In May 2017, I walked out of my office in New York City, got on the 7 train, and rode home to my apartment in Long Island City. I haven’t had a job since.
I’ve never been good at imagining the future in a detailed way, but on that day, I had even less of an imagination about the future than normal. The last 9+ years have been far beyond anything that I ever could have imagined and mostly in a positive directions.
Through the years, I’ve been obsessed with how we navigate life transitions and how one can build a life beyond the default path.
Here are some of my reflections,
Before you leave
Destructiveness is the outcome of an unlived life.
1. Most people just need a break
People mistake the desire to escape their current path for an interest in taking a completely different path in life forever. Quitting a job is thought of as an all-or-nothing decision that can’t be reversed. This just isn’t true.
Most people just want permission to take a break from the madness. To be able to pause the inertia of the busyness treadmill and having to continue to go through the repetitive motions of their lives.
David Vaucher wrote a viral post called “I’m 33, and I’m Ending My Career to Start My Life.” A few years later he was back at full-time work and happy about it: “I’m in the most creative period of my life.” I’ve talked to many people like him who thought they were making a drastic change, only to return to their jobs much happier and feeling much more in control. (quote from the other newletter guest posts where someone left and came back)
2. Don’t wait too long
The reason people fear things like “losing their edge” is usually because they sense they already have started to lose it. People typically aren’t worried about life changes if they are happy and crushing it on your path. I’ve found that most people that take a leap often regret nog leaving earlier.
For me, the first doubts about my path started off when I was out of work for several months, recovering from some health challenges at the age of 27. When I returned to work, I didn’t care about the same things as everyone else. But I didn’t quit until I was 32. Those 3-4 years before I quit required me
Walking away from a successful career was the most important decision in my 30s. At the time, it felt scary and foolish. Now I wish I had done it earlier.
Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move toward a path that is.
When I finally did leave, it was half by accident. I sent my boss a frustrated email saying I should just leave the company. He took it as my resignation, and I didn’t push back.
2. We can ride out low-grade anxiety for long periods of time
We can remain in a state of certain discomfort for very long stretches of time. Think about that friend who has been complaining about their job for years.
They complain, but its a familiar discomfort.
For most people the uncertain discomfort of taking a leap or making a change is far more terrifying than the familiar torture of having a manager micromanage your work, or having to pretend to care about clients you’ve long lost interest in. Our coping strategies (mine were getting drunk on the weekends, job hopping instead of deeper questions) help us avoid the deeper fears and can keep us running in circles for years.
3. Don’t mistake a good career trajectory for growth
When I worked in executive search, we went through the same quick mental checklist on every resume. No gaps in their resume…check. A steady string of promotions…check. Good brand names…check.
Clinging to this ideal of a steady career trajectory keeps most people in the business world in a state of low-grade anxiety about their “employability” and continued ability to stay relevant.
Early in my career I loved my work at McKinsey, but everyone around me kept leaving to keep progressing in their careers, applying to business schools, law schools, and fancy NGOs and non-profits. I was seduced by the promise of business school but it’s the biggest regret of my career. I had a great situation, good managers, and interesting opportunities. I should have stayed a couple more years.
while I absolutely loved being in school again and all the friends I made, I ended up desperately trying to break back into consulting again after graduating, despite thinking I would head in a different direction.
4. You don’t have to leave forever. You can do one year at a time.
When I quit, I didn’t think past a year. I wasn’t quitting forever; I was just going to test the waters for twelve months. The worst case was that my savings would go back to where they were a couple of years earlier. I could get a job again and move on.
I think one year working on your own, trying to do freelancing or something like that, just trying to make money, go out on your own, see what it’s like, see what it feels like, then go back into a job. Many people do this, and then from there just keep iterating, right? A pathless path can include full-time work, right?
Almost everyone who leaves soon sees that the one-way door they thought they walked through is a two-way door. (actually pull in the leaving work and returning guest post here)
5. Prototype the leap
For most people, life is not based on all-or-nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state.
