I recorded an episode in 2021 with a friend, Kris Abdelmessih. After finishing the conversation I remember being excited about what we talked about but it wasn’t until listening to it a second time that I realized how many great ideas I took from the conversation.

What follows below is a link to our conversation as well as eleven ideas that resonated with me.

Meet Kris

Kris Abdelmessih has one of the most unique perspectives on life and works I’ve stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models.  I enjoy his perspective – unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.

We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I’m spending my time with my work.

The conversation dramatically shifted how I’m thinking about the possibilities of my path.  If you are on a self-employed path, this is a must-listen. We talk about:

• Financial insecurity and its relationship to the creative path
• Using creative pursuits online to make friends and make your life better
• How to think about the options in an emerging space like the creator ecosystem
• The challenges with using an “options mindset” to make career decisions
• His experience spending time and teaching kids
• Brainstorming options for his next adventures with work

Eleven Lessons On Valuing The Solo Path

#1 I used to believe in Creativity, Inc.™

Early in my career I never thought of myself as creative. Creative people had titles like “creative director,” or sold paintings, or did crafts with their friends.

Now I realize that turning information into stories that resonate with people is also a certain kind of creativity. One that I can use in many different ways and that I can improve at over time.

Another kind of creativity is being able to navigate modernity. Landing interviews, figuring out how to complete bureaucratic tasks, and getting accepted into grad school all require a certain kind of creativity. I don’t like being creative in this way but can I do it? If needed.

#2 “You realized you didn’t have to be dissatisfied”

You don’t know what you don’t know. When I was working on my former path, I thought that being dissatisfied was part of work.

On the podcast, Kris said to me that on my current path I learned that “I didn’t have to be dissatisfied.” I never thought about it that way.

I’m not sure what this is worth but it’s definitely a superpower for knowing when to stay no to the projects that might drain my energy.

#3 A job is a kind of work where its harder to get fired

When I was employed I didn’t behave as if this were true. I worried too much about doing what everyone else was doing instead of putting all my energy into doing the things I was good at. It’s clear now that if I took a job I’d behave much differently.

People undervalue looking at life from different perspectives and this is one of the biggest reasons to experiment with structuring your life in many different ways.

#4 Turning a one-way door into a two-way door

Many people fear leaving their jobs because they might not be able to ever get their jobs back. Some believe that if you leave for too long no one will hire you. This might be true in some places but it is definitely less true than in the past.

Almost everyone that leaves their job or embarks on a new path almost immediately recognizes the one-way door that they thought they walked through is definitely a two-way door. Many people continue to dabble in that old world either as freelancers or on their own but many never end up going back through it.

#5 Undervaluing Space

Kris was surprised by how valuable it was to take time just to think and reflect on his life. Something about full-time work makes this hard. Or at least, that was my experience. I’ve written about valuing space and my experience in the first few months in Taiwan, where I couldn’t find any work and embraced the opportunity to walk around and read in parks.

On my current path, I build in sabbaticals and extended breaks because I know that is what keeps me energized. I haven’t come close to burning out or considering leaving my current path once and continuously cultivating time and space for reflection is a big reason why.

#6 You play the games that the people around you play

We both reflected that we got sucked into money and promotion games that we never would play now. Before I left my job I was fighting for a promotion and a raise and was upset that they were not giving it to me. I haven’t made 50% of what I made in that job in almost five years but I have plenty, I’m happy, and I know for sure I’d never play those games again.

#7 Cutting expenses is lowering your cost of personal capital

When I first quit my job in New York and again in Taiwan when I couldn’t find remote freelancing work, I cut my spending a lot. The story I told myself about this was about financial fears and insecurity about money.

Kris said. “oh you were lowering your cost of personal capital.”

I like this lens. From this perspective, anything I spent my time on would have to meet a much lower bar for “approval” by the internal investment committee in my head. When your personal cost of capital is low, you can “invest” in much riskier projects and ones that can’t be valued clearly.

This was probably one of the biggest reasons I was able to make a shift from freelancer to the creator economy stuff I’m making money from now.

#8 “If you make money every day you are leaving money on the table”

Kris shared this popular quote in trading circles. It resonates with how I’m trying to approach my path. When many people talk about leaving their jobs, they talk about their desire to “replace” their income.

If I had focused more on freelancing I could have done this. However, I realized within a year that I wanted to play a longer game and learning a bunch of different skills, finding work I liked doing and living in different ways was going to help me much more in the long run.

