Staff Software Engineer

I'm Twenty

I know it might come as a shock, but I’m actually twenty years old. This is a fact that I do my best to ignore most of the time, but the past week has shown me there’s been a cost to that. You see, a typical twenty year old is in college, probably working a job on campus in between attending lectures, inviting themselves to parties, and doing countless hours of homework. That life was certainly a lot more familiar to me at nineteen, before I took a year’s leave of absence to work full-time in San Fransisco. Eight months into my tenure in San Fransisco, and eleven months after I drove away from my dorm at the end of my first year at UChicago, I’m ready to take stock of what, exactly, this experience has done to me.

When I drove East from Burton-Judson last June Thirteenth, I was clearly a changed person from the one would moved into college housing a mere nine months earlier. For one, I was a hell of lot better educated, having been able to stretch my academic muscle far better than was ever possible in high school. But beyond the question of academics, things were a lot murkier. I’d spent my first year away from home, but I’d done so in a veritable pressure cooker, where students took pride in spending more hours in the library than anyone else. I also hadn’t taken well the notion that an entire academic quarter was devoted to being locked up, trapped by a bitter and cruel Chicago winter. Instead of relishing the opportunities of youth, I was embittered by the follies of a young adult who was convinced beyond a shadow of a doubt that he had absolutely no growing up left to do. In retrospect, I can see how stupid that was.

I was a stranger to serious romantic relationships, my last one ending at the start of my sophomore year of high school. I substituted intimacy with hard work on open-source projects, and soured towards those who were ensconced in happy partnerships. I had friends, sure, but in deficient quantities both throughout high school and in college. There were always the stalwarts, sure, but I found myself often frustrated that I couldn’t make plans when I wanted to. I was also reluctant to commit myself to any sort of group membership, for some reason or another. And thus I felt very lonely. I still do, in some respects, but as I shall describe later on, those sorts of emotions have morphed to be something far less destabilizing than they once were.

The duo of working my ass off for many years in a row, without any serious respite (I was also quite studious in high school, probably much more so than was strictly necessary) and the bout of intense loneliness no doubt spurred on by the distance from any family caused the most intense sensation of burnout and frustration that I’ve ever experienced, and it didn’t go away. No success was sufficient to buoy my spirits, and every temporary setback made me feel even more distant from everyone around me. Even though I was in college, I was incapable of having fun for more than a few hours at a time, and even then it usually required a fair dose of alcohol and some coaxing to loosen up for once. Even as my career began in earnest, and I rose to prominence through open source projects such as RestKit and CocoaPods, and landed an internship on the incredible Tumblr iOS team, none of that made me happy. There were scant minutes of celebration, always followed immediately by a nagging feeling of what’s next.

I confided in some developer friends that I thought I needed a break. I couldn’t imagine another nineteen years where I was struggling so hard to find a baseline level of contentment. I couldn’t find respite, much less happiness – I was just too jaded. And let me tell you something – you don’t want to feel jaded at nineteen. So I harbored a desire to somehow take some time off, but I knew deep down that it was a pipe dream. My dad would certainly not approve of me leaving university, and I had no where really to go for any period of time that could possibly be construed as a constructive use of my prime years. And then Elóy told me about Stripe’s open source retreat, and there was a concrete port towards which I could dream of anchoring my desires. As I’ve written more than once before, I has nearly certain that my application wouldn’t be accepted, but it was a solid opportunity that had clearly explainable benefits, and wouldn’t sully the image I was trying to project about my trajectory in life. It wasn’t a break from college, I could say, but an opportunity to do something even better before returning for a year! I’m not sure I really believed that, but I was convincing. It also turns out that I was right.


I left my first year of college disappointed in my lack of progress. I was nine months older, twelve classes wiser, and yet I felt like I’d barely been treading water for that time. Where was the immense growth that was supposed to come at this crucial juncture in my young life? Was I not on the bridge that picked my up on the rocky beaches of adolescence and safely delivered me to the sandy beaches of adulthood? Apparently not. I’d had a short fling at the end of the year, but apart from that I hadn’t engaged in any other relationships. I’d made friends, even confided in them, but that wasn’t enough. I barely slept, and had trouble keeping my eyes open during classes, even when I desperately wanted to. I had holed up in my room too many nights to count, putting off doing work, and then feeling absolutely miserable with myself for my inability to be productive. It was probably worse than in high school, although it’s quite honestly hard to say, given the myriad differences, such as lack of parental influence and also much more flexibility with which I could slack off. I was binge-eating more than ever, I was running much less than before (both of which are, of course, partially attributable to winter). Things flat out were not getting better.