John Zeratsky wrote an article titled “I Quit My Job to Sail Around Central America for 18 Months.” The real story took years. He and his wife started with small sailing trips: one night, then a long weekend, then a week, then two weeks. A couple of years before the “big trip,” they went for two months. The headline “Quits to Live on a Sailboat” is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition While Aggressively Saving Money over Five Years.”
Diania Merriam paid off $30,000 of debt in 11 months. Then, after a successful year in her sales job, she asked for a two-month unpaid sabbatical instead of a pay raise so she could walk the Camino de Santiago. Her manager said yes.
My story is not one of courage, but of pragmatic and safe experiments, experiences, and questioning over several years. Before I quit, I sent an email announcing a career coaching side gig to 100 of my closest friends and family. Sending it was terrifying.
If you want a place to start, map out three versions of your next five years with an Odyssey Plan.
6. Name your fears
In hundreds of conversations, I’ve found that people’s fears fall into five areas:
- Success: “What if I’m not good enough?”
- Money: “What happens if I go broke?”
- Health: “What if I get sick?”
- Belonging: “Will I still be loved?”
- Happiness: “What if I am not happy?”
Writing about fears has helped me transform abstract worries into concrete issues. When I wrote that I was afraid of going broke after I quit my job, I realized that there were 50 different things I could do to make money.
Tim Ferriss’s fear-setting exercise, which I adapted for career changes, ends with the question I find most powerful: “What is the cost of inaction in 3 months, 12 months, and in a few years?” Years later, I ran my own worst case. If I just broke even for the rest of my life and then collected Social Security, I could live on about $40,000 a year. It delighted me. That’s a pretty good life.
7. Your number is a feeling
When I hit $50k in savings, something shifted. With some small reductions in spending, it was a year of living expenses. A year felt important. I don’t know why. It was arbitrary but also personally persuasive.
One guy told me straight-faced that he’d take a break to write his book once he had $10 million. Angie quit her job and traveled for a few months with only $7,000 to her name. The number matters less than the feeling it gives you: I am not completely reckless.
Saving more doesn’t fix the fear. From what I’ve seen, money fears are completely independent of actual money quantity. If anything, people with more money tend to have higher anxiety. That’s how they acquired the money.
After I quit, I was scared as hell to spend a dollar on myself that I hadn’t earned. What helped was thinking of my savings as a gift from my former self.
I’m not sure why this worked so well, but it cracked me up thinking about my spreadsheet self making a presentation telling me why he was investing in my wanderings and creative experiments.
8. Will the people in your life love you less?
I hid my move to Taiwan from my parents for more than two months. They didn’t even find out from me; they heard it from my cousin. A month before I left, at a family wedding, the questions came. Wasn’t I worried about healthcare? Would I ever have a “real job” again? What was my long-term plan?
Instead of sharing my own fear and uncertainty, I tried to convince them. But the pathless path can never be fully explained, so trying to convince people is usually futile.
I didn’t want to disappoint my parents. I desperately wanted to convince them that I was doing the right thing. However, had I understood that I feared losing their love, I would have realized that the wiser response would have been to open up my heart and be vulnerable.
It still happens. I can get 50 notes of praise, and then my mom will say, “Are you going to get a real job?” And I’m right back at square one.
The first year
That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.
9. Take at least a month off
Unfortunately, a typical one- or two-week vacation isn’t going to cut it. I believe that the minimum effective dose is at least a month away from work.
Most adults spend 500 or more months working between 22 and 65. A three-month sabbatical is less than one percent of that. Almost everyone who’s taken an intentional break from work has told me they wish they’d taken one sooner. It might be the only “hack” I fully endorse.
It takes a while, though. Jacqueline, who took a structured three-month sabbatical, told me it took her four to six weeks just to get to a base level of being able to think about what she wanted.
