Time To Reintroduce Myself, I'm Paul | #239
September 29th, 2023: Greetings from Taipei! I’ve been reflecting a bit on what I’m trying to do with my writing and realized it might be a good time to reintroduce myself and share a bit about how I think about my writing here and what comes next.
👋 Hey Again, I’m Paul
The majority of this list has joined in the last 12 months which for me is an interesting thing because your conception of my writing and thinking may be of various things I’ve written recently. For me, my writing all fits in a neat, but complex web of ideas that started sometime around 2015.
That was the year I paid a career coach to ask me the obvious question: “What are you waiting for?!” I didn’t have an answer so I started taking action on the things I claimed I cared about. I started writing about the modern working world and all the flaws I saw as well as all the ways you could hack a career to maximize your own potential. If I look back now it’s clear that I was trying to search for some reason to stick around on a path that on paper seemed so perfect.
It took another couple of years of writing on the side, hosting meetups and events, moonlighting as a career coach, and volunteering, for me to realize that I had unintentionally forked my attention toward a different direction in my life one that started to pull me forward.
Outsiders saw someone walking away from a path that made sense. And it was just as confusing to me. I hadn’t reached any sort of financial independence but I had saved an amount that felt safe - $50,000 in savings. I figured that would buy me a year to follow the new energy that had shown up in my life. If I went back to $0, so what?!
If I had been paying attention more closely I would have realized that I had no idea what I was doing. I had a plan to work as a freelance consultant but I didn’t actually like the kind of consulting I was trying to do.
And so this is what I’ve been writing about for the last six years.
In that first year after piecing together some consulting income and making $20k in a single month, I decided that I had “earned” a year of living expenses (which I had gotten down to $36k a year in Boston) and that I should just stop working for money to see what would happen. This was my own frustration with work and inspiration from two main sources. First, Charles Eisenstein’s Sacred Economics where I learned about the “spirit of the gift” and trying to align our lives around offering what we truly want to give. The second was Andrew Taggart’s writing, and his idea that we lived in a work-first reality, something he called “Total Work.” He wrote an article titled If work dominated your every moment, would life be worth living? Upon reflection, I saw that everything I had done up to that point in my life had been downstream of the assumption that the most important things in life were work and money.
The most interesting thing for me to do then was to test in my own life if I could decenter work as the most important thing. My working conclusion is that while you certainly can’t escape work you can definitely make some interesting tradeoffs worth pursuing if you don’t accept that adulthood is mostly a time when you should be continuously working for a company. The hard thing about this is that it requires constant tweaking and reflection. This is fine though as I like thinking through this puzzle and enjoy writing about it all. I’m six years into this stubborn mission and I’m gaining more and more confidence that I don’t need to surrender 100% of my time to the demands of work and money.
Some people like to dunk on me for this pursuit and that is okay. It’s the cost of writing online, one that pales in comparison to all the positives of being able to share ideas and find others. I know that I am privileged in some ways but it is always funny to experience it from my perspective because while half the people I encounter think I am living out their ideal life, the other half are horrified at the tradeoffs I’ve made and can’t believe I walked away from a promising career right before it took off and actually started to generate large salaries and bonuses.
In 2018, a year after quitting my job, I moved to Taiwan without a plan and ended up falling in love with writing and Angie, who is now my wife. Those were slow times. I stayed in Taiwan for most of 2019 while Angie was navigating her career shift into the fitness world and I was trying to get to know myself better while dabbling in all sorts of creator-type pursuits like writing, online courses, and podcasting. I had lowered my cost of living to about $1,000 a month and at that level of spending, I realized I had many years to figure things out. I lost interest in trying to make money and this was probably one of the most important shifts in enabling me to eventually do things like write a book. Because what really happened was that I was finding out what I actually liked. If you can commit to something without a promise of a payoff for a long enough time, you probably like it, and experiencing this can lead to a completely different perspective on how to spend your life.
