Carpe Annum

My 2020 Gap Year Playbook (for Startups and Tech)

Wednesday, July 29th, 2020 · 23 min read

But she won’t drop out, her parents will look at her funny
Now, tell me that ain’t insecure
The concept of school seems so secure

— Kanye West, “All Falls Down” (2004)

A beach in LA

When I wrote about leaving college back in February, I had a rather subdued conclusion:

It’s highly dependent on your individual situation and the only person really qualified to make a decision is you.

“Why I Dropped Out”

A lot has changed since February — including, potentially, those “individual situations.” With many schools going partially or even fully online this fall, taking a year off of school is making a lot more sense for some people — especially so for CS students. A few reasons:

  1. College is offering a lot less (at least, perceived) value — $50,000 for Zoom University? — so the opportunity cost of a gap year is unprecedentedly low (there are no on-campus experiences, roommates, or football games to miss out on). For a CS student who never attended class anyway, virtual school eliminates almost the entire value-add of college.
  2. The scope of potential opportunities in technology has expanded with the accelerated transition to remote work; you don’t need to live in a tech hub or go to Berkeley or Stanford to have a side gig with a tech company anymore (although with increased demand, these opportunities may be more competitive — which is why it’s important to land an internship before taking a leave of absence).

Although many of the considerations I touched on in my previous discussion (financial aid, student visas, progress towards your degree, etc.) still apply — and the economic and geopolitical impacts of COVID-19 have undoubtedly complicated those considerations — for those who are able, who ideally have a bit of coding experience, there’s no better time than now to consider taking some time off.

Here’s the playbook I recommend.

Syntax highlighting in VSCode

Step 1: Learn to Code, Startup-Style

Besides programming, I can’t think of any other profession that employs so many self-taught people who often have degrees in completely different fields, or even no degree at all.

Besides programming, I can’t think of any other profession that hires teenagers with little to no prior work experience for six-figure salaries.

And besides programming, I can’t think of any other profession that’s already so accustomed to remote work that there are companies that have existed for years without ever having an in-person office.

Coding is one of the most accessible fields to self-teach, one of the most in-demand skills in the market right now, and one of the most adaptable jobs to remote work. It’s quite frankly the perfect skill to have in a COVID world. And especially for someone interested in working in tech, there’s no better way to break into the field than as a programmer.

So if you haven’t already, I’d recommend learning how to code, specifically with the tech that’s hot right now with industry and startups; think Node.js or Python rather than whatever C++ or Java they’re teaching you in school, so you can be immediately useful. If you already have some prior experience, do some real projects with these technologies.

If you’re not sure what’s “hot” right now, the Stack Overflow Developer Survey is a great way to find out. For instance, “TypeScript” is #2 in the “Most Loved Languages” section and “React.js” is #2 in the “Most Loved Web Frameworks” section (and we use both at Jupiter). Both are great to know for work at an early-stage tech company.

When I was starting to learn how to code, I first read a book about JavaScript fundamentals, and afterwards applied that knowledge to several personal projects. I’d recommend a similar approach for new learners, because working on fun personal projects doesn’t feel like work. Even better, as your projects grow and change, you’ll pick up extra skills along the way.

For example, the only reason I know how browser cookies work is because I needed to learn how to set them correctly to scrape my class schedule off my high school’s student portal. I learned how to buy servers in the cloud because I wanted to make a project available to others that didn’t shut down whenever I turned my computer off.

I’m not saying here that coding is the end-all be-all skill to learn for the rest of your life, but the bottom line is that knowing how to code — especially with the languages and technologies that are most commonly found nowadays at startups — makes putting together a productive and profitable gap year significantly easier, especially so for those looking to work in technology.


  • Making a Website for Free — if you have zero coding experience, this will teach you the basics of HTML/CSS.
  • Eloquent JavaScript — A book to learn JavaScript fundamentals.
  • — I made my first web app off of a tutorial from this website.
  • Enlight — Learn to code with mentorship and peers through projects (made by a good friend of mine at the University of Michigan!).
  • freeCodeCamp — A very popular website for coding tutorials (founded in October 2014 — I didn’t know about it when I first got started, but I’ve heard good things).
  • React — The most popular user interface library right now. The tutorial on their website is great.

Flying out of Philly

Step 2: Land a Fall Internship

Some of you who read Step 1 have probably already tried coding and hated it.

Unfortunately, I recommend coding because it makes this second step — landing an internship — so much easier, especially if you’re less experienced.

Although you might come across nontechnical internships as a product manager, growth marketer, or in business development, these roles are typically reserved for older students. They are also primarily hiring pipelines, meaning that the company wants more senior students who can commit to working at their company longer-term in the immediate future. To be fair, most internships are hiring pipelines, but switching companies frequently is more common for software engineers, and companies are aware of this.

