#26: My Career Break Blueprint 🗺

wtf am I doing lol

It’s been two weeks since I left my job as a product manager. I’ve actually known that I would write this post for months now. As I was putting together the final plan to quit, I had the impulse to share what I’m planning for this nebulous, undefined period. To make the timeline a bit clearer, I have a small confession. By the time I published #23: Chronicles of the Career Breakers, I had already put my notice in. Although I had come to terms without the input of the Career Breakers, reading the responses after the fact still brought a wave of relief as I discovered shared feelings of nervous excitement and irrational worries.

I’ve had a lot of time to think about what I want out of this next chapter. Before my last day of work, I already had plenty of notes jotted down for what I wanted to cover. It’s funny now because so much has changed in just the last two weeks that I scrapped what I originally planned and rewrote it all. A testament to how uncertain this path can be.

I’ll share what I thought I would be doing and what I’m actually doing now. What I have planned and what I have left intentionally unplanned. Hopefully my blueprint can be a frame of reference, but certainly not gospel for how to escape the religion of modern work culture.

What are you optimizing for?

In the tech bubble, there’s this commonly repeated question, “What are you optimizing for?” The bearer of this question might be an interviewer, mentor, or peer and the setting might be an interview, casual one-on-one, or late-night quarter life meltdown accompanied by a tub of ice cream. I’ve noticed that one response has risen above the rest and been deemed the most virtuous: “I’m optimizing for learning.” This answer signals to the asker that you’re smart and ambitious because you prioritize personal growth. Also, by not answering with “money” or “prestige”, you position yourself as someone who’s in it for the experience rather than the fat paycheck or clout.

Donning this virtue-signaling mask has become somewhat of a charade from my vantage point. Just like if an interviewee asks you “What’s your favorite part of your job?”, you’re obligated to answer “the people” with a smile on your face, and just like how we would stand up every morning and recite the pledge of allegiance in school, we must now go through the formality of responding with “I’m optimizing for learning.”

Looking back, I know for a fact that when I uttered those exact same words a couple years ago, I didn’t truly mean it. In reality, I was seeking a high salary, recognition from my LinkedIn network, and projects that would look good on my resume so I could perform the zig-zag motion of changing jobs every 2-3 years for a more senior role with a bigger paycheck. We can’t possibly all be optimizing for learning. If that were true, we would be in the library reading books rather than taking job offers that pay $500K to optimize the click-through-rate of ads by .001% to increase a trillion-dollar company’s revenue by another few million dollars.

Now that I’m in career-break-mode, I’m still not optimizing for learning. I don’t want to waste time going down rabbit-holes or understanding technologies that don’t interest me. Instead, I’m trying really hard to figure out what feels like play to me and let things flow from there.

What am I even doing??

At first, I thought I would frame this career break as a “DIY MBA”. It’s fitting since most people pursue an MBA to change careers or grow their professional network, and if the current recession vibes follow ‘08s path, there should be an increase in grad school enrollment. But when I googled “DIY MBA”, all I saw were lists of books on business, entrepreneurship, and productivity. While I do plan to read a bunch, thinking about starting something is not the same as actually doing it*.*

My second attempt to conceptualize what I’m doing required me to split myself into two beings. Viewing myself as my own patron helped me tolerate staying in my job while I traded away my creative potential for fiscal security. I even compared my career break to existing programs like the Thiel, 776, and O’Shaughnessy Fellowships. It’s like I’m creating my own fellowship! Except I’m all alone and instead of someone giving me free money, I’m living off savings.

Third time’s a charm. A career break implies a temporary period and then it’s time to get back on the (corporate) horse. But just two weeks in, I’ve already realized that I’m not trying to go back. What I’m going through is more of a career transition. Calling it a transition implies that there’s this other life that I’m marching towards, but it’s so illegible, amorphous, and uncertain. I’m hesitant to even call it a transition because it’s still possible that I try these projects, they don’t work, and then I need to get a job. It’s tough to stomach because that would feel like failing.

