Reflecting on 2025 + Reader Survey | #318
December 30th, 2025: Greetings from Chishang, Taiwan! We spent the last few weeks of the year down in the south of Taiwan. It’s been a great place to disconnect from the frenzy of the city, reflect on our year, and spend more time with each other for the holidays.
Please fill out the Pathless reader survey:
I’m doing a survey of Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.
Reflecting on 2025
For the eighth time, I accomplished my only real goal: don’t go back to the paycheck world.
The reality is that this year felt like a year of treading water on the business front. I kept feeling a bit stuck, trying to find my way out before concluding at the end of the year that my priorities weren’t really to crush it on the work front anyway. My priorities for the year were:
Being a dad
Supporting Angie and helping her finish her book, Made in Taiwan
My hardcover book launch
All the other stuff
I spent too much time worrying about #4 and not giving myself credit for doing quite well on #1-3.
#1 Wrote a bunch of stuff
I spent lots of time tinkering with AI tools, contemplated my relationship with creating and sharing ideas, poked fun at the hustle bros, celebrated my eight pathless anniversary, shared 40 lessons on learning 40, riffed on AI & Work, explored rabbit holes like protocols and seapunk, launched my biggest project, the premium hardcover, and riffed on “wise agency” after giving a talk on the subject.
Looking at these posts from the year, I have a couple of thoughts
Yes, I was all over the place
I was a bit more generative and creative than I thought
Behind the scenes, I dabbled and wrote quite a bit in a few book drafts. Those books didn’t really find flow toward a finishing point, but I intend to revisit them in 2026 and see if we can ship 1-2 of them and/or experiment with new ways of producing and publishing books and mini-books.
As always, the goal remains: “write most days.”
#2 Did some podcasts
I published 13 podcast episodes, and 3 of these were me being interviewed on other podcasts. It’s clear, I can’t quite sustain the podcast right now, and I’ll still post episodes here and there, but don’t expect to spend much time on it in 2025.
Some of my favorite episodes this year include the convo with Nat Eliason on writing books, Steven Foster on his pathless path and living in Idaho, Andrew Taggart on The Yoga of Work, Pranab Sachi on “attentional co-piloting”, and Dennis Owen on The Art of Retirement.
#3 Business Kept Operating
Behind the scenes, my businesses kept humming. Most income flows are down year-over-year, but still enough to fund my life. People kept buying The Pathless Path, and my consulting skills course seems to still have a market despite declining over the past couple of years. I also did a few corporate workshops, which helped my confidence throughout the year. I plan to share more, but here is a high-level picture of the year:
Most of my income and profit came in the fourth quarter from sales of the hardcover and black friday sales from my consulting course. This was the first year I was in a bit of a panic financially in terms of needing new sources of revenue, but it feels good to finish the year solidly in the black, earning about $10-15k more than our cost of living.
My margins were about 43% this year, but if I subtract out the hardcover investment, they were closer to 70%.
I’m looking forward to getting back to running a leaner and more profitable operation next year.
Here are some reflections earlier this year on my eighth! year in business:
#4 The Hardcover Feels Like A W
I’ve never made a big bet like this before, but for me it feels like a W already.
My modest mental goal was 100 books, and I ended up selling about 325 via 250 of the launch and premium buy-one-gift-one bundles. This generated about $35-40k in revenue, which paid off about half of the investment. I had a huge bill of $36k in November for the remainder of the printing costs for the notebooks and books, and it was nice to be able to pay for it with sales rather than have to dip into personal savings.
I was able to fully fund the investment from cash flows from the business, and my mental accounting is seeing this as a past sunk cost, meaning 2026, all sales will be cash flow positive.
This tested me mentally. I’ve never frontloaded money into a project at this scale, and it definitely stirred up some anxiety. I wrote a bit here, and if you didn’t read my essay on the “why,” you can check that out as well
#5 Expanding My Store
The direct sales experience has gone really well, and I’ve decided to expand the selections in my Shopify store. You can now purchase paperbacks, ebooks, notebooks, the pathless hat, and bulk copies of the premium hardcover directly from me.
My hunch is that direct sales will be a big part of making this author path work by producing one-off collectible items, offering bundles, and also signed books.
The premium hardcover bundles will continue to be available with gift wrapping, free notebooks, and illustration cards until I decide otherwise, but you can now buy the notebooks (which people really love and are nicer than you’d expect) on their own now:
Still figuring out Shopify and such, so if you have any feedback, do let me know!
#6 The Community Is The Most Energizing It’s Been In Three Years
I launched a community in 2023, and the first year never quite worked with the monthly payment model (too much churn and admin work to handle it). Since shifting to a one-time fee, it has grown, attracted a vibrant group of people who are active in sharing and connecting with others, and it resulted in us shipping our first print project (via The Pathless Collective), not to mention many offline connections.
One big improvement was shifting away from Circle and to a WhatsApp community, which is about 10x more active and a medium I am better at engaging with.
It doesn’t make much money right now (about $4-5k in 2025) but it is something I find myself pulled to more these days. If you’d like to join us, one of the members is going to be hosting a deep reading group starting in January (will share more when I have it), and Brian Wiesner also hosts weekly serendipity sessions.
#7 Had so much fun being a dad
I’ve been thinking about the idea of “quantity not quality” when it comes to being a parent to a young child. This is mostly because when you’re with a young child, especially a 2-year old, the time is not “high quality,” its usually pure chaos. Yet the more time I spend with me daughter and the more time we spend together as a family when we are not rushed or stressed, the happier I am.
I feel so lucky to have a delightfully happy, silly, and fun daughter. I’ve had so much fun spending ton of time with her over the last 2+ years and its by far been the highlight of the past few years. I've become sillier, more playful, and happier despite many challenges on the health and work front.
Sometimes I feel like my path is a bit crazy and that eventually, its not going to work anymore. That may be true but I think I’ve been to stressed about it. My “compensation” for this way of approaching life has been tons of quantity time with my daughter. And I wouldn’t sell it for anything.
#8 Taking Some Time off At The Beginning of 2026
I’ve taken half-action on too many small things over the last couple of years and am not finding forward momentum on enough things. Instead of trying harder, I’m going to take my own advice: “Have you tried doing less on the problem?”
We’re starting the year participating in a “Traveling village” with 20 other families in 3 different countries from January to May. I decided I’ll take a break from January 7th until the end of the first location, February 21st, and likely until the end of February.
I used to take “leisure weeks” every seventh week, and they really helped me both connect with what I’m deeply driven by AND take action/ship stuff. That’s fallen off since I finished Good Work in 2024, and I’m going to see how this mini-sabbatical goes.
Please fill out the Pathless reader survey:
I’m surveying Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.
Finally, thank you!
You have no idea how grateful I am to people who engage with my work. The fact that this path is still going and I get to work on interesting things and spend my time in a way that feels good most days is remarkable.
If you aren’t getting what you want from my writing or work, though, please unsubscribe.
There is so much good stuff out there!
Glad to see your fruitful 2025
Happy a truer 2026!
Appreciate these reflections and sooo curious to hear more about this traveling village!!