So, if you’re on the younger side (think freshman or sophomore), coding can be your ticket to an opportunity where your resume otherwise wouldn’t get a second look. Companies of all sizes hire younger students for engineering internships, and startups are especially willing to take a chance on someone less experienced. If you can show your initiative and be a valuable team member, early-stage startups generally care less about where you came from, whether you went to (or finished) college, or that you’re on a gap year.

In terms of landing an internship at the best possible startup, I would recommend specifically reaching out to Y Combinator (YC) startups (like the one I’m currently working at full-time, Jupiter).

If you’re not already familiar with the program, YC is a startup accelerator based in San Francisco. Twice a year, about 200 companies go through their program, and YC gives each company about $100,000 for a small percentage of ownership. The accelerator is famous because it has had some wild successes with multi-billion dollar companies like Dropbox, Airbnb, and DoorDash.

Due to this track record, YC companies have a bit of a “halo” and get a lot of interest from the venture capital community. These companies are perceived as being much more likely to succeed than your average startup (although that’s not to say it’s much easier — the perceived chance of becoming a billion-dollar business might go from 0.00006% to 0.0006%). YC companies also tend to have access to great mentors and resources that other companies might not have.

That said, a YC startup is still a startup, and it will be just as grueling as any other early-stage company. Speaking from personal experience, these companies have as much of a need for any help they can get as any other early-stage venture.

That said, with the support of the greater YC community, they typically have enough funding to comfortably sustain themselves for the immediate future. In other words, YC companies can usually focus their efforts more so on growing quickly and improving their product — the important things — rather than trying to raise money and stay afloat.

To recap:

  • Startups are the easiest place for a nontraditional student (like gap year, low on experience but high in hunger to learn) to find work.
  • YC startups are often the best of those startups.
  • Even if “YC” seems exclusive or elite, if you’re hungry to learn and ready to take initiative, your offer to help will surely be appreciated — so don’t hesitate to reach out! Even if there isn’t a great fit at the time, there may be one in the future and it’ll be good to establish some sort of relationship with the company now if you’re truly interested in their product and/or mission.

Unpaid internships are not a common practice in software the way they are in other fields. You should be paid at least a nominal wage for your hours, and I’d say $15 to $25 an hour is “fair” for someone with less experience (keep in mind that some bigger companies pay their interns $35 to $50 an hour). I’d try to get at least that much, and a company that can’t offer at least that much is probably not a great one for an internship now (although it may grow and become a good one later on).

Afterwards, another benefit of the YC community is that if you do a good job, your current company can refer you to other great YC companies to work for down the road.

If you’re not interested in startups, doing freelance development (e.g. making websites for local restaurants), volunteering through technology-focused organizations such as the U.S. Digital Response or Code for America, or taking free CS courses through MIT’s OpenCourseWare are also great ways to spend your fall, but working at a startup is the most direct way of putting yourself in a good spot for a career in tech and what I’ll focus on in the sections going forward.


  • Work at a Startup — A directory of YC companies looking to hire. In response to increased demand for fall internships, YC actually just recently updated their Work at a Startup internships page specifically for Fall 2020, so definitely check it out.
  • YC Companies — A list of all publicly-launched YC companies. Some companies (especially more recent ones) may not have registered on Work at a Startup but might still be looking for help. Use this to supplement your list of target companies from Work at a Startup.
  • Founders’ email addresses — If you can write a good cold email and the founders have publicly shared their email address, emailing them directly could set you apart and demonstrate initiative (but be respectful — I know I don’t mind a good cold email but I’m not 100% sure about others).
  • There are a lot of great resources about writing cold emails on the web, but here’s one template you could use, building on the skills you developed learning how to code:

    Hi {{startup}} founders,

    My name is {{name}} and I’m a {{year (freshman, sophomore, etc.)}} gap year {{major}} student at {{college}} looking for a fall internship. I love the work you’re doing with {{startup}}, and I’m especially interested because {{why the company piqued your interest on the directory}}.

    I’ve also been learning {{tech you’ve learned, like JS, React, Node.js, etc}} and I viewed the source code on your website and noticed you’re also using {{tech they’re using}}. I’ve built {{links to some projects you’ve built while learning}} with {{tech they’re using}} and I’d love for the opportunity to continue honing my skills this fall and help build your product too.

    I’ve attached my resume in case it’s helpful! I know you guys are busy, so no need to respond now (happy to circle back in a few weeks), but I’m super excited about your product and I’d be honored to have the opportunity to help bring it to market.



Michigan boys

Step 3: Disenroll (“Drop Out”)

I specifically put this step after “Land a Fall Internship” because you really should have a good idea of what you want to do before actually leaving. (For what it’s worth, committing to a gap year and filling out the paperwork before worked for one of my friends, but I would not recommend it).

