October 17th, 2022: Greetings from Austin. I’m pumped to be sharing this with you. It’s about 5,000 words and took me longer than I expected to write, but I think you’ll like it. Please share if you think it would help others too.
The Great Digital Creator Arbitrage Opportunity
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27 months ago, I wrote to you from a small apartment in Barcelona. I remember sitting down to write and looking out to a small but densely packed street alive with energy.
I was writing issue #100 and it felt like a good excuse to be a bit bolder. In that issue, I made a call for 100x more creators. I wanted to encourage more people to take a chance and put their ideas out there, find the others, and in some cases, become self-employed or do something entrepreneurial.
Those ideas were seeds that evolved and grew into The Pathless Path and in the time since I decided to write the book in late 2020, I’ve seen more people from around the world lean into this new way of living and working.
However, far too many people are still sitting on the sidelines.
I believe that we are in the early days of what will be remembered as one of the greatest times to be alive for hyper-curious people who are willing to be creative, connect with others, and share their ideas online.
Leaning into this new kind of path still involves fear and insecurity, real and perceived losses of status, and a lack of a good story for what you are doing to tell others.
While these fears and costs are real, many are not as bad as people think and on top of that, the stigmas of creating online or following a path like mine are rapidly decreasing.
When I left my job in 2017 I thought I was a rare exception. Since then, I’ve connected with thousands of people around the world and a mini-scene has emerged of hyper-curious weirdos who are sharing ideas online. Each year I’ve been self-employed I have underestimated the opportunities in front of me and it seems that there is still a massive disconnect between the quality of opportunities and the real and perceived “tax” that one needs to pay if they want to create online or leave the default path.
This disconnect can only last so long. This means there is a massive arbitrage opportunity for a certain kind of person that loves engaging with ideas, enjoys connecting with others around those ideas, going down obscenely deep rabbit holes, teaching people, and helping others in specific domains.
If you are a curious person and want to build your life around exploring ideas, this is a great time to be alive and selfishly, I want you to join in the fun.
Here’s a mini-roadmap that might help you make it happen:
Step 1: Assess Your Reality Tunnel
Robert Anton Wilson argued that people go through life existing in a “reality tunnel.” As he says, these are “…a model, an abstraction, which is comforting when we do not know what to do about the muddle of existential reality or ordinary experience.”
Many people are mapping their experience of work to a reality tunnel I call the “default path.” The default path view of work says that good careers are a product of getting good grades, picking the right majors, and getting your career sorted in your twenties, and then putting your head down and grinding it out until retirement. The default path tells you that taking a break from work is not possible, and that life without a steady paycheck is reckless.
Wilson argued that the more we are “hypnotized” by our perception of what we think is real, the more of our “existential experience we then edit out or blot out or blur into conformity.” Most of us, including me, have done this in our careers. When we face setbacks, limited paths to promotion at our companies, changing jobs and skill profiles, meaningless work, and layoffs, we explain it away and continue to look for proof that we are doing our best to map into the default path reality tunnel.
Until we find a better story.
Step 2: Find A Better Story, You Can Steal Mine For Now
“The Pathless Path” was my humble attempt at a better story. Instead of an ideological “capitalism is evil,” missionary “burn it down,” or modern-HR “work is broken” perspective, I tried to tell an empowering story that shifts focus to the individual but also is a term people can embrace to give themselves permission to remix their own work and life scripts as the old story loses its influence.
That’s not to say I don’t have issues with the default path. In his review of my book, Venkatesh Rao called our modern world of work a “success cult.”
While success cult wasn’t a phrase I had in mind while writing the book, it is powerful and gets to the heart of one of the traps in our modern world of work. That even if you leave your job, you are still part of a broader culture that looks at life through a work lens. No matter what path we are on we feel the pressure to always be doing and orienting ourselves in ways that might help us in our careers. It convinces us we need to ship, produce, have an impact, and make money, or we are a failure.
