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The End of Certainty

The End of Certainty

Man in a white dress sitting in front of a mural of a bubble bursting, with his head in his hands

The water at the bayfront was a mirror the morning after graduation, reflecting the colors of the sky as the sun came up.

Sunset in Sarasota was fiery, leaving the sky awash in shades of pink, red, and orange. By contrast, sunrise brought periwinkle and mauve in muted, peaceful tones. Every few minutes, a fish would break through the surface with a splash.

It was the perfect ending to a night spent wandering around campus. Commencement had been the night before, followed by a school-wide party. I still had on my dress from the celebration. My makeup was smudged, raccoon-style, around my eyes. In my hand, I carried a pair of black high heels that I’d given up wearing hours ago.

I’d skipped the festivities in favor of hanging out with Kristina, who I’d known since I’d thrown a party in their room that had caused them to puke over their balcony second year. Kristina had spent the last year studying abroad, and we were both leaving Florida soon. This would be the last opportunity to really spend time together for a while. We’d talked and walked around the whole night, re-visiting our old campus haunts, reminiscing about the night-trips to the beach, doing our best to come to terms with the fact that we were alums now. 

Okay, that last part was actually just me. Kristina was more than ready to get out. They’d been accepted to one of the best business schools in the country and wanted to start the next chapter of their life as soon as they could.

“We’ve played the game and won,” they were saying now, turning their back on the bay so that they could gaze up at College Hall. “It’s time to do real things.”

Kristina started talking about their new goals — getting an apartment where they could live alone with maybe a pet or two, finding a long-term partner who wanted to settle down, networking and landing internships that would lead to a high-powered job. “In short, no more fucking around,” they concluded. “Those days are behind me now. It’s time to grow up.”

They knew how much I’d wanted to “grow up” and “do real things,” too. Kristina had been one of the only people I’d been comfortable truly talking about my ambitions with — despite the fact that I wrote about goals often, I felt uneasy discussing them in real life. 

And yet …

“Silicon Valley. Are you excited?”

I nodded, even though what I really wanted to do was sit here and talk to Kristina and enjoy the sunrise forever. I’d spent an inordinate amount of time in the library of my own accord, and I was only beginning to see what I had missed out on. In the last four years, I’d seen exactly one sunrise — the one I was looking at now. 

I wanted to absorb all of the beauty I’d missed while I’d relentlessly gunned for a bright future. If the sunrise couldn’t go on forever, then I wanted to sit at the bayfront until the sun came up, then spend the day at the beach until the stars were high in the night sky. I wanted to run away to beautiful places and spend a summer driving around with the windows down and laugh with my friends. All my summers in college had been taken up by one commitment or another, by desks and computers and deadlines and the promise that each little sacrifice was going toward my “bright future.”

That morning, the last thing I wanted to think about was work.

“I’m looking forward to seeing your accomplishments,” Kristina continued, delving once more into how hard we’d both worked, how much time and effort and energy we’d given to land our spots in the Real World. I thought about the previous evening, where I’d walked across the stage dressed as the red Teletubby to get my diploma. I was now an alum — and I’d be starting my new job across the country in two weeks.

Fuck, my new life is beginning.

Instead of making me excited, though, the notion made my stomach turn. College had been a marathon, an exercise on keeping my eye on the prize, and I’d really and truly given it my all. I was exhausted. Could I really do it all over again in two weeks, indefinitely this time?

A fish leapt out of the water. Damned if I know, buddy, it seemed to say. Figure it out. You’re an adult now.

The shaky Jenga tower of life decisions

If you’d told me in January of that year that by May, I’d be uncertain if I wanted to go to San Francisco at all, I would have asked you to stop fucking with me.

In the winter of my last year, I had finally gotten in my groove. I’d always worked hard, but December through March saw an unprecedented level of output. I was in peak workaholic mode — every second of my day was given to either my internship, my blog, or basic life-sustaining stuff that I couldn’t not do, such as eat or sleep. Graduation was nearing; I was determined to set up my post-grad life to run as smoothly as possible.

This meant securing a solid software engineering job and having an executable vision for Fake and Basic, both of which were much easier said than done. For the first few months of 2018, my life was the very embodiment of those “WORK. SLEEP. REPEAT” T-shirts I saw people in downtown San Francisco wearing unironically. I wanted to be both an engineer and a content creator — I needed it, goddammit — and I was going to make it happen.