I like animals and I also like metaphors so the following combines both: I feel like a crab molting. I’ve outgrown my old shell and reluctantly crawled out into the dangerous world. I’m exposed and in an incredibly weak position, but if I can stay out of the way from predators (not run out of money), then I’ll gradually develop a new, better fitting shell. Yeah, that sounds about right. It’s not a DIY MBA or self-funded fellowship, it’s me channeling my inner crab.

Introducing my projects

In a nutshell, I’m working on three personal projects: this blog Game of One, my climate newsletter Build in Climate, and my podcast On The Rise. I wish I could claim I channeled my inner Magnus Carlsen and forecasted this masterplan with my next ten moves, but truth be told, in April, when I started saving up for this career break, I had no idea what to do with my life. My plan at the time was to do the stereotypical travel-the-world for a year to “find myself”. It’d be like Eat Pray Love, but instead of a 34-year-old divorced woman, it would be me, a single 26-year-old dude who also doesn’t know what to do with their life.

Slowly, but surely, once I put the intention out there to leave the corporate world, things started to unfold. At first, there was a false start in leaping at the shiny, alluring path of being a startup founder. From spending three months voraciously searching for the “right” climate startup idea which ultimately dissolved because of a cofounder breakup, I realized that I actually genuinely care about climate. It seems pretty straightforward now, but at the time, gaining this conviction felt like a revelation. At this point, I affirmed my passion for climate, but still didn’t have a clue for how to apply myself. During my startup search, as a function of subscribing to literally every single climate newsletter, I started to notice gaps in - let’s call it - the climate tech content space. That ultimately led me to start Build in Climate where I’m writing for emerging founders and jobseekers looking to build a company or career in climate.

In November, my friend Abe had the idea to start a podcast and reached out since (in his own words) “You have a very different perspective than me but a similar drive.” I vividly remember in our initial conversation we were thinking about doing a product management podcast (since we’re both PMs), but that quickly lost steam when I eventually asked why would I delve into a job function I was actively trying to leave. We kept jamming and settled on this concept that seems so obvious now. It went something like, “Why don’t we just talk to cool people?” and then once we accepted that we were nobodies starting from scratch, we started reaching out to our friends doing dope things since we knew they would actually be down. And that’s how we ended up with On The Rise, a series of curiosity-driven conversations with creatives, athletes and entrepreneurs about the life and career that they’re building.

Last Tuesday, I voluntarily subjected myself to a 5:30am wake-up call so that we could record a podcast episode with my photographer friend Terry who’s currently traveling around the world. He’s been trekking in the Himalayas and diving in remote Indonesian islands without internet access so when this two-day window appeared when he’d be in Bali, I knew we should push to make it work, even if that meant recording the pod at 6am. I remember in high school I’d wake up feeling like a zombie and only after hitting snooze multiple times. This time I jolted out of bed before my alarm even went off. I guess it’s different when you’re working on your own stuff that you actually care about.

Creating for my own benefit

From the outside in, it’s easy to think that creators churn out content transactionally for attention or money. It wasn’t until I was on the other side and started to produce more that I realized the act of creation can be highly rewarding by its very nature. Game of One (this blog) has become my mental weight room where I can stress test the strength of my beliefs and stretch my imagination. I only launched my climate newsletter last week, but it’s already become a forcing function to further investigate areas that I only comprehend at a surface level. In the case of the podcast, conversing with our guests about their respective domains has prompted me to take action in my own life. From our episode with elite swimming coach and teacher Michael Sabala, I overcame the hesitation to reach out to my former teachers that have left an impression on me. Sharing what I’ve been up to led to this heartwarming response from my 7th grade history teacher:

I’m just getting started with no line of sight to monetization, but still, it’s nice to notice the fruits of my labor, even if they aren’t fruits made out of dollar bills.

Am I hedging my bets or just interested in multiple things?