#9 Translating “normal” expenses into dream life scenario expenses

Self-employment exposed a clear tradeoff between money and time. When I see a car, I see the equivalent time I could spend not working. When I hear about a home someone has bought I think about the life experiences it could buy me instead.

There are a lot of Teslas in Taiwan. When I see someone driving it on a commute from the office, all I can think about is the two or three years traveling the world that money would fund instead.

If you start to think about a lot of purchases like this, pricing them in the “dream life” scenarios you imagine, it might expose hidden possibilities in your life right now.

#10 Portfolio Theory of Indie Creation

One of the most interesting examples Kris shared was a perspective from portfolio theory. If you are thinking about creating something as an individual, it can be easy to overlook the value the higher value it might have if it were part of a broader portfolio of content.

For example, he could create a course on options trading and it might do well but if he did this for a company like Robinhood it might have even more value for both parties.

I value working on my own but this made me realize I’m probably a bit blind to obvious opportunities where I and another person or company would both be in better positions if we figured out how to partner.

As more people become self-employed, enter the creator economy, and dabble in this broader new economy, the possibilities will continue to increase. Developing a better view of how I might fit into all of that is going to be something I reflect on more deeply in the coming months.

#11 “highest and best use is…”

Kris mentioned that it’s clear that the economy says his “highest and best use” is doing something in finance but he has a hunch that he hasn’t quite figured out his broader highest and best use.

To me, this seems like the ultimate and real work of our lives. Many people are content to accept the economic answer (and for some people that may be their best use) but I am not. I have a hunch that my highest and best use is continuing on this journey and seeing where I might be useful along the way.

The hardest part about this is that if you don’t let the economy decide, you can’t measure or prove that you are right.

Jeremy Finch from The Fire Jar Summarized This Convo Too

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 How a Trader Models The Solo Creative Journey – Kris Abdelmessih (Podcast) appeared first on Boundless by Paul Millerd.

“You can’t study or learn your way into a new identity” – I love this quote from Darren Joe.  

He’s been thinking about carving a different path from 2003 to 2004 when he graduated college. This was before Tim Ferriss’ 4-Hour Workweek and before becoming a digital nomad was a thing. I asked him what his inspirations were and he wasn’t quite sure. He just always had a natural drive to be independent and do his own thing.  

He recently published a book titled The Fail-Safe Entrepreneur.  In it, he argues that almost all solopreneurs strive for three things: Freedom, Adventure, and Meaning.  I definitely agree.  However, he says many fail to reach these aims because they ignore the shadow side of this path.  He details four things – FAIL: Failure, anxiety, instability, loneliness.

We explore many things in this conversation including:

• Grappling with the achiever identity
• Longing for independence and freedom
• Parental approval
• Building Community
• Experiments
• Defining success

You can buy his book the Fail Safe Solopreneur on Amazon

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 How To Tame The Shadow Side Of Solopreneurship – Darren Joe (Podcast) appeared first on Boundless by Paul Millerd.

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I connected with Visa on twitter, where he’s made many friends over the past several years. I wanted to interview Visa to talk about his leap to self-employment over the past couple of years, but we talked about so much more. We talk about:

• What the word “nourish” means to him
• His evolution on procrastination and getting started
• How to find like-hearted humans on twitter
• The “asshole problem”
• The curious humans of twitter
• How he creates his own work

Thinking On Twitter

Visa has gained a reputation on twitter for being someone that’s building a transparent “second brain” (h/t Tiago Forte), sharing whatever he finds with his followers.  

He says he does this mostly to keep track of what he’s learning and finding, but it also seems to be something that many people find value from.

• Link To All His Threads: Visa’s Threads

I asked him for his most overrated thread:

…and his most underrated thread:

His tips for getting started on Twitter

Many people worry about attracting attention of influential people. Instead, he suggests you just focus on building genuine connection. Here are the five steps he recommends for anyone that wants to dive in:

1. Don’t follow institutions – if its interesting, people will retweet it
2. Don’t follow people that won’t reply (+3,000 followers): 
3. Follow people with max of 1,000-ish followers
4. Have conversations with people
5. Make friends with their friends

Taking the leap to self-employment

I love his own tips on self-employment. The following tweet summarizes how he’s thought about his own leap (he say’s he us currently on step 4!)