Pair this with the default path idea that it is noble to suffer and toil in the present for a far-off payoff and you have people that see their own struggles as proof that everything is okay. We inherited this idea from previous generations but they had fewer alternatives, faster promotions, more economic growth, and pensions. For young people today, I believe this way of orienting toward the future has an enormous cost. It short-circuits people’s agency, self-awareness, and ability to take even the most minimal of risks.
And most of all, it convinces them to abandon their dreams.
Step 3: Admit That You Have Dreams (aka: “The Inspiration Deficit”)
I’ve probably talked to a dozen people who have told me that they have millions in the bank but feel absolutely and completely stuck in their jobs and careers. They don’t know what to do. They don’t think they can leave and do anything else. It is a bizarre state of the world where people making hundreds of thousands of dollars per year with even more in the bank feel powerless.
When I get these people to open up they tell me about lapsed hobbies, buried curiosities, and abandoned dreams. “Aren’t those worth pursuing?” I ask.
Buried beneath the surface ambitions of millions of office and knowledge workers around the world are dreams of working on things that are more challenging.
There’s a reason this tweet got six million views:
Instead of this, we have the most educated population in the history of the planet spending their time working on things far below their level of capability. Plenty of people are hungry, curious, and want to be challenged but are stifled by the bureaucracy, credentialism, performance, success scripts, and hyper-specialization of modern jobs and careers.
This is the inspiration deficit. Almost any path that can be mapped and planned in today’s world has likely been sucked dry of the challenge that people desire.
People complain that too many college graduates go work in fields like consulting, banking, and Big Tech. I think this criticism is slightly off. Those fields are some of the best places to start your career and if you can get those jobs, take them! The better criticism is that once trained, people fail to walk away. When people are approaching a level of competence (usually 5-10 years) it coincides with a dramatic slowing of the pace of learning but a dramatic rise in income. The money convinces people that it is far too risky to do anything but keep going. This transforms once hungry and determined people who fought like hell to get these jobs into prisoners of their own success. “What else could I possibly do?” they tell me.
In a famous speech given in 1986, the scientist Richard Hamming talks about his experience at Bell Labs and walking up to another scientist in the lunchroom, pestering him with three questions over a series of weeks:
What are the important problems in your field?
What important problems are you working on?
If what you are doing is not important, and if you don't think it is going to lead to something important, why are you at Bell Labs working on it?
These are powerful questions and I the version of it I would ask you today is:
What are you most curious about?
What is your unique perspective or way of helping in this domain?
Given the infinite resources available to you today, why are you doing nothing about this?
Step 4: Imagine Counterfactuals - What Accidental Entrepreneurs Teach Us
A pattern I’ve noticed from interviewing people on my podcast is that many people end up on their paths by accident. They didn’t aim at the specific version of the life they are living but are often surprised at how happy they become once they are living it.
This was the case for me, and it convinces me that this is the case for more people than they think.
What are the odds that you are in the optimal work situation, and it happens to be the exact default way people work in the time you are alive and in your specific company and role?
What hidden upsides to your life might you discover if you were forced to figure it out for a year?
Austin Church, who’s been working independently for nearly ten years talked about this during our podcast conversation. He described how six months after college he got laid off. Luckily, his former boss came to him and asked him to freelance. Austin, desperate for work, said, “yes I can do it.” He had no idea what he was doing and when he proposed $40 an hour he expected to get laughed at.
He reflected, “people think that label or entrepreneur or being your own boss is predetermined and is something you have, or you don’t. I think that’s not true…for me, once I got a taste of setting my own hours, and the autonomy and freedom, I was hooked.” He’s since gone on to work in many different ways over the last decade, starting various businesses, working as a consultant, course creator, writer, and more.
Anne-Laure Le Cunff, who’s been on a solo path for almost four years, initially intended to become a startup founder after leaving her job at Google. That was the script that she and many of her peers saw as the obvious next step in the tech world. After a year she realized, “that was not the life I wanted to design for myself.”
