That may be the right path for you but I want to convince you that there might be another path.

I want to share my version of how I’m playing something Packy McCormick calls the “great online game.” A version that focuses on building a life where I can work in different ways to pay the bills, have plenty of time for creative pursuits, and don’t have to be tied to a full-time job.

What follows are five principles that have emerged that have guided my path. They have emerged slowly and organically. Only now do some of them seem obvious. I fully expect that they may morph over time. These principles serve as a compass for me as I navigate the infinite possibilities of the internet.

I think that nearly everyone, including people on the default path, should develop their own principles. This is because the stories of how we think about our work and lives are outdated, one based on a 1950s reality. This story worked in a time in which people worked for one company in their life when growth rates of 5% were normal, and most women didn’t work.

The trap of this story is that it actually works in the first few years of anyone’s career. Many companies still believe in this story and this is why the first five years of your career are still filled with promotions and a clear career path. Anyone that’s made it past that point, however, knows the truth. That there aren’t many clear career paths left and because of slowing growth rates, competition and politics are more central to getting ahead than some may think.

Developing your own principles and strategy is the only choice left if you don’t want to play those games. For the self-employed, developing your own game and set of principles is not a choice but a necessity. It is the only way to survive over the long term.

Here are five principles that help guide my path.

Principle #1: Coming Alive Over Getting Ahead

In April of 2020, my strategy consulting skills course started taking off. This was a weird moment because it took off at the same time I started dealing with extreme fatigue following complications from a tooth extraction. My course was selling like hotcakes and I was either wandering around the Canary Islands talking to doctors or sleeping in bed. This is one of the weird things about being a self-employed creator. Your financial reality can shift dramatically in a short period of time and often due to things outside of your control.

I had spent hundreds of hours to get it to that point but it was never my intention to hit a monthly revenue goal. I genuinely thought it would be fun to figure out how to create an online course (If you want to go much deeper, the full story is here). If you had talked to me in January of 2019 you might have thought my principles of keep doing stuff I like, give generously, and don’t work too much were pretty stupid because I had made less than $3,000 doing so in a year. Two years later I’ve somehow made a decent American salary for two straight years.

After a strong year of sales, I reflected on my success with StrategyU. My inner consultant knew that the obvious solution was to double down, add more courses, level up the marketing, create more content, and see where it goes. I was even invited to an accelerator program for proven course creators to make this happen. I could see the path and had a reasonable level of confidence that I could 4-5x my course sales if I wanted to.

But then I challenged myself, “what would you do once you had that money?” I realized I would write. I then reflected upon the fact that I could simply do that now. I was already making enough to support myself and still save a little money each year.

With this in mind, I decided to make a commitment. In 2021 I would write a book. This would be a way to commit to what I claimed to care about and also be a way of testing out this principle of “coming alive over getting ahead.”

My course has remained steady but has not grown much more than the previous year. However, the act of committing to writing a book has been one of the most thrilling commitments of my life. I’ve never felt so alive, challenged, and excited about anything I’ve worked on.

If a choice emerges between spending more time on making money but means I’ll have to cut back on some of the things I like doing like learning, writing, and connecting with people, I plan to walk away from that choice.

Principle #2: Don’t Be Attached

While my online course continued to succeed, I realized that I had come to expect that income.

With a few hours of maintenance per week, I was able to keep a profitable business running while writing my book and studying Chinese full-time for a three-month stretch. In one of those months, I even worked with a client to run a four-week consulting skills bootcamp which led to my best month since being self-employed. Then in May, the sales of my course tanked, likely driven by a change in the google search algorithm, people returning to the office after covid restrictions, and travel for the summer.

These kinds of ups and downs would be terrifying if I had a high fixed-cost lifestyle or if I had not experienced them before. To anyone that’s been self-employed for a long period of time, they learn to deal with these shifts. Here is an example of some various swings in different income sources I’ve experienced over the past five years.

With this in mind, I try to make sure that I’m not assuming that any of these income sources are permanent. I’ve embraced a visualization exercise where I go through an exercise of visualizing all my digital properties and revenue streams evaporating and then asking “am I okay?”