He thinks people should be bolder in creating their own work and using your curiosity as a guide

you can do unpaid work for yourself. I suggest do anything you find interesting

He gives the example of a mean girls essay he wrote that (Power & Social Dynamics In Mean Girls) got a lot of attention from people that were “above his pay grade:

The trap some people fall into is they think they need to do what they think other people will be interested in…that;s like guesswork…and your guesswork is probably off by some degree that you don’t realize.

I love that model. Check out the episode and let me know what you think!

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 Visakan Veerasamy On The Curious Humans Of Twitter & Creating His Own Work appeared first on Boundless by Paul Millerd.

In the months before the trip, I lost several projects and then lost a great project because they weren’t comfortable with me working remotely while I was in Asia.

I was feeling pretty crappy. I had turned down projects for a couple of months prior to focus on some creative projects, but was feeling pretty desperate to land some work so I didn’t feel so worthless in a busy American city.

A couple weeks before my trip, I had a client reach out about a potential project which was right in my wheelhouse. Towards the end of my pitch, I said “sooooo I have this trip planned to Asia. Would you be open to me proposing how I could still do this work remotely?”

They said sure. I was shocked.

The next day I sent them a proposal to spend 25% of my time working on this project from Asia for an hourly rate that would easily support my life over the next couple of months. They accepted it immediately.

A few weeks later in a surf-side cliff town in Uluwatu on the island of Bali, I spent about 5 hour working on the project for the first time from the location pictured below.

As I worked that day, it was one of the first times I was working and didn’t really have any resentment towards that work. How could I with such a view?

It was also the first time where I felt a little silly that I had spent almost a year freelancing and didn’t think about leaving Boston or New York to explore more of the world or visit friends. Especially if I could live here for $20 a night.

Almost a year later, I visited this same place traveling with my partner and realized that this moment, this day of working remotely and abroad at the same time, was a moment that forced me to dream a little bigger and question my own limitations I was putting on my life.

And now I always wonder, am I dreaming enough now?

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 Are You Dreaming Big Enough? appeared first on Boundless by Paul Millerd.

However, in this article, Thompson still seems stuck in a systemic view of work and the symptoms of that system. By doing this, he fails to address the fundamental question of how to build a life around work. Perhaps his inability to get there comes from his own internal struggle:

This is the right time for a confession. I am the very thing that I am criticizing.

As someone who has spent the last two years of my life trying to solve this seemingly impossible puzzle and writing about it through the eyes of others, I know there are many ways to “hack a living” as the practical philosopher Andrew Taggart would put it.  Taggart has written one of the most powerful assessments of this crisis in his book “The Good Life and Sustaining Life: An Inquiry Into Our Great Vexation” where I believe he correctly frames the challenge:

There may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life.

As he identifies in his inquiry, “One cannot deny that the question of the good life must come before that of sustaining life.”

This is Aristotle’s good life, not the Kardashian good life.  

If we look at Thompson’s essay through this lens we start to see the problem. Many of the workers he details have the Kardashian good life, or at least the modern professional equivalent. They have solved many of the problems of sustaining life and but lack their own deeper definition of the Aristotelian good life.  It is choosing pour over coffee and luxurious vacations rather than the ability to do whatever you want on a Tuesday.

Anne Helen Peters actually gets closer to a possible question towards the end of her “Millennial Burnout” essay, which Thompson references, but never takes us any further.

It’s a way of thinking about life, and what joy and meaning we can derive not just from optimizing it, but living it. Which is another way of saying: It’s life’s actual work.

Thompson and Petersen’s articles were shared like crazy, but they never offered any ideas about what to do next.  

Our social media environment incentivizes this. It’s much safer to share something that shows vulnerability and gets a “me too!” reaction than something that might challenge the status quo.

I’ve read articles slamming co-living communities for being utopian, privileged, escapist and out of touch paradises. So last year when I went to visit one of these communities, I was shocked to find people from all over the world who were craving (and achieving) a deeper connection to others and aspiring to build a life-less centered around work.

