths. To reinvent. To step into the unknown.

What we lack is not courage, but a deeper set of mindsets, tools, and models for navigating the modern world and making sense of what the journey might look like. We don’t need another article telling us that pursuing our passion is going to make us happier. We don’t need to be told that our boss doesn’t know how to manage.

We need an updated map of reality and better approaches for thinking about stepping into the unknown. Here are six ways that work and carving your own path in the world are different than we think.

We need to update our expectations of what work actually provides

Less than a third of people work in full-time jobs. Even less have jobs with great healthcare, benefits and a path for personal and income growth. Yet our assumptions about the working world are based on a myth of the “organization man” from the 1950s:

As Seth Godin says:

The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve.

Follow the path and be taken care of.

I get e-mails and have conversations with people on a weekly basis who “played by the rules.” They got the degrees, credentials and jobs that were supposed to guarantee them everlasting fulfillment. Yet they face misery, anxiety or unexpected failures in their jobs.

Here is a friend who had followed the default path of success and had experience at a top consulting firm and had a top-tier MBA:

As an amazing example of big corporate bullshit, the new position I was going to accept was then re-orged into oblivion as part of an unrelated org change that wasn’t coordinated with the first one – effectively laying me off for a second time in six weeks. From there, the guy who would have been my boss kept putting me in touch with internal people who had open positions, which I felt I might as well explore.

Half of those conversations were about mind-numbingly boring jobs or resulted in the hiring manager saying “I’ve heard great things about you, we had a great conversation and you seemed great to work with, but I need to hire someone with more specific experience here”. Those reactions highlighted that whatever cachet I had as a high-potential general manager was evaporating before my eyes as part of this acquisition of my business unit.

This story is all too common. However, our conventional beliefs about the working world is that it is working just fine so they don’t tell anyone. It is surprising how many people I talk to in these situations that have not told anyone in their life. There”s probably a deeper question about why they are telling me, a stranger on the internet, but that’s not worth exploring here. Career stagnation and finding yourself lost on the journey still brings enormous shame because we are operating with broken assumptions.

For many, they do get what they deserve. At least in the beginning of their careers. For many college graduates, there is a somewhat straightforward path that looks something like this:

…but then things get wacky. Many companies still promote a clear career path but struggle to fulfill their promises because of slow growth rates. Many people expect some sort of easy path to a senior Director or executive role. The reality is a bit messier. This means that people’s careers start to look a little more like this:

Navigating a career and more importantly, a life, in the modern world is hard. You used to be able to bank on steady income rises to cover a 3-year mortgage, but how do you bank on that now?

I wish this wasn’t the truth, but as I’ve talked to hundreds of people over the past few years, I’ve realized that the people who have mastered reinvention – dealing with uncertainty, keeping flexible financial obligations and experimenting with new work identities – seem most excited about the future.

So while that senior executive tells you “work hard buddy and you’ll be taken care of one day” look at him and smile, not because you’ll be taken care of but you know something he doesn’t know. That there are no guarantees and that counting on that kind of path is a bit crazy.

Quick quiz: What do the following items have in common?

• Data scientist
• SEO Manager
• Substack Paid Writer
• Chief Happiness Officer
• Blockchain Developer
• Remote Fitness Instructor
• Online Course Designer

These are all jobs that barely existed when I graduated in 2007. Now, there are literally hundreds of thousands of people doing these jobs around the world.

How would I have planned for that? In one of my consulting gigs last year I had to rely on my website building skills which I first taught myself for fun when I was about 10 years old. I certainly didn’t plan that – I was just lucky I could help.

Unreasonable ideas of success prevent us from taking action

Everyone has seen an article like this. It exists (and works) because it taps into our deepest insecurities about money, status and power. This is great for clicks, but this line of thinking convinces us that being successful means making a lot of money and convinces many that its not even worth getting started.

Over the past 2+ years I’ve fielded countless questions about my plans for hiring employees and growing. The assumption is that everyone is an entrepreneur and that everyone must always want more. This assumption is so strong that it convinces countless people to invent plans for scale even though deep down they know they have enough.

Paul Jarvis, who wrote a book called Company of One, once wrote about a new business venture he joined with two other people:

‘If this company needs business growth beyond the three of us, I’m out.’

…Not because I’m afraid of success, but because “success” to me means being able to get what needs done, done without having to hire a team

When I was thinking about launching a podcast, someone asked me how I was going to monetize it. I told him that wasn’t my goal. I just wanted to try something new and see if I had fun doing it. My gut told me that it was a forcing mechanism to be creative and push my thinking to the next level. It only cost me about $75 for a microphone to get started.

I talk to many people who have been stuck for years. They would love to try out working on their own or some creative project but have a deeply embedded fear of failure. Part of this comes from our ideas of what success looks like.

We don’t see stories of the solopreneur like Jarvis who is more focused on “having enough” than getting rich. We think instead in terms of the brands and personalities that capture our attention. If you are thinking about becoming a freelance consultant you worry about competing with Mckinsey and BCG. If you are thinking about starting your own thing, you think about Gary Vaynerchuk and Tim Ferriss. If you are thinking about starting a podcast, you are competing with Gimlet and NPR.

It’s easy to fall into this trap. Here is a screenshot of my podcast in Apple’s mediocre podcast app:

When we look at this, it seems like we are in direct competition with each other.

Except This American Life operates like a Fortune 500 business unit instead of a fledgling startup and this is only one of NPR’s many podcasts. Let’s take a look at their team compared to mine and the number of listeners.

If I’m comparing to NPR, I’m an absolute failure. Yet those 200+ people that listen to my episodes? Some of them include you and I think you are some of my favorite people in the world.

I’ll take my people any day of the week.

When people think about carving their own path, they immediately think about whether or not they will be successful and by successful, they mean money and what other people think of them. While this can keep people working and hustling for years, its not a path to building a sustainable life.

The real challenge of carving your own path is finding the work that you want to keep on doing. This will create a feedback loop that gives you energy, enables you to meet people that are excited in similar ways and keep coming up with ideas to experiment with.

When people think about the internet, they assume that everyone is engaged in some form of molotov cocktail verbal warfare. What I’ve found is that most people on the web aren’t actively engaging in negativity and instead are just looking for interesting ideas or interesting people to connect with.

As of this year, Mary Meeker tells us there are 3.8 billion people connected to the internet. What this means is if you are looking for the people that might resonate with something you are creating, working towards or sharing, your search might be easier than you think.

You just need to find your relevant speck of the universe. If you are working as a freelance consultant, you likely need no more than 5-10 steady clients to support your life for the next 5-10 years. If you are selling a course for $200 and want to earn $100,000 a year, you only need to worry about finding 500 people who are excited about what you are creating.

You’re also probably not thinking weird enough.

For Marielle Chartier Hénault. In 2015 she started a Mermaid School and now has 10 schools across Canada and the US. She supports her life with this:

She likely started the business to find out if there were other people that shared the same interests. The same driving force led me to start my podcast, keep my newsletter going, and to keep experimenting and trying new things. She found a bunch of people that wanted to go on a journey with her and I’ve found a bunch of people that keep e-mailing me or having curiosity conversations with that say “keep going.”

Maximizing wealth and size are only two options for orienting your behavior. The internet has enabled even more options for sustaining your life than ever before.