When my consulting course struggled for a couple of months after doing so well for more than a year, I was able to reflect on the fact that I’ve started from scratch in the past and I could do it again.

Principle #3: Build An Income Floor & Optimize For Income Streams

About a year into self-employment I realized I really want to stay on my path longer than my initial plans for a one-year experiment. I realized that if I wanted to commit to this path, I needed a better strategy for earning money than only freelancing.

Freelancing is one of the best ways to get started with self-employment. It enables you to leverage your existing skills while giving you more flexibility with time to spend on other things you want to work on or to simply work less. This worked well for me. I had much more time to work on creative projects but realized that following that path was a lower-income and precarious version of my previous path.

I wanted to embrace an antifragile approach, one in which I would not be as susceptible to stretches without income or to shocks in the broader economy. Freelancing is one of the best ways to make money in a strong economy, but it’s also one of the quickest things to disappear when companies are cutting costs.

With that in mind I set out to focus on two goals:

• Earn money in as many different ways as possible
• Build a portolio of income streams that act as a high probability “floor” of income

This lowered my income in the short term but boosted my confidence and resilience. Knowing how to make money in a number of different ways gave me practical skills and an expanded imagination about what I could do to make money.

While I had a hard time realizing it at the time, my overall income also steadily increased over time with this approach. I now have had at least three sources of income generate over $200 for more than a year and have had at least six income sources for longer than that.

In my first year of self-employment, I had high earnings but it was inconsistent. I had six months with less than $2,000 income and three months with more than $10,000 per month. The second year I shifted away from consulting and had seven months with less than $2k income. The last two years? I’ve made at least $2k every month.

This is much more valuable for the game I’m playing as it dramatically lowers the odds that I will run out of money and gives me more freedom to walk away from any type of work I don’t want to do without feeling like I might go broke

Principle #4: Start Slow & Keep Trying Things

I like trying a bunch of different things for a few reasons. First, I genuinely like creating new things and experimenting. I find the process of turning ideas into my head into things that can be helpful for others to be fun. This is a unique advantage in the world that is emerging and I’m fully aware of this.

Second, it keeps things interesting and also exposes me to a number of different ways of engaging in the world such that I can help others do the same.

Finally, it helps me build a portfolio of “small bets” as Dan Vassallo shared in this conversation with me – any one of which could have unexpected payoffs.

With my newsletter and podcast, both started as ways of sharing what I was up to and without any intentions of turning them into businesses. I didn’t promote them or share them widely because I wanted to be able to quit without people noticing. Tim Ferriss took this strategy with his podcast. He told himself that he would do six-episode and if he was having fun and didn’t hate it, he would keep going.

Conventional wisdom says to grow fast, to take advantage of every launch. However, that increases the odds that you end up doing something you don’t want to do. My approach has been to take a slower path. Five years into this journey, almost everything I’m doing I want to be doing and this has been from a series of incremental “yeses.”

I recently launched a freelance consulting skills course. This course was the result of helping a couple of freelancers that were doing work for me level up my skills. I realized I was having a lot of fun helping them be better and they were finding the information and feedback useful. I had validated both the idea and the feeling. That second part is often ignored. Too many people don’t think about the fact that once they build something that makes money, they have to spend a lot of time doing that thing. I only built the course because I enjoyed helping people become freelancers. Right now it’s still a small bet but when the opportunity emerges to take it somewhere else, I will consider it and if it feels right, I’ll say “yes.”

Principle #5 Make Friends. Be Helpful

This is the most important principle and the one that makes everything else more fun. Yet, it is also the one where I struggle the most.

I’ve always been the person that likes helping other people. In college, I proactively volunteered to help fix people’s computers and help with resumes, job searches, and interviewing. After I graduated I helped people make career changes and write essays for grad school. At my jobs I always took on extra roles to help with training and coaching.

It was fun. But the world tells you that these are silly things. People tell you, don’t get taken advantage of. Adam Grant writes books showing how to avoid being a pathological altruist and to make sure you balance yours gives with your takes. Others ask “why you don’t charge?” You spend your time at work helping your struggling colleague while you watch the skilled politician land another raise.