Make sure you get familiar with your school’s gap year policy. By what date do you need to disenroll to avoid any tuition charges? How long can you take off? What’s the process for re-enrolling?

If you’re on a student visa or receive financial aid, there may be specific conditions that you should be aware of.

You might also want to think about taking a community college class or two online — if you entered college with a decent bit of AP credit, you likely can still graduate with your grade if you take an extra class or two. Look into your school’s transfer credit policies for more information.

Taking community college classes might also save you a lot of money — Michigan costs me upwards of $2,000 a credit, while I’m currently paying $50 a credit (40 times less) to take a four-credit physics class from a California Community College (go Cougars!). If I go back to Michigan to finish up my degree, that’s $7,800 saved.


  • The University Registrar — If your school’s website doesn’t answer all of your questions, email your question to the “University Registrar” or “Department of the Registrar.” The email address for Michigan students is
  • Your school’s transfer credit equivalency page — Your school will likely have a website which shows which community college classes transfer in. One example of such a page is Michigan’s Transfer Credit Equivalencies search. If a class is not listed, email the department you’d want to transfer it into (e.g. email the math department if you’re planning on taking differential equations) and they might be able to grant you an equivalency.
  • — For students attending public universities in California, this site has all the information you need for transferring community college credits to your school.

Remote work on the Jersey shore

Step 4: Work Remotely in the Fall

This step is pretty straightforward — spend your fall gaining valuable experience (remotely).

There’s been a lot written already about how to make the most of your internship, so I’ll be brief here, but I want to emphasize that you should make sure you schedule regular one-on-one meetings with your mentor or manager, so you can get feedback on your work as the internship progresses.

In addition to getting a sense of how you’re doing in your job, these one-on-one meetings can also be an opportunity for you to ask for things that might be out of the scope of your role but still can be extremely valuable to your overall experience, like the chance to prototype a new technology for a new project, or a meeting with the CEO or other senior leaders.

Outside of work, try and find a community of other like-minded students. Especially if you’re just out of high school, it might be hard to develop a daily routine and find a sense of community without the structure of school; even more so while working remotely. There are a bunch of new online communities popping up in response to increased interest in gap years this fall, so consider joining one. Also, COVID has seemed to make people more open to making friends online, so don’t be afraid to Twitter DM or email interesting people, and create your own little community, too.

In the physical world, it might be fun to get an Airbnb somewhere with other friends who are also taking gap years (or even just online classes), but assess the virus situation and make sure you stay healthy above all.


  • Gap year communities — There are a bunch popping up on Twitter and LinkedIn right now, so searching those sites for “gap year community” might help you find something. Hiatus is one such community, founded by another friend at Michigan.
  • Xoogler School — I’m part of a Google alumni community called Xoogler, and they’re putting together an 8-week program this fall for gap year students taught by tech industry veterans. It’s a paid program and I’m not sure if it’s feasible to have a full-time internship at the same time, but it was a unique opportunity that I didn’t see posted in many other places so I figured I’d share it here.
  • YC Internship Program — Y Combinator puts together a great community every summer for interns at their companies, and due to increased interest in fall internships, they may create a fall community too. If you’ve landed a job with a YC company and this sounds like something you’d be interested in, feel free to email Ryan Choi, who runs the program, and let him know! (Or email me, and I can let Ryan know too, although he’s always open to suggestions from anyone and is generally super responsive to email).


Step 5: Learn Personal Finance

If you haven’t worked full-time before, now is also a good time to learn how to get your finances in order. I’d set up a personal checking/savings account (separate from your parents’) to deposit your paycheck and open up a Roth IRA (a type of tax-advantaged retirement account) to stash retirement savings. Max out your company’s 401(k), if they have one and offer it to interns.

In addition, if you’re living on your own and spending your own money for most of your personal needs, it might be good to get a credit card and start building your credit. A longer credit history will help you get a lower rate on car and home loans in the future.

Once you do these things, use tools like Mint and Credit Karma to keep tabs on all of your accounts.

Learning these things now will prepare you for when you get your first “real” full-time job and HR throws terms at you expecting you to know what to do.


Google Bikes in Silicon Valley

Step 6: Apply to FAANG for Summer

Both small startups and big corporations have things to offer in terms of learning opportunities. Even though the pace of growth might be faster somewhere smaller, to round out your experience, it doesn’t hurt to apply to a large FAANG-type company for a traditional summer internship sometime during the fall too (applications for the following summer will typically open up in the late summer or early fall of the previous year).

