Reinventing / Getting Unstuck On A Pathless Path | #302

Embracing "Crazy 40" as they say

July 17th, 2025: Greetings from Chiang Mai. I haven’t been writing here as much but have been feeling energized after participating in a series of workshops with Seapunk Studios this week (more on this soon).

+ I published a couple of podcasts. One with Lawrence Yeo on his recent book Inner Compass, which I read in about a day. We are both a bit obsessed with doing work on our own terms, so if you are wired like that, you’ll like the pod or video.

+ The other with Jack Moses. We had an in-person conversation in Chiang Mai about the upsides and challenges of embarking on a weird path earlier in life (for reference, Jack said he was inspired to drop out of college after reading my book, he has since returned though!). Pod and video are here.

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Crazy 40

Last May, I had tickets to the ConvertKit conference. It’s an interesting conference for people doing creator-type things on the internet. Basically, people like me. I bought tickets because I thought it might be a good way to continue to promote The Pathless Path and give the second book a boost when I finished. But in writing Good Work, I realized that my reasons for going were more “getting ahead” than coming alive. I had become slightly addicted to the royalty income that helped fund a very extended paternity leave and time to write another book, and was pulled into the game of alliance building that is quite common in this world. But as I wrote, I could see that I was being pulled into the identity of a creator rather than starting from my own curiosity and interests.

I wrote about this challenge in Good Work:

Sometimes I feel the pull to embrace labels like “CEO of a Training Firm,” or “Published Author,” or even the recently popular “Creator.” While I may use these labels in a pragmatic sense in conversations and even sometimes in formal bios, I reject them as a way to see myself completely. I don’t write for awards or for financial rewards. I am not a Writer; I simply write. I write because I enjoy it and it matters to me. Identifying too closely with a specific work identity narrows my imagination and creates artificial constraints that are unnecessary. The book writing may be the “sexiest” thing I do, but I am all of the work I do, including the “bad” work I must sometimes do to pay the bills. Despite this, people often demand that you use labels. I’ve found it freeing to adopt ambiguous ones like “curious human” which don’t come with a prescribed work path.

I took a step back and asked myself what I was really trying to do with my life and work. I realized that it was simple: follow what’s interesting, try to do challenging and creative things, and remain energized about this way of showing up for a long time. Self-promotion as the main aim wasn’t the way forward.

So I sold the conference ticket, and instead bought a ticket to Edge Esmeralda in California. I was following my interests in connecting with and meeting other families with parents on weird paths like ours. I wanted to explore the question of “what does a thriving family life look like with two pathless parents, especially from different countries?” That seemed like a good place to start.

This doesn’t mean I was able to quickly resolve my feeling of being a bit stuck. More simply, I was just trying to go against what I had been. I was trying more stuff as my friend Calvin Rosser suggested we do when lost.

Recently, a Burmese friend here in Chiang Mai Yan introduced me to the term အရူးလေးဆယ် (pronounced a-yuu lè hsè). Its direct translation is “crazy 40,” but is a slang term that many young people have repurposed to mean essentially, “doing random absurd things.”

This has been my strategy. For more than a year, I’ve been embracing turning 40 and trying random shit to get unstuck. Looking back, it’s interesting to see how many things I actually did that helped me reorient:

1. I’ve mostly stopped trying to connect with other creators, especially “big” ones. I want to double down on supporting and helping the people who have already helped me, especially the ones who did so without me ever asking.

2. I spent considerable time “professionalizing” my StrategyU online course and workshop business, making it a lot easier for me to deliver standardized workshops for companies and also bring other people in who might be able to do some of the facilitation work with clients. I’ve realized that having a “part-time gig” is still a cheat code for taking risks and fully unleashing my creative work (this returned to a majority of my income in 2024).

3. I’ve slowly moved away from X, spending more time on Substack Notes as it’s less outrage-inducing and nudges me to think in longform much more.

4. I’ve taken book writing much more seriously and have spent far more time working on a few different books (though one thing I’m struggling with is that my best work is there, and I don’t end up sharing it as much here anymore).

5. I realized I want to start working with others. I’ve launched the Pathless Collective on Metalabel and am currently working on our first physical Zine with members of the Pathless Path community. It’s been slightly challenging, but I’m learning a lot and now see a path to future collaborations and am very excited about this thread.

6. Angie and I decided to embark on a number of living experiments, which included a month in Boulder, a month in Oaxaca, deciding to move back to Asia, doing a month of daycare, hiring a nanny, and now living in Thailand with Angie’s extended family helping with our daughter. From these experiments and reflecting as we go, we now have a much clearer sense of what a life might look like with kids in the future.