We need to stop ignoring our craving to create and express ourselves

What would you do if money didn’t matter and you couldn’t tell anyone about it?

I like this question because it helps remove prestige and status from the equation. However, when thinking about getting started, people stumble in two areas:

First, most of us think about creativity as something we need permission to do. We need to get accepted into a job before we can create something. We need to be formally part of certain organizations.

While there are still some gatekeepers, you don’t need permission to publish your own book, publish your own music, share your writing or thoughts, sell your crafts or even offer your services. You can even become a cab driver via Uber or Lyft.

Second, people are terrified of putting something out there. There is that internal voice that says “what will people say?”

I can’t cure this for you. In fact, I still feel like a fool every time I hit publish or share. This is from George Leonard in Mastery:

The early stages of any significant new learning invoke the spirit of the fool. It’s almost inevitable that you’ll feel clumsy, that you’ll take literal or figurative pratfalls. There’s no way around it. The beginner who stands on his or her dignity becomes rigid, armored…

The only way to overcome this is to get started. This is what I did when a career coach challenged me to e-mail 100 people I knew in 2015 and tell them I was taking the leap to become a career coach. That small step was one filled with terror and a feeling I can’ only describe as peak feeling like a fool.

I still feel silly, but I’ve done a number of experiments over the last five years as you can see by some of my below-average logos:

All of these experiments started simply – typically with a conversation where someone was excited about the same thing or asked me “why haven’t you done this?” My rule is that if three people ask me to do something, I probably should. Despite a number of experiments under my belt, launching my podcast in December 2017 was was still a nauseating thing to do.

Each of the experiments has been valuable. Some have turned into things that help support my life. Others have helped me realize what I didn’t want to do.

We’ve already talked about our unreasonable mindset of success, but what is a good model for thinking about creation. Shouldn’t we have a goal? For me, my model is simple. It’s all about finding out what’s in the unknown:

People write about the hacks for getting started, but overcoming your own insecurities is just not that easy. This is why the most “successful” often tend to rub us the wrong way. Let’s just say that their inner voice saying “you are a loser” is just not as powerful as yours.

What does work is finding people that believe in you. I get a bit too excited when others share their creative ideas with me. I tend to turn into an instant cheerleader and supporter, asking them “why not?!”

Earlier this year, while spending some time in Bali, I put a post in a coworking community that I would help anyone launch a podcast in less than an hour. A brave group of three people volunteered and 70 minutes later, we had a podcast launched.

I’ve turned this into a sort of personal mission, helping anyone and everyone launch new creative ventures. There are plenty of people that will tell you how your idea sucks, how it won’t work, how you haven’t thought through the business model or that it already exists. Get away from them. Find a crazy weirdo like me who thinks you have something worth sharing.

Overcoming friction to getting started is hard. We need to embrace tools My personal favorite tool for doing this is called the Most Dangerous Writing App. In fact, it’s how I ended up writing the introduction for this article. Set the timer and write. If you stop typing, everything disappears. Try it out for 5 minutes and let me know what you think.

While you may be thinking you have nothing to share, nothing to create I bet that deep down there is something there. If you are subscribing to this newsletter, you probably have a small drop of creativity waiting to be released. David Whyte offers some powerful questions about where to look:

1. What is the work that brings you alive?
2. What are the places that bring you alive?
3. What are the conversations that vitalize you?
4. In who’s presence simply by being in their presence do you find becoming your best self?

Life is (incorrectly) framed as all-or-nothing leaps

We glorify the leap. The person that takes a bold leap into something new. We wish we could be them, but shit that looks scary.

We tend to judge people’s actions by an external interpretation of what’s happening. One day they’re working full-time and the next day they are not. One day someone is working as a glorified telemarketer at a startup and the next day they are in nursing school. I’m sure many people saw my personal leap without any clients as madness.

What people didn’t see in my own journey were the years of small experiments, the new connections I made through my writing, the growing courage through stepping into uncertain opportunities and my dreams about carving a new path. Leaving the corporate world was inevitable. Many small experiments got me to a tipping point where I had enough courage to leave. I just had to pick a day.

Some of you may have listened to the podcast I did with John Zeratsky. He wrote a viral article titled, “I Quit My Job to Sail Around Central America for 18 Months.” While the title of the article makes sense to get people interested, the truth was a bit more nuanced. He and his wife had dreamt up the plan five years prior and had already delayed the trip once by two years. Prior to taking the big leap, they tested their plan:

“Before we left…we would take small sailing trips, we would go somewhere for one night…later that year we would do that for a long weekend, then for a week and then for two weeks. A couple years before we left on the “big trip” we went for two months.”

Instead of taking a leap, they “prototyped” their life seeing how smaller trips felt, what skills they needed to learn and to see if they wanted to keep going.

I’ve been living in Asia for the last year, living as a “digital nomad” in Taipei, Bali and Chiang Mai. Four years ago I never would have imagined living in such a way. As I started my self-employment journey, I found myself having more flexibility than before and found I could often design my work around my life. I took two one-month trips and on the second trip ended up doing some work while traveling. Only on that trip did it dawn on me that I could reinvent the way I was living. I decided to prototype a longer “trip” of three months in Asia. That trip has turned into a year and who knows what’s next.

Alastair Humphreys once traveled the world for four years straight and has gone on some incredible adventures. However, as he has started the next chapter of his life and is raising a family, he has found a way to embrace that adventure that was core to his life. He works with people and challenges them to think smaller and embrace “micro-adventures.” He describes them as:

an adventure that is short, simple, local, cheap – yet still fun, exciting, challenging, refreshing and rewarding…for normal people with real lives.

You don’t have to pack up your life and become a nomad, but you also don’t have to be scared of shifting in a new direction.

What is the dream you have that you might be able to prototype?

Our craving for security is real, but the pursuit of money & traditional metrics will not solve that

In 2015, Kevin Durant left his team of nine years to join the best basketball team in the world. In the NBA, great players like Durant are judged based on whether or not they win championships and this undoubtedly factored into his decision to dramatically increase his odds at a title.

Except when he ended up winning a title, he was disappointed. In the off-season, his friend Steve Kerr could tell that winning the title had only made him realize there is more to life than achieving other people’s goals.

Many people face this same realization after landing their dream job, making $100,000 for the first time, getting promoted to Partner or getting accepted into their dream school. They realize that they need to pick another more challenging goal or come up with some deeper perspective for how they want to live their life.

Daniel Kahneman won the nobel prize for his work on how the brain works. Earlier in his career, he started studying happiness, but ultimately decided to abandon it and work on something else. Here is what he found:

“People don’t want to be happy the way I’ve defined the term – what I experience here and now…it’s much more important for them to be satisfied, to experience life satisfaction, from the perspective of ‘What I remember,’ of the story they tell about their lives.”

People want a story about their lives that they can be proud of. When we chase easily defined metrics they leave us inevitably empty. People in their early twenties can more easily come up with new goals to chase (think about the cliche of the 27 year old deciding to run a marathon) because they have accomplished so little in terms of traditional metrics.

At some point people reach a “wtf” moment, where they start to reflect on their life in a certain way and realize that there is a deeper game worth playing. While money can lead to happiness and life satisfaction, there are limits. Research has shown that in terms of day to day well-being:

health, care giving, loneliness, and smoking are relatively stronger predictors of daily emotions

This makes intuitive sense to most of us and even more sense to people that have faced a health crisis. Such a crisis is often a “WTF” moment for people. For others it is getting fired, losing a loved one, an end of a relationship or even just a moment of desperation after years of a slow, creeping sense of dread.