She freelanced for a bit which gave her some time flexibility. That led to writing and leaning into her curiosity about neuroscience. She decided to write articles for 100 straight days and many people started following her work. She ended up building an online community, decided to pursue a Ph.D. in Neuroscience, and is now planning on writing a book. She couldn’t have aimed at this kind of life if she tried but now said, “I wake up feeling excited most mornings.”
What if Austin had never been laid off? What if Anne-Laure hadn’t started writing online?
Would they be inside big companies convincing themselves that taking a leap is too risky? How many people are sitting on a future potential path they might love but are afraid of taking that first step?
I am quite sure it is more than zero people and the good news is that I think most people, given enough ingenuity can do what it takes to sample a new life mode.
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Step 5: Minimum Viable Dose: A Three-Month Break Sometime During Adulthood
The thing is, I don’t think you need to quit your job.
If I had infinite money, I would offer people a money-back guarantee on a three-month sabbatical sometime after the age of 30. I would have people take three months off, actively shift away from “worker mode,” and do at least one small creative project. If they didn’t have some sort of “a-ha” or moment of clarification about what they wanted to do with their life, I would offer them $25,000 no questions asked.
I’ve literally talked to only one person out of close to 100 that took some sort of sabbatical in the last five years and said, “yeah, didn’t do anything for me.” The other 99% of people? They typically report dramatic shifts.
Here is an amazing thread from Cecile who is logging her reflection on a current sabbatical experiment.
Here’s what she wrote about her mindset before taking the leap
“I had always been curious, ambitious, and productive within the scope of my job and within the companies, I had worked for but I had no idea whether I would end up being as curious, ambitious, and productive once I had stepped outside of those worlds. I was terrified at the idea of letting go of my identity as a successful leader - and terrified of being boring.”
In an attached essay she details what so many others report:
She reconnected with her body: “As I practiced listening to what my body wanted more and more, I started hearing stronger signals from it to do or not do things. Eat less sugar. Drink no alcohol. Exercise in the morning. All of those things felt like embodied invitations rather than rational decisions and it has been feeling really good and relaxing to lead more of my life from my body rather than from my mind.”
She awakened creative energy: “I also felt an urge to start being active online. This is coming from someone who had only ever been a consumer of online content rather than a creator. My only experience of posting anything online had been limited to a few posts on LinkedIn from the time when I was recruiting to fill some roles.”
She went down curiousity rabbit holes: “I also got curious about design and web design - I spent more hours than I probably should have on learning how to use Figma, Squarespace, and Webflow well such that I could create a website that felt like me and illustrate my writing to make it more appealing. I got curious about neuroscience and spent hours distilling podcast teachings into visual summaries which I then shared on Twitter. I started reading classic books, old and new, and posting commentaries of the ones that resonated most - some short, some detailed like this one.”
And a broader shift: “I’ve slowly been shifting from a scarcity mindset to an abundance mindset.”
Here is something I strongly believe: These are the kinds of people that are not only going to thrive on unconventional paths but in the broader working ecosystem. The world of work is increasingly being driven by creativity, art, and storytelling.
Learning to tap into these modes of being (and reminding yourself they are there) is not only a vital part of human existence but is increasingly table stakes for an energizing career and the path to doing great work.
Many people that take sabbaticals often go back to their jobs too. And this is good! The difference is that many of them now approach it completely differently. They see the tradeoffs they are making and know how to inject the things that matter to them into their jobs.
Three months. That seems to be the minimum effective dose. If you prioritize it as one of the most important things in your life that you need to do – elevate it up there with a big ol’ wedding and taking time off for kids – I think you can pull it off.
Three months out of the almost five hundred you are supposed to be working.
Step 6: Pay A Status Tax
There is a cost to sharing things online and an even higher cost to walking away from the default path. I believe this will fade away but right now it’s still the cost of entry.
I talked to Ali Abdaal while he was on a sabbatical from practicing medicine. He had been crushing it on YouTube and was fully alive making with his many entrepreneurial ventures. His viewers saw him detailing how he was making millions doing what he loved but when he talked to me about potentially leaving medicine, in regard to his family, he said “they probably would think less of me.”
