Why I Dropped Out

Tuesday, February 25th, 2020 · 33 min read


Winter in Ann Arbor

Winter ‘19: Ann Arbor

The dark morning sky, a blast of cold air, and the sound of construction workers beginning their day: it’s 7am in Ann Arbor, Michigan. Although spring is supposed to start in just a few weeks, temperatures above freezing seem months away. I’m walking out of the math department, where I’ve been holed up working on a problem set since 8pm the night before. It’s hazy outside, but I’m not sure if it’s just in my head or the frigid air condensing my warm breath. As I begin the half-mile march down South University Avenue to my dorm, I see students making their way to breakfast.

By the time I make it to my room, the sky has lightened to a monochromatic white. Trying my best not to awaken my roommate, I shuffle into my dorm room.

It’s now 7:15. I set my alarm for 12, which will hopefully give me enough time to finish writing my proofs before class starts at 1, and I collapse into bed.

In high school, I always enjoyed picking my own schedule. I read the course catalog, threaded through prerequisites to enroll in something I was really excited about, and otherwise tried to take the most challenging classes I could. The coursework wasn’t too bad — straight As became my baseline — and I fortunately still had time to make it to cross country practice every day during the week. I spent my weekends coding apps and hanging with the boys. It was a comfortable suburban high school life.

I had developed a reputation for getting good grades in high school, so, eager to reassert my academic prowess in college, I took a similar approach to choosing classes at Michigan. The summer before my freshman year, I spent hours browsing the course catalog and reading departmental websites to pick my classes. Taking full advantage of my AP credits, I planned prerequisite chains for upper-level classes and aimed to pick the most challenging schedule available to me. By August, I’d done so much research that I had my entire collegiate coursework mapped out, even creating two variants of my schedule for if I wanted to graduate in three years or four.

So when registration opened at orientation, I executed my plan: I skipped the intro CS class for the second-semester programming course and opted for proof-based linear algebra for math majors instead of multivariable calculus for engineers. I enrolled in cognitive science and a first-year writing seminar to round out the quantitative classes.

Outside of class, I joined the running club, became a member of the startup club, and began working on an app outside of my normal CS coursework. I was excited to tackle college head-on and couldn’t wait to get started.

It took only three weeks for my average in linear algebra to drop to 60%, and I was seriously considering dropping the course. Had I really underestimated college by this much?

Even now, I still recall the chilly September night of the drop/add deadline, the sense of foreboding as I went to bed with the thought that when I woke up the next day, my GPA might be tarnished forever. Midnight passed amidst a fitful sleep.

Linear algebra soon became the hardest class I’d ever taken. My attendance at the running club’s practices declined from my high-school level of six days a week to a paltry two or three.

I’d never been more academically challenged than that semester, but as I slowly ran less, slept less, and went out with new friends less, my grades began to improve. I surprised myself with an A+ on the first exam which brought my 60% into the mid-eighties. By the end of the semester, I had a cumulative A+ grade in the class and an overall 4.0 GPA.

Although I had few friends outside of my classes and a level of physical fitness that would’ve been appalling to my high school self, I’d still made it work: I wanted straight As, and I got straight As. At the time, that was all that I thought I needed. I’m making the most of college, I thought.

But I can do even more. So, I ratcheted up the intensity the following semester, electing to take more pure math with an honors analysis and a combinatorics class, and tempered the math with two 300-level humanities classes.

It also took only three weeks for my average in the analysis class to drop to 60% — but this time, the thought of dropping the class barely entered my mind.

Yet, even just three weeks into the semester, I was regularly crashing overnight in the math building with my fellow analysis classmates to work on problem sets. I usually left at 7am, but even then I wouldn’t be the last to leave. Some of the later stragglers joked about seeing our professor when he came in to teach an hour later at 8.

My health was deteriorating precipitously, and I couldn’t remember the last time I went for a run or hung out with the boys. Consumed with academics, I realized I’d made barely any progress on my app since the very start of the school year.