I was cynical about this for a while. I wanted the working world to change. I wished there were paths for people to progress and get raises while remaining a front-line manager. My first blog was called “better working world project.” Eventually, I realized it was better to create my own game rather than try to swim upstream.

So I experimented. I started a career coaching business on the side. I started writing. I eventually went out on my own and was able to be the kind of freelancer I wanted to be. I had more time to spend helping people for fun without feeling like an idiot (though sometimes it still feels silly to do things for free).

As I continued to do this and built an audience through my writing, people starting sending me thank you notes. I received one note from someone that I had a conversation with a few years earlier. She told me that her conversation with me completely changed her mind on what she wanted to do. Now she was doing something she loved and wanted to thank me for the inspiration. I’d be lying if I said that these moments are fucking awesome.

I did an exercise in which I had to rank my “yearnings” or the things we really crave. My top two were appreciation and freedom. Appreciation was something that surprised me but it felt true. Leaning into that and realizing that it is something I need but can also be fuel is a powerful thing to know.

A couple of years ago I did another exercise in which I had to write down my “purpose.” The person that created it said to keep writing versions until you cry. I thought it was silly but I’m always open to trying new things. It worked and this is what I landed on.

Connect as a real friend to people to give them the courage to create, help simplify the world to enable people to imagine new possibilities, and continuously be more brave in discovering the people and things that matter in my own life

I know that my desire to help others might be a little pathological and after reading Adam Grant’s Give and Take it seems that I’ll probably succeed financially a little less. But I don’t buy his argument that this is something to fix. I have realized that I want to design a life around making this weird quirk a great part of my life. I know that it undermines my ability to be financially successful sometimes and that’s okay.

I’ve just decided that it matters.

The Bottom Line

I don’t know what will be paying the bills next year but the longer I play this game the more confident I become. It could all blow up at any second, but the whole point of the game is to enjoy the journey.

I spent ten years on a path where I was always focused on the next project or the next step.

This is way more fun and I hope I’ve convinced you to find your own game worth playing.

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 Designing Your Own Infinite Game In The Creator Economy appeared first on Boundless by Paul Millerd.

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Years ago, Ben wrote that his personal mission statement was “to help people reach their full potential” and our conversation touches on this theme in many different ways.  Ben is a former car rental pro turned consultant turned HR executive. His work in HR landed him on the cover of Human Resource Executive. It’s pretty cool, so I wanted to share it here:

He then decided to leave the corporate world and has been on an entrepreneurial journey for the last six years as an executive coach and startup founder.  In our conversation about coaching, Ben mentioned a fact from an HBR article on coaching that I thought was fascinating.

“It’s rare that companies hire business coaches to address non-work issues (only 3% of coaches said they were hired primarily to attend to such matters), yet more than three-quarters of coaches report having gotten into personal territory at some time.”

This disparity really gets to the core of what people like Ben are about – being more human at work.  Ben joked in our conversation that everyone’s real issue is with their parents. While certainly funny, this gets to a deeper point that many people are waking up that we can’t just show up as robots to work anymore.  There has been a wider embrace of being our full selves at work, led by people like Ben who started the first LGBT group at his consulting firm more than 10 years ago.

Our conversation touches on a number of issues including coaching, entrepreneurship, how his relationship with work has evolves, management versus leadership and what he wants written on his tombstone.  Some other topics we touch on:

• Ben’s motivation to work at Enterprise Rent-a-Car after college and what he learned
• His early entrepreneurial “ventures” starting at 12 years old
• How his mindset about work shifted as he became successful in the corporate world
• His experience hiring working with an executive coach in his late 20s
• His experience coaching and favorite exercises
• Why companies are scared of trusting their people
• Why being a manager is actually an incredible opportunity for people
• The learning and ownership upside of carving your own path
• The value of having advisors, friends of confidants to celebrate “wins”
• Balancing life & work and his personal sustainability
• Deciding to give himself a raise as an entrepreneur

Links Mentioned:

• What coaches can do for you (HBR)
• Pilot: Executive Coaching For Organizations
• Ben Brooks Coaching
• Connect with Ben: LinkedIn, Instagram & Twitter

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 Ben Brooks on coaching, trust, the art of management & entrepreneurship appeared first on Boundless by Paul Millerd.

