Sabbatical lessons: Interview with matt yao
Introducing Interviews!
I started writing about the sports world because I wanted to learn what it is to cultivate an inner game that allows individuals access to self belief in the face of uncertainty and incredible odds. In addition to the sports world, I believe that there’s a lot we can learn from business leaders, creatives, and professionals that have developed the inner game to explore roads off the beaten path and to take risks in pursuit of playing big on their own terms.
Rather than focus on what they’re doing, I want to explore their inner game and talk to this brave band of individuals directly. What mindset shifts did they have to make to pursue their path? How have they learned to cultivate belief in themselves? What have they done in moments of uncertainty and doubt? What are they discovering about themselves in the process?
On that note, I am thrilled to feature my first interview with guest Matt Yao. Earlier this year, Matt made the decision to leave his job as a product manager and embark on a sabbatical. He caught my attention with the wisdom and vulnerability he shares about his decision and journey via his blog, Game of One. In addition, he writes a climate newsletter called Build in Climate and co-hosts a podcast, On the Rise. Highly recommend checking them out!
A fun opportunity to connect with Matt directly is featured at the end of the interview :)
What are you up to in life right now?
I am about six months into my sabbatical. Right now I’m in New York City. At a high level, I have 3 projects. My personal blog where I write about my life and whatever I’m thinking about. I write a climate newsletter that focuses on the problem of climate change as well as what I think some of the solutions might be. And I also do a podcast with a friend called “On the Rise” where we interview entrepreneurs, creatives, and athletes and ask them about their lives. It’s been a very inspiring and rewarding process. Those 3 projects have a bi-weekly cadence. Every other week one of those things will go out and that’s about as much structure as I have in my life right now.
Outside of the three projects I spend a lot of my work time and my intellectual time reading whatever is interesting to me and I don't set any limits or boundaries. And then with all the free time, I like to do the things that I want to do but might not be able to do when I have a full time job: traveling, meeting interesting people, working on my health, and also hobbies like skiing and surfing.
What were you seeking in your life when you made the decision to leave?
It’s interesting because when I decided in February 2022 to take the sabbatical, I basically didn’t have these three projects in my life at that moment. It’s not like I had this well thought out, intentional plan of “now that I’ve quit my job I’m going to spend all my time writing, researching, podcasting, and reading.” It was a realization that what I was doing in my full time job as a product manager just wasn’t something that I could do long term. I think it was easy for me to be a mediocre product manager but I came to the realization that it would feel very inauthentic and therefore like a slog, like moving through quicksand for me to become a great product manager. I didn’t have the motivation to level up in those certain skills.
Once I realized that I don't want to rise up the corporate ladder, I knew that I had to do something. What’s interesting is that in the 10 months before I actually quit, these projects that I’m working on came into my life. By the time I actually quit, I knew what I was going to do.
Have you experienced moments of uncertainty and doubt during the sabbatical?
So much. I feel like uncertainty is the main theme in all of this. I’ve had to decouple uncertainty and negativity. Because we go through a rigid education and work system, we’ve been conditioned by society to think that having certainty is good and having uncertainty is bad.
I’m sitting with really high levels of uncertainty but I think what has helped me decouple uncertainty and negativity is realizing that I don't know what's going to happen but I keep seeing signs of progress. I can’t plot them on a graph with a straight line and they happen very sporadically but there are these little qualitative moments that help me know that what I’m doing is good, that I’m making progress, and I just need to trust myself and keep going.
How has your relationship to the idea of a career changed because of the sabbatical?
Leading up to when I quit, I was telling people that I was going on a career break; someone that either breaks the notion of a traditional career or is taking a break. Now I view it as more of a transition.
But then the next question is, well, what are you transitioning to? And I don’t really know. But with the extra slack and the free time, I’m trying to orient myself against these long games and areas. An example is climate where I know that I’ll be doing something for decades to come, but I’m pretty sure I’m not going to be writing about climate for decades to come. I don’t know necessarily the role I’m playing but I know the game and what field I’m going to be on. It’s easier to figure out the role organically by being in the right place once you know that you are committed to a certain area.
There’s a paradox that commitment can be freeing because you spend so much time thinking about what to actually commit to that you can never commit all of your mind towards the actual thing. Once you reach a point where you’re actually committed to something there’s a sense of relief that you no longer have to worry about whether it’s the right thing or not because you’ve decided to spend time on it.
You haven’t used the work a lot as we’ve been talking. Where does “work” fit into this version of yourself that you’re becoming and how has your relationship to work changed?