I somehow managed an uncurved 90% on the first midterm, but frankly, I was burning out and had no idea if I could repeat the feat — let alone if it was even worth it. About halfway through the semester — in a decision made in the haze of a drowsiness so all-encompassing I don’t even know where I got the idea from — I resolved to go to bed at 12 midnight no matter how close (or far) I was from finishing.

As the remaining weeks of the semester trudged on, I was still spending all my time doing problem sets (I was just the first of my classmates to leave the math building now) but at least I was feeling better.

It was around then, as I exchanged declining grades on half-done problem sets for increasing health and well-being, that I began to reflect what I was doing to myself, and more importantly, why. Was this really the most effective method of getting my education? What was that my mom was saying about “growing” as a person? Admittedly, I was learning a lot from my coursework — meditating on readings of Joan Didion and E. B. White and the writings of Rousseau and Mahatma Gandhi, and I could tell I was much, much, much better at math than when I came to Ann Arbor — but at what cost?

Slowly, the idea of taking some time off of school began to creep into my mind. I very much felt like I needed a break, and I began contemplating the canonical gap year: traveling to Europe, living in Spain for a few months, learning a new language, and immersing myself in a new culture. During those last few weeks of studying before finals, I started looking at flights to Barcelona in September, and I began reaching out to clients for contract software work I could do to support myself.

Finally, it was all over, and I was sitting at home, back from my first year. I had gotten back into running an abridged, three-mile version of my favorite route from high school cross country because I wasn’t fit enough to finish the full five, and I had just gotten back from a run when I got a notification on my phone that my final grades were in.

I opened the Michigan app to see that real analysis was my coup de grâce: my first final B grade, ever. Although I’d been a straight-A student my entire academic career to this point, there really wasn’t much of a shock. I followed my 90% on the first midterm up with a 60% on the second, and all of my problem sets past week five were halfway done or less. For me to have gotten an A would’ve been a disservice to my classmates who toiled until they could say good morning to our professor at 8 every single week of the semester. I was just grateful for the generous curve.

Although I might not have been able to prove the Fundamental Theorem of Calculus on my final exam, in that moment — back from my third or fourth run in weeks, seeing that B grade — I had some real proof that I could trust myself to make the right decision for myself, even when it might not be the immediately obvious one. Despite my worse GPA, I’d learned much more this semester than last.

The great grades I got my first semester let me ignore a lot of things I should’ve been paying much closer attention to, but now I understood. That vital choice I made halfway through to at least have some semblance of normal sleep every night — maybe at the expense of a GPA with a leading digit of 4 — felt like a sign that my other idea to take a break from school wasn’t as crazy as it seemed.

But I still had a whole summer ahead of me before I had to figure out my plans.

Google Bikes in Silicon Valley

Summer ‘19: Silicon Valley

In recent years — perhaps in response to market demands — the computer science major has effectively become vocational training for software engineering. According to the 2019 Stack Overflow Developer Survey, only about 30% of developers with bachelor’s degrees elect to pursue further education; of those who do, many seem to regret it; compared to more traditional industries like law or finance, the field’s largest employers care demonstrably more about skills than any sort of credential or deep theoretical knowledge; and it shows in compensation for undergraduate software engineering interns: Facebook, Google, and Amazon pay their summer interns — some with only one year of college educationannualized salaries of over $100,000 a year. In fact, I know a few people who took extended time off from school before completing their degree just to work at tech companies, and with the rising cost of higher education, that’s the only feasible way I see someone paying their own way through college debt-free today.

On the flip side, with so many undergraduates coming out of school already having industry experience, just having a CS degree often isn’t enough to get the attention of many tech companies. Working a summer internship allows students to show employers that they are ready for full-time software engineering work, and it tends to make the recruiting process much, much easier. In fact, I’d argue that a single Big N/FAANG-type (Facebook, Apple, Amazon, Netflix, and Google) internship can be worth more than an entire CS degree.

