2023 Reflections: New Additions, New Heights & Open Questions | #252

2023 was the year I became a dad and for the first time, pressure—tested this life that Angie and I have been building over the last several years. In terms of enabling me to be present and enjoy the beginning of the “magic years” of my daughter, it was a complete and unambiguous success. Financially, it was also my best year I’ve had, mostly due to my book selling almost four times as many copies as last year. But in terms of how I think about my path and where work fits into my life going forward I feel more uncertain than ever.

The addition of my daughter to our life has made this past year one of the most laugh-filled and joyous in years. It was also a challenging time, but in the best way. From the outside it might appear like my life became filled with a chaotic mix of childcare, feedings, and middle of the night soothing sessions. I found myself frustrated a lot but something about looking at the cutest face in the world and seeing them come “on line” more and more each weeks seems to add a depth of meaning to every moment that is simply hard to explain.

The highlight of the year has been seeing Angie become a mother. She is a natural. She loves children and it supercharges the playful side she has that so many of her friends and family love. It’s so cool to see how much joy she gets out of our daughter as well. She inspires me to be a better dad and better person.

Some highlights from the year

• Countries Lived In: US, Taiwan, Spain

• Countries Visited: Netherlands, Indonesia

• Places Visited: Fredericksburg, Texas; Sebago, Maine; Connecticut; Taipei, Taichung, Toucheng, Taitung, and Hualien, Taiwan; Amsterdam, Netherlands; Bali, Indonesia; and Barcelona, Spain

• # of Podcast Episodes Published: 39 new episodes and 7 replay episodes

• # of Newsletter Issues: 42 main issues, 6 guest issues, 4-5. other kinds of issues

• # of Copies Sold (Audio + Print + ebook): ~34,308 (3.64x of 2022)

• # of Scheduled Work Hours I’d Skip If I Could: Probably 20-30 total hours

• Revenue in 2023: ~$319k

• Profit in 2023: ~ $245k (76.8% margin)

Revisiting 2022 Reflection Questions

I thought it might make sense to start our revisiting some of the questions I had for 2022.

On Uncertainty: Last year I wrote, “This next year feels wildly uncertain but not in a way that stresses me out. I am feeling more secure and confident about my path than at any time in my adult life.”This remains true but I have a better sense of how a child might fit into my life and this path whereas I couldn’t really predict what it has felt like over the last year.

Parenting Scripts: I thought I’d feel more pressure to have a plan about how we want to approach parenting but the first year felt a lot more about reacting to day-to-day changes than executing a coherent strategy. I sense this is also why people love clear plans and paths with kids: there is just less time to think and reflect on big questions. It seems like the elephant in the room for parents is education and it has surprised me how many parents worry about future schooling decisions even in the first year of life. It has also surprised me how different parents vary on when you need to make these decisions by. One parent said “everything is pretty easy until they turn seven,” while another said “you really have to figure everything out by the time they turn three.” I usually pay the most attention to the parents who seem the least anxious about the future 🙂

Invest Like A Business: I committed to spending $20k on my business. I didn’t hit this relative to last year but was MUCH less hesitant to spend on things that were aligned with what I want to be doing like booking podcast studios, co-working spaces, freelancers, and paying for software or tech equipment. I’m probably still a bit fearful of boldly spending in a bet-the-business-to-scale kind of way and I sense that will more or less remain the same in 2024 (though I am playing with hiring an operator for the StrategyU business)

Writing Over The Past Year

I feel good about my newsletter consistency over the past year but feel that overall, my writing was lacking in depth and quality. This was mostly due to fitting in work around everything else in my life throughout the year which was a bit more difficult with a child in the mix.

The only longer piece I shipped of note was The Way of Mediocre Man which I am quite happy with. It feels like the start of an essay collection that revolves around working with a spirit of non-doing that will include reflections on losing my edge and others. I’m still trying to figure out how to think about future publishing projects. Stay tuned for more this year.

The newsletter issues felt good but also a bit scattered and I wrote too many issues last minute. I could have done better with more iterations. I’m planning on being a bit more deliberate with the newsletter this year and have someone helping me to go a bit deeper and help with cadence.