If a month is scary, block off a random Tuesday afternoon. Don’t tell anyone. Go for a long walk or sit by a river, and pay attention to the feelings that come up. For a longer break, my sabbatical planner works out what it will cost and how many months your savings cover. My sabbatical guide makes the case for taking one.
10. Expect the crash, then the guilt
The day after I quit my job, I woke up and started to write.
I wrote about being burned out, something I would have denied a day earlier. I felt broken and it shocked me that I had spent the previous six months in a numbed state, going through the motions, and pretending everything was okay.
A job hides this. The limits on hours worked and the hidden camaraderie of others disengaged with their work can convince you this state is normal.
Then comes the guilt. I spent five weeks in Europe after quitting. In the second week, I started to feel extremely guilty. I became hyper-aware of the script in my head that said I should be working, or at minimum trying to make money. By the fourth week, I started to relax.
A couple of years in, I tried an experiment: what if I just didn’t work or try to make money? It felt terrible. I felt like an idiot. But then I’d wake up, go about my day, and realize I was having a pretty good day.
11. Grieve the achiever
On the flight out of New York, I started to feel the subtle pangs of grief that come from letting go of an important part of yourself. I was leaving behind my identity as an achiever.
I do miss telling people about my impressive achievements and watching their eyes light up with instant respect. It was so simple and the lack of that kind of reaction is still clearly noticeable on my current path. Now, instead of igniting admiration, I often trigger people’s deepest fears.
If my script were still to maximize my earnings based on my skills, I’d be an utter failure. Compared to my business school classmates, I’m probably in the bottom 1%.
The shame surprised me. The voice in my head said, “you are a bad person.” I know this is crazy to feel, but it also means the people terrified of taking time off from their jobs are judging the risks accurately.
Eventually, I admitted to myself that I wanted appreciation, and that it was okay to want it.
12. Fire the manager in your head
On my first freelance project, I had 100% control over when and how I did the work, and I still went to a coworking office five days a week. I felt guilty when I wasn’t working during typical work hours, Monday through Friday. Many self-employed people are surprised to find they still have a manager in their head.
Most of us know that work days are Monday through Friday, and when many people become self-employed, they go through a phase of still showing up Monday through Friday and performing a normal workweek.
I urge people, however, to remember to fire the “manager in their head” and take the next Tuesday off.
Burnout comes faster when you work for yourself, because there are no limits on how much work you can do.
In 2024, Angie and I split the week. I worked Monday, Tuesday and Friday, and she got Wednesday and Thursday. There are no mandates of working five days per week. You are allowed to work three. Or two. Or one. Or none!
13. Money panic makes you frantic
Without a paycheck, I said yes to every opportunity. My first gig paid me $1,000 to walk around New York City, find people wearing Allbirds shoes, and ask them four questions. On day two, I bought a large cardboard sign, wrote “Do you own Allbirds?” on it in big letters, and held it up at the farmer’s market in Union Square. I’ve noticed this period of frenzied activity is a common stage for people who leave their jobs without an income.
Later, I took a consulting project because I was scared.
It paid $7,500, which would fund my life for several months, but when I started working on the project, I realized I had talked myself into the project in order to calm my fears rather than as something I was excited to work on. I committed to not making the same mistake again.
I still get financially anxious on this path. I just don’t make decisions from there.
14. Change your surroundings, but don’t stay lost
I floundered around the US for about 15 months, taking freelance gigs, booking random trips, and wandering around Boston. Then I booked a one-way flight to Taiwan. Arriving there was enough of a shift that I finally gave myself permission to not have a plan.
There is something natural to feeling lost while living abroad that is hard to experience in your home country. Feeling lost at home often also feels like failing.
This is also why sabbaticals might not deliver their promised results if you don’t leave familiar surroundings.
But getting lost can be a trap too. If you spend too much time being lost, distancing yourself from the default world, things can quickly turn into escapism. I spent two months in Bali in 2019, about a year and a half into my journey, and it was perfect. The key is to embrace places like that so you can eventually leave them.