Lydia Lee was a self-described “multi-potentialite” growing up and loves to experiment and play games growing up.  You can probably draw a straight line from her hosting television shows for the stuffed animals in her room to her current YouTube channel Screw The Cubicle TV.  However, life is never that simple.

In University Lydia was drawn to many different things but did not know anyone who was taking a different path so she kept exploring within the context of the corporate world.  To deal with her underlying curiosity, she kept moving to different jobs: “two years was the maximum that I could last.”

Burning Out In Moscow

Lydia was working 60 hours a week, “thinking about work the whole time” and had not taken a vacation in five years.  The stress caught up to her in Moscow when she was traveling on a work trip.  It was burnout.  It presented itself not only as a feeling that something was “off” (she said that had been there for years) but as something that was physical.  She had a panic attack and a feeling of “agoraphobia” and not wanting to leave her hotel room.  She also reflects now and believes that burnout is often a deeper call for more creative expression.  She said: “part of the burnout for me was that I was a creative person.”

Meeting That First Friend

Many of us can grasp conceptually that different options are available to us, but it does not become real until we connect with another person who has done it.  This happened to Lydia during a two-month vacation to her home country in Malaysia.  While on a boat, she struck up a conversation a man from Germany who was running a business remotely.  This piqued her interest and planted the seeds for her to start to think about her work and life in a new way.  When she returned to Canada, she re-visited Tim Ferriss’ 4-Hour Work Week with new eyes and started to apply some of the lessons to how she might work with more freedom.

A Journey Of Learning & Experiments

A question I often get from people who want to leave the corporate world is “how do I get a job doing x?”  Lydia and I talk about how this is often the wrong framing.  Creating your own job is more about a series of experiments and evolution of where your creative energy takes you.  Even this language can be a bit uncomfortable for people to grasp.  We live in a world that operates around getting “access” to a job, not creating it.

Lydia now lives in Bali building a business she is passionate about.  Was that the plan?  No.  Often with many entrepreneurs, the first thing they do is not what they end up sticking with.  The shift from full-time work to a different world often comes with a deeper shift about what is possible.

Lydia was running her first business and blogging on the side about her journey when someone reached out about coaching them on helping him carve his own path.  Freeling a bit hesitant about her coaching skills, she decided to create her own “internship” if you will so she could get the experience.  She decided she would reach out to her network and ask eight people to commit to eight weeks with her.  She offered the coaching for free and in the process created a priceless 64-hour coaching training for herself which enabled her to understand who she liked working with, what she still needed to learn and help her figure out if she wanted to do more of it.

What About The Pineapples?

If you go to Lydia’s site, you will see purple pineapples. Like this one:

I asked her about this and she said that a client she worked with described her as a pineapple: someone direct and firm on the outside, but inside really cares about the people she works with.  She likes working with people that are comfortable being challenged and has had such success with her clients because of this approach!

Connect With Lydia

• Screw The Cubicle
• Bali Retreat: April 2019

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 Screw The Cubicle With A Side Of Pineapple (Lydia Lee) appeared first on Boundless by Paul Millerd.

Nemo Ashong’s bold vision is “a truly inclusive and empowered world”  He helps people to be fully expressed and to be more authentic, be more unique and be more powerful.

He grew up outside of Camden, NJ and often struggled with his identity growing up as a first-generation African-American: “I wasn’t quite African and I wasn’t quite American.”  He found that he didn’t really “fit in” with the black community, but found a home in the gifted program early in his life which exposed him to a very diverse population and forced him from an early age to carve his own path.

Using Agreements To Unlock Powerful Conversation

He is a fan of inviting people to be their full selves in the world and challenges people to think about how they can be “1% more themselves” each day.  In order to help people as a coach, he is very tactical about creating the understanding and space for such conversations.  He typically outlines three core agreements with his conversations partners:

• “I choose to hide nothing and hold nothing back”
• “I choose to serve, rather than please”
• “I have a track record of having life-changing conversations, and at this point, I refuse to have anything less than that, are you open to having a life-changing conversation?”