These were some of my favorites and reader favorites:

Personal Reflections

• Reintroducing Myself

• Escaping The Meatball

Creator / Pathless Path Stuff

• Leaving Money On The Table

• How To Play The Creator Game

• Become More Serious

• Follow The Clues

• Be Someone People Can Root For

Travel Reflections

• White Guy Without A Swim Cap

• Go Wander, Abroad

Book Stuff

• Betting On Myself (Rejecting A Book Deal)

• 71-Page Slide Deck On Self-Publishing

Corporate Commentary

• The End Of The “Purpose” Era

• People Won’t Work

• Organizations and Network Swarms

Roundups / Admin Posts

• Top Books of 2022

• Roundup of Boundless Newsletter 2022

• Why I am renaming Boundless to Pathless

Fiction

• I did one experiment with a longer fiction piece, Nomad Dreams. It got the worst reaction from readers including an angry post from someone that said I shouldn’t write fiction anymore 🙂 But it was fun and I’ll keep experimenting.

Three Big Reflections On 2023

#1 I’ve Never Worked Less And Never Made More

This was the first year I made more than I ever made in consulting and it was also the year I worked the least in my life. After March I didn’t work more than three days in any week and didn’t get to really do focused work for more than 10-15 hours each week. I have mixed feelings about all of this and will be taking steps to be a bit more intentional with my time in 2024 but overall I feel incredibly blessed to have such time freedom.

Most of this comes from the unexpected success of my book. I sold about 34k copies throughout the year, most of which came after a video about my book from Ali Abdaal that led to a huge spike in sales followed by what seemed to be a sustained boost in the Amazon algorithm. At an average of $5 per book across all formats, this easily paid for all our living expenses and taxes in 2023.

Pretty cool. A single book, paying for my entire year. Not something I’m expecting to continue but the serendipity of this aligning with the birth of my daughter felt like permission from the universe to really be present through the year. I am filled with gratitude.

It also gets to one of the more interesting things about this path, that financial success, if it comes at all, doesn’t always align with when the work actually is done. The book rewards are downstream of work I did from 2018 to 2021, a time in which I didn’t make more than $1,000 in writing and when I had internalized the idea that writing was something I did for fun and for free. I could easily drop some cliches telling you to do what you love but even me in 2018 wouldn’t have believed me.

The book success has me thinking differently and has motivated me to create more books. But I’m also weary of over-identify as “author dude”. For almost seven years on this path I keep leaning into the things that give me energy and those things almost always lean somewhere interesting.

I’m thinking a lot about what might pay dividends 3-4 years from now. Is the community the thing? My newsletter? Do I make more money as a part-owner of StrategyU? Future books?

This sort of question can be crippling on a pathless path. And it has been bothering me recently. Did I do too little in the last couple of years promoting my book and leaning into that? Is the podcast a waste of time?

But this is why I write. As I wrote this out I laughed. Who cares? I’m not doing this to turn my life into some sort of business optimization exercise. I’m designing around actually liking what I’m doing. And so I’ll keep going until I get some dramatic signals telling me I’m taking more risk than I thought.

Let’s see what happens.

#2 I Happily “Purchased” 10 Months Of Paternity Leave This Year

For me, time freedom has always been the goal. When I was single and working, I hated the fact that 260 days a year were owned by a corporation. When I quit, I actively avoided anything that gave my time to anyone else, and over the last six years, I’ve learned how to create my work, play long games, and make money in dozens of different ways. Along the way I gained comfort with earning very little, missing out on opportunities, and pushing the limits of doing less when the “smart” path is to do more.

When people asked when I was “returning” to work, I felt immense gratitude that there was no return. My entire body tightens up picturing myself having to return to some office after a far-too-short paternity leave (Side note: Three months maternity leave is far too short and paternity leave should probably be at least three months. I really don’t see how anyone is doing this without struggling and/or outside help).

While I didn’t really prioritize work, I still got stuff done, and focused mainly on the writing, which I love doing. I fit it in around naps and sleep and staying fit and travel when we were in Taiwan and Spain but more or less I wasn’t really close to seeing work as a top priority for most of the year.

What is the cost of this?

It’s pretty obviously more money. Self-employment is weird in that once you figure out how to make money you can clearly see ways to ramp up OR down things to make more or less money.

For the most part, I find it more interesting to ramp down and then to see what happens.

What has happened for me is that I’ve developed a better relationship to money, gotten healthier, had more time with Angie, and become more at peace with myself.

I was able to spend a lot of time in that mode this year and I don’t have an ounce of buyer’s remorse on what felt like a solid 10-months of paternity leave and time freedom.

#3 Some Random Parenting Riffs

I haven’t written a ton about parenting this year like many have asked but I did want to share some quick reflections.