15. You don’t need a plan
In the fall of 2018, I rolled out of my twin bed in a small Airbnb in Taipei, started the coffeemaker, and thought about my day and my week. I realized that there was nothing to do. I was 33, had no clients, and had recently told my friends I was giving up on dating and shifting to the “cool uncle” phase of my life.
Not long after, I met Angie at a teahouse in Taipei. A year later, I was planning a tiny wedding.
People underestimate how well things might work out if you don’t have a plan. This is because they don’t have much practice sitting in the present and noticing the abundance of wisdom and clues that surround us.
John Steinbeck told his son, “Nothing good gets away.” I’d add: as long as you create the space to let it emerge.
16. It takes longer than you think
People think that the moment you quit your job, your new path begins. Mine began almost two years later, on a bean bag chair on Batu Bolong beach in Bali, eating Mie Goreng and drinking a mango smoothie. I felt tears of joy welling up, knowing I was finally headed in the right direction.
For the year and a half before that, I had been flailing. I had “bought” time by lowering my cost of living, then traded that time for work I didn’t want to do.
From quitting my job to feeling a sense of forward momentum took about 21 months and mostly involved doing less for long periods of time until my natural drive started to push me forward. The hardest thing about this is that you often feel like a failure, and are constantly reminded of such from others.
Looking back, the first three years on my own were hard emotionally and personally. I had to go slow, because I was working through personal issues, not business issues.
You can reorient your life in a new direction quickly, but rewriting the scripts and rewiring your nervous system takes much longer than you’d ever expect. I mapped out the common stages in 12 Common Experiences of People Making Life Shifts.
17. Get ready for “What do you do?”
When you work full-time, you have a story called a job. A job is the most accepted story of adulthood. Even if you hate it, no one cares that much. It’s a passable story.
When I lost that story, I was scared to tell people close to me what I was doing, or really what I wasn’t doing. I lied. I made up fake plans. Years later, a guy at a gathering in Austin heard that I write about our relationship with work and asked, “Is there really anything more to say about that?”
My mom once asked me, “What am I supposed to tell my friends?” I told her to just say entrepreneur or business owner.
As I wrote in 2024, you need three stories.
A boomer-compatible story
The first one is for those anchored to a traditional view of work or for someone you simply don’t want to defend your path to.
“I am doing some part-time work and looking for my next job.”
“I’m trying to build a business” instead of the more accurate “I’m dabbling with podcasting, writing online, and trying to post my way to Twitter fame.”
The key with this group is to keep it neutral and pivot to other topics ASAP.
A curiosity trigger story
You want a balance of a “normal” answer and one that is a little weirder.
“I just left my job but am excited to explore mindfulness and breathwork.”
The real story
The third story is for your fellow travelers. These people, god bless them, want to know everything and actually are curious about what you are up to.
“I’m doing a bunch of stuff; writing, podcasting, online courses, consulting, and different ways of working and living.”
You should always be changing these stories and noticing what happens.
18. Don’t grab a title just to answer people
Ben Hunt writes about the “industrially necessary egg.” “Good” eggs meet specifications, are perfectly clean, and can legally be sold in a supermarket. The eggs from his farm are often dirty and come in various shapes. On the default path, you are automatically a “good egg.” On the pathless path, people default to seeing you as a “bad egg.”
This means embracing the pathless path requires grappling with the feeling of being a bad egg. This often drives people who leave the default path to eagerly embrace new identities that are still recognizable as legible to the “traditional” economy. They gravitate to titles like founder, entrepreneur, freelance consultant, or creator.
I did this too. I thought I needed a company called Vivo Strategies, with service offerings and transformation programs. Then I realized clients were just hiring Paul, who could help with stuff.
Early on, the word “work” triggered me, so I’d just say I was dabbling on some random creative stuff. Then I’d meet other people dabbling on creative stuff, and we’d hang out.