Understanding this requirement, in the fall, I applied to twenty-plus companies (which seemed like a lot then, but I realize now is actually a pretty low number) for summer software engineering internships. Unfortunately, as a freshman, applying then with barely even one semester completed as a CS major, I didn’t have much on my resume besides school, and I was rejected or ghosted by every company I applied to. I don’t blame them — if I was hiring engineers and saw my own freshman resume, I’d probably toss it because there’s really not much signal at that point (although maybe that’s an opportunity to rethink the way hiring for developers works, as some companies are doing).

While I still wanted to take my gap year, I didn’t want to take it without anything to show for. At the time, I thought that if I didn’t have work for the summer and took a year off, I might not end up getting work the summer after, which wouldn’t bode well for future years. Of course this is a slippery slope — and admittedly, a very freshman-esque outlook — but the bottom line was that I wanted to leave school on my own terms, from a position of strength — with some work experience and the security that I had opportunities elsewhere — rather than leaving burned out, simply fleeing academics.

Through a string of fortuitous circumstances — unrelated to my original job applications from the fall — I somehow landed an internship at Google in California in mid-March. I’m really not sure what I would’ve done if I didn’t have anything and just stayed home for the summer, and I have a feeling I might’ve been back at school this fall if that were the case. But with this Silicon Valley job, I finally started feeling truly comfortable with following through with my plan to leave. Regardless, I still made the bare minimum of preparations to come back in the fall — including registering for classes (which were slightly less daunting this time) — to maintain my optionality, but I’d already transferred my apartment lease for next year and didn’t consider coming back to Ann Arbor a very likely possibility.

After returning from Michigan and before leaving for California, I spent a week at home in Pennsylvania, where I had the chance to talk about my plans further with my parents. I wasn’t entirely sure what they initially thought, but by the time I arrived home it was a remarkably easy discussion — I had mostly solid grades, a productive (and lucrative) summer ahead of me, and over a year’s worth of transferred AP credits that, after a year off, would still allow me to graduate within four years, with the rest of my grade in 2022. They were on-board, on one condition — that I return to school next fall. Whenever my mom was around and I was explaining my plans to someone, she’d make sure to correct me:

“You’re not ‘dropping out,’” she’d say, “It’s a ‘leave of absence.‘”

At the end of the week, my parents dropped me off at PHL, again impressing upon me the importance of having a plan to return to school, and I boarded my flight to SFO anticipating to finish my twelve-week internship the first week of August and to fly out to Barcelona shortly afterwards.

I didn’t really know anyone in the Bay when I first arrived. I was 19 years old with one year of college in the Midwest under my belt. I’d grown up on the East Coast, and the last time I’d visited San Francisco was for a family vacation years ago. In my mind, it was some abstract hodgepodge of the Golden Gate Bridge, Google, streetcars, and startups.

But one of the few connections I had was someone I’d briefly met at a hedge fund recruiting event in April when I was still in school. He was a year above me at Stanford, and being on the quarter system he still had a few weeks left of classes. So shortly after I arrived, I sent him a message asking him if he wanted to meet up.

We grabbed lunch in Palo Alto, close to campus. I was munching on a piece of avocado toast when he nonchalantly mentioned he ended up having to renege on his summer hedge fund internship. He’d just started a company and would instead be beginning a seed accelerator in a few weeks. I did the math, and with pretty much just an idea, the company was already worth around two million dollars.

My first thought was what the hell is going on here? My second thought was that I already knew the answer: this was exactly what I had in mind when I arrived. I just didn’t expect it to be this in-my-face. Startups had always been something I read about in the news, and raising venture capital was something I watched on Silicon Valley. It was disconcerting to have this all right in front of me so fast, but there was no doubt I was intrigued.

“Let’s keep in touch,” I said, as I departed for the Caltrain station.

My first day at work, I met my intern host, who’d be responsible for mentoring me over the summer. He was a soft-spoken man from Vietnam with dark, graying hair, and he’d studied math in college in the nineties. He was a Silicon Valley veteran, with a long tenure at Yahoo in the mid-aughts before coming to Google.