Andrew Luck was at the top of his game when he decided to step away from being the Quarterback of the Indianapolis Colts. Yet his “WTF?!” moment probably happened four years prior to that decision. He was injured and for the first time in his life, he didn’t dedicate every waking moment to football. Here he is talking about the experience:

“I’ll say it right now—I think it was a blessing in disguise,” Luck said. “Absolutely. It forced me to reevaluate many, many things in my life. And the result has been … yeah, really positive. And I shudder to think of not having that. I don’t think I’m married if that had not happened. I think I eff that up. I truly do. I truly do.”

He had found that the “easy metrics” of a first chapter weren’t enough for him:

“I’d put way too much of my self-worth directly into how I was performing on the football field,” Luck said. “And then I wasn’t on the football field and I felt quite empty. It was very unhealthy, first for me, second for the relationship with my now-wife, and my other relationships.

While the circumstances of Luck’s decision, namely the fact that he’s walking away from one of the most desirable and high-paying jobs in the world, make his decision seem crazy – the same type of decision is being made around the world every day.

We need to embrace the deeper game of the second chapter.

Don’t Be Afraid To Start Your Next Chapter

Benjamin Franklin’s accomplished an enormous amount in his life. He can lay claim to inventing the lightning rod, political cartoons and bifocal lenses, played a pivotal role in the declaration of independence, became the first postmaster general and helped start the University of Pennsylvania.

However, many of these accomplishments happened in the second half of his life, only after he decided to walk away from a successful printing press and other appointments at the age of 42:

When I disengaged myself, as above mentioned, from private business, I flatter’d myself that, by the sufficient tho’ moderate fortune I had acquir’d, I had secured leisure during the rest of my life for philosophical studies and amusements.

One of the biggest challenges people face in modern times is walking away from a life that makes sense as Sophie Kleeman says:

It made perfect sense in my mind, but it felt as though most of the people around me were baffled.

We confuse “making a living” with living the life we want to live. We also confuse leisure with “idleness.” In Franklin’s time, leisure still met both reflective contemplation and active engagement in the world.

Over the next 42 years, he lived a life of adventure, experimentation, and creativity all because he had the courage to reinvent.

If you find yourself saying “hell yeah!” at the end of the post, I offer a self-paced course that will help you go through some of these activities and lay the groundwork for your own reinvention.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Reinvention Is The Most Important “Skill” You Need To Have In Today’s World appeared first on Boundless by Paul Millerd.

As I started my career, I began my own sort of philosophical and liberal arts education.  But given my limited background, I had to lay the groundwork to get to some of the deeper questions and mental models that helped me eventually take a leap to carve my own path beyond the corporate world.

I often see people suggesting deep philosophical books that question the meaning of life but realize given my own past mental models, that this approach doesn’t make sense for many people.

It is easy to dismiss books such as Dale Carnegie’s “How To Win Friends And Influence People” or David Schwartz’s “The Magic Of Thinking Big” but to someone indoctrinated in business, those may be the most reasonable books to start with.  Alas, it was these kind of books that made me hungry to go deeper.

What follows are ten types of books that you can use as a roadmap to dream of a life beyond the corporate world.  I’ve offered a “starting point” for each category which is probably the most accessible of the options:

1. Thinking About What Matters
2. Building “Human Skills” In The Workplace
3. Know Thyself…In The Business World
4. Questioning The Modern State Of The Business World
5. Finding Some Hope In The Business World
6. Mindfulness & New Emotional Mental Models
7. Carving New Paths & Wandering Into The Unknown
8. New Models For Seeing The World
9. Grappling With The Role OF Work In Our Lives
10. Going Deep – The Hard Questions

I. Thinking About What Matters

Start Here  Tuesday’s With Morrie (Mitch Albom)

Helped me to think about life from the perspective of the end of one’s life. In this story, Morrie has lived a full life and has deep relationships as evidenced by the number of people who are constantly visiting him.

So many people walk around with a meaningless life. They seem half-asleep, even when they’re busy doing things they think are important. This is because they’re chasing the wrong things. The way you get meaning into your life is to devote yourself to loving others, devote yourself to your community around you, and devote yourself to creating something that gives you purpose and meaning.

Last Lecture (Randy Pausch)

Randy Pausch is a dying professor who decides to devote his energy into a literal last lecture.  What transpires is a talk focused on never ignoring your inner child and a story that will likely deeply resonate with many.

Survival In Auschwitz (Primo Levi)

This book is a deep contemplation into what is means to live and survive in the darkest of places.

Sooner or later in life everyone discovers that perfect happiness is unrealizable, but there are few who pause to consider the antithesis: that perfect unhappiness is equally unattainable. The obstacles preventing the realization of both these extreme states are of the same nature: they derive from our human condition which is opposed to everything infinite.

II. Building “Human Skills” In The Workplace

Start Here  How To Win Friends And Influence People (Dale Carnegie)

I know, I know!  Cliche.  So What? The simplicity of the book makes it powerful.  It doesn’t need the latest and greatest psychology studies.  It just offers principles about how to treat people and is a reminder that the norms and assumptions about behavior in the modern business world lead people astray.  For example, if you want to change someone’s mind, focus more on getting that person to like you instead of attacking them with facts and to focus on simple things like listening:

Talk to someone about themselves and they’ll listen for hours.

Influence (Robert Cialdini)

This book was a bit mind-blowing, making me realize we are more susceptible to influence than we realize.  Cialdini has written extensively about how things such as social proof, reciprocity, commitment, authority, liking and scarcity drive our behavior.  Becoming aware of our behavioral biases will help you identify the decisions you really want to make as opposed to the ones you are just falling into

The Art Of Learning (Joshua Waitzkin)

This book is terrific. Waitzkin walks through how he became a chess champion at age 8 and brought Gary Kasparov to a draw at 11 years old. After quitting chess, he applied the same approach to Taiwanese push hands and became world champion. He introduces the concepts of “beginner’s mind” as well as his own framing of “numbers to leave numbers” which is a great way to show that to go fast, you first need to go slow.

III. Know Thyself…In The Business World

Start Here  How Will You Measure Your Life (Clayton Christensen)

This book is a fascinating perspective on how to define success from within the corporate world.  Christensen made me gain hope about leading with principles in the corporate world, positioning “management” as a way to have a positive impact on other people:

“If you want to help people, be a manager”

Quiet: The Power of Introverts in a World That Can’t Stop Talking (Susan Cain)

I thought I had a good understanding of introversion and extroversion until I read this book. This book also made me realize I was a lot more introverted than I realized. This is where I first heard of the term “ambivert” and realized I am energized by a mix of alone time and activity with others. I was fascinated by the history of how extroversion became such an ideal in modern society and the mistakes that can lead us to make.

Mastery (Robert Greene)

Mastery is an incredible book for anyone with a creative bone in their body.  Greene talks about the different phases one must undertake if they want to become a master at their craft or develop a wide range of skills.  He helps people understand the hard decisions that need to be made, such as leaving a teacher (see: manager, leader) once you have learned enough so that you can go out on your own.