This didn’t surprise me. I’ve talked to many creators and entrepreneurs you’ve probably heard of who are absolutely lit up by what they are doing and are financially successful but still struggle to win the support of their parents, friends, or extended family.
This is the surprising norm of taking a path like mine in today’s world. The US is probably one of the best countries in the world to take an unconventional path. But even here pressure to conform and work like everyone else is very strong. In many countries, it is judged even more harshly.
At a societal level, this is a tragedy. Not because we aren’t getting more billion-dollar unicorns. But because at the individual human level we aren’t even accurately valuing things that would lead to those unicorns in the first place – things like dignity, passion, curiosity, aliveness, and connectedness.
Step 7: Refactor Ambition
One of the biggest challenges people have when embarking on an unconventional path is disconnecting from extrinsic markers of success and listening to internal motivational cues. On the default path, you can spend an entire career playing other people’s games. At first, people on a pathless path try to fill the lack of extrinsic goals with new ones of their own creation. They hire a manager in their head.
This is a mistake and to embrace an unconventional path, especially one working online you will need to detach yourself from popular types of ambition to find a path that is sustainable.
Over the last couple of years, I’ve experienced a complete transformation and reawakening of my own curiosity and desire to do challenging things in life and work. While similar to my early career enthusiasm, this feeling is deeper, more powerful, and likely sustainable.
I believe the best way to describe this shift is as a shift from legible ambition to illegible ambition. The reason so many people cling to default metrics of success is that other people understand them. Legible ambition is a story that your parents can tell their friends. We fear that not having such legible ambition means we will be cast out of our modern work-centered culture.
Illegible ambition is personal, hard if not impossible to describe to others, and might not lead anywhere impressive, sometimes for years. But it is also immensely powerful. Illegible ambition is about connecting to who we really are and doing work in a state that friend and fellow internet weirdo David Perell perfectly describes as “hearts on fire.”
Hell fucking yes. Who doesn’t want hearts on fire in their work? At a minimum, if you knew that this state existed, and I think David is correct, why not try to see if you can find it?
For a long time, I rejected all flavors of ambition – in principle and as a term. Confirmation bias drove me to fully accept David Whyte’s reflection on ambition as, “frozen desire…the current of a vocational life immobilized and over-concretized to set, unforgiving goals.” That was me and it took me a good two or three years on this path to find my footing and convince myself that I wouldn’t do that to myself.
I realize now I wasn’t afraid of pushing myself. I was scared of pushing myself toward other people’s silly goals. The interesting thing about experiencing this kind of lasting, internal ambition is that external metrics like money seem more attainable in the sense that they are more of a question of speed and time rather than how much sacrifice or suffering I’m willing to endure. Having stumbled upon things like writing that challenge me and that I can probably do forever, I am filled with the feeling of endless possibility.
This is often hard to understand because even if someone is overflowing with intrinsic motivation, they likely share and talk about external outcome goals. But if you listen close enough, you can start to notice the raw energy and excitement that’s really driving them.
Finding this sort of internal power is an individual art to master and probably will not be clear when you first start creating online. When people start putting themselves out there fully, they are at peak uncertainty and crave a roadmap. There are dozens waiting for you and you need to ignore them. Do this for likes. Write this way for more sharing. But most of these are other people’s limited reflections on the things that worked after they found their groove.
As I like to say, don’t find a niche, find a mode or a state you can keep showing up in.
The most important thing you need to know is that this refactored ambition is possible. You can leave legible ambition behind and not “lose your edge” as some people think.
It might be hard and disorienting but it also might be worth it.
Step 8: Sharing Your Unique Interests Online Is Good. Full Stop
When I was graduating college, Facebook was filled with party pictures and dumb comments that we posted on each other’s walls. As we approached graduation we shut down or hid our accounts so that employers would not find them. We were embracing the previous generation’s norm that we should hide our “true” selves from the workplace. I internalized this deeply, and when I decided to share ideas publicly via LinkedIn’s publishing platform in 2015 I was terrified. What if my manager sees it? What will people at my company think? Will people laugh at me?