“It’s less work for me if you do well,” he said, half-jokingly, so he put a weekly check-in lunch in our calendars to make sure I was on track.

I spent much of my first few weeks browsing Moma, Google’s intranet. I was amazed at how transparent everything was — I could look up any employee by name and see their reporting chain and tenure, I could read design documents for everything from the YouTube popularity algorithm to the Google server cluster manager, and I could view the entire source code of huge projects like Gmail. I could feel myself learning so much, so fast.

As May turned into June, I sat back, enjoyed my three free meals every weekday, and began to finally sleep and exercise regularly again, averaging a little less than eight hours each day in the office. I started reading books on my own again, too, for the first time since probably middle school. Wanting to make the most of the Bay Area rent I was paying — three times as much as what I was going to pay in Ann Arbor had I come back in the fall — I made an effort to meet someone new every week, going to intern meetups and DMing people on Twitter that I found interesting.

It was really only around then — the official start of summer, having been moved in for about a month — that I think I truly developed a clear understanding of why I felt so disaffected with school. It was never the workload per se, but the feeling of not being in control. Life was good now because I was owning my learning, my health, and my friendships. I felt that the “personal growth” I’d been seeking — even if I couldn’t yet understand what exactly that meant — was finally happening. Being overworked was simply something that prevented that from holding true.

I had a whole gap year ahead of me, and when I realized I wasn’t necessarily looking for a break, but more so just an opportunity to live on my own terms, trekking to Barcelona and doing the “canonical gap year” started to make less and less sense.

Even though I haven’t done much traveling abroad, I wholeheartedly believe it when people say there is no substitute for international experiences. But for the opportunity to learn and grow — at my own pace — and the exposure to new people and ideas that I was looking for, I felt that the Bay Area offered some worthy substitutes for going to Spain.

Becoming independent? Even if I left Google, there were boundless opportunities for motivated software engineers, and I didn’t have to look any further than the two-million dollar idea founded by my 20-year old friend at Stanford. Novel experiences, people, and ideas? I was meeting so many new people, traveling to so many new places, and seeing my surroundings from so many new perspectives. Even learning a new language? It wasn’t foreign, but at Google, I was writing Java in production for the first time, and there were so many opportunities to learn new technologies across the stack.

I figured while I had the momentum that came from working at a large tech company, staying in the Bay — at least for a few months more — wouldn’t be a terrible idea.

In late June, Michigan raised their tuition for out-of-state students by 4%, pushing the cost of attendance for nonresident undergraduates to over $70,000 a year for the first time ever. I’d already made my decision to leave, but the numbers supported my choice: my Google salary for the entire summer wouldn’t have been enough to pay myself through even a single semester of school, and I already felt concerned enough making my parents pay my nonresident tuition when I could’ve gone to my local state school for less than half the price.

But it was a choice I made — out of the schools I was admitted to after high school, Michigan had the best CS program, and unlike my classmates who wanted to become doctors and lawyers and might’ve chosen to forego an expensive undergraduate program for a top medical or law program afterwards, I originally chose Michigan because I didn’t plan on pursuing graduate education.

But while my initial thought was that my bachelor’s would be a terminal degree, I started to grow convinced that having no degree could be a terminal “degree.” Part of the great reputation of Michigan’s computer science department comes from its consistent placement of graduates at top tech companies, and looking at many of the upper-level electives offered by the department — classes like EECS 484, “Databases” (which covers topics like writing SQL queries and transaction management) and EECS 485, “Web Systems” (which covers full-stack development) — it seemed like the reason for that was because the education was becoming increasingly vocational: those were the same exact technologies and concepts I was using at Google.

This was around the time of my midpoint evaluation, and I was starting to get emails from HR asking me to fill out a form expressing my interest in a returning internship. The form also had a smaller checkbox for new grads, so they could be routed to a conversion recruiter who could prepare a full-time offer. At our check-in lunch that week, I asked my mentor about full-time conversion. It was a productive discussion, and I decided to check the box.