IV. Questioning The Modern State Of The Business World

Start Here The Halo Effect . . . and the Eight Other Business Delusions That Deceive Managers (Phil Rosenzweig)

A clear and convincing case that most explanation of who is “successful” and a failure in the business world is highly subject to market dynamics and the firms that happen to have the most profitable business model of the time.  This book will make you highly skeptical of modern business “research” and stories praising or criticizing leaders.

Shareholder Value Myth (Lynn Stout)

This book is a must-read for anyone who has a suspicion that there may be other and better ways to measure success in the world than money and especially, “shareholder value.”  This book helps show that our current state of affairs is a recent innovation.

Reinventing Organizations (Fredrik Laloux)

This book highlights organizations that are typically led by truly transformational leaders that have questioned the status quo and built organizations (sometimes very large ones) that start with deep trust in people and their ability to solve problems.  This book shows that self-organization can work and that it is likely the only path forward if we want to build a better business world.

Skin In The Game (Nassim Taleb)

Taleb looks at the concept of “skin in the game” in terms of people, employees, and organizations.  His perspective on the modern state of the employee/employer relationship:

So employees exist because they have significant skin in the game –and the risk is shared with them, enough risk for it to be a deterrent and a penalty for acts of undependability, such as failing to show up on time. You are buying dependability.

He argues that the modern employee is no longer a “company man” but rather a “companies man”:

A companies person is someone who feels that he has something huge to lose if he loses his employ-ability

V. Finding Some Hope In The Business World

A big part of my career in the business world was an obsession with trying to understand first why organizations seemed to drive so much stress and anxiety in people and then second, what we could do about it if anything.  This led me to discover a number of books that not only helped me discover new ideas for business, organizations, and leadership but also develop my own perspective on what’s happening in the modern workplace.

Start Here Drive (Dan Pink)

Pink’s introduction of the concepts of autonomy, mastery, and purpose through research and company examples is a great way to discover self-determination theory, which is a foundational theory of what motivates people.  If you look at modern organizations through the lens of motivation, you would assume that everyone had lost their mind.

Work Rules! (Laszlo Bock)

The key takeaway from this book was the fact that many things you can do to improve the employee experience are free.  Too many organizations think that transformation comes at a major cost.  But as Bock shows in many examples in his experience at Chief People Officer, the hardest things to do are to trust people and give them freedom to make mistakes.

VI. Mindfulness & New Emotional Mental Models

Start Here The Heart Aroused (David Whyte)

I wish I read this book at the beginning of my business life, but I wonder if it would have been too soon.  Whyte speaks poetically about the experience of the business world in a way that well, arouses your heart. Whyte’s summary of the book:

(it) will look at the link between soul and belonging, creativity and failure, success and stasis, efficiency and malaise at work, but it sets as its benchmark not the fiscal success of the work or the corporation (though this certainly can be good for the soul) but the journey and experience of the human spirit and its repressed but unflagging desire to find a home in the world.

Nothing Special (Charlotte Joko Beck)

This was the first book I read about Zen Buddhism and mindfulness. The story is a conversation between Beck and her students and will resonate with anyone who is curious about mindfulness, meditation, and spirituality.

VII. Embracing The “Pathless Path”

Start Here: My Book! The Pathless Path (Paul Millerd)

My book, The Pathless Path, was published five years after quitting my job and carving my own path. It’s sold over 25k+ copies with minimal marketing so people seem to like it. It’s not a how-to guide but an inspirational account of my journey combined with “recipes” on how to embrace an unconventional path.

Anything You Want: 40 Lessons For a New Kind Of Entrepreneur (Derek Sivers)

Sivers build a company selling CDs of independent artists in the early internet era.  He ignored most of the advice about how to build a company.  He also ignored the advice on how to write a book.  This short book shows that “best practice” doesn’t always lead to happiness.

Field Guide To Getting Lost (Rebecca Solnit)

Rebecca Solnit puts words to the journey of “getting lost” and wandering into the unknown. If this quote resonates with you, you are ready for this book:

That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.

Linchpin (Seth Godin)

Godin has been a self-employed solopreneur and freelancer for decades.  He helps people re-frame their thinking away from needing to be “chosen” for a job towards a world where the world depends on you expressing your creativity and daring to “make a ruckus.”

Designing Your Life (Burnett & Evans)

This book by two Stanford professors was designed to help undergraduate students figure out what they want to do with their lives.  Based on design thinking, they have a number of useful question prompts and exercises that push you to expand the number of ideas and options you can come up with, rather than picking from default options.  If you want to imagine new possibilities, this is the book for you.

Crossing The Unknown Sea (David Whyte)

Whyte is my favorite writer and this book is a beautiful reflection of his own journey from naturalist to non-profit worker to poet. He talks about the inner game of doing the thing which is scary (people thought he was crazy to quit his day-job) and living full out.

The Good Life & Sustaining Life (Andrew Taggart)

A practical philosophical reflection on what it means to live the “good life” in the modern world and the many approaches one might take to sustain such a life.

There may be no greater vexation in our time than the question of how to make a living in a way that accords with leading a good life. Yet if nearly every thinking person has faced this vexation at one time or another and doubtless throughout most of his adult life, virtually no one has ventured to think it through in a well-considered, systematic fashion.

VIII. New Models For Seeing The World

Start Here A Lesson On Worldly Wisdom (Charlie Munger)

This fantastic graduation speech from Munger highlights the need for many different “mental models” for seeing the world and how to move between them.  Worth reading in full.

The Righteous Mind, Why Good People Disagree On Politics & Religion (Jonathan Haidt)

This book made me rethink how people arrive at their beliefs.  Haidt shows that morality is something that is highly influenced by your environment and biology.  This book made me much more understanding of a wider range of ideas beyond politics and religion.

Wanting (Luke Burgis)

The self-employed path is filled with hustle traps and the most powerful one is “mimetic desire.” Luke walks through his own personal journey of awakening and helps steer people toward finding their “thick desires” – things they can sustain over the long term.

Sacred Economics (Charles Eisenstein)

A bold re-imagination of our world to one based on generosity, connection, and embrace of the environment.  This book is a beautiful mix of technical economic analysis with a spiritual questioning of the status quo:

I think ultimately what is happening is that our deep ideologies and belief systems, and their unconscious shadows, generate a matrix of synchronicities that looks very much like a conspiracy. It is in fact a conspiracy with no conspirators. Everyone is a puppet, but there are no puppet-masters.

IX. Grappling With The Role Of Work In Our Lives

Start Here Bullshit Jobs (David Graeber)

Graeber looks at the modern workplace through his definition of a “bullshit job” which is when employees define their job as pointless and without meaning.  He looks at the history of work and shows that our current relationship with employment, time and money was not always the way it was and challenges readers to think beyond the status quo.

Rest (Alex Pang)

Pang’s incredible book on rest covers sabbaticals, unplanned breaks, naps, and sleep while challenging our modern understanding and definition of things like time, leisure, idleness and rest.  He boldly challIf your work is your self, when you cease to work, you cease to exist,” shares counterintuitive results from people who worked 2-5 hours a day and shows the benefits of not following the conventional wisdom that more = better.

As a result, service workers and professionals are rewarded not just for performing work but also for “performing” busyness at work.

Reclaiming Work (Andre Gorz)

Gorz argues that “real work is no longer what we do when at work” and that a lot of what we are doing in the workplace is performing a social ritual we have decided is necessary to “earn a living.”  This book imagines a world “beyond the wage-based society.”