My tunnel vision paid off. I scored an offer at a company I liked and successfully rebranded Fake and Basic to be a personal development site. Things were going well on the career front, so I turned my focus to having fun.

I’ve never been asked the classic job-interview question “what’s your biggest weakness” before, but if I had to come up with an answer, I would say that my biggest weakness is my tendency to overestimate exactly how much stuff I can take on at any given time. I pile way, way too much on my schedule, only to realize too late that I’m in over my head.  

This is something that I’m very conscious of now. Back then, I had no qualms about stuffing myself at the Buffet of Goals and playing drunk Jenga with my life decisions, which led to what happened next.

In fact, I’d say that I’m extremely careful with my schedule now because of what happened next.

Spring was coming up; the days were getting longer, and I was all too aware that my time in Florida was limited. I wanted to make a bunch of memories before I had to leave for good. I would travel to New Orleans and Miami and Palm Beach. I would have a bunch of senior-year adventures with my friends. I would take as many pictures as possible. Oh, and I’d also write my entire thesis, which I hadn’t really started yet. My plan was to do all of this within the three months I had left.

The Jenga tower had reached peak height and was wobbling precariously.

In the execution of these plans, my hand would be just a leetle bit too unsteady — that is, I would make one little mistake that would cause me to fall behind and sprint the whole rest of the time to catch up. By the time I was done, I would be well and truly burnt out.

When I returned from my San Francisco internship in late January, I had no idea that the tower would come crashing down within the next few months. I’d worked my ass off; my track record was solid. What could I have possibly fucked up?

Little did I know that the fuckup would have nothing to do with work at all.

My not-so-leetle fuckup

I’d had my nose to the grindstone for so long that one could argue that my career was my significant other. However, I also had an actual significant other — like, a human one — who lived a few hours away from where I went to school. We’d met as first-years in front of the library during orientation; he’d left to go somewhere else, but we liked each other so much that we decided we’d try long distance.

It was a bad idea, from the very beginning, not in the least because my mind was fully occupied with other things. Our sleep schedules were also the total opposite of one another’s — he worked late and often went to bed just as I was waking up at 5 AM. When combined with the tendency that my mother called “out of sight, out of mind,” this made for practically nonexistent contact, save for the few times a month I’d take a day out of my schedule to go visit.

I prioritized work over being with my partner, every single time. I’d stupidly assumed that everything would work out since we got along fabulously when we were together. As it turns out, though, if you don’t call, text, or otherwise talk to someone for weeks at a time, your relationship will suffer no matter how much you love one another.

In the words of Lana del Rey — “they said that love was enough, but it wasn’t.” We broke up after I returned from California, and instead of doing all the things I’d said I’d do, I spent weeks crying in bed and moping around. I felt terrible for taking him for granted, for being so neglectful.

This was the first time that I felt that inherent sense of motivation threaten to leave me completely. Throughout my four years, there had been times when I’d been lazy, or slacked off, or procrastinated, but I that inner urge to do and deliver good work always came back, keeping me on track. 

I tried to feel better, but I couldn’t. I tried to make myself feel better through my usual methods of socializing, taking pictures, or intellectualizing myself out of my emotions. None of it worked.

I began to wonder if it all even mattered, if leaving some sort of work-related legacy was the end-all-be-all of everything. What about friends, family, love? Would being number one in everything career-related always make me happy? 

All of a sudden, the promise of a cushy job and a shining career didn’t seem as satisfying.

The whole thing left me with a strange, unmoored sensation. The Jenga tower had collapsed — not with a crash, but quietly, silently, like those rare games where the tower still somewhat looked like a tower, when in fact it was just a mess of blocks that were piled high enough to represent something concrete.

I wouldn’t know it then, but this would mark the beginning of my loss of direction.

A truth I didn’t want to acknowledge

Slowly, very, very slowly and with no small effort on my part, my drive came back. At least, the creative part did — I started to write and take pictures again. Throwing myself into a project pushed out of my mind the things I didn’t want to remember.

