Transitions

Many of my friends, myself, and others are going through life transitions now. It could be due to layoffs recently overwhelming the tech industry. Or reaching our 30’s and still being unsure what we are intrinsically driven by after some reps at prior jobs. Or maybe just having a nagging feeling that something isn’t quite right where we’re at and needing some time to figure out where we derive meaning from.

Navigating this period can be a rollercoaster of emotions. My first month after leaving Dapper Labs, I was elated for a break after consistently putting in 60-70 hour weeks. My second month was filled with anxiety:

“Damn everyone is getting laid off. Should I hedge and find a safe job ASAP?”

“People that have done big things in their careers specialized early. I’m already late!”

“If I want to have kids and afford a house in 3 years, is this my last chance to take on risk?”

Thankfully, I’ve calmed down a bit the last few weeks. It’s ok to “not be ok” for a bit and deliberately figure things out. I’ve been reading a bunch and wanted to share a few of my favorite sources I found helpful and have helped transition my mindset towards gratefulness about transitions, curiosity to explore what’s next, trying to hack small habits on getting started, and appreciating some structure for consistency.

Discomfort With Laying Fallow

I stumbled on two great resources by Ed Batista - an exec coach and lecturer at Stanford GSB (thanks Dan for sharing!). First on navigating life transitions: we might feel uncomfortable because we tie parts of our self-identities to our lines of work so having to transition away requires the psychological act of letting go of that prior self. Ed quotes William Bridges’ Transitions: Making Sense of Life’s Changes:

Changes are driven to reach a goal, but transitions start with letting go of what no longer fits or is adequate to the life stage you are in. You need to figure out what exactly that no-longer-appropriate thing is… Whatever it is, it is internal. Although it might be true that you emerge from a time of transition with the clear sense that it is time for you to end a relationship or leave a job, that simply represents the change that your transition has prepared you to make. The transition itself begins with letting go of something that you have believed or assumed, some way you’ve always been or seen yourself, some outlook on the world or attitude toward others. [pages 128-129]

Discomfort and ambiguity in this period isn’t a bad thing! If you weren’t satisfied with your prior life, it could be good to shed that part of your identity to leave room and craft a new one. Ambiguity leaves the opportunity to try out something different that might become a better fit.

Ed and William move onto a concept of “fallow time” which typically refers to the period between crops when arable land is left unplanted and parallels our transitionary periods between work. We often fail to acknowledge that we’ve entered fallow periods and get stressed about them. However, they are critical for reflection:

One of the difficulties of being in transition in the modern world is that we have lost our appreciation for this gap in the continuity of existence. For us, “emptiness” represents only the absence of something. So when what’s missing is something as important as relatedness and purpose and reality, we try to find ways of replacing those missing elements as quickly as possible. [page 133]

You should not feel defensive about this apparently unproductive time-out during your transition points, for the neutral zone is meant to be a moratorium from the conventional activity of your everyday existence. [page 135]*

There are three main reasons for the emptiness between the old life and the new. First, the process of transformation is essentially a death and rebirth process rather than one of mechanical modification… The second reason for the gap between the old life and the new is that the process of disintegration and reintegration is the source of renewal… The last reason for the emptiness between the stages of the life journey is the perspective it provides on the stages themselves… The neutral zone provides access to an angle of vision on life that one can get nowhere else. And it is a succession of such views over a lifetime that produces wisdom. [pages 140-142]

Fallow periods are important for rest, reflecting and acknowledging that things weren’t right before, and figuring out where your curiosities direct you next. Average humans work anywhere from 40-60 years over the course of their lives. Assuming our finances are ok, what’s a few months or a year to pause and aim in a better direction? Embrace this period.

Exploring Curiosities

Alright, now that we have time to explore - what next? I’ve spent a lot of time the last few years probably overthinking this. I don’t think there’s a right answer for everyone because every individual is motivated by different things. Some chase extrinsic motivators like money and fame. Others find their intrinsic callings and impact the world. 80,000 hours thinks we need to prevent and fight off our impending AI overlords. Many find meaning in their families, friends, and experiences. Since there’s inherent variance in everyone’s preferences, I think the best thing one can do when uncertain is to explore and experiment.

My baseline assumption is that most people don’t actually know what they want. There’s an infinite amount of possible paths for ambitious people to chase, it’s very easy to get caught up on social media with whatever the current thing is, and many people’s stated preferences are drastically different than their revealed ones. Given those assumptions, I don’t think you’ll really know what you resonate with until you try a lot of things. So the best thing one can do when uncertain is to increase the pace of trying things that pique their interest and pausing each time to reflect on whether it’s working out.

Chris Dixon has a great post (Climbing the Wrong Hill) where he makes the parallel of people choosing their careers with hill climbing in computer science. Imagine you’re randomly dropped at a spot on a map and your goal is to climb to the highest possible hill. One strategy would be to immediately start climbing up the hill closest to you and stop once you reach the peak. However you risk that you were randomly placed at a spot with a small hill. An alternative strategy would be to randomly place yourself at multiple other spots on the map, climbing for a bit to gauge the max height, then ultimately move back to the hill that you found was highest. He closes with this:

But the lure of the current hill is strong. There is a natural human tendency to make the next step an upward one. He ends up falling for a common trap highlighted by behavioral economists: people tend to systematically overvalue near term over long term rewards. This effect seems to be even stronger in more ambitious people. Their ambition seems to make it hard for them to forgo the nearby upward step. People early in their career should learn from computer science: meander some in your walk (especially early on), randomly drop yourself into new parts of the terrain, and when you find the highest hill, don’t waste any more time on the current hill no matter how much better the next step up might appear.