The Normal Chaos Of Love (Beck & Beck-Gernsheim)

While this book is very much about love and relationship, it also frames those relationships and our modern ideal of a family in contrast to the workplace.  The authors (a married couple) argue that the modern reality of having everyone be workers is great for the workplace and freedom, but creates chaos and complexity at home – complexity that we have yet to fully grapple with:

Everybody – including parts of the women’s movement – has the right to expect that offers once made to men should now be extended to women, and assert that women are as useful as members of the job world as men are. They should however realize that this road does not lead to a happy world of co-operative equals but to separateness and diverging interests.

Leisure: The Basis Of Culture (Josep Pieper)

In the late 1940s, Pieper wrote of a crisis of “overwork” and a disconnect from the classical sense of leisure.  He wrote that we “mistake leisure for idleness, and work for creativity” and was skeptical of Max Weber’s assertion that “One does not only work in order to live, but one lives for the sake of one’s work.”  In today’s world, “leisure” often just means a break from work.  Pieper argued instead that leisure was:

the disposition of receptive understanding, of contemplative, beholding, and immersion – in the real. In leisure, there is, furthermore, something of the serenity of ”not-being–able–to–grasp,” of the recognition of the mysterious character of the world, and the confidence of blind faith, which can let things go as they will; there is in it something of the ”trust in the fragmentary, that forms the very life and essence of history.

X. Going Deep – The Hard Questions

Start Here: Not a book, but perhaps better than a book? Brain Pickings is perhaps the best source for wisdom on the web.  A voracious reader and learner, Maria Popova pulls the most powerful parts of great writers in history on topics such as love, creativity, art, poetry, philosophy, life and work into compelling synthesized posts.  Start with one post and you’ll end up opening up a ton of tabs in no time.

• Recommended posts: 10 lessons from 10 years of BrainPickings, Ursula K. Le Guin on Busyness, Reclaiming Our Human Dignity in a Culture of Workaholism, or David Whyte on Work/Life Balance

The Great Work Of Your Life (Stephen Cope)

Stephen Cope’s The Great Work of Your Life is a spiritual guide to finding your life’s purpose. The book uses the ancient text of the Bhagavad Gita to frame stories of famous people who have followed their dharma, including Tubman, Whiteman, Frost, Keats, and Susan B. Anthony.

Zen And The Art Of Motorcycle Maintenance (Robert Pirsig)

This book has been around since the 1970s and its central argument still rings true (perhaps more so?) that in our continued acceleration towards the future, we are losing touch with a deeper, spiritual side of ourselves.  Pirsig contemplates what got us to this point:

The range of human knowledge today is so great that We’re all specialists. And the distance between specialization has become so great that anyone who seeks to wander freely among them almost has to forgo closeness with the people around him.

At the Existentialist Café: Freedom, Being, and Apricot Cocktails (Sarah Bakewell)

What does it mean to be free?  How should one act in accordance with that belief.  Bakewell tackles these tough questions through the lens of the existentialist philosophers that emerged in the early and mid 1900’s featuring the philosophies of Kierkegaard, Sartre, de Beauvoir, Heidegger and more.

The Wisdom Of Insecurity (Alan Watts)

Watts contemplates our desire to continue to put life into neat little boxes:

The more one studies attempted solutions to problems in politics and economics, in art, philosophy,and religion, the more one has the impression of extremely gifted people wearing out their ingenuity at the impossible and futile task of trying to get the water of life into neat and permanent packages.

and on following the default path:

To keep up this “standard” most of us are willing to put up with lives that consist largely in doing jobs that are a bore, earning the means to seek relief from the tedium by intervals of hectic and expensive pleasure. These intervals are supposed to be the real living, the real purpose served by the necessary evil of work. Or we imagine that the justification of such work is the rearing of a family to go on doing the same kind of thing, in order to rear another family . . . and so ad infinitum.

Meditations (Marcus Aurelius)

While it was written over 2,000 years ago, we get a peek into the Empreror of Rome’s private journal and his meditations on life:

When you arise in the morning think of what a privilege it is to be alive, to think, to enjoy, to love …

and

Leisure lives on affirmation. It is not the same as the absence of activity; it is not the same thing as quiet, or even as an inner quiet. It is rather like the stillness in the conversation of lovers, which is fed by their oneness.

Essays (Ralph Waldo Emerson)

Emerson’s collection of essays are a great read and accessible for being written in the 1800’s.  Emerson on self-reliance:

There is a time in every man’s education when he arrives at the conviction that envy is ignorance; that imitation is suicide; that he must take himself for better, for worse, as his portion; that though the wide universe is full of good, no kernel of nourishing corn can come to him but through his toil bestowed on that plot of ground which is given to him to till. (Self-Reliance)

Nature:

The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles.

…and Education:

The book, the college, the school of art, the institution of any kind, stop with some past utterance of genius. This is good, say they,—let us hold by this. They pin me down. They look backward and not forward. But genius always looks forward. The eyes of man are set in his forehead, not in his hindhead

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post 35+ Books Recommendations To Help You Quit Your Job appeared first on Boundless by Paul Millerd.

The question “what do you do?” increasingly does not make sense. Five years ago, I would have said “I’m a consultant.” People really just want to know “how do you make money?”

Increasingly, that question is coming to mean “what do you work on?” For me the answer is complicated — I create a podcast, I interview people, I write, I read extensively, I coach people in their careers, I volunteer. Some of those things help me make money and some don’t.

In organizations and in the emerging freelance economy, I have seen a steady, but dramatic shift. The people that are able to thrive are the people that are able to create. The people that are energized and excited are the ones that are doing what matters to them.

Yet, we pretend that the old markers of success — climbing the ladder, getting a promotion, having a “good” job — are what matter.

They don’t.

The Nature Of Work Has Fundamentally Changed, Yet We Operate As If It Is Still 1995

Consider the following:

The decline of full-time work: There was no net increase in full-time employment from 2005 to 2015 — all employment growth was in “alternative work arrangements” such as on-call and temporary as well as contractors and freelancers.

Work continues to increase in complexity: BCG has measured “complicatedness” of work showing that it has steadily increased 6.7% a year for 50 years. This has dramatically outpaced productivity improvements.

Limited connection between traditional education and our work: Less than three out of ten people work in fields tied to their major.

Dream jobs don’t exist: In 1997, Amy Wrzesniewski found that work that is a “calling” is a result of a mindset, not our underlying skills.

People prefer autonomy over control: Researchers found that when power is framed as autonomy versus power over people, people were much more inclined to seek power positions. Autonomy is also highly linked to job satisfaction and performance.

Money is not a motivator: In 1949, Professor Harry Harlow introduced incentives to reward monkeys and ended up destroying their intrinsic motivation. We then found the same result in humans. Yet, almost 70 years later, in organizations, we still use the language of “carrots” and and “sticks”

People are meaner at work: McKinsey found that people experiencing rudeness at work increased from 49% to 62%from 1998 to 2015. YIKES!

Failure to understand these shifts means one thing:

People are stressed, miserable and fed up, playing a game with rules that no longer exist.

In my own career journey, I made multiple career changes and eventually carved my own path as a freelancer. At every step of the road, I encountered endless amounts of bad advice, pseudo-science and buckets of hogwash about the choices I was making. Despite this, I was quite happy and engaged.