Personally, I thought I was a pretty good coder going into my Google internship having worked at a local startup after high school and having shipped a bunch of side projects beforehand, but the things I learned while at Google — stuff like how to structure my PRs, how to do code reviews, what makes a good deployment process, and how to formally approach designing good software — no doubt made me a better engineer, and much better prepared for my work at Jupiter as a founding engineer.

From a more career-focused perspective, it can hopefully be the start of a flywheel: working at a small startup will give you the “experience” that’ll help you land a job at the big company, and having the big company on your resume will help you work for the hottest startups (if that’s what you’re interested in) and might help you get more attention elsewhere where previously you might’ve been overlooked.


Cave rock in Tahoe

Step 7: Travel?

Fall will come and go. By now you’ve hopefully been working for a few months and have a decent bit of money saved up. If you’ve been staying home, enjoy the holidays with your family, and if you haven’t, maybe take a trip back (but get COVID tested first).

Now is also a great time to start thinking about what to do in the spring.

It’s up to you as to whether you want to keep working or not, but if you’ve got enough saved up, a big company internship coming up in the summer (in which case you’ll surely be well-taken-care-of financially), and COVID is hopefully being managed better, it might be good to ease off of the grind and travel a bit.

Maybe you were going to study abroad last year and it got cut short by COVID. Perhaps visit that country and live there for a few months — make your own personal study abroad program. Maybe you’ve got a bunch of friends at different schools all over the country. Plan a road trip and visit them all! The possibilities are endless.

You can do things in your early 20s that you can’t do as well before or after, like plunge deeply into projects on a whim and travel super cheaply with no sense of a deadline. For unambitious people, this sort of thing is the dreaded “failure to launch,” but for the ambitious ones it can be an incomparably valuable sort of exploration.

— Paul Graham, “Before the Startup” (2014)

If COVID is still ongoing, perhaps look for something closer. If you’re from the Bay Area, get a cabin in Napa or Tahoe for a few months. You could definitely keep working for the same company, and it might be a nice change of pace from home.


  • Airbnb — Airbnb’s great for this type of stuff. My first summer in SF, I ended up booking an 84-night Airbnb because I was having too much trouble finding a non-scammy-looking sublet. If you’ve never created an Airbnb account before, throw my referral link some love and you’ll get $20 off your first booking (and I’ll get $30 of travel credit too).


Step 8: Intern in the Summer

It’s a little bit harder to predict what the world will look like next summer, but regardless, you’ll want to take a similar approach to a big company internship as you did at the startup: make the most of it.

Schedule a regular one-on-one meeting with your manager. Take initiative by emailing VPs that are leading projects you’re interested in. Since these companies often offer free food, the bar is so low to asking other employees to meet over lunch (maybe search LinkedIn for people at the company who went to your school). Among other things, you can get great career advice from these meetings — for instance, you could ask these coworkers why they chose the big company over a startup, since that’s something you’ll have to figure out as well once you graduate.

Outside of your company, summer is also a great time to meet other interns, too (if quarantine is over). Join summer intern communities to meet other people at a similar stage of life and career. In addition to sharing referrals (they might help you get your next job) and company lunches (I was able to try the food at Uber and Airbnb last summer), these communities are also great for finding a group to split a car rental to Big Sur or Yosemite on the weekends.


  • Summer intern groups on Facebook — Search for stuff like “Bay Area Interns Summer 2021”, “Google Mountain View Interns”, etc. There are always a bunch every summer.
  • Slack communities like and — These are classic summer intern communities that have been around for a few years now. These communities may also be adapting to COVID and offering off-cycle (i.e. fall and winter) activities as well, so do check them throughout the year.
  • Intern recruiting events — Companies often host recruiting events over the summer, and they’re a great place to meet new people, too. You’ll typically find out about these through the intern groups linked above — I went to one at Twitter and one at Apple last summer.
  • VGraupera/1on1-questions — A great list of questions you can ask during your lunch meetings with coworkers to keep the conversation going.


Step 9: Return to School (or not)

The working world can be seductive. Every day, you gain skills that you know will actually be useful for your career. You (hopefully) work with ambitious people that push you to do your best and you make a tangible impact on a real product. It’s probably less stressful than school, and you’re getting paid too.

So by the time your gap year is over, maybe you won’t want to go back.

I’ve had a lot of time to think about this decision, and there are a lot of things I’ve loved about taking time off, but to be honest, as of now I think I’m leaning towards going back to school (though this is a discussion for another time).

Regardless, what I end up choosing to do doesn’t matter — because at the end of the day, the only person really qualified to make a decision is you.

But back to now. This year is a special one. Whatever you do, get out there and seize it.

Thanks to Jeong Shin, Neehar Banerjee, Alex Becker, Cynthia Chen, Kirti Shenoy, Shiqi Sheng, and Kelvin Yu for reading drafts of this.

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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.

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