If you go back and read some of my writing from 2018 and 2019, you’ll find someone projecting his own uncertainty into a dismissal of the default path as well as a powerful sense of emerging wonder. I was open to the world and not in a rush. I didn’t do anything to try to grow my audience and only read and shared what I found most exciting. It’s probably why this same approach is so easy for me today too. I don’t work for the algorithm because I’ve known so clearly from the beginning of this journey that I didn’t want to work for anyone.
The Taiwan chapter of my life was supposed to end for a couple of years as Angie and I got married and then decided to leave on a two-year around-the-world trip, starting in February 2020. While that obviously didn’t go as planned, we still ended up spending time in Spain, Mexico, the US, and then back to Taiwan.
2020 was an interesting year because I didn’t change anything I was doing and despite this, there was much more interest in my writing. I responded to it by having as many conversations with people about what they were experiencing and then writing about it weekly. For all of 2020 and 2021, I was in an exciting slipstream of ideas. That work ultimately culminated in my book which was published in 2022 upon returning to the US and I think accurately captures a lot of the energy I experienced on my path. Rob Hardy has this beautiful idea of creative emotional transfer which says that “the emotional state you're in when you create a piece of content or art, directly transfers to the people who consume it.” I think this is spot on and if there’s any explanation for how my book has taken off that I favor it’s that I feel the pages really do capture the raw sense of wonder, curiosity, and authentic interest in what I’m writing about.
In November 2021 Angie and I returned to the US and have mostly been in Austin with some time in New York, Lisbon, and Connecticut. When we were flying back in 2021 I was a bit terrified that I couldn’t “make it” in the US having only made about $45k the year prior and having no real plan for how I was going to make more money to afford the increasingly expensive American life.
In December of 2021, a recruiter from Stripe reached out and I ended up having a call with a hiring manager at who was starting a new strategy group reporting directly to the CEO. I told him I’d be interested in short-term or part-time support but they kept saying that they’d only hire full-time. They asked how much I’d want to make in such a role and I threw out a crazy number: $350k. When the hiring manager seemed to indicate this was reasonable, I was shocked. I knew that salaries had increased a lot in the economy since I had left the workforce but since I had never worked in BigTech, I hadn’t realized how much. They said they loved my background but said full-time was non-negotiable. It didn’t take me long to realize this was a silly idea and I emailed her and said, I’m not your guy.
I ended up doubling down on my StrategyU training workshops and dabbled with being a little more ambitious. It seemed to be good timing as companies were finally “giving up” and deciding that in fact, remote work, and more importantly for me, remote training, could be a thing.
In Austin, I befriended many fellow creators and I felt a little more comfortable betting on myself and leaning into sharing my ideas a little more boldly. I had a book I thought was pretty good and after five years of playing small, I figured I might be a little braver and put myself out there.
And so for the last two years, I’ve been spending a lot of energy on promoting the book and leaning into my podcast again while still writing here and continuing to follow my curiosity. It’s been such a fun journey and I don’t know where it all goes next. Especially since we had our first child in March.
After my daughter was born I was able to spend a lot of time with her and my wife. This is still the case six months in and it delights me so much that this is possible. I am thankful for my past self for actively designing a life and work around time freedom rather than trying to stay on the default path or trying to aim at financial success on the solo path as fast as possible.
Before having a child, Angie and I rarely operated with any sort of schedule. Most of our time was unscheduled and flexible at a day’s notice. It was a nice life and it worked because I liked my work enough and could fit it in whenever inspiration struck. But with a child, we are sensing that we will need a new strategy. I am not sure what that looks like but Angie and I are planning on doing an ongoing podcast series discussing our attempts to figure this out among other questions. It should be fun.
One thing I’m reflecting on being back in Taiwan is that doing a lot of stuff often doesn’t mean you are doing what matters. I think in the US I got caught up in the collective anxiety and obsession with money. I think this is unavoidable in the US and was useful for me as I was moving back and needed to make more money but now that I have some time and space to think I’m feeling a renewed excitement to embrace the unknown.