During the period of time where I felt lost at my last job and knew I needed to change, identity-wise I felt like a slacker because I wasn’t working hard. It’s been very nice just to realize that it’s not that I am not a hard worker, I was just working on the wrong things. I’m now working harder than ever and I’m learning faster than ever. My conception of work is what I spend my time on, the reading and writing that I do. But there is this cliche that if you find what you love, you never work a day in your life. That's a cliche until you realize that it’s true. If you are not working on what you love, then you’ll read that phrase and think it’s a load of BS or that it’s a cliche. If you’ve ever experienced it, then you know that it’s true.
What are the biggest things you’ve realized during the sabbatical?
The best thing about the sabbatical that I didn’t expect is how fast I am able to learn. All the things I was worried about have not been as bad. I had all these worries about money or just not being sure about doing what I set out to do. I’ve thought about quitting the climate newsletter multiple times. Just sitting with those feelings and having to work through them.
When you take a sabbatical in most situations you are more on your own than before you went on the sabbatical. During the 9 to 5 most of your friends are going to be working and you are just left alone to think about your thoughts. You don’t have a boss or maybe you don’t have people around you who know what you are going through. All of these problems that you feel, you have to solve them yourself. This sounds obvious but when you are in your job and you have a paycheck you find ways to neutralize those problems without facing them directly. For example, if you have a problem at work you can rant to your coworkers or your boss or HR. Or you can take your paycheck money and treat yourself to a nice meal or retail therapy or drink your problems away.
When you can’t use money in that sense to solve your problems you just end up naturally staring at them and realize that you have to face whatever it is straight on. For me, I spent the first three months of my sabbatical struggling with waking up every morning and being disciplined and motivated enough to sit down and read and write. It sounds super simple to just do the thing but without any external forces or pressures, I had to choose to do that every day.
For the people that are where you were in 2022 that are thinking “I don’t think my current job is for me but I’m afraid to leave” - what would you say to them based on your experience thus far?
This one guy, Kevin, who contributed to a blog post where I was interviewing people that had been on sabbatical said, “if you are thinking about it, it’s inevitable.” I don’t want to make blanket statements but I think that’s probably true.
In terms of actually what you can do, there’s the pragmatic, checklist type things you can take care of like stockpiling cash, looking at your paycheck and what you’ll save month by month, looking at credit card statements of how much you spend and what you think you’ll spend in the future. These are things everyone should do but it’s actually the easy side of things.
What gets people hung on actually leaving is not the personal runway but the “who am I without my prestigious job?” I spent all of my years of school and college grinding so that I could get this job and now I realize it’s not what I had hoped for. It didn’t solve all my problems - there’s something else lingering for me to go explore. Getting over that hurdle is the more challenging part than solving the financial and practical constraints of taking a sabbatical.
I don’t think I can give advice on how to overcome that. I can’t give advice because what you need to do is get off your phone, sit in a room by yourself, and be comfortable with being alone, thinking thoughts, and letting whatever comes into your head be processed.
I spent five days last year backpacking on Kauai in Hawaii and I didn’t listen to anything or read any books. I found myself multiple times sitting in a cave, not sleeping or meditating, just eyes open being still. Whatever that looks like for you - it does not have to be sitting in a cave for two hours - you just need to go do that type of thing. Then a lot of the personal, individual blockers for you and your identity will come to the foreground of your mind. It sounds very “woo, woo” when I say it but I can’t prescribe a step by step routine because it’s such a complex thing.
What I hear in that (which in many ways is what I’ve found through the coaching process) is the ability to just sit with uncomfortable thoughts and be curious about what’s on the other side of them.
Being aware of your thoughts is the simple version of what I'm trying to say. Be aware of what’s getting in the way of you quitting your job. Be aware of how much of your identity is wrapped up in your work. Be aware of the things that you’re interested in that you haven’t given yourself permission to explore because of your demanding job.
In the 10 months between deciding to quit and actually quitting, the projects I have now came into my life and I don’t think it’s a coincidence. I was able to search farther and broader because I was actually searching and looking for things that I would love to commit myself to and work on. There’s something about setting the intention to quit and then trusting yourself and the universe that you’ll figure it out.
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Opportunity to connect with Matt: Matt is starting to explore coaching and is creating space for open-ended conversations with folks who are interested in his story or ideas. He’s inviting anyone interested to reach out over Twitter or email him at matt.r.yao [at] gmail [dot] com!