Being Yourself In The Workplace 

We talked about the challenges of diversity & inclusion in the workplace and discussed Nemo’s initial aversion to getting involved in diversity events at his past companies.  He feels that we do not focus enough on inclusion and an inclusion in the sense that it gives someone:

the ability for someone to really feel that they can bring all their experiences to the table.  That ability for someone to really feel that they can present a new way of going about it because in their community and their experiences and the things they have done they have seen it work out differently.

By not fully embracing inclusion, he feels that “we miss out on leaders that can challenge the status quo” or at least explore and discuss difficult issues.  He asks a provocative question:

Are we creating a generation of leaders and people who will be able to really engage in dialogue and feel confident in themselves to respectfully invite other ways, other perspective other methods into the pool of knowledge?

Nemo’s core message to people is to look for the “hard lines about how life should be in the corporate world that we are taking part in perpetuating” and to question them and he feels that the best way to do this comes down to a simple message to people:

“Be more you.”

Not “be yourself,” but to look for opportunities where you can be yourself at least 1% more, whether it’s in a decision you are making or showing up to work as a different person.  These changes will lead you to more fulfillment and hopefully, more joy.

Reflecting On This Conversation

This conversation brought out some vulnerability in both of us and we barely scratched the surface around these topics.  I live for this type of tough conversation and appreciate that podcasts give the kind of space to explore topics with nuance.  I’m not sure we ended up with any clear answers, but I think had the type of conversation filled with respect and curiosity that can enable us to go deeper with each other and with other people.

Connect With Nemo

• Nemo Ashong: Empjoyment
• 1-On-1 Coaching With Nemo
• World Joy Movement

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 Name Is Nemo and I Don’t Do Small Talk” appeared first on Boundless by Paul Millerd.

Romy is an employee engagement consultant turned coach. She built her career consulting for and working in Fortune 100 companies on all challenges employee-related. Her mission is to drive meaningful and behavior-based change for mid-level leaders that helps them operate in a more productive and human way in the workplace. There are a lot of coaches out there, but what makes Romy stand out is that she has a lot of experience working with senior executives in her consulting career and she has deeply studied what works and what doesn’t. Hear more in our conversation…

Romy Rost – Website

Empower Your Conversations – Work With Romy

Podcast Information: #BoundlessPod

Support: Support The Podcast For $1 a Month

Join the conversation: #boundless VIP facebook group

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

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The post Boundless Podcast: Romy Rost on leadership, freelancing & coaching as a skill (Episode 13) appeared first on Boundless by Paul Millerd.

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Janet is one of my favorite people. We have a similar belief that people are capable of more than they believe and that alternative paths are more realistic and the reality than people realize.

Not a fan of default paths from an early age, one quote stood out from Janet that she has continuously asked herself throughout her life:

“The conventional path is not going to work for me, what can I do instead?”

Life Hacking From an Early Age

Janet first started “hacking” life in high school when she decided that the standard curriculum wasn’t for her. Despite pushback from parents, teachers and peers, she followed her curiosity and negotiated an alternative path — avoiding things like Math to go deeper with teachers in social studies, religion and politics.

Her next “hack” was to apply to college in Canada. Starting with the constraints that she wanted to avoid debt and that her parents would support the equivalent of in-state tuition she looked for different options and found a way when her uncle convinced her to look at Canadian universities.

Although taking a non-conventional path, she learned a lot about being able to adapt that would help her later on in her career.

But first, a normal job….

In her first job as an oil spill responder, she found she enjoyed the work but felt something was missing. This led her to pursuing a masters degree in education where she learned about the path of career counseling. She felt it would be a perfect job for her because she had often struggled with making sense of her career herself and wondering “how she could do things differently”

Paul’s Side Note: In many people I’ve worked with, I’ve found that they often stumble upon work they are passionate about by addressing their own needs, much like Janet did — she wanted to figure out how to navigate a career for herself, which led her to be really valuable to others

Putting her story into the world, aka starting a blog

In college she “decided not to become a teacher” after talking to teachers and realizing that many of them were not as happy or energized as she expected. Yet it was pursuing a masters in Education which led her to her freelance career.