That made me wonder, why do ignore science and reality when talking about careers? In the last year as I’ve been carving my own path as a freelancer and in my work as a career coach, I’ve become obsessed with one question:

How should someone think about navigating their life and career in a way that enables them to have freedom to do the things that matter to them?

The deeper I looked, the more good ideas I found. From Pryor and Bright’s “Chaos Theory of Careers” to Adam Grant’s work on original thinking to Ryan and Deci’s self-determination theory to the fascinating research on curiosity, creativity, and solitude.

Our Deep Attachment To Work

How did we get here?

We place so much emphasis on work, yet the labor force participation rate is still less than 65%. We live in a time where we have a belief that much of meaning, dignity and identity can be unlocked through work. This cultural meme runs so deep that we tend to value any work for work’s sake and leave unquestioned the deeper questions of what it means to live a good life. It also results in bizarre phrases like “working poor” being a commonly understood and accepted phenomenon.

We need a radical mindset shift in terms of how we think about work and how we are meant to do things that matter

At the core, we need to stop praising someone for merely being employed or dutifully going into an office every day and we need to embrace the ambiguity and reality of the world.

Let’s ask people instead:

• Does your work bring you alive?
• Are you creating value for other people?
• Are you doing things that matter to you?
• What can I do to support your life?

The Framework

Foundation: Perspective, Motivation & Compass

Perpetual optimism is a force multiplier. — Colin Powell

Perspective:

We are operating under the assumption that the default path is the only path. The reality is that the default path is mostly an illusion. Most people that end up doing something that energizes them end up there through serendipity. We need to shift our thinking to embrace optimism and think about work as a life-long journey that will be reinforced by continuous learning and a flexible and open mind to new experiences, ideas and opportunities. Too often, organizations stifle motivation they tell people what not to do — numbing them into a state of learned helplessness. The reality is, for organizations to thrive and for people to thrive, we will need to push people to think on their own, question the status quo and become “original thinkers.”

We are operating under the assumption that career paths still exist and that successful people are the ones with the most money or highest rank. There are jobs and industries with great paths, but these are increasingly reserved for people who know how to acquire the right degrees and credentials. The truth is, we need to destroy the idea that a “job hopper” is somehow a lesser qualified person. We need to encourage people to try more types of work and embrace planned happenstance theory putting emphasis on optimism, open-mindedness and flexibility rather than specialization or the illusion of career paths.

Motivation:

We are operating under the assumption that having a job is enough. Unfortunately, most jobs are not set up to enable you to thrive and at worst, they may also destroy you. You are also more at the whim of the success of your industry, the pace of change in your job, and the “strategic” moves of large companies than you realize. The truth is you will need to continually self-reflect on the work that motivates you intrinsically, prioritizing mastery, autonomy, and relatedness, and continually re-assess your values, definition of success, and a connection to doing work that matters to you.

Compass:

We are operating under the assumption that companies will take care of us. Deep down, many know this is not true — just google the word “layoff” and see who was axed today. Here, I’ll do it for you…and this is only in the last 24 hours:

The truth is, we need to shift instead to approaches like Stanford Professors Bill Burnett and Dave Evans “Designing Your Life” that starts with a focus on living a good life and then helps you find work to do that fits into that. This does not mean living paycheck to paycheck— it means being thoughtful about mitigating risk through lowering expenses and eliminating debt such that you can have the freedom and flexibility to spend time how you want across all aspects of your life.

#2 How You Create: Environment, Connection & Action

It’s the way I study — to understand something by trying to work it out or, in other words, to understand something by creating it. Not creating it one hundred percent, of course; but taking a hint as to which direction to go but not remembering the details. These you work out for yourself.

Professor Richard Feynman

Environment:

We are operating under the assumption that work means going to an office 260 days a year, 5 days a week, working from 9–5 (at least). The reality is, more and more people are not working this fixed schedule and that it is often impossible to do 40+ hours of the types of creative work we will need to do in the future. We need people who are more comfortable in diverse global, virtual and remote teams and understand how to optimize their environments to maximize flow and creativity.

Connection:

We are operating under the assumption that investing more in corporate culture will make us happier. The confusing reality of this is that many of these efforts backfire since they are not built on a foundation of meaningful work. We need to instead align our work and lives around communities that share our passions and values (which can be done in companies sometimes!). We also need to shift beyond the “transaction mindset” which pervades our world and look for ways to be generous and support each other in their work so more people do the work that matters to them.

Action:

We are operating under the assumption that work is easily understood and can be documented in a process. Not to mention that it should be done full-time! The reality is, work is increasingly happening in projects and the companies that thrive are the ones that think in this context instead of keeping employees from quitting. Workers and companies will need to think about experiments — especially ones that will fail. As Adam Grant showed, original thinkers often run enormous numbers of experiments (for example Edison has 1093 patents, but most of them likely had little impact).

#3 How You Adapt: Knowledge, Progress & Vitality

Without continual growth and progress, such words as improvement, achievement, and success have no meaning. — Benjamin Franklin

Knowledge:

We are operating under the assumption that our employers and universities will train us and give us the skills we need. The data shows that most of the $150 billion spent on learning & development every year is wasted. Universities are failing to give people the skills to compete in the economy. The truth is, we need to embrace the mindset of learning through doing, thinking about learning as a lifelong project instead of something that happens from ages 5 to 22, and creating opportunities for apprenticing or projects as a way to continuously develop skills. Finally, we need to more quickly shift to and give more credibility and support to alternatives to on-campus learning.

Progress:

We are operating under the assumption that employers and managers should tell us what to do and that the hierarchy determines our value. The truth is, permission is increasingly an illusion and those who seek it are going to be left behind. Hierarchies are outdated and more concerned with power than helping us develop the skills and experience that will help us build a career and a life. This leads to unnecessary suffering, the lack of growth and people in the wrong jobs. We need to shift from external markers of success to internal ones — are we energized?, are we learning? — and think about our careers as a portfolio of different projects, connections and skills. As Marc Andreessen offers: “The first rule of career planning: Do not plan your career.”

“ Do not go where the path may lead, go instead where there is no path and leave a trail.” — Ralph Waldo Emerson

Vitality:

We are operating under the assumption that two weeks of vacation a year is adequate and that “work-life balance” is a worthy goal. This mindset starts with the assumption that work is the most important thing and you need to be some sort of productivity ninja that carves out meaningful time for health, love, relationships and fun. We instead need to start with our work and time and think about how we can invest in other people and communities to get the best out of each other. Finally, we operate under the assumption that workplaces are the source of all dignity, meaning and energy. However, with this mindset, we avoid the solitude and reflection that will unleash our naturally creative spirits. We need to flip our thinking to ask ourselves what the conditions are for us to thrive!

Are You Ready For The Future Of Work? Take The Assessment Here

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Nine Future Of Work Mindsets You Need For The Weird New World of Work appeared first on Boundless by Paul Millerd.

I’m here to make a plea with you: please stop watching the news?

Our addiction to the constant flow of news, whether it be about the latest political crisis, sports soap opera, hunt for a missing airplane or a moral crusade against someone who said something 30 years ago, it is all doing the same thing. It is hijacking our brains and distracting us from being in the world with each other, distracting us from getting started on that creative project we’ve been telling our friends about for five years and holding us back from spending time on things we might otherwise derive some joy from.