Google’s generous internal transparency also eventually led me to face some of the thorny issues that I’d heard about the company in the news over the past year head-on. I read archived email chains in Moma while my code compiled, and I watched executives dodge pointed questions from employees at all-hands.

There was another intern on my team, a few years older than me, who sat next to me. He was returning, and worked in the New York office the year before.

“What have you seen change between this year and last?” I asked him one day after lunch.

“Well, the food at the New York office is better.”

“I’ll have to visit next time I’m home!”

“The company overall has definitely changed a lot in the past year, though.”

He told me his account of the intrigue that filled the previous summer — from Project Maven, Google’s AI collaboration with Department of Defense, to Dragonfly, their censored Chinese search engine. Compounded with allegations of sexual harassment levied against senior executives, the backlash from employees culminated in worldwide walkouts in November 2018.

He said that there were many projects that he couldn’t access now that he used to be able to browse. Code that was previously accessible was now siloed off to specific teams. Executives didn’t share as much as they used to, and they stopped taking live audience questions at the weekly company-wide meeting.

Next week at lunch, I asked my mentor what he thought about last year’s issues. He briefly mentioned that he hadn’t been following it too closely and that he had two young daughters to send to college. We chatted only a bit more before I got the sense that he had many, many other things to worry about when he began recounting the time he attempted to escape from communist Vietnam on a boat.

“They caught me, but I was very young, so they just sent me back home.”

Google gave me a generous housing stipend, and I made a deliberate choice to pay extra to live in San Francisco and commute ninety minutes each way to work, instead of living closer to campus in the peninsula. I’d long held entrepreneurial aspirations, and from Airbnb to Zenefits, it seemed like startups were increasingly opting for the city over the valley stronghold of FAANG. I wanted to be closer to this burgeoning center of gravity.

Every day after work, I’d take a Google bus from Mountain View to my apartment in San Francisco’s Mission District. I got my internship offer in mid-March and only spent one week at home after school ended, so the research behind my decision to live in the Mission over other neighborhoods was scant: a few positive reviews I read in the San Francisco subreddit. Although I’d get off the Google bus just a few blocks away from Dolores Park with a flock of fellow software engineers, I quickly deduced the neighborhood’s working-class, Hispanic roots from the mariachi playing at the BART station on the weekends and the relatively affordable prices at the three taquerias I passed on the way to my apartment.

As the summer went on, I began to grow more and more attuned to the crises faced by the city that I’d heard about in the news — things that I was frankly rather ignorant of by virtue of having lived my entire life up to then in a quiet suburb. I watched shops and restaurants in the neighborhood close due to high rents, and I was overwhelmed by the number of homeless people on the streets, everywhere I went.

While the questions raised by Project Maven and Dragonfly — of working with ICE or the Chinese government — might have been more far-reaching, I was honestly most moved by witnessing the human impact right outside my door of the massive influx of tech money into the city. Living right down the street from Uber and Twitter took on a completely different meaning.

Google wasn’t perfect, and new grads allegedly now have more “hesitation about the moral qualities” of big tech, but whether I worked for a Khan Academy or an Uber, I began to doubt if it was even possible to “get paid a ton of money but [be] socially responsible.” If tech workers’ demand for housing in the Bay Area outpaces the supply, basic economics says it’s we who are raising rents and exacerbating the crisis.

I wanted to better understand what was going on, so over the summer, I read as much as I could about rent control, YIMBY movements, transit-oriented development, land-value taxes, and the planning commission. As a fan of public transportation, I avoided Uber and Lyft as much as I could, developing an appreciation for my proximity to a BART station in the Mission and an understanding of the importance of bus rapid transit when I moved to Western Addition and began taking the 38R. I’m admittedly biased, but I think there are many cities which would be thrilled to be such a vibrant magnet for talented, ambitious young people, and I grew passionate about finding a solution to the housing crisis that worked for everyone, tech or not.

In terms of how I wanted to spend the next few months of my gap year, though, it was hard for me to characterize Google as more or less “moral” than say, Facebook or a startup. I felt like I couldn’t in good faith claim anything of that sort in the midst of the crisis happening right in front of me.