While working in her first job as a career counselor, some colleagues recommended that she start writing and she started a blog. She started a blog, found she had a following and then decided she would start offering career coaching services.

By putting her learnings on navigating her own career and her work with students, she found that it resonated with people and she was able to turn it into a business.

Chaos and Planned Happenstance — Two theories of how careers actually work in the real world

I have to credit Janet with introducing me to two awesome academic theories of careers that seem to address the issue of what actually happens (versus what we pretend careers look like).

They are Planned Happenstance theory and The Chaos Theory of Careers. As Janet summarizes these ideas: “we can only plan so much in our lives and the successful lives come by planning for coincidence — putting yourself in the right place at the right time”

How to make a shift

When working with clients, she starts with helping them think about three main things. The core questions are:

1. Whats wrong with your current situation?
2. What’s working with your current situation?
3. What are your values (she recommends this survey)?

Then, she gets people to think more creatively about what they could bring their skills into the world. Her general advice to people, especially students is “get out of your own head, get out from being under expectation” and connect and create out in the world to see what might happen.

If you want to learn more about her work, check it out here.

How she defines success now

Success for Janet is all about “her energy and her levels of joy.” She knows that when her energy is low, things need to change or she needs to change what she is working on in her business. She finds that doing work that is meaningful and helping other people helps lead to the unintended side effect of being happy, which attracts others to want to be around you and work with you. She finds that people who are happy “see more opportunities” and that this mindset is actually the key that leads to real financial or business success.

Links:

• Janet: www.careerjanet.com
• Planned happenstance theory
• Chaos theory of careers (video) and research paper
• My Life Values (assessment)

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 Janet Matta, Rock Star Career Coach On The Alternative Paths We Fail To See appeared first on Boundless by Paul Millerd.

Asking someone “what do you want to do?” is a terrible question. Yet we ask this question over and over to young people.

If I were asked this question, my response would be complicated:

“Since the half-life of skills is rather short and I can’t predict what types of work will exist ten years from now, I am going to work on a wide range of challenging problems, focusing on work that enables me to learn on the job and exposing myself to risks such that I will be more comfortable with change when I get older so I can stay energized throughout my career.

Cue the eye roll. It’s easier if someone just says, “I want to be a lawyer” right?

I spend a lot of time talking to people trying to make sense of their careers. I talk with college students, young professionals and even people at the tail end of their career trying to figure out what’s next.

For many, career choices have never involved much thought. You pick a major and take a job in that field. You stay within a department at a company. You stay within a certain industry. You follow the default path.

However, default paths are mostly an illusion. Even people who may have a resume that looks linear will likely tell you about their many speed bumps, rejections and course corrections along the way.

Given how fast our economy is changing, more people are having to take a step back and take a different approach that just following the default path. In my experience working with people as a career coach and mentor, I have found three approaches that help people take a different approach to planning their career:

Lens #1: What skills do you have?

You have two choices in all career decisions:

1. Strengthen current skills
2. Build new skills

The first step is to understand what your current skills are. People often do not give themselves credit for some skills that they have. I like to break down skills into two categories. First is “fundamental” skills — these are the ones that would have been relevant 200 years ago and will be relevant 200 years into the future — and are things not traditionally thought of as skills. These are things like listening, problem solving, adaptability, compassion and energy. Second is “technical” skills — these are abilities that are more relevant in today’s world and can be things like coding, language skills, software skills, writing & synthesis skills and video production.

When you take an inventory of these two types of skills you can look back on previous jobs and often figure out why you were so frustrated (the environment did not help you strengthen those skills) and also look forward to figure out what environments will work best with your current skills and help you develop new ones.

What is your unique combination of skills?

I was recently speaking with someone who had written a book, had a masters in engineering and was good at coding and data analytics. There are not many people with that combination of skills. If you are able to identify an environment that helps you maximize a diverse range of skills, you will be well on your way to carving out a meaningful and energizing career.

