My Annual Review: Leaning into Ambition and Not Destroying Myself
Greetings! My goal is to post every day this week as a way to reconnect to writing and set an intention of going a bit deeper this year. Below is an excerpt of my annual review. It’s a bit long, so you can read the full thing on my site.
If you missed it, I launched “Find The Others” a community for people looking to find others on unconventional paths and get started creating and sharing ideas online.
You can upgrade to subscriber here on Substack or even easier, join on Circle and I’ll update your status here so you can see the occasional subscriber posts.
Here’s the plan for the rest of the week:
Tuesday (Subscribers): I will share my financials including sharing how I more than doubled my income in 2022 and break down all the fun details. I will release these to the public in a couple of weeks but if you want to access them right away, subscribe or join Find The Others
Wednesday: Going to do a review of some of my favorite reads from the year
Thursday: Some of my favorite essays, articles, podcasts, and up-and-coming creators
Friday: I will celebrate one year of my book launch with some reflections and sharing of all the details and earnings
Saturday: Not sure!
Leaning Into Ambition & Deeper Commitments: (Still) Enjoying The Journey in 2022
2022 was a year of commitment. Commitment to a place (Austin), my next chapter (becoming a parent), and a deeper sense of connectedness toward my life and my work.
It was a year in which I showed up fully as myself, unable to hide because I had spent 220 pages boldly outlining how I intended to live. It was a year in which I found new friends in Austin who invested in Angie and me and actively supported us, encouraged us, invited us into their homes, and never laughed a single time when we shared our silly and crazy dreams for life.
It was also a year of unexpected financial success, making about 2.5x what I did in 2021. I’m still processing what that means and how to think about a path in which past success certainly does not mean future success but might indicate hidden opportunities I had not considered.
It’s a year of generational shifts in which we were able to share with my grandmother that Angie was 5 weeks pregnant a few weeks before she passed. Michelle, our daughter, would have been her 17th great-grandchild.
2022 was a year of leaning into “ambition” and realizing that my related fears were tied to the compromises I would have had to make on a previous path, not my current one. I am no longer in danger of ending up stuck and cynical on a path I don’t like. I have more than five years of carving my own path with more self-awareness of how to design a life around the things I actually like doing. Ultimately, I realized that the “ambition” that many of us were steered toward has been corrupted by the default path. Each of us has an inherent ambition to do things that matter to us and that won’t always come with a paycheck, promotion, or title.
In 2022, I discovered that there was nothing to be afraid of in putting myself out there. Hiding a bit in the first couple of years on my path probably made a lot of sense. I had to “leave the world” to re-enter the world in the Joseph Campbell sense. I said to Angie many times this year, “Wow, I’m okay, I really love everything I’m doing, I am not going to wind up trapped on a silly career path again!”
The review that
Countries Lived In: US, Portugal
Places Visited: Johnson City, Seattle, San Francisco, California and Oregon Coast, Portland, Connecticut, New York City, Boston, Lisbon, San Antonio, Porto
# Of Books Launched: 1
# of Estimated weekday “days off”: 60-70
# of Copies Sold (Audio + Print + ebook): ~$10,000
# of Scheduled Work Hours I'd Skip If I Could: A bit higher this year, probably 200-300 or so
Revenue in 2022: ~$230,000-250,000
# of Expected Children for the Wang/Millerd Family in 2023: 1
Learning To Celebrate
Last year, inspired by my friend Chris, I tried to embrace “celebration” a little more in my life. It emerged out of a conversation about my book and with me mentioning that I had no plans for a book launch or any sort of celebration.
Celebrating myself, especially on this path has always seemed silly. I’ve never been overly attached to external achievements and genuinely enjoy most of the things I like doing. What did I want to do after I published my book? Keep writing. Keep living my life.
But it felt like something worth exploring. Over the past year I’ve realized that I like celebrating in two ways:
Generally celebrating life with friends
Leisure & reflection
On the first, I hosted a party inspired by Nick Gray’s amazing book, I hosted a gathering of internet friends. I sort of made this a celebration of my book launch but not really. I gave out some books and that was pretty much the only book-related event I did for the year. However, I ended up hosting tons of small meetups, writing sessions, pool parties, and small dinners throughout the year and it’s something Angie and I realized that we both want to be part of our life.
