when should you gap year or quit your job?

~4 minute read, shoutouts and resources at the end

every week, i get at least one friend saying they're considering a gap year, and many ask for my advice since i've taken two self-organized gap years and built The Residency, where people come to take gap years to work on their startups full-time.

as you'd imagine, there is no black and white answer. but there is an algorithm that i am confident works. and, you can figure out using it if a gap year is the right option for you.

the structured gap year:

if you're considering a gap year with structure (an internship or preparing for Olympics), my opinion is it is usually a no-brainer. if you truly are hyped about the internship and are intensely motivated to prepare everyday for the Olympics (and have the discipline for it!), i have seen this usually go well. little ways that it’d go wrong.

the self-organized gap year:

if you're considering a gap year to start a startup, work for other startups part-time and/or travel, it gets more tricky. while this may sound like a dream, it can also turn out to be a year you hated if you don't plan it right.

let me explain.

scenario 1

you have already been diligently working on your startup or side project with college/job, and now the only constraint to your growing startup is you putting in more time, then i think it might be worth it to take a gap year. especially if you are an above average disciplined person.

i'll give you an example with aaron. aaron is my man. he graduated from his masters in robotics in europe and instead of going for a job right after, he decided to continue working on his robot arms project full-time on a gap year. he had previously been working on this side project on nights and weekends after school obsessively.

when aaron took his gap year, it was a smooth transition for him. he wanted to work more on his robot arms and the project he was already working on nights and weekends now was his everyday thing. i lived with him at the time he was working on this, and he was locked in 9 AM to 12 AM in one study room every single day.

he didn't watch movies, didn't use social media. didn't listen to music. he didn't even have the urge. i can't think of days he wasn't in his study room.

he had a direction of what he wanted to do: make cheap robotic arms accessible for all. he had this insane obsession with working on this project. so, he went for it. months later, his startup raised millions.

W decision to take a gap. and while aaron is insanely stoic even for silicon valley standards, most people who i have seen have successful gap years happen to have this obsession and above-average self-control on their urges.

scenario 2

you hate your job/college right now, don't have the time to work on your side projects/startup or if you have the time, you don't have a project to focus on right now but want to get out of this vicious 9-5 cycle and explore the world.

this is the scenario where caution is necessary because if you take the uncalculated risk of just diving in a gap year with no plan, there's a good chance you'll spiral into a bad phase.

i did this.

i did this. summer 2023: finished 1st year of uni, hated my major, working 15-hour days between summer school, internship, starting a podcast, hackathons, and figuring out The Residency. i was obsessed with The Residency's potential but had no momentum. i still went full-time on it.

bad decision. the first 4 months were completely wasted (not the entire gap year itself). suddenly i had all this time, grant money in the bank, and no gun to my head. you'd think the more time i had, the more i'd work on my podcast.

though, i did record 10+ episodes w/ people, i never published them because quite frankly, i had a lot of time, and avoiding boring tasks was easy. i could always do it tomorrow because my calendar was free for a long time.

i got distracted by road trips, rock-climbing, SF events, endless Twitter scrolling and philosophical convos. i let my inaction decide for me and my podcast died.

for a bit, i thought i was broken but after witnessing many people’s experiences, i have come to realize this is not uncommon.

there was a resident in the residency, let's call him, Arjun, who was making good money in his job at a manager position at just 21 y/o, but he wanted something bigger. he took a break from his job for 3 months to build his startup which was just an idea. he was non-technical and he was working on a software product, so many of his days were spent figuring out who (a technical co-founder) to build the startup with, or how to code it himself using GPT.

at the end, it didn't work out, he was never able to figure out how to get the first beta version out and he ended up going back to his job. there’s countless examples i know like this.

"exploring" with little idea of what you are going to do is a dangerous game to play and i have seen it go wrong more than i have seen it gone right.

consistently, the people who win at gap years are those dedicating more time to pre-existing projects they're already obsessed about. and i think the way to go if i don’t have such a project is to keep trying to work many side-projects until i find that one — this gives me still some basic structure in life w/ my college or job and keeps pushing me.

but that’s just my take.

who knows spiralling down in a bad phase in exploration may even teach a necessary lesson and build resilience for you. maybe that’s a part of the process?——————————————————————————————————————

shoutout to friends with high agency:

1. Ying: from Montreal, lives in Toronto and nomadically. works as a Chief of Staff at a startup called Onova. she hosts banger events. this one time at Onova, the Software Engineers were away, the CEO was away and something had to be shipped urgently. instead of blaming it on SWEs or anyone else, she gets her boyfriend to look at the codebase and they both work 15 hours to make the product shippable.

2. Samarth Jajoo: from India, lives in Berkeley. one of my good friends from my gap year. found a bug in Amazon’s kindle when he was 11 and got invited to their office with his parents. in his teens, he made hella internet money and now is almost done with his degree at Berkeley. and might be starting a pharma company soon.

3. Sulaiman Khan Ghori: he’s from the US, went to college in Germany, dropped out after a month to become quazi-CTO for a company whose founder he met at a coffee shop. he came to the residency and built Invisibility, a SaaS software. his childhood dream is to build a space company so he learned how to build a rocket engine from scratch and within weeks fired it in his backyard. he also randomly just got a job at xAI recently.

asks:

1. my friend aili who works in growth who recently took a startup from $30k MRR to $200k MRR in 3 months is looking for full-time non-technical roles with hardware companies. her DMs are open! i vouch for her hard.

2. i have been asking myself where can I learn to be the best video storytelling recently. Pixar, Disney, Vox YouTube series. any companies or youtube channels come to your mind?

resources for you:

1. katie’s great and she is hosting a rippleX afternoon hang for Socratica Symposium

2. focusmate is a cool app if you are like me, have no attention span and want to co-work with other people online

3. if you want to create insane graphics like on these stickers in the corner, buy midjourney and use this profile “--profile mzsjtzp” with the prompt