Doing this inside a large organization can often be a challenge, especially at junior levels where employees are expected to specialize in one function or task. More and more people are realizing that achieving personal growth and challenging themselves in new areas is harder and harder to do within a big organization and instead are pursuing “side hustles,” creative projects and freelance careers with a portfolio of different projects and responsibilities.

If you assess your fundamental and technical skills and combine that with your curiosity, you can often identify areas to further push yourself to learn and develop new skills and unlock new opportunities. This doesn’t have to be a full-time job, but can be getting involved in a club, volunteer opportunity or side hustle. Since there often isn’t the pressure of keeping a job, I’ve seen many people’s passions explode into something bigger that eventually replaces their former “career” on the default path.

Lens #2: What is your definition of success?

In the corporate world, if you do not have a personal definition of success, you are accepting a default definition of success. Whether you like it or not, this means you are valuing making more money, getting promoted and attaining authority positions. When asked, people rarely say they value these things and research shows that these type of extrinsic rewards can be demotivating at worst.

Developing a definition of success is not easy and you may face backlash if you start making decisions based on it. Early in my career I decided that personal growth, learning and working with inspiring people were my guiding decision making principles and definition of success. This meant taking pay cuts, leaving jobs before I could have been promoted and quitting jobs where I was working with people who were not inspiring (brilliant jerks). Based on the defaults of the corporate world, I was insane. Based on my own definition of success, everything was according to plan.

Lens #3: Re-define risk — What is your worst case scenario in 10, 15 & 25 years?

It is useful to visualize your worst case scenario ten or more years ahead of time. For me, I pictured myself sitting in a cubicle, slightly overweight, staring at the off-white color of the office and so distraught that my boss had criticized my work and counting the hours until I was allowed to leave.

If you know what you fear most, you can avoid it. You don’t need to know what you want to do, but by knowing what you don’t want to do, you can use that to make decisions.

Jim Koch would have never started the Boston Beer Company if he wasn’t able to re-frame risk. He had been working at Boston Consulting Group for six years in what he described as “a great job.” However, he reflected:

“I asked myself do I want to do this for the rest of my life? The answer was no. If I don’t want to do it for the rest of my life, I don’t want to do it tomorrow.” — Jim Koch, Founder of Boston Beer Company

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

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It was July 2014 — I was at a networking event in Boston and ended up having a conversation with someone who just made the jump to being a career/life coach.

I ended up sharing one of my dreams with her:

“I’m want to be a career coach one day. I’ve helped a lot of people land great jobs and figure out what they want to do. I love it.

What she said next scared me:

“You already are a coach, you just need to start doing it”

Damn. Now I had to do something.

I could tell you about taking massive action immediately after this conversation, but that’s not what happened. I was still scared. It took me several months to take action on this thing I knew I had to do. You know what held me back? Picking a name. At least that’s what I told myself. In reality, I was a bit scared of doing something out in the open.

What would people say?

Everyone has something that holds them back. For some, it is perfection — needing everything to be perfect. For others, it is creating such massive goals that they become overwhelming. For me, this was the first time I was attempting something outside of the

On a quiet day in February 2015 in snow packed Boston, I finally landed on “Careers with Paul.” I registered the domain name and put up a quick website. It felt great to take action. It felt like I was moving forward on something that I was excited about.

Within a couple months, I had enhanced the website even more and had re-learned HTML, but was not sharing it with the world or actively finding clients.

Lingering doubts still held me back:

What was I doing?

Can I do this?

What if I’m bad at it?

How do I get started?

But the biggest thing: What will people say? But more on that later…

At this point, I saw a mailing from my alma mater about a career coach that was beginning to work with alums and was intrigued. I quickly sent him an email saying I’d love to connect and see how I could help with alums as well.

That conversation turned into a deeper discussion of what I was trying to accomplish. He asked me the same question: Why haven’t you done anything yet?

I didn’t know it yet, but having someone that saw opportunity and not limits was addicting — I decided to hire him on the spot. Plus, how could I coach other people if I hadn’t put myself through the same challenge?