In terms of celebrating achievements, I finally realized I had already been doing it. My friend Sky gave me the idea that reflection and leisure could be a way to celebrate. This is something I’ve been doing for several years. and even more purposefully with my “every seventh week off” approach.
2022 Lesson: Celebrations take many forms. It doesn’t need to look like a party. It can be a slow, quiet walk by myself where I have enough space and time to smile and laugh a little at this crazy little thing called life.
In addition to walks, bike rides, and taking time away from active work, one form of leisure for me is writing. This is great because it’s been the source of almost all the success I’ve had with working on my own and it rarely feels like “work” in the way that my old office job did.
So here are ten things worth celebrating!
Getting to spend time with my grandmother and let her know that we were expecting a daughter before she passed
Expecting our daughter, Michelle, and that Angie’s pregnancy has been healthy and smooth to date
Publishing a book and selling far more than I ever could have projected
Finding an amazing group of friends in Austin and after several years of being nomadic feeling like we found a “home” of people that support us and want to be part of our lives
Angie finding her groove with her work, feeling comfortable in the US, and finding a good group of friends (especially girlfriends) in Austin
Reprioritizing my health and joining a gym and going most days I’ve been in Austin
Becoming much faster at turning ideas in my head into actions in the real world
Being a little more ambitious (which was scary!) while not losing touch with who I want to show up as in the world
Hosting a few meetups throughout the year inspired by Nick Gray’s book
Meeting some amazing men in Austin that want to live lives built around vulnerability, healthy ambition, and friendship
Revisiting Questions From Last Year
#1 How do I use my happiness, optimism & energy to support others?
In asking this question last year, I was defending against my biggest fear: falling back into cynicism I had my final couple of years of full-time work. I associated moving back to the US with that experience and the reality that the US culture values full-time work and steady (and climbing) incomes. I was scared that I would need to hide from that pressure much like I did the first couple of years on my path.
My conclusion: I’m fine. Moving to Austin has been huge for finding a group of people that are not only supportive but root for me to succeed. This was something I was missing in my life previously and I realize the effect was that I always tried to hide or “play small” and not really believe in myself. Finding people that support me has been the path to reclaiming my optimism from when I was younger.
#2 How do I level up the ambition in ways that are exciting and sustainable?
I was more ambitious over the last year and I was able to do it on my terms which surprised me. Ambition took the form of leaning into things I already cared about like reaching out to popular podcasts and relaunching my own podcast. I made a list before re-launching the podcast of the top people I want to interview. When I did it I assumed it would take a couple of years to build up the courage to ask but I’ve already had a number of them on and I just confirmed a date with the #1 person on that list. Stay tuned 👀
Ambition is something I want to write a bit more about this year. I sense that the word has been poisoned by our modern obsession with full-time jobs and money. Ambition is independent of employment status which is hard to see because so many people pair it with legible monetary success. The kind of ambition I care about is something we might label “alt-ambition” (thanks @vgr) or illegible ambition. An internal drive that we all have and that far too many seem willing to extinguish for the sake of comfort or the appearance of security.
#3 How do I help Angie succeed?
This was a big year for Angie and something I thought about a lot throughout the year. When we first got to the US in October of 2021, she spent a lot of time trying to apply for jobs in Tech and the corporate world. I was a bit saddened by the lack of imagination of recruiters. She has an amazingly diverse mix of interests and never quite fit into anyone’s box.
Luckily after taking Write of Passage in March she made some friends in Austin, started sharing her story in English, and started to believe in following her own "pathless path” on the work front. Over the last six months of 2022 she not only landed multiple freelance projects, but she had to turn down multiple projects because she became too in demand.
It’s really hard as someone’s partner to see them struggle and many times I just wanted to help her fast track through the challenges she was facing. But that’s not how life works. The cool thing is that every time she faces a challenge she persists and doesn’t give up. It’s been inspiring to see her overcome so many challenges so quickly.
#4 What are the business or personal things I’m not thinking about (yet)?
Probably a question I’ll keep asking for the rest of my life. One of the hardest things about this kind of path is figuring out where you are headed and what to focus on in the present. This is true for any human but the potential options and potential randomness relative to paycheck life is an order of magnitude higher.