I know this isn’t much of a resolution, and there’s definitely a spectrum — for instance, Google internally seems to have a much stronger culture of thinking things through and thoroughly testing code whereas Facebook (from what I’ve heard) still moves pretty fast. And it’s not exactly fair to compare a company like Khan Academy with Uber — different problems call for different solutions, some not as clear-cut as others. It’s just that I found that the differences between many of these companies to be much less consequential than they were made out to be (Microsoft ended up winning the big Department of Defense cloud contract after Google employees complained), and it still didn’t change the fact that all of tech was in some part exacerbating the most conspicuous issue, the housing crisis.

If anything, living in San Francisco taught me how little I really knew about how the world worked. I’d been programming since high school, and it was a prescient professional decision to pick up that JavaScript book in ninth grade. It was hard not to feel like I’d “made it” when that first fat paycheck from the world’s “best” tech company hit my bank account. But by the end of summer, I knew I still had a lot, lot more to learn.

The daylight hours were getting shorter, and my internship was soon coming to a close. By then, I’d very much grown to cherish my weekly lunch check-ins with my mentor. I’d always learn something interesting, and my mentor presented a refreshing side of Silicon Valley entirely distinct from my original expectations.

It was one of our last lunches, and I was talking to him about how I should best spend my next few months out of school. Becoming a full-time Googler was still in the works. I was musing about other possibilities when he remarked, invoking the name of our mutual benefactor, “Nathan, you are richer than Larry Page.”

He dug his chopsticks into his pho and pulled out another bundle of rice noodles from the steaming broth as I sat there with a quizzical look on my face.

“You have time.”

A view of San Francisco from Marin

Winter ‘20: San Francisco

And so, September arrived without any Spanish departures. As I finished my internship, my mentor offered to continue helping me stay at Google, but by then, I knew that I needed to make the most of the flexibility and “time” that came with being a nineteen-year old.

I wanted to optimize for learning, and (for better or for worse) my only marketable skill was software engineering. Other than going back to school, joining a startup seemed to be the move that made the most sense to me. I’d learn the basics: validating ideas, building something from end to end — but also hopefully how to navigate the vagaries of the real real world outside the cocoon of big tech, in the myriad challenges that any early-stage company faces. Knowing how to code was the crucial piece that would allow me to get paid for that learning.

I’d been talking to a few other companies in my last few weeks at Google, but my friend at Stanford had just finished the accelerator, and fortunately, they were looking for new hires.

As of this writing, it’s been about five months since I left Google, and nine months since I stopped going to school. I became the first hire at that company that came out of the accelerator, and I’m still the only non-founding employee.

It’s been a wild five months.

It goes without saying, but life at a startup is tougher than at Google. I don’t have catered lunches, an excessive salary, and “normal” hours anymore. But one perspective I’ve heard on Google’s pay and perks is that they are as much a defense mechanism as they are marketing tool: a way to keep turnover low and prevent employees from starting competitors. If anything, maybe a takeaway right now is learning that there are “perks” that are more important to me than free food and nap pods. I have unparalleled autonomy to work on what I think is interesting, I build things that customers can use instantly, I’ve learned everything from increasing SQL insert performance to the metrics that can determine product-market fit, and I actually know how to cook now.

Large companies do pay better — but I’m luckily getting stock in addition to my startup salary. It’s amazing to have some real, legal ownership in what I’m building (I’m pretty pumped to be on the cap table!), and I sincerely hope things work out — for me, and for the entire team that took a chance on me and let me be a part of their vision. But from a purely economic standpoint, rudimentary calculations show that the company will have to exit for at least nine figures for it to be comparable to what I’d get at a big company assuming I went full-time, and ten figures for it to be undeniably life-changing money. In the most likely scenarios, I’ll either be able to pay my way through a semester of school or will have some nice kindling for the next time I go camping.