On Getting Started

I think what I’ve struggled with the most since being off on my own has been missing an external accountability source, getting over analysis paralysis, and actually starting. Especially coming recently from leading a product team where most of my work was research, providing user and problem context to teammates, influencing others, and the increasing amount of team-related processes to build, I’ve had to slowly re-learn getting back to the basics of building things directly again (which I love! but it’s been awhile). When faced with what feels like an ambiguous and gargantuan task (achieve financial freedom! improve the world!), I think our natural inclination is shy away, do something comforting and familiar, or just procrastinate.

I recently re-read and was inspired a lot by James Clear on habits: the most effective way to get over big scary tasks is to convert them into the smallest possible atomic unit you can think of and make that an “incredibly small habit”. These examples can be better but some examples of things I’m considering:

Suddenly something that seemed scary before is now decomposed into a more approachable set of tasks that don’t feel as bad. Plus you can try the tasks for a bit and figure out whether they feel right for you.

For most things, there isn’t much downside risk to trying something new aside from fear of failure or perceived negative social perceptions. I’ve usually overcome that the same way I overcame being fearful about going to school dances in middle school which was realizing:

  • Nobody really cares because they’re mostly thinking and worried about themselves.
  • People don’t actually have their shit together when they get started and that’s ok.
  • Most people don’t actually have their shit together even when they’re successful and that’s ok as well!

All of us are still figuring things out. Just do it. Like Nike. But just start with smallest thing in the beginning so you can build familiarity and comfort then do it continuously.

Marveling at Consistency

I was inspired most recently after stumbling on an article by Michael Dean on Beeple. Beeple is an artist that took over headlines in 2021 for selling his “Everydays” piece as an NFT for $69 million. Yes, I know nobody cares about NFTs right now but the background context to how he arrived there is incredible. According to the story, Beeple sat down every single day for at least a 2-hour session and it became a non-negotiable religious habit for him. He would sit down for a session, start something new, finish what he could, then move onto the next. He apparently did this every day for 14 years and accumulated over 5,000 days of artwork.

Creating something everyday for 14 years. Absolutely legendary and insane. But Beeple went ahead and did that.

The journey is cool because Beeple acknowledges that his style and work in the beginning looks like disjointed shit (IMO I think it’s pretty good!) and ranged across random topics across portraits, anime, Powerpuff girls, and other doodles:

But Beeple got better over time so what he was able to accomplish in that 2-hour interval gradually improved to incredible pieces of art:

My takeaway was to try and build consistency in some practice. It’ll lead you to experiment, discover or create your style, and the habit becomes apart of your identity and muscle memory. And once that consistency became a part of your self identity, it can spontaneously lead you to weird but incredible places. Whatever you do is going to suck when you start but that shouldn’t prevent you from starting. As Sam Altman says: “the days are long but the decades are short” - so make use of the time you have and you might be surprised at what can be accomplished as the decades pass you are consistent.

Closing for Myself

I’ve had an uncomfortable but also useful fallow period to reflect a bit. I’m still not sure what the right next path is but I have started establishing some principles and experiments to chew on:

  • Build friendships with friendly peers: the best thing I got from Amazon, Opendoor, and Dapper were peers that became meaningful friendships. Being able to connect authentically on shared values and interests was crucial for leaving a happy impression on me. Whenever I had to deal with internal politics instead of shipping product? Not as exciting.

  • Excellence and ambition are contagious: having peers with high-talent bars around you improves your quality standard and motivates you to do your best work. The teams where I was challenged least led to lower motivation levels and quality of experience. I never minded long hours as long as I felt like I was being challenged in the right way.

  • Beneficial for the world: I tend to overthink and worry about which industry or sector to work on but I’ve ultimately been most happy when I know what I’m grinding on is beneficial for the world. Helping entrepreneurs start in-person or online businesses to chase their dreams? Felt great. Empowering people to move easily using data/ML/ops? Also great. Building speculative lottery products but in a fun consumer space? Not sure at times.

  • Mix of Making vs Managing: Having a calendar over-indexed only on IC or manager work was tough. I loved sitting down for hours jamming on SQL and building analytical frameworks but hated not “playing ball” and directly executing after discovering insights. I loved dreaming up and executing product ideas and strategies but hated sitting in 6 hours of meetings straight daily. I think I want a healthy mix between strategy and technical work in what’s next.

  • 1→N versus 0→1: I’ve been lucky to try out many company stages but do think I favor early stage more. It feels great to run through a full problem identification → launch → learning loop and this happens much more frequently with a smaller team. I’ve never properly done the 0→1 so that’s a frontier I’m most curious about.

I’m getting close to fully recharged and ready to jump into what’s next soon. In the meantime, I’m mostly focused on improving my habits and starting off with a few simple input actions per day: shipping at least 1 Github commit (however trivial!) while learning, exercising everyday, doing some research or interviews in spaces that I’m curious about, and hopefully writing a bit more to structure my thoughts better (however bad the notes are!):

We’ll see how far we can get when we set up better systems and inputs.