Eight Years Pathless & Money Reflections | #299

June 2nd 2025: Greetings from Chiang Mai! We are here for a few months so if you are planning on coming through or have people I should connect with, please let me know!

Eight Years Of Pathless Pathing

Last week was my eighth anniversary of walking out of my New York City office, boarding the 7 train, and heading back to my apartment in Long Island City. It’s still mind-blowing to reflect on this day. 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.

At 40, I find myself having spent 22 years as an “adult,” six in school, and sixteen working. Those years are not split 50/50: eight years full-time and eight years self-employed. While the thrill of achieving impressive things and landing jobs at prestigious companies in my 20s was exciting and satisfied my ego, the past eight years of self-employment have been far more satisfying and energizing. I hope that at 50, I can look back and count the large majority of my adult life as self-employed.

Without further ado, here are some reflections on making it to eight years:

#1 The writing remains the fuel and creation of my path

Since 2018, when I first woke up to the fact that writing was something I enjoyed, it’s been the main source and outlet of this path. While I’ve made money in many different ways, most of my energy in terms of work has gone toward writing. For the first five years, I didn’t make any money directly from writing. 2023 is still the only year I’ve made the majority of my income from writing, via The Pathless Path book sales.

Don’t get me wrong. It’s been amazing to make money from my writing. It feels great to make money from The Pathless Path, a book I made no compromises on, and as more people have shared it, I’ve certainly enjoyed leaning into promoting the book in ways that feel good.

But the creative risks I took with that book were made possible by making money from other things. I’ve treated StrategyU like my part-time “day job,” the serious money-making endeavor, and this has enabled me to approach writing with a sense of curiosity, joy, and play. I think this is an underrated strategy, especially for early creators. Not having to make money from my writing probably enables me to do things to stay writing, and have chances over the long term to make money from writing I’ll be proud of.

I decided on the mantra “write most days” very early on, and I’ve mostly stuck to that. The last two years have been somewhat of a challenge in terms of maintaining my creative spark, but mostly because I found that I preferred hanging out with my daughter to working most days.

The pull to write never faded, though, it just became a new puzzle I had to figure out how to fit into my life.

#2 I’ve now spent as many years “self-employed” as “employed.” Interestingly, the income trajectory has been about the same…

Money is weird.

Early on my path, I didn’t earn a lot. Most of this was by choice. I avoided taking the kind of contract consulting gigs that were a freelance version of my new job. I bought “time” instead, spending time creating, writing, not working, and experimenting.

It’s interesting to look back, however, and realize that the trajectory of incomes is curiously similar in both paths.

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. There are many potential explanations for this. One is simply expectations. Someone who thinks, “I’m someone who can earn and is worth this much,” will look for opportunities to do so again. I had a conversation with a fellow creator recently, and I was shocked when they dismissed an opportunity that would “only” earn them about $80,000 a year. Damn, I thought. Am I aiming too low?

A big part of my journey has been improving my relationship with money, something I’m attempting to write a book about. I thought I had a good relationship with money before quitting my job, but I was actually avoiding messy beliefs about money that a steady paycheck had masked.

I think a bigger part of my income trajectory is a simpler explanation: I became a beginner again. Most of the things I am doing to earn money now were skills I had to develop and cultivate over time. There could have been ways of speedrunning this, but for the most part, I’ve chosen to do everything myself.

#3 My eight-year journey has been a hyper-independent one. I think this has mostly been a positive thing.

At almost every point, I’ve optimized for working by myself and doing everything myself. This has been amazing from a learning standpoint. I’ve developed skills in audio, video, and general media production. I’ve improved my coding skills and now with vibe-coding can do quite a bit across many different languages and platforms. I’ve done every aspect of producing, publishing, and printing a book. I’ve created, designed, sold, and delivered consulting work, doing ads, live trainings, paid speeches, online courses, books, and many more one-off creations. The confidence I’ve developed from this, both in terms of being able to make my path “work,” and in terms of being able to start and try new things, is far beyond what I had on my previous path, where I was dependent on people hiring me to do work for them. I’ve seen a lot of people outsource almost everything they do as fast as possible, but I think they probably underestimate how much they are then always dependent on working with (and more importantly, paying) others to make things happen.

The other side of this is that I haven’t done much working in teams or groups. In consulting, I was part of several teams where I completed projects at a level of quality far beyond what I could do alone. It was quite fun. I suspect I’ve left some of this kind of satisfaction on the table by not pursuing more collaborations. I’m hoping to remedy this in the coming years. A few things I’m planning on pursuing:

• Publishing essay collaborations with others via platforms like Metalabel and testing out what it might look like to publish as a “collective” (The Dark Forest collective is a great model here).