I’ve gone back and forth on why I’m pursuing several projects at once. Back in college, we would spray-and-pray our resumes at internship applications in the hopes of getting an interview. That wasn’t optimal, but it still worked to some extent because it is kind of a numbers game. That’s completely different now. The stakes are much higher and you can’t just spray-and-pray creative endeavors that require actual brain power. Everything I’m pursuing right now is attached to my name and by extension, my reputation. Every blog post, newsletter, or podcast episode takes hours to produce, refine, and launch into the ether. When you’re indefinitely living off savings in pursuit of personal projects, it can sometimes feel like there’s a ticking time bomb strapped to you, but instead of seconds, you count down by what’s remaining in your bank account.

The challenge for me is just as hard as knowing which color wire to snip. Not only do I have to figure out what I can do well enough that it can generate income, I also have to genuinely enjoy it. I got into this whole career break situation because I was working a job that I didn’t deeply resonate with. Exploring and searching for what I find fulfilling, to me, is even more important than trying to figure out how to make money from it. A good problem to have.

In some ways, I am hedging against each project not working out, but also praying that (at least) one does. If one project takes off and another is struggling, I might cut my losses and double down on the winner. On the other hand, I want to challenge this notion that everyone should dedicate themselves to just one thing and stick with it. I think by anchoring to the default of a singular full-time job rather than multiple fractional jobs, we ignore the fact that most people are multidimensional - we care about (and are good at) more than one thing. I don't think you need to be “all-in” on something in order to show that you care. You can care deeply about something without signing yourself up for 40-hours-per-week of it.

Leveling up

I know that my creative outputs in the form of a blog, newsletter, or podcast are only as good as my inputs. As much as I need to protect my time to create, I still want to make sure I have space to breathe and time to explore my curiosities. Since leaving my tech job, I’ve already noticed a stark contrast in the books I’m reading. Instead of reading about business, startups, and pseudo-psychology, I’m gravitating towards books about the creative process, philosophy, and exploration. I’ve even gone as far to sequence the order of books to be “just-in-time” for what I’m currently going through. A few weeks ago, I was struggling to sit down and write so I picked up The War of Art. In early January, I could already sense my aggressively-set new habits were slipping so I bumped up The Power of Habit to the top of my reading list. It’s been envigorating to craft my own career break curriculum. I’m finally back to learning for the sake of learning. I can’t remember the last time I felt this way.

Leaving room for slack

With an ambitious roadmap of three distinct creative projects, I know that it’s important to carve out time for wandering. Typically we value rest so that we can maximize our performance as athletes or knowledge workers. However, on the pathless path, leaving unstructured time is vital for serendipity and these mystical things we call “inspiration” and “luck”. It’s only been two weeks into my career break, but I’m already starting to see how having slack leads to unforeseeable opportunities emerging. It’s not so much about taking time to chill and watch TV, but more so lifting your head up every now and then to see what’s out there. We can often fall victim to thinking the world revolves around us when in reality the world is changing even when as we sleep.

All that said, it has still been a challenge for me to not get too fixated on my projects and I always feel more behind than I actually am. I’ve set aggressive deadlines for myself and then had to repeatedly push them back once I realize that I would need double the amount of time (and coffee) to get everything that I want done. Fortunately, I have built-in breaks in the form of ski trips and other travel later almost every month this year. I was in Jackson Hole in early January and I’ll be skiing in Salt Lake City, Bend, and Colorado in the upcoming months. I don’t plan to work during those trips and instead just enjoy the time with friends. What I’m iteratively learning is that I need to focus when I’m in the ideal work environment and then completely surrender the pressure to work in all other spaces.