Now it seems wild that I channeled 100% of my own interest and curiosities into work products for my company and planned to do that for the rest of my life. When I was at McKinsey, one of the best resources on lean manufacturing was a blog run by Mark Graban called leanblog.org. He shared unique perspectives, dug up information from books, and shared case examples from clients he worked with. He was literally one of the best resources for my research in my client work.
I got a chance to meet Mark when I was in grad school in 2012 and I was star-struck. I put him on a pedestal and never thought once that I could do what he was doing. That was wrong, clearly, but many people probably have that same stance toward me now. “Oh Paul can do this because of ___________”
It’s a lie. You are good enough, you just need to get started.
In issue #100 I proposed a simple diagram, which my friend Jeremy Finch has since made a little prettier:
The idea still stands. Almost 100% of the people who want to be heard are pulling that off. Some of those are annoying, sure. But the way to deal with that is not to get angry but to enter the area. Turn your envy, disappointment, or outrage into better work.
Far more than you will expect, people will likely be delighted by your sharing. You will find others that get excited about your strange viewpoints. They will thank you for letting them feel seen. They will be inspired by your words. They may reach out and try to be your friend in real life. They may try to hire you.
The worst-case? No one will say anything.
Throughout history, people have risked death for the ability to share their ideas. Now almost everyone has unfettered access to the internet and most people are sitting there and thinking “eh, I’m good.” People will look back at us and wonder what the hell was wrong with us.
Sharing your ideas, offering to help people, and teaching people can be a useful stand against the default consumption mode that most of us are in a lot of the time. We are in a digital age whether we want to be or not. Even if you aren’t scrolling for hours every day, most conversations are flooded with swarms of memes and ideas that were first a/b tested on social media and the internet.
Many people make the case for writing online as a way to build an audience, make money, and build businesses. All of that is true and possible and largely underappreciated. Yet the real power of writing is captured by this quote from Rebecca Solnit:
“As a writer, you withdraw and disconnect yourself from the world in order to connect to it in the far-reaching way that is other people elsewhere reading the words that came together in this contemplative state.”
Creating online, in a counter-intuitive way, is a way to disconnect with the very-online world we live in and a way to reconnect with yourself.
From there the whole world might open up.
Step 9: You can take it slow
In Venture Capital, they talk about a pipeline problem. There is an abundance of capital but not enough people to start companies. I think that one thing they should be doing is funding more people to become self-employed and then waiting a few years.
Many of my guests who have founded companies did so about 2-5 years after taking a leap to work independently. Solopreneurship forces you to practice self-management and all sorts of a/b testing on how to structure your life. I got to know Tiago Forte and Khe Hy when they were solopreneurs, working on their own which they did for several years. Over the past year or two, they’ve both scaled their efforts and started hiring employees. I’ve been impressed watching that they are still doing it on their own terms and seem to be enjoying it.
Mr. Beast is the ultimate example. He started making YouTube videos when he was 14 and now at the age of 24 has more followers (106 million) than the populations of all but 14 countries. While he worked independently for most of his journey, he’s building a company and currently hiring for 21 roles.The companies of the future won’t look like GE but will literally be one’s run or shaped by the influence of people like Mr. Beast.
I’m 5+ years into my journey and that seems like the amount of time I’ve needed to try different things, build my confidence, find my footing and have the courage to lean back into bolder intentions with my work. While I love working solo, I see multiple paths to running a small company without burning out or losing myself and that’s been a pretty powerful realization even if I remain independent.
The takeaway is that you can take it slow. Creating online, doing your own thing, and dabbling here and there might dramatically expand your possibilities in the future.
Step 10: Get Started Now. It’s Still Early But The Gap Is Closing.