• Potentially working with others to write books, and/or having a hands-on coaching role with authors who are writing books, where I might be a good partner (I’m very tentatively open for this now, feel free to email me)

While I’ll likely lean independent on most things I’m doing, I’m very open to ideas. Please nudge me if you think it might be interesting.

#4 Perfectly passive income doesn’t exist, but there certainly are ways to make money that require less than 40 hours a week of constant energy

There’s a common refrain in the solopreneur world that “passive income is a myth.” Some of this is driven by insecure grinders trying to validate their non-stop work, but another part of it is the reality that, without maintenance, things will decline. But almost every long-term solopreneur I know has some random income stream that keeps on giving. And I think this is a good argument to at least make some bets in a portfolio of projects that produce passive income, even if it means it will be a relatively low amount over time.

One example: In 2019, my StrategyU YouTube channel monetized, and I’ve been getting a check each month. Even though I haven’t really posted many videos in the past few years (you can see the numbers below), I still keep getting views and payments. In the last year, I’ve made $1,000 from the channel. It’s not a ton, but it’s also not nothing.

Here’s what it looks like over time.

As you can see it’s declined steadily. But this income requires almost no energy in the present, as long as I’m willing to continue to see it decline (which I’m fine with). However, the odds that it will go to zero in the next few years are almost zero, which is kind of cool.

I joke that this is “less than grind income” (LTG Income): income that does not require constant effort. You don’t need to clock in and do “maintenance” 8 hours a day, five days per week; you can do it intermittently. I could decide to do a few videos over the next year, and maybe one of them pops off. But I can do it in a way that aligns with my energy, not a schedule.

My consulting course is a better example of LTG income. Over the past six years, I’ve had this self-paced course, which I’ve steadily maintained. I probably spend a couple of days a month on it and then every 2-3 years, do a 4-5 week sprint overhauling everything. Each year, likely anchored by the default ways of thinking about work, effort, and money, I am still convinced that income is going to drop to zero. I tell myself, “This is it, it’s over for sure this time.” But it never quite does. It’s certainly been dropping for the past couple of years, but I just did another two-week overhaul of it last month, and it’s starting to turn around from the recent trend.

Here’s a breakdown of some of that effort

Courses were hot among creators from 2019-2022. Many of those creators have now shut down or moved on because they scaled rapidly but couldn't sustain the economics when growth stalled or they lost interest in running them. My approach stays profitable even with minimal sales, AND more importantly, it doesn’t rely on me working on it every day. I've written about choosing not to scale my course in Good Work despite real upside, and part of why I didn’t expand it was that I thought it raised the risk of burnout. I suspected that if I turned the project into a constant effort sort of thing, I might lose interest. And so it’s pretty cool to see that the course is still running, years after many people in my world abandoned similar things. It gives me eight years of evidence that my principle of designing work for not burning out does seem to be a decent one.

So yeah, maybe pure passive income isn’t real, but I do think people on alternative paths should consider that they might be able to build things that don’t require constant energy to maintain, and these sorts of things can be amazing complements to playing longer games, especially with things like creative work that just take time to blossom.

#5 My first income drop was quite dramatic. It didn’t feel like failure.

When I was employed, I had a paycheck mindset. Success was when income increased. As you can see in the chart at the top, my income has mostly increased every year. The only time it didn’t was when I had to take an unpaid leave of absence for health issues right after business school. At the time, I would literally adjust my salary in my head to account for this. I’d do the mental math of “well, if I were working, this is what the income would have been.” Increase that number every year, and things are good.

2022 and 2023 were wild years for me. My income was 2.5x over 2021 and then grew 30% more in 2023. I sold an insane amount of books, had some big wins for my training work, and had some economic tailwinds pumping money through the US economy, and I didn’t really increase my spend that much.

It was all sorts of shocking, and it broke some of my mental scripts about my path. Since I had been scraping by for five years but loving what I was doing, I assumed it would always be that way, and I was already happy about that. But I think I had underestimated that things might go really well, and it might not require a crazy shift in my effort levels. It would just be downstream of the things I was doing consistently.

As part of this, I had to develop two skills:

1. Learning how to actually celebrate success

2. Learning how to spend money without feeling reckless

The first is still very much in progress, but I did take a whole morning to celebrate the eight years with Angie last wee,k which is only something I’ve done in the last three years. The second was something I leaned into in 2024, and we decided to spend a bit more on an apartment that felt really nice to live in, and also to spend a little more on convenience so that we felt like we were thriving in our daughter’s first couple of years of her life. The result? The first year, we spent more than we made.

