I’ve always been conflicted about my path after college. This is how I completely reversed course, and why I’m excited about it.

Entitlement

I had a hidden thought all throughout college I never really noticed. I consistently worked hard and actively pursued new projects, but at the same time, I felt I was owed something because of what I did in high school.

During senior year of high school, I held three major leadership positions and maxed out my schedule with AP courses, with an online AP Spanish course for good measure. So that was my day-to-day while I was summarizing 18 years of existence into essay form to prove myself to college admission committees across the nation.

Most days on the trek to school that first semester, I literally slept while I walked, opening my eyes every few steps to make sure I wasn’t about to stumble into the nearby creek. Once, I was nauseous and threw up in a bush on the side of the path. I gathered my breath, spat out bile while my little sister watched in abject terror, and then I kept walking. I couldn’t afford to miss a day.

Even as I write this, I feel a sense of pride and indignation stirring within me, like that bush vomit is a badge of honor. I pushed myself to the edge of sanity and got into Stanford as my reward. My classmates validated this mindset as well. I humbly soaked in the praise on Facebook, in yearbook signings, and in person: “Congrats on Stanford — you deserve it!” Why would I ever have to apply for anything or prove myself to anyone again after enduring that?[1]

Internship

As soon as I got to Stanford, I discovered that life had moved the goal posts. No time to rest — I had to apply for internships so I could later apply for jobs. I was resentful and jealous of peers who spent their summer at Google or Goldman because in my mind, they had reached the finish line. They got the Brand-Name Internship™ and now they could coast for the rest of their lives.

Spring quarter freshmen year, I rushed and ended up joining Phi Psi. One of the reasons I joined was because I admired how smart and hard-working the people I met were. Ironically, those qualities became a source of dread and competition once I moved in. Even though I liked CS, I felt like I showed up late to the party. It seemed like half the guys in my year were already section leaders[2] or had been coding since the womb. There was no way I could compete with them to get an internship.

I grew afraid. Any rejection would be a rejection of who I was as a person, that even my best wasn’t good enough compared to the best of everyone else at Stanford. So I didn’t apply. I couldn’t fail if I didn’t play the game.[3]

Ownership

Every year would start off with some initial dread as career fair dates flooded my inbox, but I would suppress it with the affirmation that I wouldn’t even apply. Dread would give way to an uneasy sense of relief, like I had dodged a bullet by not showing up to the shootout.

My brain rationalized the decision, as brains are wont to do. The interview process was an artificial barrier for those who don’t know the right people. Because I didn’t know the right people, it wasn’t worth even trying. People I knew from high school were working at software companies now. Then what was the point of busting my ass to get into Stanford if I just ended up in the same place as them? I didn’t get into college by following the standard path of science fairs or math competitions, so I wasn’t about to step onto the standard path now.

I’m interested in a lot of things, and that’s reflected in my work experience. Looking back, the common thread across my summers was ownership: I had control over what I was doing. As the sole graphic designer for Stanford Student Enterprises, I called all the shots for how print and web products would look across campus. As a CS researcher, I proposed and designed my own study on human-drone interaction. As the sole software developer on a Stanford Med School project, I worked from home, set my own hours, and traveled when I wanted to. Why would I ever go to the effort of competing, just to end up as the cog in some giant corporate machine?

At the start of this school year, I applied for Pear Garage with Will and Andrew, the two other kids from my high school who got into Stanford my year. We shared the motivation to forge our own paths and had complementary skill sets.

It was exciting when we got in. We were on our way to making new wealth and taking control of our lives! Yet over the quarter, both Will and Andrew dropped from the program, leaving me on a team of one.

Facing reality

The turning point happened at the end of winter break. My mom asked what I was doing after graduation several times, and I waved my hands about how I would do Pear on my own now that I was taking winter quarter off. I had to admit though, I wasn’t motivated anymore. Without a team, I was back to how things always were: working by myself.

In a similar vein, I also planned to spend the quarter off exploring my artistic interests, which I had once again shoved aside during the fall. Yet throughout the entire three weeks of break, I never once picked up a pencil to draw in my sketchbook. I would open it up, but then I would feel guilty about making art when I should have been working on getting a startup off the ground. I was making zero steps towards either goal.

My mom was worried I was going to limit my opportunities by not even considering full-time jobs. I defended myself, as I had for years. I didn’t want to work on a fraction of a codebase to increase corporate revenue by a fraction of a percent. All my friends who worked regular jobs were so boring now, and I didn’t want to become boring. I would be too tired to make art after work. My 20s were the best time to take risks. I had read The Crossroads of Should and Must by Elle Luna and decided that applying for full-time jobs was my Should, but I couldn’t articulate what my Must was.

I began to have my doubts about my current “plan.” As great as control and ownership were over the past few summers, they literally came at a price: I earned enough to make Bay Area rent but not much more. I had ownership because they were relatively small projects. I told myself I didn’t need a lot of money in my 20s, but I couldn’t say I was working towards eventually making more as a startup founder or artist either.

Was I stunting my future purely out of stubbornness? I considered if I was avoiding the job search for reasons other than ownership. I considered fear.

Identity crisis

As I’ve mentioned, I liked CS, and I grudgingly acknowledged that software jobs were flexible and paid ridiculous entry-level wages. After talking with my mom, I decided that instead of spending the quarter off doing art and halfheartedly attempting to work on a startup, I would buckle down and prepare for technical interviews and apply for jobs.