7. I restarted my “curiosity conversations” - 45-minute no-agenda calls for members of my community. I realized I had become too disciplined with my time around book writing and wasn’t having enough random conversations

8. This is also why I restarted casually doing my podcast and am inviting people who are in the flow of my current interests. I’ve realized conversations are vital to how I process ideas and find energy to create.

9. I took a month in February and used all my “work” time to play with the new AI coding tools. This was simply fun and expanded my imagination for what I might work on in the future.

10. I’ve been spending considerable “study time” reading and exploring in new directions. I’ve gone down the Protocol rabbit hole and wrote up my summary of the research in an attempt to protocol-pill myself, but am still not quite sure what my contribution might be. It’s still an open thread.

11. In addition, another curiosity rabbit hole has been to understand Asia more broadly. My wife is from Asia, and my daughter is half Taiwanese. I want to help her learn about her culture and understand her role in the world. What does it mean to be a third culture kid in today’s world? I’ve read about 10 historical fiction books from Asia and use them as jumping off points to learn more about the history of Asia.

12. I’ve also recently been involved in Seapunk Studios and am currently participating in a week-long “studio” (going to do a bigger writeup) and am feeling incredibly energized from this. I’ve realized that outside of being a facilitator for company workshops, I haven’t participated in a single in-person “meeting” or whatever you might call it, in nearly seven years. With this and the Pathless collective, I am going to attempt to slowly shift from individual contributor to something more collaborative and participatory.

13. I’m also slowly researching and learning more about the nomad scene in Asia and planning to do some writing around the Chinese modern working world (potentially checking out places like Dali, aka Dalifornia) and in other countries.¹ In some ways, the modern situation with work is much worse for people in Asia in terms of opportunity (especially in middle-income countries), while at the same time, other people are radically changing their lives by participating in the digital economy.

14. I’ve been working on a premium hardcover edition of The Pathless Path over the last year and a half with Saeah Wood of Otterpine. I’ve invested a considerable amount of money in this project and have enjoyed working with a true pro and a creative. It’s helped me imagine a sustainable book publishing path without selling my soul. While I’ll likely have to play “creator mode” a bit in the fall as I launch this, I feel way better about this now. I’m simply going to let invitations emerge and reach out only to people who already love my work. (Join this secret list for early updates on this book.)

15. Finally, we are continuing to learn about living in different ways with kids and are planning on participating in Traveling Village 3 in 2026, which is twenty families living together in three countries over four months. More to come on that.

As I sit here writing in July 2025, I am feeling incredibly energized and excited about exploring all these threads in my life and work. I don’t know where they will take me, but I’ve always been excited about the unknown.

I’m also sharing this because I think this sort of reorientation isn’t really talked about in detail. While I’ve written about feeling a bit stuck a bit over the past couple of years, I haven’t talked as much about what I’m doing behind the scenes.

It’s sort of funny to observe a lot of hustle bros online who talk about doing “hard things” and grinding endlessly toward bigger goals. They riff endlessly on the epidemic of people who are wasting their potential or not grinding hard enough. This kind of path, something we might call the “way of achievement,” is one path forward in life. But from my perspective, there aren’t many people in the world who don’t yet know about this way forward. It is the default mode of life for many.

There is another path, however, one that I think is more challenging in different ways. It is the way of unfoldment:

The way of unfoldment involves letting go of things that are “working” and creating space in your life to let other things to emerge. It is about learning to trust your natural curiosity and interests and doing this again and again throughout your life This is the path I took after leaving the default path. 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.

That is the hard thing to do and it would have been easier to go to that ConvertKit conference and double down on creator mode. Build more alliances, trade recommendations to pump my books, maybe even sign a big book deal, and try to pursue the speaker circuit.

But none of that felt exciting for me, and if I projected that life forward, it felt incredibly risky. I might lose energy and enthusiasm for writing. I might become a bit cynical.

That alone, though, is rarely enough.

The reason people embark on the way of unfoldment is that they are pulled by something deeper, something they can’t quite explain. This is often enough to keep going and you know you’re being pulled in this way because you don’t feel the need to preach to others that they should be doing it too. It’s just a choice one can make.

And so last year, I embarked on my shake shit up at 40 plan. အရူးလေးဆယ်. It’s still in progress and has no destination or end date. But for the first time in a while I’ve felt lost while also feeling confidence over a number of weeks that I’m moving in the right direction. I don’t know for sure if I’ve unstucked myself but the only thing to do is keep seeing where I’m being pulled.

In a conversation with a friend earlier this week I described the feeling of pathlessness as feeling both sad and deeply confident at the same time.

Sad because you are always mourning emergent forms of yourself that you must let go of. For me it is the “creator Paul” that could have pushed a little harder.

And confident because I know from eight years being on this path that this is exactly where I’m supposed to be headed. I am genuinely excited to see where life will take me next.

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Thanks for reading and making it down to this bottom section…

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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