Spring break rolled around, and my other overachiever blogger friend and I fucked off to Miami. The plan was to write articles in the early morning, go on photoshoots during the day (we’d pose in front of every cute Wynwood mural we saw, we promised ourselves), and party at night.

We shot the shots. We penned the posts. We were too exhausted to party. I published “How I Pulled Myself Out Of A Gigantic Rabbit Hole of Sadness” on one of the first days we were there, talking about the strategies I used to get myself out of the strange headspace I’d been in after the breakup. 

“The past three weeks were not a happy time of my life; it was the one dark period of the year that took me almost completely by surprise,” I wrote. “However, I’m really grateful that it happened, and even more grateful that I was able to snap out of it. I am now a lot more in touch with myself and can see even more clearly why self-care is so important. I like myself a hell of a lot more than I did before this happened.”

A year and a half later, I want to shake myself for being so naïve. Oh, you sweet summer child! Stop using that story arc where you go through dark shit, get slightly better, and say that everything’s fine!

Because everything was, in fact, not fine, even though I thought that I’d gotten over “letting my life slip away.”

Reading fiction as escapism, journaling regularly, and timeboxing my wallowing may have helped get rid of those negative emotions, but the “gigantic rabbit hole of sadness” had never been the real issue. Sadness and loneliness were common visitors after a breakup, and it was perfectly normal to be a little out of it while feeling sad and lonely. 

No, the real issue was that my fundamental beliefs were changing. “I still largely pick and choose what I believe in, but I started having an open mind to different ideas,” I wrote under the section titled “I Got Into Spirituality.” I was referring to how I no longer scoffed at woo-woo shit, but I’d also started questioning what I really wanted. Was it a career in software development?

I enjoyed thinking about code, breaking down systems in my mind until they made sense to me, but I lacked the “I love building shit so much that I’ll sit here hacking and debugging all night if I have to” mentality of my other hackathon-frequenting friends. Instead, that all-encompassing, borderline obsessive (okay, maybe just obsessive) passion was reserved for content creation. I could shoot in the extreme Miami sunshine all day, spend all night editing those pictures and making sure the color balance was just right, then rise before the the next morning and bang out an 11-page article.

What, then, did that make me?

What, then, did it mean that I’d agreed to take on a full-time role that practically required me to be obsessively passionate about programming?

What would it mean for my future success?

That was the real issue.

But I wasn’t thinking about these things so carefully that sunny day in Miami. I figured that I’d gotten over slumps in the past and would again — I had a few months before graduation, surely I’d be back up to a hundred percent before starting at my new job.


One more block on the tower

Well, maybe things would have worked out if not for the fact that I still had to write my entire senior thesis, which was a requirement for graduation from my school.

I call it a “thesis” because that was the terminology everybody used, but my thesis was really more of a project — it consisted of an iOS app and a book of tutorials on creating iOS apps. I had been working on it throughout the year, but I’d come back from Miami on a content-creation roll, taken one look at what I already had, and declared it all to be absolute trash. I decided to throw everything away, shut myself up in my room with a bunch of caffeine, and get to work.

For the record, I brought this upon myself — one more block on the tower, I thought. I certainly didn’t tell my thesis sponsor too much. I worked on my new idea for a week, then realized that it wasn’t enough to qualify as a thesis … so I threw that out, too, and started a new project from scratch.

By then, my deadline was two weeks away. I worked throughout the night, researching and coding and typing as fast as fast as humanly possible. I fixed one bug after another and wrote one draft after another, until I had a version that I was proud of. 

If you’re a current student at my alma mater and you’re thinking about doing this to yourself — don’t. It’s objectively bad for your mental (and physical) health, and I would suffer the consequences long after the process was over.

But I wasn’t thinking about consequences at the moment. I submitted everything and danced around my common room to celebrate. At long last, everything felt like it was complete. Now, all I had to do was defend my thesis and graduate.

Shifting perspectives

I successfully passed my thesis defense a few days after I submitted my work. I had a few weeks before graduation to do whatever I wanted.

I wanted to work on creating content— creating content for Fake and Basic, above all. I’d channeled into my articles all of the things about ambition and achievement that I was uncomfortable saying aloud, and to my surprise, they were resonating with others. I woke up to multiple e-mails and messages about how my content was inspiring, how I made people want to get up and do shit with their lives. I could, it seemed, make this blog of mine into a real thing.

