Optimistic | #156
Reflecting on optimism and results of my 2nd eight-week sabbatical
October 9th, 2021: Greetings from Kenting, Taiwan. We are here for two weeks before heading back to Angie’s parents to spend some time with them before moving to the US.
🗽 Our plan is still a bit unclear but it looks like we will spend November and December in New York City before moving somewhere else for the winter and then likely Austin for three or four months. If you are going to be in the city in November or December, let me know. I’m hoping to organize a couple meetups!
Consider becoming a paid supporter of the newsletter. All members will get free copies of the book!
#1 Optimism & Moving Back Home
I’ve become more optimistic and lighter in the last year. Being happily married and finding a sustainable path in my work has played a big part but it has also been a result of being on this pathless path and going through a journey of both finding out and remembering who I am.
One of the traps of self-employment or any unconventional path is that your existence is in tension with the large number of people who have no interest in any sort of unconventional path. It was not until I quit my job that anyone ever asked me “why are you doing this?” Before, my path was obvious.
When I first faced these questions, I was defensive. The working world was broken and it was breaking me. Don’t you see it?!? I wanted people to see the world as I saw it. Why? Not because I wanted to be right but I wanted reassurance. On a pathless path, there is no next step, and it’s easier to try to fight battles getting people to see the world as you do than developing the capacity to exist in that space of not knowing.
As I learned to be more comfortable in that space and learning to appreciate solitude, I found myself withdrawing from relationships and the world. Part of this was the simple reality that I was 12 hours away from many of the people I had gotten to know in my life and another part was the fact that I wanted to protect myself. I needed to get stronger.
At the end of 2019 I read William Zinsser’s book On Writing Well. I found inspiration in two passages:
Sell yourself, and your subject will exert its own appeal. Believe in your own identity and your own opinions. Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going.
You are writing for yourself. Don’t try to visualize the great mass audience. There is no such audience—every reader is a different person. Don’t try to guess….what you think the country is in a mood to read.
Through writing, I was able to come back out of my shell while still playing it safe. I published an essay “I’m not writing for you” that detailed the people I wasn’t trying to reach and outlined the people I did want to reach. This was a turning point that enabled me to move past seeing myself in opposition to the world towards engaging with it directly. “Finding the others” as Seth Godin says.
Throughout 2020 and 2021, my writing attracted many people and in hundreds of curiosity conversations, I was given the strength to loosen up and stop worrying about protecting myself. I started to laugh at myself more and got way less distracted when people criticized what I was doing. A lot of the relationships I leaned into were the ones that inspired me to write my book.
I think many people embracing a pathless path go through similar stages: exit, opposition, retreat & solitude, engagement, optimism.
Before I quit my job I lost track of who I was. In college and in my early 20s, I was an optimistic force of nature. In grad school, a friend said that he thought I was someone that “lived life to its fullest.” It surprised me because I thought I was just being myself.
Right after grad school, I went through a breakup, two challenging years battling health issues, and growing disillusionment with the corporate world. I moved to New York to shake things up. I moved in with my college roommate and it was great. But the new city energy faded and I had to grapple with the fact that the way I was setting up my life wasn’t working. I could no longer muster up the energy to want what I was supposed to want.
Over the past year, I’ve been trying to embrace some of the things I loved doing growing up: playing more basketball, spending more time outside, and even bringing back the yo-yo:
I’m starting to see the wisdom in why I was pulled into this direction five years ago. I’ve softened into the world a little more, have started to have more fun, and have confidence about being able to continue to shape the life I want to live.
I’m excited to be back in the US with this renewed optimism. One of the things that had been a trigger for me is the insane US healthcare system. It’s a horrific system for someone like me that is self-employed but isn’t perfectly healthy. But as I learned last summer almost no one has the power to change anything and even doctors have given up trying to do anything about it.
So I’ve decided to embrace reality and look at this as part of the game I’m opting into. After all, we’re choosing to move back to the US. No one is making us. I’ll just try to make a bit more money and stop complaining about it.
Part of my shift is also because I’m moving there with Angie who is coming there as an immigrant. While she’s lived there twice, both times were as a student where she spent a lot of time with other international students. Being part of a large, outgoing, and energetic white family is going to be something different. She said something to me a few weeks ago, “do you know how lucky I am to get a green card?”
With this in mind, it feels crazy for me to complain about anything. I want to help give her all the opportunities that I had access to and build an amazing life for both of us. It’s exciting to be embarking on this next chapter, optimism in hand.
It’s my longer-term aspiration that I can build a life where I can be creative and remain curious while also spending most of my time connecting with amazing people, teaching, and learning. I still don’t know what that path looks like either but that’s the point, right?
25 pre-order spots left for The Pathless Path. Or you can get a free copy by becoming a supporter on Substack
#2 Reflecting on 2nd Eighth Week Sabbatical
My wife and I took a week off last week as part of our experiment to take every eighth week off from work. We explored two islands, Green Island, and Orchid Island in our final around the island tour before we head back to the states.
My motivation to embrace this experiment was inspired by Sean McCabe who has been giving his entire team off every 7th week for the last six years. We chose eight weeks to align with the calendar this year but may change it up next year.
Sean’s original motivation was overwork. Mine was a bit different. While I can work long hours it’s usually something I’m enjoying and I tend to always disconnect after working five or six hours. Since we are both working on our own things we tend to follow the wisdom of mother nature, working a bit more on days when it’s rainy or too hot and exploring more when conditions allow.
The biggest benefit of this “work block” was that it helped me to put clear deadlines on the things I want to do anyway.
Here are the goals I set at the beginning.
I was able to complete the important things I put at the top of the list - the updated pricing for StrategyU, finishing the draft of my book, and launching landing pages for coaching and corporate packages of my consulting skills coaching.
It’s fun to reflect on the things that didn’t get done either. Why do I keep being convinced I’ll create YouTube videos? Are they really important? If so, what stopped me from doing them? How can I make it easier?
The next work block runs until Thanksgiving and also overlaps our move back to the US. My main mission is to launch the book, launch a “personal board report” to some trusted friends and followers, and explore potential partnerships, projects, or part-time gigs that might be interesting now that I’m back in the US time zone
#3 Howard Gray - The Formless Path
Howard has been on the pathless path since he was a teenager but he prefers “formless” - this was a fun conversation about grappling with multiple identities, the truth about the creator economy, becoming a parent and figuring out where to focus.
I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support me directly the best way is to consider becoming a paid supporter of the newsletter.
Alternatively, I use and love all of the following services and they give me 30% of all revenues from people that sign up. If you plan on launching a course or e-mail list and you end up using my affiliate code, I’ll gladly spend an hour helping you get set up and answering questions. Just let me know!
Teachable - 14-day free trial
ConvertKit - First 1k subscribers for free
A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.