And so I relished the chance to take a break, to back off and give myself a chance to finally reset. I’d been in high gear since late in elementary school, and the cracks were beginning to show. I not only wasn’t growing up, but rather I was exacerbating every existing bad tendency. I remain convinced that continued, uninterrupted application of that college strain would’ve caused me to finally crack before I managed to graduate. I even strove to complete three majors, sure that it offered a way for me to be content with my time in college. So much for maturing, right?

And, after my rather uneventful summer at Tumblr, in which I worked 40 hour weeks and didn’t need to push myself too hard, I packed up my life and moved out to San Francisco. I was going to live in my own apartment, and work my own job, and generally speaking take things easy. I was scared that I would become listless without the directed goals of school to guide me – after all, my life had been governed by school in one form another since I was approximately two years old – school life was basically all I knew. So this was going to be something different.


Let me make one thing incredibly clear – this year has probably been the single best thing I’ve ever done for myself. The Samuel that’s writing this while flying back to San Fransisco after a speaking trip that included six days in Hyde Park, blocks away from my dorm, is not the one that drove off last June – he’s not even the same Samuel that made a Halloween visit and came away disappointed. I unequivocally believe that I, the Samuel that’s writing these very words, has finally grown up and made good on all the things I’ve wanted to promise myself – not in material things, necessarily, but rather in the fact that I’m finally taking care of myself.

This isn’t to say that I’m suddenly a wizened, ornery old man, but rather a proper adult – a human being capable of self-sustenance in mind, body, and spirit. I have an incredibly fulfilling job that I work at about forty hours a week, and I help lead two open source projects that have a hand in vast swaths of the project I personally use on a daily basis existing. And damn if I’m not proud of all of it. I also take the time to cook dinner a couple of times a week, and even annoyingly tweet about it every time I do, because I’m proud of what I’m doing. I’m back to reading prodigiously (my current focus is on esoteric history books). I go to the symphony two or three times a week – I even took a friend there on a date a few weeks ago!

I sleep almost eight hours every night, I don’t fall asleep at my desk, and I don’t feel jealous every time one of my coworkers succeeds. I’ve lost weight, I walk to work every day, and even try and fit in a ten mile hike through the city once a week. Before leaving my apartment last Monday, I took a look at myself in the mirror and couldn’t help but smile – I felt content with what I saw, with who I am.


I didn’t really realize all of this progress that I’ve made in the past year until I took this trip, and spent some real time back at school.

Being on a college campus when you’re a former student may be one of the strangest experiences I’ve ever had. It’s almost like nothing around you has changed. People are taking the same classes as always. There are the same eternal college dramas unfolding. And while my friends were a year older, they too appeared unchanged. Some of them are a mere three weeks from graduation, but they’re still certainly college students. And now I can properly recognize how much I’ve changed in this year.

It’s not that I’ve become distant from my friends, since we’ve certainly stayed in touch. But all of the anxiety that is so clearly prevalent from their lives is now absent from mine. The anxiety and drama and fear that used to be paralytic just isn’t inhibiting me any more. I’m more confident than I’ve ever been, and more content with the trajectory my life has taken. Sure, I still have lots of things that I’d love to improve, but now I’m optimistic that I can get there. There’s no weight or raincloud hovering over me, casting aspersions on my every move. All that’s just gone.

I couldn’t have realized this without returning to my old (and soon to be future) life, and taking a step back to ask what’s different. “It’s not you, it’s me” is a stereotypical breakup line, but in asking myself what had changed, it was the only conclusion I could draw. The thing that had changed was me. And going to parties and grabbing coffees with my friends, I was finally able to delight in the fact that I’m twenty. It’s an age of fun and discovery, after all! And now I’m equipped to enjoy it. (I decided to start by going to three parties consecutively this weekend, about which I have zero regrets.)

On Friday night, I went with my housemates to the BJ Scav party, well-regarded as one of the best parties of the year. I was, of course, rather drunk, but I can still remember the entire night. I found myself in the kitchen, by the drinks, and somehow struck up a conversation with a girl I vaguely knew. Through some turn of events, the conversation meandered to the topic of her tattoo, which said “All Was Well” – of course, the final words of the Harry Potter series. As she was explaining why she chose those words, I was granted some perspective on my own life – they represent that, no matter what comes next, after everything that’s happened in the past, we’re at a point where we can be truly content. And that’s where I am right now in life.


I’m returning to UChicago in September, and I’m going to continue living on my own. But now, I know I’m ready. Ready not just to finish college and get a degree, but also ready to finally explore the world as an adult. As someone who’s willing to have their eyes opened, and as someone unencumbered by the baggage of youth.

I’m still twenty, which is of course, only one year older than nineteen. But I know I’ve undergone a disproportionate amount of growth in the past year. I’ve grown up in exactly the ways I had always hoped college would help me mature. Even though I still can’t order myself a beer in my home country, I’m an adult now.

And I couldn’t be prouder of myself or any happier. At last, I can say, without a trace of irony, All Is Well.