We are in the middle of a massive transformation in the way the world works. This is why I’m not too worried about legacy work beliefs. Every year those beliefs show their cracks and the default path loses its more of it’s grip on people’s imagination. In twenty years, a path like mine will likely seem generic and boring.
Every day I see small bits of evidence of how this is showing up in the world. Here are a couple from this week:
Newsletter writer Ben Thompson getting exclusive interviews (as opposed to traditional media) with the CEOs of Microsoft and Facebook after their recent product partnership and launch
A current student at MIT, Luke Igel, releasing his own 3+ hour documentary on the history of MIT (excited to watch)
Once you look for this you see it everywhere.
I talk to so many people that are at a local maximum in their careers and lives. They are winning at a certain game, one where success is not determined by an internal feeling but one where they map their achievements to a story of what their success is supposed to look like and they feel that something is off.
I want people to realize that there is an unprecedented opportunity available to people right now. If you are willing to pay some economic and status costs in the short term you can take advantage of this temporary arbitrage opportunity.
Worst case, you can return to your job with a little more energy. Best case? You might stumble upon a way of working and living that is far beyond your imagination.
Coming back to Richard Hamming’s famous speech, he reflected on the possibilities for people’s work:
I claim that some of the reasons why so many people who have greatness within their grasp don't succeed are: they don't work on important problems, they don't become emotionally involved, they don't try and change what is difficult to some other situation which is easily done but is still important, and they keep giving themselves alibis why they don't. They keep saying that it is a matter of luck
I’m indifferent to whether you do something great or not. All I know is that tapping into your creative potential is deeply powerful and with all the resources in the world at our disposal, we might as well see what we can become.
Step 11: Find On-Ramps - Additional Resources (Truncated In E-Mail, Send or comment to add additional ones)
There are so many on-ramps into this digital creator world. I am going to list out several which might help you get started.
Awareness: Podcasts have been some of the best ways I’ve expanded my imagination of possible paths
The Pathless Path - 100+ Interviews With People On Unconventional Paths
You can listen to Infinite Loops with Jim O’Shaughnessy who is sharing ideas around the “Great Reshuffle”
Not Investment Advice with Trung, Bilal, and Jack, all of whom are on interesting creative journeys
Creative Elements with Jay Clouse, my favorite indie creator podcast, Indie Hackers podcast, which has an extensive library of people doing interesting things,
The back catalog of Life Skills That Matter from a friend, Stephen Warley, who has a ton of valuable interviews with solopreneurs and creators
Community: There are a growing number of them and places where you will “find the others”
Ness Labs run by Anne-Laure Le Cunff
Inter-intellect by Anna Gat
Indie Worldwide, with Anthony Castrio
Creator Science, Jay Clouse
Twitter (start with @visakanv and you’ll find good people from there)
Cohort-Based Courses: The cohort-based courses are a mix of community, learning, and action and are a great way to find people at similar stages of a new journey
Write of Passage with Dave Perell
Building A Second Brain with Tiago Forte
Supercharge Your Productivity with Khe Hy
Nervous System Mastery with Jonny Miller
Many more on Maven
Have a crazy, bold idea? Emergent Ventures might fund you
Books - My favorites on navigating alternative paths
Crossing The Unknown Sea, Whyte
The Pathless Path, Me!
Field Guide To Getting Lost, Solnit
Life is In The Transitions, Feiler
Reclaiming Control, Amy McMillen
The Internet: Packy McCormick’s The Great Online Game
Lot’s of great stuff on Ribbonfarm
Ness Labs essays by Anne-Laure Le Cunff
This speaks to me at many levels! Thank you! "Illegible Ambition" is a term that will stick for long!
> if someone is overflowing with intrinsic motivation, they likely share and talk about external outcome goals.
I certainly do that particularly with strangers
Now realized because I don’t want to look and sound too weird
This is bad idea because i end up repressing the genuinely heart felt internal goals. And keep orienting my North Star based on these external goals
Had I known earlier I rather be seen weird and get to where I want to go earlier than be lost in a sea of societally acceptable goals