But the raw economics aren’t important to me right now. This may be the only time I’ll have a learning opportunity like this for a while: I “have time.” I still want to start my own thing, but if anything it takes some combination of cash and credibility to do a startup. Unless I can figure out some way to bootstrap fast or find an early-stage company that pays exceptionally well after graduation, if I go back to school, the most sensible option afterwards might be to “do a few years at Google,” build a solid resume, and save up some seed capital. And even if I opt for big tech, there’s no way to predict what life will throw at me, and I might just get complacent and decide to stay there forever. It’s definitely not the worst thing anyone could do — but I’m afraid it could be the worst thing I could do.

That is, I don’t blame anyone for taking a Facebook or Google job — with student loan debt, the rising cost of homeownership, and the plethora of other challenges posed by our new economy, there are structural incentives that make it difficult to choose anything else. And in a very pure sense, it’s just plain fun to work there.

But one thing that I think hasn’t changed about me since last year is my desire to seek out enormous challenges and, at least while I’m young, learn as much and as fast as I can. For now, I don’t think that’s something I’ll be able to find in big tech. Going forward, I would feel much more comfortable solving tough problems through my own venture or something similarly early and scrappy — a place where my determination, curiosity, and desire to do things right have the highest leverage — because that’s where I can learn the most and have the most impact. Working at a startup now is helping me get a better sense of that.

As I’ve spent the past few months working, my parents have grown more and more resigned to the fact that it might be more than a year before I go back to school. For one, my vesting cliff is in October, but more than just that, building a sustainable, scalable business will take longer than just a few more months, and I’m eager to be a key contributor to that.

There are still times that I miss college, though. In November, I was on BART in the East Bay going back to the city from a hike at Mission Peak when a bunch of drunk people wearing University of Southern California gear stumbled onto the train. Thirty minutes later, I somehow ended up at California Memorial Stadium for the Berkeley-USC game. While I can’t say the energy was the same as when the Wolverines are at home, it still reminded of my friends in Ann Arbor, who I often struggle to keep in touch with. As my Michigan friends dove headfirst into sophomore year, cool and confident, I wondered who my group of “college friends” would end up becoming. Was I missing out on my last chance to build four years’ worth of friendships?

On the other hand, I don’t think I’m entirely ready yet to dive back into the classroom. My first year was intense, and for now, I’m enjoying my work as-is and learning a lot of things that I don’t think I’d be able to get in a classroom.

But to be completely honest, I still haven’t done as much as I would’ve liked by way of truly expanding my understanding of the world. Broadly, I’m doing similar full-stack engineering work to what I was doing at Google. I read The Atlantic, Bloomberg, The New York Times, and whatever else interesting comes through my email or Twitter feed while my code compiles, but I am still just about as ill-informed on the housing crisis as I was after my rudimentary research this summer. I registered to vote in California and got a thick voter information packet that I’ve barely begun reading.

Some other dropouts I’ve spoken with who’ve chosen to return to school have told me that leaving school gave them a very clear sense of what exactly they wanted out of it, and I’ve grown increasingly convinced that college — if done right — offers exactly that broadening of my perspective I’ve been seeking.

As my mentor said, though, I “have time.” I can’t do everything at once. I’ve been giving serious thought to going back to school sooner rather than later (and if I do, hopefully I’ll be able to pay for it myself).

But I’m not completely sure yet. If anything, this past year has given me a lot to think about in terms not only how I should spend this next year, but the rest of my life. Do I want to make my career writing software for whomever will pay me the most money? What else can I do that I don’t know I can do just because all I’ve done so far is write code? Why am I building what I’m building now, and why am I doing what I’m doing now?

I have a lot more thinking to do, but I guess I have my whole life ahead of me to figure it out.

Afterword: Why You Shouldn’t Drop Out

There are a few things about my situation that made it easier for me to take time off — here are some practical considerations to determine whether it’s right for you. It’s been an awesome experience for me and I’m happy to chat at, but as many things are, it’s highly dependent on your individual situation and the only person really qualified to make a decision is you.