I want to share my own approach to the news which is that I almost spend no time consuming it. I am sharing my approach to the news because in conversations with people, no personal practice has raised more questions and more indignation than telling them “I don’t follow the news.” So I want to share with you a bit about why I decided to move away from the news. I’ll also share a bit about why the news is so outrageous, why politics is a special kind of monster, why people will likely never change their minds and how we can block it. I’ll close with a few of my suggestions on better things to read.

Let’s dive in.

The news will kill you (or at least lower your sperm count)

Countless studies show that watching, reading or listening to the news can contributed to increased levels of stress. These headlines not only stress me out but share the same story:

Stress drives a whole bunch of things we don’t want:

This study looked at 250+ patients who had a heart attack and asked them immediately after their incident what caused the heart attack:

Attributing the initial attack to stress responses (e.g., worrying, nervousness) was also predictive of greater morbidity in 8-year survivors

and more:

between 20 and 40 percent of sudden cardiac deaths are precipitated by acute emotional stressors.

for the men who hope to be fathers one day, this study found that your sperm count might be harmed by stress:

the number of “healthy” sperm was significantly reduced in both groups of stressed men compared to reference values

Newspapers have always been crazy, but the internet has turned them into click-seeking monsters

The news sells to our emotions. The more emotional we become, the more we consume. The best emotion to tap into is fear. Humans have a negativity bias that long ago would protect us from danger, but now mostly forces us to spend an unreasonable amount of time focused on news that is designed specifically to activate this reflex.

This is and always has been the business model of news media organizations. Except at one time only a small number of newspaper titans like William Randolph Heart got to control the headlines and people didn’t spend that much time reading newspapers. No longer supported by print subscriptions and having to shift to digital means to survive, most media companies are competing in a race to the bottom get-the-most-clicks competition that is the modern internet.

This is why digital news is filled with projection, outrage, spin and terrible images. This is also why you never stumble upon articles that tell you that some things are actually getting better!

Prior to the internet there was a certain amount of friction to getting the news. You either had to buy or subscribe to a paper or set aside time to watch the news. Oliver Burkeman, a journalist, notes the shift here:

It’s easy to assume that the reason you spend so much time thinking about the news is simply that the news is so crazy right now. Yet the news has often been crazy. What it hasn’t been is ubiquitous: from its earliest beginnings, until a few decades ago, almost by definition, the news was a dispatch from elsewhere, a world you visited briefly before returning to your own. For centuries, it was accessible only to a small elite; even in the era of mass media, news rarely occupied more than an hour a day of an educated citizen’s attention.

Politics is a special kind of madness

Politics is the soup du jour of news junkies these days. While people realize that politics is about power, they do not react to the news by saying “oh wow, what an interesting attempt to gain more attention and power by using divisive language.” Most tend to react to it by falling into the trap of moral outrage and disgust.

In 1990, New Gingrich had discovered that elevating the level of outrage was a good political strategy. Here is a fascinating NPR podcast about this shift:

There was one memo I write about in the piece called “Language: A Key Mechanism of Control,” that literally included a list of recommended words that Republicans should use in describing Democrats. And they included words like “sick,” “pathetic,” “lie,” “anti-flag,” “traitors,” or “radical” and “corrupt.”

The kind of broader strategy when waging these national campaigns was to reframe the kind of policy debates in Washington that may have seemed kind of dull or inaccessible to the average American and turned them into these big struggles between good and evil, or white hats versus black hats, and a battle for the character and soul of America.…

This led to a fake division on issues that had and still have broad agreement such as reforming healthcare, supporting social security and medicare, improving gun control and improving education.

Politics is about priorities. Except people like Gingrich have helped convince many people that a lower priority ranking of an issue is really a moral fight of good versus evil.

While right-leaning parties embraced these tactics earlier and more often (In 2011: “conservative media use significantly more outrage speech than liberal media”), they are now common place across the spectrum and have been adopted across the globe.

“But you don’t understand, most people have crazy ideas about politics and we have to change their minds!”

Great rebuttal, but that’s not the case. When you look at people that watch cable news on a nightly basis its only a few million people watching Fox News, CNN or MSNBC. Here is some Fox News data from 2019:

Meanwhile, Fox News’ flagship primetime program, “Tucker Carlson Tonight,” remained the highest-rated show in cable news with 3,353,000 overall viewers and 557,000 in the 25-54 demographic.

People freak out about Fox News, but fewer than 1% of the country is actually watching it on any given night and less than 15,000 people between 25-54 per each state on average are locked in. An enormous amount of elderly people seem to be sitting around watching these programs and let’s admit it, we’re not going to change grandpa’s mind.

In 2018, the “Hidden Tribes” report helped to add some nuance to the polarization meme that seemed to be accepted as gospel. They found that four divisive issues “divided” America but that 67% of the public could be described as an “exhausted majority”

A consistent finding of the study is the contrast between the more tribal beliefs and behavior of the 33 percent of Americans in the wing segments (Progressive Activists, Traditional Conservatives and Devoted Conservatives) and that of the 67 percent in the Exhausted Majority (the Traditional Liberals, Passive Liberals, Politically Disengaged and Moderates).

The report also found those that hold the most extreme views (14% of people) are the least likely to ever change their minds:

Those in the wing segments tend to hold views that conform to their tribe and do not deviate from the party line.

Being a good person does not equal “staying up with the news”

You might be saying “okay okay I get it, but what about staying up with the what’s happening in the world?” This is a good question, but I think the sentiment is disconnected from what is really happening.

The most common response people offer when I say I’ve cut the news is “well how do you find out about things?” The implication being that one needs to know. Here is Oliver Burkeman again:

But the creeping colonisation of our personal sense of reality by “current events” has also seen the emergence of a strange new moral imperative – a social norm which holds that ignoring the news, or declining to grant it preeminence in our lives, is an irresponsible indulgence, available only to the fortunate.

The problem with this mindset is that the act of immersing yourself in the news literally makes you more stressed, takes you away from other things which might have an actual positive impact on the world and keeps you in a state of energetic addiction waiting for the next bombshell to drop.

Learning why we react the way we React

It is easy to fall into the trap of believing that people carefully work through their beliefs via reason and rationality, but that’s not how it plays out in the real world. Studies on twins have found that genetic factors influence greater than 50% of many of our beliefs about the world.

One of the best books I’ve read on this is by Jonathan Haidt, The Righteous Mind. The book has an apt subtitle: “why good people are divided on politics and religion.” In the book, he gives us a sense of what’s at stake and is at the core of what I’m trying to convince you:

If you think that moral reasoning is something we do to figure out the truth, you’ll be constantly frustrated by how foolish, biased, and illogical people become when they disagree with you.

Another book worth reading if you are intrigued by how our brains operate in the world is Thinking Fast and Slow  by Nobel prize winner  Daniel Kahneman. He breaks down our brains processes into “System I” and “System II.” System I is our automatic reactions to the world and System II is our more well thought out rational brain. Many people think System II dominates, but when we start to realize that System I is calling the shots most of the time, we can become more aware of what the news is attempting to trigger

If you’re not the book reading type, this video is worth watching:

Okay, you’re convinced…First step: block the madness

In order to find better stuff to read, you first need to spend time building some walls to protect you from the social media barrage of fear and outrage driven content. Here are some steps I recommend:

Step 1: Delete all the news apps on your phone. I hear you saying “but I like staying informed!” Lets take a look a a sample of what is keeping you informed:

These are the headlines that get blasted to your phone as notifcations 24 hours a day. Are you “informed”? Sure — but have you learned anything new or shifted your perspective on anything? Doubtful.