19. Don’t over-share early
In my first week after quitting, I wandered around New York and ended up at the Cloisters, at the literal frontier of a city I had failed to fully explore in two and a half years. When others asked how I was doing, I felt compelled to give them proof that I had a plan and knew what I was doing. I didn’t.
This will be a confusing time. You may feel the urge to tell everyone about your new insights, questions, and curiosities, but this can be a mistake. Your ideas may make others uncomfortable and any doubt, skepticism, or criticism they express could convince you to run away from the frontier.
The philosopher Agnes Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.” You can’t explain that to people yet. You’re still trying it on.
Money
It is not necessary that a man should earn his living by the sweat of his brow, unless he sweats easier than I do.
20. Earning less shows you what you value
When I quit, I audited my spending and was shocked that I had been spending nearly $6,000 a month living in New York City. A lot of it was what Thomas J. Bevan calls a “misery tax,” the spending that keeps you going and functioning in the job. For me, it was a mixture of alcohol, expensive food, and vacations.
Making less after making a high income is a cheat code for figuring out what you value. When I went from making six figures to $30k after quitting my job, I saw how little of my previous spending was on things I valued.
For my first three years on my own, I made about $30,000 to $40,000 a year, roughly 20% of what I made before. I was having the time of my life.
21. Define enough, or you default to more
On the pathless path, knowing you have enough is what gives you the freedom to say no to clear financial opportunities and say yes to something that might bring you alive and might even pay off much more over the long term.
If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no. Very few people would ever walk into their manager’s office in September and declare, “I’ve made enough money for this year. See you in January!”
You can also set enough too low. Once I moved to Asia, I got my costs down to under $1,000 a month, and I was probably pushing that too far. I got very neurotic about spending money. But it accidentally created a cocoon for me to really deepen into the work. If you’re curious how far your money would go somewhere else, try my location arbitrage calculator.
22. Keep a good-enough job
Philip Glass drove a taxi early in his career to support his music. “It was the quickest and easiest way to make an honest living,” he said.
However, rushing to directly monetize your good work can be a mistake. The right approach is to treat the work that feels good as sacred, protecting it as long as possible by making money doing something else.
My version is StrategyU, which I treat like my part-time “day job.” I keep it running with about 15-20 hours of effort each month, and it gives me a “basic income” that lets me approach my writing with complete independence. To work out how much yours needs to earn, try my target income calculator.
23. Leave money on the table
During the pandemic, I could have run a live version of my StrategyU course and charged $2,000 or more per person. Some friends were making nearly half a million dollars from a single course. I asked myself, “Then what? What would I do with all that money?” It was obvious. I would “buy time” to write. So I wrote my book instead.
Every time I make a decision not to pursue an opportunity, it doesn’t feel like losing money, it feels like I’m reaffirming my commitment to this path.
Think about what you won’t leave on the table. Soul? Your relationships? Time freedom? Your health? That book you want to write?
24. Your income will probably drift back
I’ve noticed on my path and observing others that there is a gravitational quality to money. Within 3-5 years, many self-employed people seem to end up earning a remarkably similar income to their former incomes.
For me, it took longer. I don’t think I crossed $50,000 a year until I was five years in. But when I did my eight-year review, the total I’d earned working on my own was almost exactly the same as my eight years employed.
Part of that is expectations. Someone who thinks they’re worth a certain amount will look for ways to earn it again. But I think a bigger part is simpler: I became a beginner again. Most of the things I do to earn money now were skills I had to develop over time.
25. Ask what you’d pay to do the work
Too many people searching for good work short-circuit their own interests, curiosity, and energy by worrying first about what people will pay for. Instead of searching for skill-market fit, start with person-interest fit.
One of my favorite filters is “How much would I pay to work on this?” It flips the frame from working for money to paying for the right to work. When I ask this question, very little work other than writing passes the test.