One random thing I didn’t expect was for my book to succeed at the scale it did. I treated some of the initial success as a cue from the universe to keep writing and talking about these ideas. This led to me relaunching and renaming my podcast The Pathless Path podcast and continuing to write on the newsletter.
#5 What are the experiments I can do to continue to grow?
Over the last year, I did a bunch of stuff and feel like I’ve expanded my own imagination a ton. Some experiments include:
Took DJ lessons in a studio and did a couple of “gigs” for my family
I hosted several events and was able to decrease the time from thinking of doing something to sending the first invite substantially
I did a 6-week experiment with YouTube with a coach that was way more fun than I expected and turned YouTube from a chore to another fun outlet to create and share ideas
I got a little more ambitious with my podcast, re-launching it as The Pathless Path podcast
I took sponsors on both my newsletter and podcast and while it’s probably still a bit early to lean into these opportunities fully, it unlocked another “income stream” that I know I can potentially count on in the future.
Some Favorite Places of the Year
Creator Cabins: This is where we spent our first week in Austin and it’s also where I finished my book. This will always be a special place for that reason.
Austin: I find Austin delightful. It’s sunny, filled with happy people, and a place that many fellow creators have decided to call home. I wrote more about Austin here.
Lisbon: This was our “last hurrah” of nomad life for a while. We spent the whole summer traveling around the US, Connecticut, and then Lisbon.
Lisbon is simply a world-class wandering city.
After living in so many places for the past several years, I enjoyed this opportunity to really cherish the joys of adapting to a new place in a month. At the same time, it was interesting to see how eager Angie and I were to return to Austin.
The Pathless Path – Wow!
I sense that publishing The Pathless Path will become an important inflection point in my life. The book seems to have taken on a life of its own, one which seems out of my hands at this point.
In December, Ali Abdaal published a top 15 books of 2022 video and it drove about 2000 sales of my book in a couple of weeks and will likely help me reach about 10,000 copies sold in one year.
People are reading it too because a couple of weeks later I’m receiving 5-6 messages a day thanking me for writing the book.
Writing the book was transformational and I think it’s because in a book there is no point in hedging. If someone is going to spend several hours with you, they want to know what you think. So much of life is filled with people bullshitting, hedging, and half-assed takes.
I really give a damn about helping people thrive on unconventional paths and I’m going to build my life around continuing to make that happen.
(This doesn’t feel scary to type, which definitely would have a couple of years ago.)
Self-publishing a book was also very profitable. The first year will likely end up generating about $50,000 in revenue and 10,000 in book sales. More on this in a future post!
StrategyU Also Had A Record Year
Everything did better this year which is equally terrifying and exciting.
Can it last? What do I do next?
Constant companions on the pathless path!
One of the best things I did was hire Nate Kadlac to help me redesign my brand for StrategyU. I was surprised at how powerful a color palette and brand theme could be for unleashing my creative impulses.
The slides on the right just feel better, right?
Nate radically shifted how I see design in many aspects of my work and I think one of the biggest mistakes I made was not working with Nate earlier!
2022 Lesson: Design inspires creation
Hacked-together PowerPoint graphics are fine for speed but over time there’s probably a slight cost to the hanging desire of always knowing it could be better.
After redesigning everything, I started to see new patterns in the ideas and ended up spending a couple of hundred hours this past summer rebuilding my Think Like A Strategy Consultant course.
This also made me realize the returns of playing long games. Because I have worked with so many students and also so many companies, I have been A/B testing phrases, terms, and ways of presenting ideas that help me figure out what works. Also inspired by people like David Perell and Tiago Forte, I looked for ways to ramp up the performance factor that most other people offering training in the corporate space simply aren’t doing.
After re-launching, sales improved and I ended the year making about $100,000 in revenue (probably $80k in profit) from the course in 2022 and another $50,000 from workshops and multi-week and consulting with companies.
The workshops were a big surprise. After packaging the workshops and selling them as a clear offer (I do these starting at $6,000 for one-off trainings and now $25,000 for a four-week offering), I got a lot more interest. I was able to raise prices and position myself as a unique provider in the space.
The crazy thing is that I rely 100% on inbound requests from clients via YouTube and SEO and send everyone the same standardized offer. This runs as a pretty efficient thing right now and there’s no reason I couldn’t scale this up 2-3x with minimal effort. My biggest roadblock is that given free time, I tend to bike around, sit in the sauna, or write about our relationship to work, and in March, I’ll likely want to nap with my daughter 😂.