I hugged my mom good night, but no matter how I sliced it, I had reversed a core tenet of my identity — don’t apply for “mainstream” jobs — and my identity was having a difficult time adjusting. Had I just been making wrong decisions for five years? It took me hours to fall asleep that night. I woke up the next morning with a sore jaw because I had been clenching my teeth the entire night.

I moved back into Palo Alto as winter quarter started, and the sense of dread mounted as I read articles on interview prep and realized how far behind I was. By avoiding any experience with the application process for four years, I had created a self-fulfilling prophecy. I tried to protect myself by not playing the game, but that left me way out-of-shape once I decided I wanted in.

I thought bitterly about how cowardly I was. If I had sacked up just one quarter earlier, I would be chilling right now. Even as dejected and overwhelmed as I was at that point, I’ve always believed regrets are pretty useless thoughts to hold onto. I pushed forward, and as the week progressed my outlook began to change.

Things change

At the time, I was reading a book by Scott Adams, and two points stuck out to me:

• View failure as a tool, not an outcome
• Success is a slot machine if you have the tenacity to keep pulling the lever

The book is a good read overall, but those two points jumped out as the most relevant to my identity crisis. Failure was not an assault on my character. Because I got into Stanford, I subconsciously set the bar for my post-college life ludicrously high: that whatever I did had to at least match the prestige of getting into Stanford. It was my inner high school senior, demanding that I get my reward for working so hard at Stanford and to prove to the world that I was still impressive. I had forgotten that I was rejected from twice as many schools as I got into.

I would still wake up thoroughly unmotivated to study, but I reached out to friends and was surprised to find how generous and helpful they were, giving me all sorts of tips and offering to help me prepare. Not only that, simply opening up about my nervousness somehow motivated me to start working.

I assumed I was the hero in an underdog story, and all my friends were frightened mainstream sell-outs grasping for easy money while I was bravely forging my own path. After talking with my friend Matt and thinking about the friends I’ve caught up with recently, I realized that this obviously wasn’t the case. I assumed that my graduated friends’ entire identities revolved around their jobs because I was projecting and anxious that it would happen to me.

For some people, the job does become identity. A startup founder or CEO is the brand of their company. But my friends hadn’t changed just because they were working now. We still talked about our miserable love lives or passion projects we were working on. The only difference was they weren’t worried about money anymore.[4]

I was impatient to have everything right out the gate. I toiled through high school and Stanford — where was my reward? But as my mom, Tim Urban, and Simon Sidek pointed out, I wasn’t old at 22 years old. It felt that way because the past decade of school and soul-searching currently accounts for almost 50% of my existence. But that percentage decreases with every passing day.

Besides, there’s no reason to let my past dictate my present.

Even if software is a “standard” starting point out of Stanford, the path I pave will still be my own. I told myself I would hate working at a software company to protect myself from rejection, but I admit I have no idea whether or not I would. I always assumed I would be working on an infinitesimal fraction of a code base, but I’ve been talking to startups and smaller companies and realize that more ownership is possible.

Right now, I’m looking to get a job because I have so much to learn about software engineering and because it will free up my headspace to actually work on creative things again. I’m not forcing myself to mix the two anymore. My artist block over winter break stemmed from anxiety over supporting myself, and once that’s secured, I’ll be relaxed enough to start again. I was worried that I would be too tired to make art after working all day, but Scott’s book has taught me how to generate the energy I need to stay motivated and crank out dope stuff.[5]

Whatever I end up doing, my job will challenge me to grow technically and as a person. Just as important my job will allow me to pursue what I want outside of it. I’m applying to jobs now with a clear head and reasonable expectations.

So here we are

Although it’s possible that I would be chilling now if I had gone through this change-of-heart last quarter, it’s more likely I would have been recovering from a panic attack. If I was grinding my teeth over this during winter break, I would have broken my jaw if I made this decision during fall quarter, while I was leading sections and grading as a TA, taking the most agonizing class of my life[6], and generally adjusting to off-campus life.[7] In general, I operate better when I can focus on one thing at a time, so this quarter off might be the best opportunity I have to catch up in job prep.

I don’t know if there’s anyone I could have talked to who would have changed my mind anyway. It always felt like I was spinning my wheels when I was talking to people my age about this, and I don’t know of any older role models with similar backgrounds whose path I could have mimicked.

In the end, I had to explore the other options first before I could convince myself it wasn’t the right time to do them. If I jumped right into a full-time job without hesitation, I’d probably be kicking myself for selling out and fantasizing about how successful I’d be if I had instead started a company or pursued art full-time.

If it wasn’t obvious from the stuff I wrote about high school and summer experiences, I was cocky. Scared and cocky — what a winning combination. But just looking at the job descriptions for the companies I’m applying for has knocked me down a few pegs. In terms of what I’ll learn working on a team at a company, I don’t know what I don’t know.

I still believe that the 20s are the best time to be risky, but I inadvertently took the risk of not applying for jobs earlier. Thankfully, I still have the opportunity to bounce back. Failure is a tool, not an outcome. Ultimately, I don’t have the obsession/motivation to put in the hours needed to start from scratch, and I definitely don’t want to do it all on my own. I’ll meet new people once I’m working, and new friends become new co-founders and collaborators.

I just want life to be simple for a little bit. I need to catch my breath after a five-year sprint of exploration and soul-searching. Then I can either continue climbing the mountain I’m currently on or discover new peaks from my new vantage point.