One challenge on my path, now that I have a lot of things I really like doing, is making sure I purposefully maintain a certain level of non-doing into my life. For me, the active work mode only is possible if I am continuously feeding my soul with non-doing and non-work. The secret to writing seems to be not writing. - Paul Millerd

What I’ve learned in just two weeks post-quitting

Money beliefs

In the months leading up, I would battle test my personal runway trajectory by simulating how much I would spend each month. I spent hours tweaking numbers in spreadsheets, thinking that more analysis would lead to less worrying. Now that I’m on the other side, I haven’t worried about money at all. I’m sure this will change as I start to dip more into my savings, but I’m still surprised that I haven’t thought once about money. It seems counterintuitive, but now that I have no source of income, I think I’m actually more generous. For example, I recently bought a couple books for friends and I’m not sure I would’ve thought to do that before I left my job. My theory is that going to sleep with a six figure salary and then waking up the next day without it while remaining intact, if not better, made me realize that my sense of wellbeing is far less correlated to my bank account than I thought.

Explaining myself

A common question I’ve been getting lately is “How are you going to support yourself?” I know what they actually mean is “How are you going to support yourself financially?”, but part of me wishes they would instead ask “How are you going to support yourself without the defined, legible container of a full-time job?” I have no idea how to describe what I’m doing or who I am anymore. I don’t even think it’s accurate to say that I’m on a career break right now because I’m already working more than before I quit (which I’m happy with). I’ve settled for “I’m working on personal projects” because it conveys a sense of passion while maintaining a level of excusability if nothing works out.

Opportunities are abundant

While I was still working, I viewed opportunities that exist within a narrow cone of reality. A random recruiter sliding into my LinkedIn DMs is an opportunity, but saying hi to a stranger at the grocery store isn’t. Since reliquishing a significant part of my identity, I’ve started to notice myself noticing more opportunities. I’ve started to strike up conversations with strangers, but also reach out to existing connections. I’m not suddenly more extroverted. I’ve just started to pick up my head and care more about non-work things. Opportunity is everywhere; you just need to seize it. The thing is, you can only respond to what you notice.

On the pathless path you have no markers

Since losing my job title, salary, and OKRs, I’ve realized that there aren’t any milestones assigned to you by default. There’s no feedback loop in the form of a paycheck, promotion, or praise from colleagues to let you know that you’re on the right track or need improvement. Sure, you could look at well-defined metrics such as likes, views, and subscribers, but that isn’t necessarily the optimal way to assess your value. You’re left to come up with your own heuristic for value creation. There’s a reason why your primary objective is called your north star. On the pathless, you’re given a compass with a general direction, but no map with trails to follow.

I’m currently not being paid in dollars, but I am being paid in attention and that honestly might be just as valuable. I’ve been measuring progress by my own judgement, but also with feedback from readers. To keep track of these illegible milestones, I started a Notion page called “Celebrate the Ws” where I just paste screenshots of whenever someone says anything positive about my work. Substack and other platforms barely give any insight into who is actually reading my stuff so it’s always nice to hear it directly. But this record-of-praise also has an evil twin page called “Doubters”. So far, it doesn’t contain much beyond a long Instagram DM that includes:

I don’t see anything in your writing which convinces me you’ll be happier because you have that time. - a Doubter

Both types of feedback are valuable. The kind words are a sign of encouragement and indicate that I’m heading somewhat in the right direction. The doubt is a worthy challenge to prove wrong and frankly it doesn’t bother me that much. After all, the greatest doubt is self-doubt and in that sense, I’m already on a quest to prove myself wrong.

There’s also been early signs of progress. A couple of people have DM’d me on Twitter to chat. I’m about to call one of them now. Paul Millerd, author of The Pathless Path, references my last blog post in his newsletter Boundless. Steve Schlafman, executive coach, writer, and ex-VC, also mentioned it in his newsletter Where The Road Bends. A writing coach generously offered me her time and guided me through some key prompts. She has even graciously offered to keep in touch. Lastly, this weekend I was at The Commons, a dope third space in San Francisco, for their weekly writer’s club, and it turns out my How To Quit Your Job guide had been shared with the community members.

Closing thoughts

I’m grateful to be in a position where I could even consider going down this route. There’s so much uncertainty, which I’m learning to view as a neutral canvas rather than a fog of risk and anxiety. I have projects to create, things to learn, but I’m also planning for the unplanned.