The question works in reverse, too. Years into self-employment, $25,000 for a consulting project felt like too much to turn down. Then a C-level executive on one call tried to make me feel small, and I remembered why I had moved away from that kind of work.
Another time, I realized I’d pay $1,000 to avoid a project. That gave me the confidence to make a strong counteroffer on my terms, which turned it into something I was excited to do and paid me twice as much.
Finding your work
Things take the time they take. Don’t worry. How many roads did St. Augustine follow before he became St. Augustine?
26. Don’t rebuild the job you left
Nine months into self-employment, I had landed four projects and proved I could make it on my own. They were the same kind of projects I had done in my consulting career. One needed a client update email that would take fifteen minutes. I started it on Monday and sent it at the end of the day on Thursday.
Consulting projects could earn me money, but I saw them as a trap. What was the point of quitting if I was just going to recreate my former life?
I was so afraid of creating another job for myself that I secretly stopped working and just started writing.
The other trap is anger. Early on, I wrote many essays about how broken organizations were. There’s money in selling escape, but I’d have spent my time with similarly frustrated people. Reject the default path, but don’t turn rejecting the default path into your personality.
27. Look at what you already do for free
For years, I told people I wanted to escape work. I didn’t want to escape work; I just craved work I cared about.
But often, there are clues. Like the report I had so much fun writing while at BCG. Or the articles I wrote for fun in college and grad school. Or the seven different blogs I launched and maintained over ten years.
None of them paid or impressed anyone, which made them harder to fake. Still, I was writing for years before I saw it as work worth doing. What might you be missing that’s right in front of you?
28. Start from what made you come alive as a kid
One of the biggest concerns people have when they talk to me about quitting their job is how to make money. That is certainly important, but a more interesting path is possible if you start with what brought you alive in the past.
I remember the day my father brought home a copy of DOS for Dummies. By typing in a few words, I could control the computer. I was hooked. In high school, I built a weather site that predicted snow days for my friends, called “Paul Says It Will,” and wrote a funny article about declaring for the NBA draft. In college, even as I started to want a prestigious career, I spent my free time making DJ mixes as “DJ PoPo Shizzle” and learning to code. It took me 15 years to see the thread.
Erich Fromm wrote about two kinds of freedom: “freedom from” outside control and “freedom to” engage with the world in a way that is true to yourself. Quitting gave me the first. The second took much longer.
For that, I’ve found no better advice than Dolly Parton’s: “Find out who you are and do it on purpose.” Two exercises can help: a values inventory and Tim Urban’s yearnings template.
29. Ship, quit and learn
Many of us were raised with the idea that you should never quit anything. This is useful for some things but absolutely terrible advice for creative pursuits. Quitting lots of things is probably the best way to find the things you want to commit to.
Since 2018, I’ve run my experiments with three questions. What can I ship quickly? What’s the off-ramp, and how do I design it for quitting? What does the experiment tell me about what to do next? When I launched my podcast, I made the cover in PowerPoint in five minutes and didn’t spend money on anything else.
Most of us grew up in schools that taught us to get an A on everything. That’s a bad approach on a new path. The goal is to keep learning without re-creating the path you’re moving away from.
When you’re employed, a new experiment looks like a dramatic job change. On your own, you can spin something up or shut it down quietly within a couple of days.
30. Rest is part of the work
When I noticed how good ideas seemed to emerge if I stopped writing for a couple of days or went for long walks, I decided to experiment further. I declared every seventh week a “leisure week.” When the Friday of the sixth week came around, I stopped writing and didn’t do any kind of work for another week.
I’d wander and ride my bike, and I started to realize I got more done. The best ideas for my book came out of those weeks off.
If you observe me on any given day, you might think I never work. But if you zoom out over a number of years, you see hundreds of newsletters and blog posts, thousands of social media posts, and two books.
31. Go the long, slow, stupid, fun way
My approach, which I’ve even jokingly coined the “long, slow, stupid, fun way” works well because I stay hyper-aware of what I’m actually interested in doing. I ask myself the question, “What if I went slower?”