This is something I need to explore in 2023. Can I find someone that is wired similarly that would want to help me run this? So far I haven’t really found people excited about building something, most people want a job. Unfortunately, I’m not a very good manager.
Will be cautiously making bets here in 2023 but there’s no reason the course and some coaching won’t continue to be opportunities.
Coming Alive Over Getting Ahead – Podcast & Community
My biggest problem is that StrategyU feels like “getting ahead” mode and I can only last in that mode so long which is why I’ve built the business to run on less than 30-40 hours or attention per month.
This is also why I’ve leaned in the direction of some of the things that don’t really generate any money at all, like my podcast.
With the success of my book early in the year, I felt called to re-launch my podcast. Much of my book emerged from conversations and the urge to share interesting stories and be able to channel my curiosity into interesting questions was too exciting.
I sat on the new name “The Pathless Path Podcast” for two months before finally taking action. I’ve been trying to get better at turning ideas into action as soon as possible and launching my podcast was a turning point for this. One day I got fed up with the idea sitting in my head and I ordered a CamLink HD, Better Microphone, and created a new podcast cover, and renamed it. I also created some sponsorship packages and was able to land an initial sponsor that inspired me to hire an editor. I now have a great editor in Poland who I just gave a raise and am planning some bigger things in 2023.
Lesson from 2023: Given that I’ll never be a hyper-optimizing type, getting ideas into a testable action as soon as possible doesn’t have much downside. I’ve “failed” at many of the things I’ve done on this path and I shouldn’t think that should change moving forward.
This past week I also finally launched a community on top of my newsletter, Find The Others. This came from paying attention to the conversations and requests from people who were reading my book. They saw that I was able to “find the others” through my writing but didn’t have platforms of their own to do the same. I hope the community can emerge as a gathering spot of generous, kind, unconventional path-ers who want to help each other succeed.
I am not sure where these two bets will lead but they feel true to my principles for this whole journey I am on.
Coming alive over getting ahead.
Thanking People Who Shared My Ideas
There are many people with large audiences who thought my work was good enough to share with their audiences and many people behind the scenes who have supported me.
As a creator one of the most important things to think about with an audience is trust and I am appreciative of many people who took a chance on me.
Special shoutouts to:
My “Unpaid Marketing Intern” Ali Abdaal: Ali mentioned me about five or six times on his main YouTube channel (which has 3.7M subscribers), interviewed me on his podcast and shouted out my book so many times in his newsletter that I lost count. Ali is inspiring for his love of learning and ability to move fast. He just also happens to have a massive YouTube channel. I’m most excited about his book too. I sense based on Ali’s interest in my book and his other work rabbit holes that his book is going to be a banger.
Venkatesh Rao: Venkatesh has given many shoutouts to my writing and wrote a nice thread on my book this past year that lead to a ton of sales. A lot of my writing is ribbonfarm / Venkat inspired. It was fun to return the favor by reviewing his excellent book Art of Gig over the past couple of months.
Chris Williamson: I’m inspired by Chris’ incredible focus on Modern Wisdom and his impressive curiosity across a wide range of domains. I messaged Chris when I launched my book not knowing he had moved to Austin and then found myself in a conversation with him a couple of weeks later. It’s been cool to see how energized and alive Chris is with his podcast and I also appreciate him giving me a chance with his massive audience.
Jim O’Shaughnessy: I like to ask a question on my podcast, “who is your path role model?” If I had to pick someone it would likely be Jim. Why? Mostly because of his infectious curiosity and optimism. At his age and experience, he is an outlier in his stance toward life. In addition, he loves finding, connecting, and investing in hidden talent. I’ve gotten to know several people around the world who Jim has discovered and already hired. I got to meet him in New York over the holidays and I sense we could have talked for hours. Which is also what makes his podcast so great. Despite audio difficulties, we had a fun conversation.
Rolf Potts: Probably my biggest fanboy moment this year. I cold emailed Rolf telling him I quoted his podcast in my book. He asked me to send him a copy and he liked it enough to ask me on his podcast. Rolf’s Vagabonding was such a powerful book to read before going nomadic in 2017 and again before I left Taiwan with Angie in 2020.