As usual:

This is an opinion and is for informational purposes only. You should not construe this information as legal, tax, investment, or financial advice. This is not a solicitation to buy or sell securities. You should consult your own legal, tax, investment, or financial advisors before engaging in any transaction.

Financial Aid

If you drop out and lose full-time student status, you might have to start paying back your student loans or lose your grant aid (I lost my National Merit Scholarship). You should read the terms of your aid and understand the financial consequences of disenrollment before making any decision.

Student Visa

I’m lucky to have U.S. citizenship, but if you’re an international student, dropping out of college might compromise your visa status.

I don’t have much else to say other than that the system is messed up; two of our founders are international and we’ve spent a significant amount of time figuring out work authorization.


Having a well-known tech company on my resume opened a lot of doors, and with a week or so of grinding Leetcode I think I can reliably pass technical screens. I was fortunate to be considered by other companies and to have the option of staying at Google, but I’m not sure if I would’ve been comfortable with dropping out first and trying to find work second if I didn’t have those options.


I’ve been coding since I was a freshman in high school, was set on majoring in CS when I applied to college, and generally saw the Bay Area as the place to be after graduation. I had a pretty clear understanding of the direction I wanted to take during my year off. This has made finding stuff to do relatively easy.

If you don’t have that clear direction, it might be difficult to make the most of your gap year. On the other hand, a year off is also a great chance to explore a wide range of potential career paths. In that case, it might be good to do a bit more planning and have a few specific jobs/positions/activities locked down so you can make the most of your year.


Although more and more kids are taking time off from school, it’s definitely not for everyone. It’s understandably difficult to leave a tight-knit community of people your age, and leaving college might be the first time you ever do that. It should go without saying, but if you choose to take time off, you should be capable of living independently and handling being wrong about your decision. I might be completely delusional about leaving, but I know it was a decision I personally made and I’m comfortable living with it.

Finishing College

I’m 19 years old and college is still very much a possibility at this point. Having a solid amount of AP credits puts me on track to graduate with my friends if I go back after a year and I wouldn’t be opposed to hanging out with other fifth years in my grade if I took two years off.

We’re trying to hire a new engineer at the startup to start within the month, and there are quite a few juniors and seniors in college we’re trying to recruit who seem like great fits, but they want to graduate and start in May or June. It makes perfect sense to me — they have significant sunk costs and the most valuable year of college is the year when you get your degree. If you’re close to finishing college, it might make more sense to stay.

Thank you to Leanne Shen, Jason Shu, Samay Shamdasani, Noah Finer, Neehar Banerjee, and Jessica Miao for reading drafts of this.

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by Nathan H. Leung

Hi, I'm Nate. I taught myself how to code before college, and I entered the University of Michigan in the fall of 2018, where I discovered interests in math, economics, and personal writing.

College was a serious step up from what I was used to in high school, so one especially late night my second semester, while working on a problem set in the math atrium — I decided I had enough. I needed a break from school.

I began planning a gap year in Barcelona and reaching out to old web design clients from high school for contract software work. Those plans went out the window, though, when I miraculously landed an internship at Google for the coming summer.

So, when school let out in May, I flew out to San Francisco and moved into a place in the Mission District instead. I soon realized that much of what I was looking for in my gap year — the unparalleled personal and cultural growth that comes from living alone in an iconic, bohemian city; a hungry market for entrepreneurial software engineers — was right where I was in San Francisco.

In August, I officially disenrolled from my sophomore year of classes. I got my travel fix in September, zooming across America and visiting Los Angeles, Ann Arbor, Boston, Philadelphia, and Chicago as part of a ten-state excursion, before heading back to San Francisco by way of 52 hours on Amtrak.

In October 2019, shortly after the founders completed YC S19, I joined Jupiter as their first hire. Outside of establishing a strong engineering organization and codifying our guiding development philosophies and practices, I've spent the last few months building end-to-end systems with TypeScript, React, Kotlin, gRPC, and Kubernetes.

I started this little blog to share some of these experiences — I hope you enjoy.