I believe that most of us really are on a pathless path and if this is true it means that we don’t know where we are going. Sometimes we mistake our busyness and calendar for the destination but given some time and space we can remember that’s not what it’s all about. In the US I was saying yes to every podcast request to talk about my book. For the past month, I’ve done none and plan to do none with some exceptions and it seems the book is still selling.
The fun thing about the game called life is that no one really knows what we are doing here. And once you can really accept that you realize that finding out what comes next can be quite interesting. In the words of Jed McKenna:
When it’s all over it’s time to be a human being in the world again, and that means slipping back into costume and getting back on stage.
Some of My Back Catalog & Themes I Tend To Explore
A lot of my subscriber growth came after I published my book, The Pathless Path, in January 2022. 62% of the current list or about 9,100 people have subscribed since I put the book out.
But in January 2022, I had been writing this newsletter (and others) consistently for four years.
165 issues of Boundless (full archive here) started in 2017
139 Issues of Boundless Reads started in 2016 (last published in 2020 here) - a newsletter I ran where I sent out 5 things I liked reading each week
Probably 100+ posts on think-boundless.com and now dead sites like careerswithpaul.com, vivostrategies.com,
In terms of themes, I’ve realized there some value in nailing down what I’m talking about (and also how this might be a good way to think about feeding into future books).
#1 Our relationship with work: history, modern news, trends, our default scripts, philosophy, default path vs. pathless path.
This is mostly covered in The Pathless Path and many newsletter issues
#2 Freelancing & Gig Life: Don’t write about this a ton but have quite a bit of experience working as an indie consultant on all sorts of projects. Here is one I wrote on restructuring StrategyU around
Organizations, business strategy: I don’t touch on this as much as I used to early on mostly because I don’t spend enough time inside of organizations or in traditional consulting projects anymore
Too Big To Think (2022)
The Crisis at Work (2017)
The creator economy: how to create and share ideas in public, mental models & recipes for playing the long game, quitting your job, how to make money and think about money, self-employment, freelancing
Random travel & life reflections: More freeform, thoughts on living in different countries, cultural differences, wandering, non-work
Guiding Principles
While I have been pragmatic in asking people to potentially add me as a recommendation, I haven’t done much around trying to juice growth. Despite this, it seems after five years growth is starting to accelerate and I’m adding about 1,000 people per month. This is pretty surprising to someone who only had 1,000 subscribers after several years of writing.
While there may be some interesting opportunities to lean into the newsletter a bit more I suspect that I’ll more or less approach it as I have been for the past six years, sharing what I am most curious about or thinking about each week. This is the best strategy for me because I only want to grow if the readers I am attracting actually give a damn about what I’m excited about too.
I plan to continue to write this Saturday version for free and will monetize using the community, my book, and my consulting workshop work. When that strategy fails to continue to work, I’ll have to come up with a new plan. But for me, writing is easy because I enjoy it. So after #239 issues, see you next week!
I’d love questions or feedback: One thing I do want to do is an ongoing Q&A series that perhaps I’ll do monthly. If you have questions you want me to answer submit them here.
Thanks For Reading!
I am focused on building a life around exploring ideas, connecting and helping people, and writing. I’ve also recently launched a community called Find The Others. There are weekly writing sessions, monthly “find the others” (literally) virtual meetups, and general supportive vibes.
You can join Find The Others if you want to hang with us too, or if you are already a subscriber, get access here.
If you’d like to support my journey, the best ways are to:
Buy or listen to my book, The Pathless Path (or message me if you want to bulk order at a lower price)
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Subscribe to my podcast and leave a review.
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Fun read! I know a lot of your story but it was cool to hear it in one take.
This comment resonated a lot:
"One thing I’m reflecting on being back in Taiwan is that doing a lot of stuff often doesn’t mean you are doing what matters."
Hi Paul, I recently came across your newsletter and can relate to a lot of what you write about. Your post today was well-timed -- I enjoyed learning about your story.
I recently left my job to pursue my writing full-time. I don't know how it will end up but I am excited to give it a try. You cover insightful topics that I have been thinking about these past few years and look forward to following your journey!