You can go fast to win the race, but I’m trying to go slow in order to go far. The hardest part of going slower is feeling “stupid,” or like you’re not doing your “best.”
I couldn’t speed anyone else up, either. For more than five years, I tried to convince Angie that writing could be her thing. She tried personal training, a podcast called Curious Barbell, a fitness course, freelancing, and job interviews. Then, on a crowded bus in Taipei, she pulled out her laptop and propped it on the diaper bag in her lap. “What are you doing?” I asked. “I’m writing,” she said. I looked at her and said, “This is it, this is it!” She smirked and kept typing. That became her memoir.
Staying on your path
Ambition eventually wears out and probably should. But you can keep your zest until the day you die.
32. Bring the fear along
For my first few years, the voice in my head was a pain in the ass, shouting, “You’re a bum!” or “You wasted your career!” These days it mostly says, “Get a job, you dummy.” I can make a decision from the fear, or I can take it with me.
If fear is always a companion, it is futile to push it away. If uncertainty can never be solved, you have more freedom in terms of how you choose to spend your time and which risks you take.
And if doubt creeps in, you can welcome it: “Oh it’s you, the doubt monster? Nice to see you again!“
33. Cynicism gets you out, hope keeps you out
The biggest challenge to creating your virtuous cycle, and one of the most dangerous failure modes of the pathless path, is cynicism. Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind.
I once heard Maria Popova say, “Critical thinking without hope is cynicism. But hope without critical thinking is naïveté.” I hit rewind and listened several times. I knew she was talking to me. My essays back then were convincing, but they weren’t inspiring.
I once sketched the person I don’t want to be in ten years. He angrily tweets about how stupid everyone with a traditional job is.
34. Find the others
I like to joke that Seth Godin was my only friend on the path before I quit my job. Books and podcasts help at the beginning, but you need people.
A few months after quitting, I met Noel Boyland, who left a promising consulting career in his early 40s after a health crisis, and Nita Baum, who seemed to know everything about me without needing to ask. With people like them, you skip the “What do you do?” question and start a deeper conversation. Later, Jonny Miller handed me David Whyte’s The Three Marriages, the book where I found the phrase “the pathless path.”
The value of freedom depends on the people around you using it too. If you’re free on a Tuesday and no one else is, so what?
Reach out to people a few steps ahead of you. Nine times out of ten, they’ll be glad to talk, because they’re still searching for people to learn from on their own journey. From 2017 to 2022, I had more than 400 of what I called Curiosity Conversations, agenda-free calls with curious people around the world.
To embrace the pathless path, you need friends, and all you need at the start is one person.
35. Reclaim your ambition
When I quit, I tried to stop working and stop making money. Ambition felt bad. In 2021, after a podcast recording in Taipei, my friend Kris told me, “You’re one of the most ambitious people I’ve met.” I thought, “Me? Ambitious? Nah.”
One day, about a year after launching my book, I looked at myself in the mirror and said, “I am ambitious.” My voice faded as I said the word. I still couldn’t fully say it.
So I said it again, and I was okay. It took me about five years to accept the word. Ambition can mean becoming a present parent. It can mean lowering your income and wandering around for two years, listening to a voice inside you.
I wrote more about this in Ambition Without Trying.
36. It gets less risky the longer you stay on it
People ask if this path gets riskier as you get older. I reject the premise.
The further I go on this, it feels less risky because I have more confidence and evidence that I can continue to make it work. What gives me the courage to keep going is I have 10 years of experience on my previous path where I never felt right.
Keep going
So the only reasonable answer I can give to the question of “How can I do what you are doing?” is this: fully commit to the journey, challenges and all. Once you do, don’t give up. Keep going. Take the search for good work seriously.
For the longer version, I wrote The Pathless Path about leaving and Good Work about what came after. The exercises I mentioned, and a few more, are on my tools page.