I’ve found that if something is worth knowing, you typically find out about it via word of mouth within 24 hours. Try it out and let me know if this holds true.

Step 2: Delete the twitter and facebook apps from your phone. In addition to saving valuable battery life, you will have to go out of your way to check them in a web browser. You’ll use it less, trust me.

Step 3: Go through this long piece of 45 tricks to make your “phone work for you and not against you” and pick and choose some of the hacks that work for you. My favorites were:

• Removing e-mail from my phone
• Turning off almost all notifications
• Using app limits to limit twitter, facebook and instagram to less than 10 minutes a day (works for browser-only access too)
• Turn off “raise to wake”

Step 4: Install the chrome extension “News Feed Eradicator for Facebook.” a and LinkedIn Feed blocker. This replaces your news feed with a motivational quote. After you go to facebook a few times and find nothing, you will eventually stop checking it out during the work day.

Step 5: Another chrome hack. Install the Momentum extension. Instead of opening the new tab page (where your most visited pages are likely facebook, etc…) you’ll see a lovely greeting, an amazing picture and another inspirational quote:

Step 6 (for Twitter): Change your trends to Japan or another country where you can’t read the language. Also make sure to mute key words that are caught up in outrage. You find find the mute options in setting & privacy => privacy and safety =>safety => muted. Also don’t be afraid to mute or block people that spend all day on twitter peddling outrage.

Now that you blocked the worst, you still need to search for the good content

There is a common belief that “everything is getting worse” especially in terms of content. Steven Johnson challenged this belief in his book Everything Bad Is Good For You by showing that the quality and complexity of television, writing, movies and other popular material have steadily increased over time. The mistake comes from when people take today’s worst content and compare it to the best content of the past.

I do think Johnson missed something, however. He didn’t factor in that it was incredibly easy to find the best content in the past. Today, a lot of the best writing, movies and music are harder to find, part of niche groups and communities.

Luckily, if you embrace some of the tools available and find individual people worth following who share high-quality content, you can start diving deep into the good side of the web.

My reading tools

• Kindle Paperwhite: No brainer if you like to read on the go
• Instapaper: When I find good things to read, I save them here. Install their handy “bookmarklet” in your browser to save articles for later. I prefer longform, so I often don’t have time to read I have a weekly digest of articles delivered to my kindle automatically.
• Book Recommendations: I keep a notepad on my iphone of book suggestions. I ignore most books until they have been recommended at least two times. Then I read it
• Goodreads: A must have for keeping track of books you want to read and getting ratings from other bibliophiles

I’m currently in the process of updating my favorite books, which can be found here.

My Media Diet & Reading Recommendations

Longform Aggregators

I typically check these at least once a week and add any interesting articles to instapaper to real later:

• Longform: The best Longform on the web — has a great app as well to find out what is popular and also has a useful “staff picks”
• Longreads: Similar to longform with suggestions of the best “Longreads” of the web
• The Browser: I check this almost daily — they have a curated selection of 4–5 articles worth checking out
• Reddit’s Investigative Journalism and Longform pages
• The Sunday Long Read Newsletter by Don Van Natta Jr.

Blogs I Check Semi-Regularly (Bookmark These)

• Marginal Revolution: Tyler Cowen is a beast — he seems to read like 1000 books a year. Always has interesting article suggestions, deep economic analysis of current events or random musics about food and music.
• Stratechery: Ben Thompson has a knack for synthesizing complex topics in a way that make them approachable. His free weekly blog always adds a unique perspective too all things happening in tech, media and the internet.
• Seth Godin: I love that Seth sticks to a daily writing practice. Blogs can be hit or miss, but worth checking out every week or so.
• Ribbonfarm: Great longform essays on all ranges of topics, but written in a unique style. Essays often leave me thinking in new ways. (Updated: not updated as frequently these days)

E-Mail Newsletters

E-mail newsletters have increasingly become my largest source of incoming content consumption. This enables me to pick and choose people I trust and their own curation or screening of writing that may be worth reading.

One of the biggest “hacks” I’ve found is to send out a weekly list of “five good reads” every Sunday, which I’ve been doing since 2016. If you want to join, feel free to subscribe here:

Some of my favorite newsletters (I keep this updated

• Brain Pickings — Maria Popova’s site excels at summarizing the wisdom and insights of all sorts of ancient and modern writers, philosophers and leaders. For example, check out this post on “Why We Fall in Love: The Paradoxical Psychology of Romance and Why Frustration Is Necessary for Satisfaction”
• Farnham Street Brain Food Newsletter: Their own mini articles in addition to some of the best reads from across the web both current and past (Shane Parrish)
• John Mauldin’s Thoughts From the Frontline: A weekly macroeconomic / financial newsletter reflecting on all things happening across the world from a financial perspective. These can be hit or miss depending on your curiosities (John’s run deep) – but I love the non-sentimental analysis and simple style of communication. It keeps me sharp on world and economic issues
• Breaking Smart: Venkatesh Rao, as he says on his website RibbonFarm has “unusual takes on familiar themes.” I’m not sure if he popularized the “tweetstorm” but he sends a newsletter where he does such a thing about interesting topics. Sometimes the language is a bit complex, but worth checking out nonetheless
• The Journal — Kevin Rose just started a monthly tech oriented newlsetter. A curious person who also embraces the goal of forwarding “shit worth reading”
• Tim Ferriss’ 5-Bullet Friday — A simple, short newsletter from Tim that usually has at least one or two interesting articles or interesting things from the internet a month
• Barking Up The Wrong Tree: Short buzzfeed type articles from Eric Barker— “top 3 things about X” but fascinating topics backed by research.
• Ritholz’s Reads: A daily curation of news from around the web from Barry Ritholz. Longtime successful financial blogger — he has a good sense for cutting through the BS and giving you things worthwhile to read.
• CB Insights: Technology & business insights plus a huge dose of humor and awesome visualizations.
• Andrew Taggart “Total Work”: Fascinating newsletter (check out the back issues) about work taking over our modern world of work
• Curious Humans: Great newsletter by Jonny Miller on what he finds curious in the world
• Ryan Holiday has a great Reading Recommendations list I enjoy
• Khe Hy, Rad Reads on money, productivity & what matters
• Azeem Azhar, Exponential View tech
• Jocelyn Glein, Hurry Slowly
• Austin Kleon, Weekly Newsletter
• David Perrel, Monday Musings a collection of fascinating things
• Future Crunch, A Positive News Newsletter
• Total Annarchy, Ann Hadley
• Scott Galloway, No Mercy, No Malice
• Nat Eliason’s Medley a collection of interesting things & book notes

No longer subscribe:

Some of these people seem to be shifting away from what I’m interested in or are shifting into outrage which I just am not intrigued by

• NextDraft: Dave Pell is the king of internet curation. His daily newsletter will keep you informed (he sometimes has a little too much news) but always balances it out with shit worth reading. He also has a standalone app you can use to read on the subway and replace your CNN app. (shifted to politics)

What else should I be reading?

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Why You Should Stop Consuming The News & My Media Diet (August 2019) appeared first on Boundless by Paul Millerd.