#1 Perception vs. reality: Before people have kids, they talk about grand strategies or belief systems. But after day three of being a parent almost all that goes out the door. You’re just trying to keep up and figure out what’s going on day by day. Are you really against screens or have you just not yet spent 2 hours with a baby who has a fever and is teething? For us, we’re going to open YouTube and put on some CoCoMelon

#2 It is an intimate and personal time: And I sense this is why so many new parents go through such a profound shift: it’s not really what you imagine it is like because no one really talks about what it’s like in a way that makes sense to anyone else. Overall, I found that this experience really brought alive a sense of “family” for the first time. While Angie and I spent tons of time together before we had a little one, we were still two very independent adults. Now, we really are a team and we have a share sense of purpose that has been really cool to experience. Nothing really beats sitting around with them two and trying to make our daughter laugh.

#3 So Many Parenting Scripts!: People want to know what you are going to do in terms of educating your children as soon as they are born. And even more so when you don’t own a house or have “normal” jobs. Are you going to send them to college? Homeschool? Will you live abroad? The honest answer to all these questions, is that I don’t know. I think it’s interesting how strong the scripts are with kids and how little agency is actually given to the kids in question. For me? I plan to pay attention and see what might feel best for my children. Might we explore unconventional approaches? Sure. But not in a dogmatic or ideological way.

#4 Schedules Do Work Well: I was schedule skeptical before kids but now totally understand. The first seven months we more or less did not operate with a schedule and this worked really well because neither Angie or I were optimizing for work or anything like that. Not to mention babies will sleep at anytime. At around 7-8 months, however, it was clear that our daughter was struggling when she didn’t sleep well. We used the sleep training approach in Taking Cara Babies and it worked magically. Not only did she start sleeping better, she was a lot happier too. Now we have a bit more predictable life and Angie and I are experimenting with a structured schedule headed into 2024 (more below).

State Of Work: More than 50% From My Personal Stuff For The First Time

In terms of income streams, my 2023 looked like this:

• $137k StrategyU

• $148k Book Earnings

• $29k Pathless Path Community

• $5k Other

This is the first year that my Boundless/Pathless/Writing earned more than StrategyU and the income streams continue to shift over time.

The interesting thing about this is that my income streams don’t always match what I spend my time doing. While most of my work time was on writing and my podcast this year, I didn’t really make much money directly from that. The bulk of my earnings were from my consulting course that I updated in 2022 and from a book I wrote in 2021.

But the shift in income is something I’m certainly paying attention to. Mark Manson said something like “your identity lags your reality by two years” and it’s something I’ve been thinking about a lot this year. I still see myself as this hack-a-living write for fun and see what happens without any goals while the metrics are telling me that making money from writing is clearly something that is now possible.

So the question is: to aim at the money from writing or stay the course, writing for fun and paying attention to what is emerging

I think the answer is somewhere in the middle of that. I want to definitely publish more books and have been surprised at how east and lucrative self-publishing can be. There’s no reason I can’t run the same playbook for pathless path for additional books.

#1 Pathless Path Community: Small Put Some Potential

One new income stream has been the formerly named “Find The Others” community that I’ve since renamed to the Pathless Path Community. It has a vibrant group of 150+ people and after a strong start, I struggled to stay engaged after having our daughter. I set the group up as something where I would be spending lots of time in virtual hangouts and that was unsustainable especially after going to Taiwan for a few months.

The biggest unlock was hiring Sri Karnic to help me organize everything and to proactively shape the direction of the community. She has a bold task (and is doing great) trying to get me to be organized and not “go with the flow” as I tend to prefer to do. In the first month of bringing her on, we reframed the positioning of the group around three things:

1. Help People Find The Others On Pathless Paths

2. Serving as an on-ramp into life as an Internet Citizen

3. Help People Build Confidence To Keep Going

I plan on creating a lot more stuff for the community in 2024 including a potential Pathless Path Course and some in-depth breakdowns on people’s journeys, something that could lead to a book that might tentatively be called Phases of the Pathless Path. I’m very open to ideas from people.

One highlight was the newly launched “let me pay you $100 to host a local event” initiative, which has already led to a number of events. Here are some pictures from recent and past in-person meetups. The San Franscisco event (led by Cissy Hu)had more than 50 people!

I plan on doing much more of these in 2024 and am thinking about a potential summer mini book tour so if you have a location you want me to visit, let me know!

#2 The Pathless Path: Will It Keep Spreading?

Will the book continue its trajectory? I have no idea but I and still getting emails every week and sometimes every day from people telling me the book rocked their world. It seems like this is going to keep spreading. I’m thinking a lot about how to lean into that energy.

My end of year book stats from 2023:

A few things I’m thinking about moving forward:

• How do I actually get foreign rights deals (I seem to be getting no traction even with an agent)?