This wasn’t unexpected. I knew the massive spike in book sales wasn’t sustainable and expected it to drop, and so in 2024, my income did plunge 50%.

While this was a bit uncomfortable, I honestly didn’t stress about it too much. I was helped out by my frame of seeing some of the savings I had accumulated as a “gift from my former self.” In the past, I would have panicked if my spending was anywhere close to or above my income levels. But now, especially with a two-year-old, I was trying to lean into “buying” the freedom I had won in working for myself. Because what’s the point of working for yourself if you don’t get an unlimited vacation policy?

#6 It’s pretty wild to see one of my early goals pan out. One of my early goals was to make money in many different ways. This year is the most diversified I’ve been in terms of income sources:

The last three years have been a healthy mix of different income sources. The main ways I make money are:

• My Book

• StrategyU Corporate Workshops

• Online Course (Think Like A Strategy Consultant)

• Community one-time memberships

• One-off consulting projects (only one in the past three years)

The cool thing about this is that early on I decided I wanted to maximize the number of “income streams” I had generating at least $200 a month. At first, as you can see it was a bunch of small-dollar things (see 2018). But for the last three years, I’ve only had one year (the 2023 book sales) where one item was more than 50% of my income.

Does this mean I’m antifragile? No. I’m the main resource behind all of these things and as we saw above without some effort, incomes will drop. But I do take it as evidence that my approach of aiming at diversification does have some upside.

#7 I leaned into parenting over the past two years. It has been the best experience of my life. My work and creative energy have suffered, but that was the point all along?

A lot of my writing is about leaning into life. Over the past two years I’ve been doing that. I’ve taken care of Michelle on my own about 2-3 weekdays per week and almost every weekend, balancing everything with Angie. While sometimes the days are long and tiring, they are always filled with laughs and joy.

I’ve also started to notice many subtle shifts in how I’m experiencing each day. Hanging out with a growing infant and now a toddler is like a nervous system bootcamp, if you allow it. Each day, I’m pushed to be more emotionally resilient, more playful, more loving, and less serious. Some days it feels like I’m not doing all that great, being distracted or not handling being triggered all that well, while other days I feel like I crushed it as a dad.

I think the part where I have struggled is in terms of finding a new, consistent relationship to my work, especially with my writing. I had a ton of fun writing Good Work (which took about seven months), but outside of that often felt lost, a bit disconnected, and didn’t quite know how to find my groove again.

More recently, I feel like things have been falling into place. A friend texted that, “your writing got its juice back.” I think mostly what I did is just keep trying stuff, tinkering, and seeing what emerges.

#8 Creative things take a long time to pay off

If two things summarize these above reflections, it’s that:

1. Creative work takes a long time to “pay off.”

2. Creations can continue to “pay off” longer than you expect

This past year, after failing on my own to do my own foreign rights (Traditional Publishing forces 1, me 0), I hired a new foreign rights agent. They quickly helped me land deals in China, Taiwan, India, Malaysia, and France. My Russian translation was also released. I am not sure what to expect from these deals, but it is interesting to know that my book is about to be re-released in several countries (the Taiwan version will go to Hong Kong and other places too) by legit traditional publishers pushing my book into bookstores. I’m likely going to do some book launch stuff in Hong Kong, Chiang Mai, and Taiwan, and maybe Singapore around these editions, which should be pretty fun.

It’s pretty wild that something I wrote five years ago is still making its way out into the world. What does this all look like in five years? I don’t know! Will a traditional publisher in the US be more experimental and release a print-only edition for me? Maybe! Will I become famous in Taiwan? Will Good Work take off eventually? Will most of them just flop and go nowhere? Who knows?!

The takeaway for me is that I should just keep releasing things into the world. And in that regard, I am trying to be a little more experimental in the coming years. I’d like to release at least one book every 12-18 months and then maybe take a few more shots with smaller experimental books and collaborations. To do that, I’ll need to be a little less risk-averse and a little more willing to try new things. I sense I’ve gotten a little “tight” as I’ve gotten some success.

Bottom Line:

It’s pretty awesome knowing that eight years in, I still enjoy my path so much, and it has been pretty consistent throughout. With this kind of inner knowing, I have a deeper faith and trust that things will work out. All I need to do is continue doing what I’m already doing.

To eight more years!

Thanks for being part of this journey :-)

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Thanks for reading!

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like this full-time for eight years now.

If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

grab them here

If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community.

Some things I endorse: Crowdhealth, an alternative to US health insurance; Kindred, a home-sharing app; Collective for handling your S-Corp accounting needs; and Nat Eliason’s Build Your Own AI Apps course

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