The only problem was that my exhilarating, feverish sprint through Thesis-Land had left me feeling massively burnt out. I wasn’t feeling particularly inspired myself. I wanted to write, but everything that came out was shit.

Maybe you need an actual break, I thought. Like, one where you’re actually just hanging out and not thinking about making stuff or networking or getting ahead.

“I laid out by the water, shot outfit looks at the bougiest areas in town, listened to copious amounts of dream pop, bought myself daiquiris, curled up in bookstores, learned how to make sushi, allowed myself to stray from my regimented sleep schedule, went shopping, and spent days spaced out in my own head,” reads “Inside My Unplanned Blogging Sabbatical,” which chronicles the events of that time.

“This was relaxing,” I write in the same article, “but it also brought about an unintended side effect: I began questioning everything in my life. Why did I continually burden myself with obligations? What exactly triggers my gender dysphoria? What maladaptive behaviors did I pick up from living in a super-white, relatively conservative, heteronormative community before coming to college? How much internalized racism, misogyny, and homophobia was I harboring, and how was that affecting how I carried myself? Why did I care so much about being diplomatic regarding the unpopular opinions I carried? Did I really believe that a productive life was a good one? And so on.”

I was beginning to bump up against the edges of the worldview I’d carried for so long. It was uncomfortable, but not in a bad way — it felt like my world was opening up, like I was actually growing as a person rather than just saying I was while repeating whatever thing I’d read in my latest self-help book.

What would happen, I wondered, if I dedicated the entire summer to exploring these shifts in perspective? I could think deeply about all of the questions I’d raised above, repair relationships I’d damaged in my rampage for glory, and “influence” my readers to do similar work with themselves. I could then start my job in the fall as someone who really knew himself and what he was doing.

I reached out to the company that had hired me, asking to push my start date back by a few months. Unfortunately, they told me, since they were a startup under tight deadlines, they needed all hands on deck as quickly as possible. If I didn’t want to start right away, they would rescind my offer, hire someone else, and re-consider me for the fall.

I didn’t know what to do. On one hand, I felt like the bottom of my world — that is, the principles that had sustained my work ethic this entire time — was falling out from under me, and I was fairly certain that I wouldn’t be a “high performer” until I regained my sense of self. On the other, this was my future I was dealing with, the one I’d sacrificed so much to build. If I let this go, I would be letting go of my ticket to California, to Silicon Valley, to everything that I thought I’d wanted.

What’s it gonna be? the Universe seemed to ask. The “success” you chased for, or your actual personal growth?

In the end, I got scared. I was scared that I’d drop off and lose everything if I took the summer to work on myself. I’d only gotten this job in the first place because I’d worked my ass off — who knew when I’d be able to do that again?

I told the company that I understood, and that I’d be happy to start in June, exactly two weeks after graduation.

Every day after that, no matter how many beaches I visited or how many diary entries I wrote, I wasn’t able to relax. A quiet panic started to grow in the back of my mind. I was breaking and wouldn’t have time to put myself back together.

I was running out of time.

Bittersweet goodbyes and reluctant hellos

Silicon Valley. Are you excited?

Kristina’s words echoed in my mind as I wheeled my stuff into the rideshare pick-up zone in the San Francisco International Airport. The last time I’d landed here, I’d been awestruck — here it was, material proof that my hard work was paying off. This time, all I felt was a heavy sense of resignation.

No, I admitted to myself. I’m not excited.

I straightened my back and tried to conjure up that confident, self-assured motivation that had been my primary mode of being for so long. I had made it at long last. The company had hired me because I was a good engineer with a strong work ethic. I had, in Kristina’s words, “played the game and won.” It was time to prove that I deserved the prize.

When these assurances fell flat — had they always sounded so empty, so exhausting? — I sighed and sternly told myself to get my shit together. I had already accepted the offer, after all. I had already made my choice. 

It was too late to turn back now. The only way to go was forward. ♚

All parts in this series

Part 1: The End of Certainty

Part 2: Worthless Unless Productive

Part 3: Decadent and Disillusioned

Part 4: Coming Full Circle

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