This attitude of “well what the hell can we do?” most powerfully came through in a recent New York Times “work sucks” piece appropriately titled “America’s Professional Elite: Wealthy, Successful and Miserable” which shares stories of people making gobs of money, but left utterly miserable. Even people who see a potential short-term solution seem utterly unwilling to do anything about it:

“I feel like I’m wasting my life,” he told me. “When I die, is anyone going to care that I earned an extra percentage point of return? My work feels totally meaningless.” He recognized the incredible privilege of his pay and status, but his anguish seemed genuine. “If you spend 12 hours a day doing work you hate, at some point it doesn’t matter what your paycheck says,” he told me. There’s no magic salary at which a bad job becomes good. He had received an offer at a start-up, and he would have loved to take it, but it paid half as much, and he felt locked into a lifestyle that made this pay cut impossible. “My wife laughed when I told her about it,” he said.

Symptoms and stories but no deeper questions.

Based on the number of people that forwarded me these articles, they are still worthwhile.  They are hitting a nerve. The pain is real and people are not sure what to do.

However, they are missing the countless people across the world (and from all countries) who are reinventing their lives and living in new ways. I’d love to see more articles exploring and highlighting two things:

1. Stories of the countless people who are experimenting with new ways of living
2. What it takes to actually transform and reinvent yourself throughout different life stages

What can we learn from people that have carved their own paths?

Over the past two years, I’ve highlighted the stories of many unconventional humans:

• Jen Morilla traveled the world until she figured out a new career for herself;  
• Lydia Lee relocating to Bali to live a more balanced life;
• Jacqueline Jensen took a sabbatical to figure out if work should, in fact, be the center of her life;
• Candace Moore accidentally building a business by generously making yoga YouTube videos to help people across the globe;
• Chris Donohoe built his own consulting firm around a 40-day workweek and bringing his full self to the world every day;
• Andrew Taggart helping entrepreneurs with the “good life question” and operating in the gift economy;
• Laura Gallaher joining Remote Year with her co-worker and employee to shift her business from an in-person one to a digital one
• Ervin Ling quitting his job at 30 to work 15 hours a week as an English teacher;
• Bryan Victor skipped the traditional path of the university in Singapore to learn through life experiments.
• Khe Hy leaving Wall Street to be a sensemaker for the miserable elite
• Christine Bader “learning to quit” rather than missing out on seeing her children grow up because of work

Experimentation is not limited to personal transformation either.  Wade Foster finds that defaulting to a remote team at Zapier has helped his team live better lives.  Tash Walker thought “flextime” was BS and implemented a real 4-day workweek for her firm in London without compromising profits. Tyler Tringas investing in founders who want to build “calm companies.”

At the center of these stories is an uncomfortable truth.  One has to leave the traditional full-time paradigm to build a more reasonable life that makes sense.  

It’s just hard to dodge the judgment and guilt that comes from “stepping back” in the traditional full-time work context. This is why so many of these people I’ve talked to have left and carved their own paths.

If you’re willing to compromise on traditional metrics of success in the short term, you mine as well do it on your own terms.

How Does Change Actually Happen?

Stories of reinvention are great, but they are not sufficient. Most people can find enough difference with another person to explain away that person’s success. “Oh they could do that because they worked at X” or “sure they probably had a ton of savings.” The reason people do this is not because they don’t think they are capable, but because change is not fun and its quite hard. I think this is why it is important to demystify the process a bit. Here are three “steps” I have seen in many people’s journeys:

STEP 1 – A Crisis?: For many, there is a crisis or major life event.  This can be a health issue, a loss of a loved one, a job loss or even a positive event like getting married, having a baby or moving to a new city.

For me, dealing with a health crisis in my late twenties and taking several months leave from work forced me to come face to face the fact that I was too deeply tied to my identity as a “successful” worker.

Yet these crises rarely lead directly to a dramatic leap despite our belief in that narrative. A crisis often shatters our beliefs and then gradually as we start to pick up the pieces, the possibility of change appears as a result of profound conversations, books or other life events that linger in the brain until the person is ready to start taking action.

For Lydia Lee, she found herself literally and figuratively burned out in a Russian hotel room, but did not start to imagine a different way of life until she had a profound conversation on a boat visiting her home country of Malaysia with a German 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.

STEP 2 – Friends: The next thing that seems to matter is that you need at least one or two friends that will support the new way of being.  This appears to help people get “permission” to move forward and have someone to confide in when they are uncomfortable or find themselves a bit lost. These people are typically friends or family that have lived life in an “unusual” way and see some value in experimenting or compromising on short term success.