• How do I get on big podcasts this year. Some suggestions recently from someone that sold books through podcasts: Lewis Howes, Mel Robbins, Jordan Harbinger, The Minimalists, Craig Rochelle, Dr. Dru. If you have any connections here or others let me know 🙂

• How do I gift a copy I have sitting on my desk to Tim Ferriss?

#3 StrategyU: Taking Ownership

This has become a reliable business with a mix of demand for my self-paced course and high-priced training courses I sell to small consulting firms and corporations. Before we had our daughter, I was able to run two trainings and use freelance facilitators which felt like I unlocked a new level in my entrepreneurship journey. I turned down several opportunities to do more of this work throughout the year so there is actually a lot more demand.

While I typically don’t spend more than ten hours a month running StrategyU, it have been spending a bit too much time doing admin and maintenance work like fixing the website or email sequences instead of value add work like writing or teaching which I enjoy. I finally came up with a plan during a clarity session with Georg Tanner. I decided that I would invest MORE time in the business and really take care of a lot of the admin I had been holding off on and really try to treat it like a real business. This wiil give me more options in the coming years in terms of bringing on an operator and/or selling a stake in the business.

I made a ton of progress over the few months and am talking to a few interesting candidates to help support me. I realized that I can actually be more valuable to the business if I’m the one delivering training sessions or coaching senior executives, which I’m great at and I enjoy.

An interesting question I’ve been pondering is: If I had to dump this business in 60 days, how would I do it? My short answer is that I’d try to sell it to a former consultant who is interested in training & teaching through something like a seller note where I would be paid back over time via the profits of a business (h/t to Justin Mares sharing how he used this to buy his first business for free).

One thing I realized this year is that I do want to stay involved in StrategyU. I do like having one foot outside the creator economy and inside the business world. I learn a lot and I have interesting and thoughtful clients. But I don’t have the energy or time to run marketing, admin, sales, emails, content, research, scripts for YouTube, video editing, newsletters, and so on anymore. I just want to teach and create and do some one-off work with select senior executives. I plan on making this happen in 2024.

Looking Forward to 2024

#1 Thinking About Money, Opportunity & Future Success

It’s interesting to feel the pull to make more money once things start taking off. I didn’t feel this as much when I was making far less and it’s been helpful to reflect on those early days and remember how much I genuinely enjoyed doing what I was doing.

Most of the time when I think about the opportunities I have, I am hesitant. I go through the mental exercise of figuring out what I might do with the money. Usually not much. I already feeling like I have enough and don’t really worry about the future financially. Things will work out.

So I tend to take it slower and let things unfold. This is the approach I took with my book. No launch, no crazy promotions or “street team” style marketing. Just put it out there and see what happens. This worked really well for the book but did I miss out on more earnings? Probably. But my goal has never been to make the most money.

One weird thing is that when you make a decent amount of money and share that publicly, most people (because they aren’t on paths like this) see that as a stable income. If you’ve made that much this year, you’ll make that much this next year is the assumption they make. In their head the probability that you’ll make that going forward is close to 100%. But in my head, I see future earnings as a probability distribution slightly skewed to the right but tend to think about my path conceptually based on the idea that there is a reasonable probability that I end up on the left side of that distribution. Just like the book took off unexpectedly this year it could easily fall back to earth next year.

While we have spent a little more loosely (especially on baby stuff), a lot of what I’ve been doing is building more cash savings (earning a nice 5% now!). More liquid cash = more freedom = more time on path. Even if things do go south there’s a good chance that I’ll still make some money no matter what. I haven’t gone a month without an income since 2019 and have a high degree of confidence that I can make at least $2-3k a month for the next several years. Which means that money runs out a lot more slowly. Even in my worst case scenario, I’d have a few years to figure things out. To me this is financial freedom. It is not so much about a number on a spreadsheet but rather the confidence that I have work I like doing, the confidence to keep going, and the agency to act.

You might be thinking “you are being too conservative!” and you might be right too. I’ve been thinking about how I can lean into a more ambitious and optimistic vision of my path and as always, its hard to unlearn our past behaviors (especially the ones that helped me to build the savings to quit in the first place).

#2 Question: What was surprising and delivered (what you think/predict will be) an enduring lesson? (from Matt Ziegler)

I think the biggest “surprise” was how much I’ve enjoyed spending time with my daughter and how much I like being a parent. I had a hunch this was going to be the case but it was hard to know before it happened.

Another surprise was the book success. Holy crap! Can you believe how many people are reading and sharing this thing? I got recognized by a stranger in Target this week, something that has now happened 3-4 times. I think the lesson from this is that yes, writing on the internet really can have an impact. It is less of a lesson than confirmation of a hunch I had that a lot of what I was doing on my previous path was worthless. It’s really inspiring to me that people are taking my ideas and making courageous choices in their own lives. I think a book doesn’t really change people directly but if it can give them more confidence or feel less crazy? That’s pretty cool.

