Thoughts on a career break

REASSESSING IS HARD

Recognizing strong feelings is easy in the moment (“I truly enjoy what I am doing”). Retroactive thinking improves abstraction (taking a bird’s-eye view) but increases biases. Something valued at 6 can be wrongly downgraded to 4 or upgraded to 8 or correctly but for the wrong reasons. Taking all variables into account is hard.

One of my best times at Habyt went from September 2022 to June 2023. I opened a new city, worked closely with the COO on two M&As, and led the integration efforts in one of them. I was on fire. But looking back, it’s not obvious how to evaluate that time to better understand what I like to do. Do I like M&A? Or did I like it because it was my first time? Perhaps it was working intensively with the team? Or maybe I simply like that it went well? Should I double down on numbers because I weirdly get in the flow while using Excel?

I am still looking, but for less multi-layered topics I just accept that I like X just because I like X. Borrowing from Vitalik, you're allowed to have preferences without needing to have a complicated scientific explanation of why your preferences are the way they are. There's a limit to how much you can change your preferences, and so if you push too hard, you end up inventing reasons for why every single thing you prefer makes sense in your life. This often leads you to try to convince yourself that these back-fitted arguments are correct, leading to unneeded conflict caused by thinking rather than feeling.

THE THEORY OF NOTHING

In January I top-down decided to do nothing for a bit and quickly became a househusband. “I’ll cook something special” became “This is the 15-day cooking plan”. “I’ll finally clean the hidden mess in the house” became “I am now a cleaning company”. “I’ll light up a candle to make a cozy environment” became “Here is my 20-step ritual before I do anything”.

I also quickly became a couch potato. “I am gonna level up my photography” became “I am gonna scroll Instagram the whole day for inspo”. “Watch intellectually engaging documentaries” became “8 hours on YouTube x espresso workflows”.

There is a full spectrum of things that fall under the “Nothing” category, but I lacked a guideline on which “Nothing” to land on. So I created one.

Introducing the Theory of Nothing:

In short, actions can be:

• productive (do X to intentionally impact Y);

• not productive (do X for X’s sake);

• positive (X is aligned with your inner motives);

• negative (X is not aligned with your inner motives).

Actions don’t belong to a quadrant, they move based on the underlying drive. Cooking can be:

• productive + positive (friends at home, food must be prepared);

• productive - negative (friends at home, you start preparing 2 days in advance with no true genuine reason)

• not productive + positive (it’s a passion)

• not productive - negative (no food is needed, you do it anyway to procrastinate on something else)

The “Negative Nothing” is anything related to the Land of the Househusband Traps or the Land of Couch Potatoes and Zombies.The “Positive Nothing” is a combination of the Land of Hedonism and the Land of Those who wake up at 5 AM (not me). You mostly want to be somewhere in there during a career break.

FULL EXPLORATION

Sam Altman took a year off and went into full exploration mode, and although most of it turned out to be not useful, the seeds were planted for anything after it. For fair context, he had sold Loopt for $43M and his options were taking over a public company or taking over YC. Yet, everybody can go into full exploration mode.

Full Exploration increases the Surface of Luck. Luck isn’t an independent variable but increases super-linearly with more surface area: you meet more people, make more connections between new ideas, learn patterns, etc.

The hard part is you’re pulled apart between rational mind A (that tells you to increase the Surface of Luck) and rational mind B (that tells you it understands the whole concept, but there is no way this very thing will bring you any luck). It takes a huge personal belief that things will turn out fine, kinda like Mr. Peanutbutter in BoJack Horseman.

This piece by Chris Dixon helped me a lot in putting things into perspective: “I think a good analogy for escaping this trap can be found in computer science, in what are known as hill climbing algorithms. Imagine a landscape with hills of varying heights. You are dropped randomly somewhere on the landscape. How do you find the highest point? The lure of the current hill is strong.  There is a natural human tendency to make the next step an upward one.  People fall for a common trap highlighted by behavioral economists: they 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. The lesson from computer science is: 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.”

PSYCHOLOGY OF MONEY IS WEIRD

All my savings are in cash, stocks, and crypto and I can comfortably live without a salary for 18 months. I am also rationally aware that I can find a last-minute job if I quickly need myself in the market. I am also irrationally aware that my cryptos will go to the moon if I quickly need myself out of the market, but this is for another essay.

Yet, my mind doesn’t care. Every two weeks anxiety kicks in and I fear the shit is about to happen. But I know the drill.

I’ll run the numbers for the nth time, calculate my runway, and see on paper the shit is not going to happen. My mind knows but needs to see it.

WTF IS A CAREER BREAK?

I needed some weeks of doing Negative Nothing the same way I sometimes weirdly enjoy reaching a maximum peak of house mess so that cleaning feels even a better job. I understood that if I did what I felt, I’d do nothing.

I need to construct a system leading me to action, rather than relying on my efforts. It took me a year of not succeeding in doing cardio to pay for a monthly multi-sport class to succeed in doing cardio straight away.

When I decided to take a career break, I wondered wtf a career break technically was. Obviously, a period without work. Then what?

Is it nothing? What does nothing mean and what’s the right amount? Should I force myself to do nothing even when I feel like doing stuff outside of the nothing-definition?

Is it full detachment only from work or from career too? When does something become career-related? If it isn’t detachment from career, how much would be too much?

Is it doing what you feel in the literal sense? Should I allow myself to scroll Instagram the full afternoon? Is it about what you truly want to do? Wouldn’t that potentially cross the career topic?

Is it entertainment and traveling? How can I avoid it simply becoming a big holiday? Would that be bad? Is it exploration? Does meaningful exploration exist apart from aimless wandering or is random exploration still net positive?

Is it connecting with new people? What kind? How should one approach connections made primarily for career reasons?

There are of course no right or wrong answers, only combinations matching with timing, goals, and needs. I decided to have a one-month horizon to then properly reassess and go forward. January was Negative Nothing. February will be writing. March will be China and Taiwan. If you’re around, let’s meet.