Candace Moore, who now is an author and yoga entrepreneur, she has support and inspiration from her mother, who was always a natural entrepreneur starting businesses in her home and adapting to her circumstances. Tony Triumph didn’t realize his family was any different until later in life, but reflected that he grew up around people that were always working in different ways to make a living.

One thing I have my coaching clients do is find someone online they can have a “path perspective” conversation with. Whatever you feel pulled towards, there is probably doing something like that already. I have them send a short note asking for advice and see if they’d be willing to offer 15-30 minutes of their time to share insights on what to avoid, what to think about and how to be prepared. People are often surprised at how willing people are to help others that want to follow in their footsteps.

STEP 3 – ASPIRE: Finally, the person needs to have a long-term vision of who they want to become.

People often arrive at this point after first questioning something they have taken for granted, like how they think about “success” and have it be a gateway to a deeper contemplation of who they really might want to be.

Then it comes down to actually shifting energy towards those new possibilities. As much as life hacks and “how-to” guides would want us to believe that change is a straight line and can be planned, the philosopher Agnes Callard gives us a different model. She believes that when we aspire to be a different person, we often have a hard time explaining our motives.

This is often the case in people I talk to. They may not have a clear vision of a future self, but they are open to experimenting in new ways. Callard might say that these people have a vague sense of “something better” in the future but have trouble articulating it. Instead, transformation is a process of “trying on values”

we “aspire” to self-transformation by trying on the values that we hope one day to possess

This is also why from the outside it is so hard to differentiate the money-driven entrepreneur from the self-employed person trying to hack a life. The people I know who are most fulfilled carving a different path are also the ones that have no idea how to explain what they are doing to anyone.

But deep down, they have a pull towards a journey or a life that tells they, “yes this is the right way.”

The “Work Sucks” Perspective Is Still Valuable

A close friend e-mailed me Thompson’s article and said “this is me.” He probably sent it to me because we’ve talked countless times over the past few years about this persons predicament. We walso talked about his unwillingness to do anything about it.

Thompson has added tremendous depth to the discussion around work. He has been ahead of the curve in questioning why we are working so much despite becoming so much more productive in his amazing essay A World Without Work. 

However, I’d love to see the Atlantic, Buzzfeed, New York Times and others do a better job of highlighting the stories of amazing people globally already starting the hard work of reinventing themselves and looking beyond the traditional path that works remarkably well for some, but leaves many hoping for a deeper connection to life.

Want to take action? Paul is launching Reimagine Work a digital online learning x coaching x experiment that will deliver activities, community and connection to people that want to carve a new path. Explore now.

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 Beyond Work Sucks: What To Actually Do If You Are Miserable appeared first on Boundless by Paul Millerd.

#1 Make A Friend Taking A Different Path

People who take a leap often cite a strong influence that gave them proof or the courage that they could do something different. For some, this person is in their own family — a parent or grandparent who lived and worked on their own terms — often an entrepreneur. 

It can also be someone you meet serendipitously. On my podcast, I talked to Lydia Lee, who had a meaningful conversation with someone who was living and working nomadically in Malaysia. It told her that this kind of life was possible, but more importantly, told her that her circumstance in the corporate world was not the only path.

This “friend” can also turn into a partner. Some people find that they want someone else to join them on this journey. This is often the case in entrepreneurial ventures where someone is starting a business. Having a co-founder not only makes your path seem less crazy, it can also be more fun as you learn and grow.

#2 Redefine Money

Everyone who pursues self-employment has to face their emotional relationship with money at some point. 

A paycheck from full-time employment is a rather peculiar arrangement if you frame it in the entire history of humans. In self-employment, you shift away from this arrangement and instead of getting paid a steady income for performing the duties of an employee (showing up, being available, doing good work) you will be getting paid for work you find, things you sell or projects you complete.

There is often an “a-ha” moment when people start a journey of self-employment that has them suddenly look at their expenses instead of their income. People realize any spending means more paid work needs to be done. People will often start taking active steps to lower their cost of living or if they aren’t willing to compromise a certain lifestyle, look for more ways to make money or charge more for their current work. 

The self-employment fear setting exercise I created can help you grapple with some of your money insecurities by explicitly stating the least amount of money you are comfortable making and how long without paid work you are willing to go. This reflection may even tell you that you don’t actually want to make the leap.

#3 Build A “Say No” / “Eff You” Fund

Build up some cash savings. This can build on #2 — you may find that you can dramatically cut your cost of living for several months to build some savings. Having savings for your leap enables you to “pay yourself” when you want to say no to a project that might drain your energy or even take a few months off to work on a creative project that is calling you.