The final surprising thing is that you can really make a decent amount of money from a book. I sort of wrote off making money from my book, declaring that “breaking even” would be a win very early on in the journey. My experience has sort of radicalized me in favor of self-publishing and to put out a book earlier than you think you should. I hope to encourage and support people doing this in the coming years.

#3 Question: What questions are you chewing on or living into this year? (from Jonny Miller)

Where do we want to have a home base for the next 3-4 years?

We really love Austin but because the summers are so intense have a hard time seeing ourselves here over the long term. It’s been a great chapter of our lives and we are excited to be here for the next year but I sense we will find another home base next winter.

How am I blocking myself right now?

I sense I’m hitting some friction in the evolution of my journey. I’m feeling a bit overwhelmed with all the things I’m working on conceptually while at the same time not really overwhelmed at all in my actual life. There’s a disconnect between the game I’m playing and the game I sense I’ll be playing in the coming years.

My gut tells me that “work more” is the answer but I honestly think being more intentional about partnering with others in a freelance capacity is probably the more effective path forward.

How can I spend more me-time this year?

With the birth and our daughter, I actively embraced the role of being the stable rock in our family. I put my daughter and Angie before myself and I think this worked well in the first six months of our daughter’s life and enabled Angie to fully live out her life as she needed. It made me quite happy to play that role. But I sense I neglected myself a bit. Encouraged by Angie, I am going to take some solo retreats this year and also make sure to spend some time in solitude and in conversation with friends.

Can a three day workweek work?

At around 5-6 months, our lets let our daughter sleep whenever she wants approach started falling apart. Angie and I got a bit frustrated with our lack of ability to have any control over our time and felt ourselves drifting day-to-day without any plan.

As two very independent people who reject structure, it took us some time to realize that we needed a little better structure to our lives. In Taipei and Spain we started experimenting with dedicated work and personal days for each of us that went really well and has gone even better after Michelle’s sleep schedule has become more predictable.

In 2024 I’m experimenting with a three day workweek where I have Monday Tuesday and Friday blocked off. This feels like a lot compared to what I spend time on in 2023. I am going to be with my daughter on Wednesdays and Thursdays as we are choosing to still watch her ourselves. I’m actually pretty excited for this mix and it’s something I’ve been thinking about doing for years. It should be interesting to see how the interplay of workdays and kiddo days will balance each other out.

How do I get people to come to me?

I am actively taking steps to creating a mini podcast studio at home, coworking space, and hosting cooking nights at our new apartment. I’m excited to host people a bit more actively and create a space with Angie where people want to come and be part of our lives.

How do I find other people like Noel I can lean on?

More below:

In Memory Of Noel

I want to dedicate this years reflection to one of my biggest supporters and mentors, Noel Boyland. He passed away riding his bike, something he loved doing. We met a few months before I quit my job and he was a consistent source of strength for me. He walked away from the default path in his 40s after a health scare and for the last 15+ years has been hacking a living taking various gigs, optimizing his life around health and family, and spending time encouraging and supporting younger people like myself.

He was always the first person to purchase anything I sold online. When I launched a Patreon in 2018 he was the first one to gift me a small amount. When I moved to substack he became a paid subscriber. He purchased every course I sold even though I knew he didn’t need them. Whenever I felt unsure about my path he was the person I would call. We would shoot the shit on video for an hour or two about all sorts of ideas and stuff we had read and I would leave the calls feeling inspired and motivated to keep going. I would tell him he was a mentor and big supporter and he would brush it off saying he was selfishly learning from me.

I don’t think I’d be where I am today without his support and he inspires me to support others on unconventional paths.

With his loss I am feeling a bit vulnerable too. I’ve realized that I don’t have many older men I can talk to about life in a deep way and I am going to take steps to find people that may be good mentors a few steps ahead of me on the path.

The biggest thing I’ve personally realized is that everyone could use a fan and a supporter like Noel. They are invaluable and when you ask people if they have someone like this in their lives, there always is 1 or 2 people who have a superpower of supporting others.

In today’s world it is easy to criticize or to be cynical or to judge other people. I see people doing that every day.

It is harder to slow down and look at where we can help and support others. Or where a nice comment might brighten someone’s day. This is a big part of what I want to do with my life, inspired by people like Noel, and something I hope you are inspired to do too.

I am lucky I have a recording of a conversation with Noel, who graciously volunteered to be guest #3 on my podcast six years ago.