There are so many others to thank but I want sincerely thank anyone who shared thoughts on my book this year.
Other conversations I enjoyed (but not limited to) include Jonny Miller (Curious Humans) Marshall Kosloff (The Realignment and Deep Dive), Bhav Sharma (Creators Campfire), and Justin Murphy (Other Life).
Questions For 2023
This next year feels wildly uncertain but not in a way that stresses me out. In fact, I am feeling more secure and confident about my path than at any time in my adult life.
I feel like I’m living out something that is true and aligned and it’s still kind of hard to explain how different that feels from my previous path. People look at me and proclaim “you still work!”
I definitely wanted to escape work after I quit my job but that faded as I found work I enjoyed and enabled me to connect with myself in a deep way. My lived experience of this path feels like I am cheating. I went from only having nights and weekends and a few vacation weeks to myself prior to 2017 to now having what feels like every single day of my life at my disposal. I guaranteed that being able to scale down some of my work this year for meaningful time with my daughter will make this feel even better.
Given the large increase in financial outcomes in 2022, I am seeing the unexpected income as “excess income” that I can invest in the ability to continue to live this life and do this kind of work. The money has been a little distracting at times this year and I’ve definitely conjured up grandiose plans of even more success. Yet I remind myself that this is almost definitely a trap and the only thing that will lead me in a “successful” direction that I actually want is staying true to myself and doing the things that fire me up in the moment.
Generally, I am having a hard time thinking about anything beyond the end of February when my daughter is expected to arrive. I am incredibly excited about becoming a dad and can only imagine how much I will have to learn.
I sense this will be a massive shift in my perspective in life but one that I feel ready for. Quitting my job in 2017 was terrible for my bank account but great for my soul and I am glad my daughter will get to see the version of me that has grown so much and is fully ready for this.
Here are some themes and questions I’m thinking about for 2023:
Parenthood & Perspective: I am heading into this new chapter of my life open-minded and humble. I don’t know what to expect but fully expect that there will be changes. I am excited to see what unfolds.
Life Perspective & Scripts: I don’t know how having a child will change my behavior and priorities around work. Many people build their lives around the assumption that most workdays are for working and then schedule childcare and support around that. That is not my base assumption for life and I am interested to see what sort of hidden scripts are at play in parenthood (from my initial conversations with people it seems parenting scripts are even more rigid than work ones!).
Scale StrategyU Or Just Keep Going?: I’ve steadily grown this over four years through constant tinkering into a business that generated about $150,000 in revenue essentially as a side gig. I like doing the trainings with companies and coaching and consulting work with executives but don’t love the maintenance and content generation. I have a 10k subscriber mailing list that I could likely monetize and the YouTube could probably grow quite a bit too. How can I get leverage here? Is it targeted freelancers with specific skills? Could I find a young former consultant that might want to use this as a platform to follow a similar path to me?
Invest Like A Business: I’ve struggled a lot with investing money in things I’m doing. I’ve had a lot of luck hiring freelancers to help with specific tasks and that works well with my inability to manage someone that wants a job. However, I still find it hard to spend money so with some help from the coaches in Malcolm Ocean’s Goal Crafting Intensive, I decided it would be best to make a fixed commitment of “R&D” spending for the year. So for 2023, I am going to commit to spending $20,000 on freelancers, support, part-time work, and other investments that might help me grow and add some serendipity to my path.
What Are Some Fun Book Bets I Can Make?: My book seems to have a bigger market than I thought. What are some bets that could 10x the sales in 2023? 100x by 2025?
Leaning Into an Emergent “Pathless Path” Movement: I love writing my newsletter and suspect I’ll keep doing it for a while. I am going to continue to follow my curiosity and am excited that I’m now pairing it with a Circle community for paid subscribers. I had a lot of experiment ideas around courses and mini-challenges that I wanted to run but didn’t want to launch something. “Find the Others” feels like a fun playground for the next year.
How Do I Write More?: In 2018 I adopted a mantra, “write, most days” and that has led to most of the things that emerged in 2022. I was probably spread a little too thin in 2022 but not in the overworked sense. More in the “I’ll do a Twitter thread” instead of doing deeper thinking, reading, and writing longer pieces. One of my goals is to write more in 2023 and I’ll be spending some time trying to be more intentional about the ideas I want to write about this year.
Thanks For Reading!
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