Mohit Satyanand built his own fun by aggressively saving early in his career:

I chose to be different very early. Within a year of joining the ranks of management trainees at a multi-national corporation, I realised that I was not meant to be a corporation man, that I needed to live in nature, to watch the peaches grow. In my spare time, I drew up business plans to run a dairy farm, or drive a tourist taxi. Most importantly, I realised I needed to build up a war-chest from which to fund my freedom. My F*** You Fund, I called it.

Even if you don’t have massive savings, dealing with a dwindling savings account can be a way to stare face to face with your fears and to bet on yourself. Despite my savings, I went through a several month period early in my journey where I didn’t earn any money. I felt terrible, but it also helped me realize how much pressure we put on ourselves to fit into a standard narrative of success.

It might even be helpful to look at your journey as a sort of Master’s education in life. Even if the leap doesn’t work out, many people find that the experience helps them deal with uncertainty, gain confidence in their work and in many cases if people decide to return to work, return in a better and higher-paying role with a bit more wisdom.

#4 Teach Others

We all have so much knowledge than many would die to know. What about your path or journey in life is different? How can you teach that to other people? I recommend creating a list of 25 things you might be able to teach people. This can be as simple as a new way to fold shirts or as complicated as theoretical physics.

One way to put this into action is to write about something you know. An article could be “Here are 5 Things You Should Know About X.” Writing it will have the dual impact of forcing you to learn it at a deeper level and put something out in the world that people might respond to. You may find that others are hungry for the insights you have to offer which gives you a clue to keep following that path.

Another option is to post on social media or e-mail your connections and give them a list of five things you are passionate about sharing with others. I suggest posting something like this:

Hello friends!

I’m doing a fun course online where I’m pushing myself outside of my comfort zone and experimenting with new ways of working. I’m doing a challenge this week where I need your help. I am looking for someone that wants to learn. Here are a few things I know about that I would love to teach you more.

1. XXX

2. XXX

3. XXX

4. XXX

All I ask is that you give me $25 for the “lesson” — this is to keep us both accountable and to raise the stakes on myself so I don’t disappoint you. If I do disappoint you, its $30 back to you so you can enjoy a free coffee on my dime.

Who wants to learn something? Message me

I suggest charging to help you stay accountable and it will help you with #5.

#5 Experiment & Get Paid

You need to have some evidence (for yourself and your confidence) that you can literally go through the process of getting paid for something outside of full-time employment. 

One easy idea that most people can do is to host a topic-related dinner around a certain theme and gather 8–10 people for high-quality food and conversation. People crave these kinds of intimate gatherings and are more than happy to pay $15–20 (or even more depending on the food).

We often underestimate our own networks and the people that may want to work with us. Many people feel bad hitting up their connections and asking them for help with their work, but find that these are exactly the people that want to support them. Plus, people could be waiting to be helped by you but didn’t know there were people in their network that could help.

Here is an example of an e-mail I sent to 100 friends and family that led to two clients hiring me. It was terrifying accepting payment from clients, but it gave me the confidence to experiment further. While still employed I got paid for two speaking gigs, a group coaching event and by several private coaching clients. These were all small fees but gave me confidence that I could make money on my own.

Don’t worry too much about the pay. A pro-bono engagement can be just as rewarding. I did multiple pro-bono coaching and consulting engagements before taking my leap, but treated them as serious commitments. I asked the same of my clients and that they offered generous feedback during and after the experience.

People underestimate the opportunities that are available to them. We are trained to think that we need to find a job before we can start doing something. However, if you are truly passionate about something and willing to offer it for low or no-fee, people are usually more than enthusiastic to be part of your learning journey. For example, if you want to start freelance consulting, you could send this message to an organization you admire:

Hello, I’m a big fan of your organization and have enjoyed how you have focused on X over the last year.

I’m currently in the process of making the transition to freelance consulting and am looking for a couple of initial clients to work with. I wanted to see if you’d be open to a low-fee or pro-bono project where I help you work on Y.

Given this is a path I’m incredibly excited about, I’ll be taking this very seriously. All I ask is that you are generous with feedback and be very direct in helping me determine if companies would be open to paying for this type of work.

Most companies would jump for the chance to work with someone with such initiative and desire to learn.

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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