The Experience Impacted me in Three Powerful Ways

1. Ignoring my self-limiting beliefs — Like many people, I have a laundry list of reasons why I can’t do something. Excuses are easy. But a coach looks past these and focuses your dreams and helps you move in the right direction. This was a powerful emotion I felt consistently while working with the coach. I would say something bold — expecting him to poke holes in my idea — but instead, he would say “that sounds great, when will you do it by?”

2. Having a safe space to consistently reflect: Building a nice website was good fun, but I wasn’t actually learning anything more than CSS and HTML. In each of the coaching session, I kept coming back to the fact that I needed to put my coaching into action to see what I was good at, what I enjoyed and even more important, what I didn’t enjoy or wasn’t good at.

3. Picking a small goal to kick-start action: When I thought about being a career coach, it seemed BIG and overwhelming. I was thinking about the end goal before embarking on the journey. I often tell my clients to pick a small goal and go do it — I needed the same advice. On my first call with the career coach, he said to me “You are already qualified to do this, why don’t you just do it?” So we decided that I would write an article explaining what I was doing and launch the site to everyone I knew in 30 days (here is the original e-mail I sent to 100 family & friends). No excuses. Once I committed to this, everything started flowing. That article was a breakthrough — it led to multiple speeches, helping a client land their “dream job” (their words, not mine), developing an e-book and online course and leading my first group coaching workshop — all in only six months.

So back to my question from above— what will people say?

I still think about it. It never goes away. Criticism is painful, but luckily it rarely comes. What has been more surprising is the incredibly positive reception I’ve received. So many people have emailed me and said how much they appreciate my help, insights or style. One friend even mentioned a small thing I did five years ago and how much she appreciated it. I have faced some skeptics, but the excitement and fun I’m having by experimenting with new ideas outweighs all the haters.

I’m excited for what’s to come and I’m here for you. Just like the coach I worked with, I’m probably going to ignore your weaknesses and when you share your dreams with me, expect to hear:

“That sounds amazing — go do it!”

The Coached Has Become the Coach.

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

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The post Even Michael Jordan Had a Coach appeared first on Boundless by Paul Millerd.

It took me about a year to publicly announce to people that I was taking the leap.  I did it in a short e-mail to 100 friends and family that helped me land my first two clients.  Here is the e-mail

Friends,

I’ve always been borderline obsessed with trying to figure out how to learn, develop valuable skills, and market myself in my own career.  At the same time, I’ve always been equally as motivated to help others achieve success.  From aggressively pushing my college roommate to apply to a job at GE (which he got!) to help my mother write “the best cover letter we have seen,” I loved seeing others accomplish their goals.

I started small, helping people find jobs, enhance their resumes and cover letters and prepare for interviews.  As I got better and I started to achieve success in my own career, more people started reaching out to me.  I noticed pretty quickly that I was pretty damn good at seeing other people’s potential (even more clearly than my own), helping them identify what they were good at and helping them accelerate towards their goals.

I gained a lot of confidence as my “clients” delivered on some big goals.  From a UConn senior that beat the odds to turn a goal of breaking into strategy consulting into a successful reality to another gaining acceptance into a top 5 business school and even another making the transition from 5th grade math teacher to healthcare research analyst at the #1 global strategy firm, I was finding myself more inspired and excited than the people I was helping.   It became crystal clear that this was something I wanted to pursue on a more serious level.

So here I am.  I’m going to pursue thison the side(no I’m not leaving my job :-] ) and I wanted to share it with you first.  Do I know where this will take me? No, but I’m excited to find out.

There are three things I want to ask you:

1. Check out my site and let me know what you think: careerswithpaul.com (RIP)
2. Let me send you updates on my thoughts: Click Here
3. The next inspiring person you meet that wants to accomplish great things – tell them they need to connect with your friend Paul

Thanks for your support and inspiration over the years, I’m really excited about this.

Eventually, I DID leave my job and pursued this on a more permanent basis, but I had no idea where I was headed at the time.  Do you have the courage to start?

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

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The post The e-mail that launched my coaching side hustle and helped me quit my job appeared first on Boundless by Paul Millerd.