It was a quiet Tuesday morning, alone under a big cloudless sky, with the sun beating down on me. Walking under the stone pines, I looked up toward the sky, thinking about all that had changed since I was last on this path. I had just finished up with my studies at the University of Cape Town, and decided quite abruptly to start anew in England, where my family was.

In spite of the surroundings having remained largely the same, I was struck by how differently I saw the world. That boy from 3 years ago went into this new chapter—university—bright-eyed, naive, and with a voracious appetite for experience. And out came someone cautious, restrained, perhaps a bit jaded. But with a deeper intuition of what he cared about.

Hazy Days

If I could describe that first year of university in one word, it’d be mesmerizing. Everything was so new, shiny, interesting. I got a pair of bluetooth earphones, and started streaming music for the first time. The algorithm hadn’t quite figured me out yet and recommended some real obscure stuff—even for someone like me who had done their fair share of digging back when I produced music. There was something very surreal about those moments, earphones in, observing the world in a sort of dissociated state: walking under the canopies with the sun glimmering through, back home from an exam in the evening looking over the city, or through the forest on a misty morning next to campus.

However, coming to Cape Town initially felt like a compromise. Being sheltered and largely isolated in high school left me with a very narrow perspective of the world, one where I thought prestige and achievement mattered above all else. Those dreams were squashed rather quickly when I got rejected from all the elite American universities I applied to. I had become so attached to this whole grand plan that when it was subverted, I was left utterly lost.

As a sort of f*ck you to the universe (talk about entitled), I vowed to never wait on the world to happen to me, to never wait on opportunity. And so a new core principle of mine was born: to say yes to everything. And honestly, it worked pretty darn well. The mixture of being in an exciting new environment that matched my gregarious nature along with my hunger for opportunity and willingness to accept what came my way, made a fantastic recipe for serendipity. And you find when you open yourself up like this, opportunity can find you in the strangest of places.

Quite quickly, I found myself at my first startup, Loop, a company with the ambition of digitalizing the taxi industry in South Africa. I stumbled on it through my driving lessons: my driving instructor had founded this company after his family had dealt with the problems of the industry for generations. It ticked all the right boxes for me (impactful, interesting, promising), and I begged to get on board. For them, it was free labour, so no questions asked.

This was exactly what I had dreamt of, what I was looking for in the States (oh, the land of opportunity), and yet I found it right at my doorstep. I recall that first bus ride to their offices. It was an immaculate day, people on the bus seemed to be dressed up for the beach (it was a university bus, so only students on board), and I was feeling all proud that I was on my way to do ‘serious business’. In the moment, it felt so right—as though I was carving my own path, doing precisely what I felt I should be doing.

I was the only software engineer on board, but honestly, I preferred it to be that way—I wanted full autonomy and accountability as I felt it was the fastest path to competence (a mistake one only learns later!). I wanted to do everything. My first major gig was to build a demo that would be used by the Premier of the Western Cape and the mayor of the city. I worked tirelessly the nights leading up to it, grinding until 7 in the morning, techno blaring in my headphones. But not so glamorous when you factor in the dry eyes, pale skin and waking up at 1pm. Nevertheless, it was a success (if you ignore the fact that it only worked like 50% of the time).

So I had my ‘15 minutes of fame’ sort of moment, and all felt good. I doubled down on the work while university and personal life shifted into the background. Months blurred together as the work became mostly routine. The friendships I had made began to fade. I’d check my phone each day, admittedly hoping to see something from someone, but was always met with a blank screen, like someone who keeps opening the fridge hoping to find something when they know there’s nothing there. But this didn’t matter, right? You’re doing serious stuff. And you’re above these sorts of feelings.

Well, my wish was granted, as the work did indeed become quite serious, all while I continued to hold the one-man fort on the tech. The responsibilities expanded, and the nature of the work shifted from exciting, socially impactful, press-attracting to more practical keep-the-lights-on stuff (staff transport—oh, how exciting). And more importantly, it became much higher stakes. While we were working on proof-of-concepts before, the work had now become something people relied on—the customers to get to work, the company to have their employees at work on time, and the drivers to get paid. I became responsible for the invoicing, which involved messy spreadsheet work and scripting for data compilation and aggregation. Staff transport is also one of the most logistically complex things to manage, especially in a place like the Cape Flats where some areas are no-gos (just to put it into perspective, we had a vehicle hijacked while waiting several minutes outside someone’s house for a pick-up… 2 days consecutively).

My boss and his wife took the lead on the logistics, working round the clock with hardly any sleep since the transport was conducted for shift workers. The pressure to come up with something that could replace the manual work was intense. And all while juggling the financials, with drivers rightfully complaining about delayed payments because our client was late to pay us, employee churn at our company…

Usually it’s these moments that are defining in our lives. If we just push through, one bit more, glory awaits us on the other side. That’s the story I told myself time and time again. But something felt off: if you asked me what I was fighting for, I couldn’t really answer. Sure, it would prove to me that I’m resilient, persistent, maybe a bit tough, but why swim against the current when you’re not sure whether you want to reach the other shore anyways?

After work one Tuesday, I made my way to my usual spot, Saunders' Rock (a rocky beach in the upmarket Sea Point suburb) for my routine cold swim, something I had grown guilty of doing since it meant leaving slightly early to make it before sunset. The Atlantic-facing water in Cape Town is pretty damn cold (between 10ºC and 15ºC), and with my low body fat, 3 minutes is enough to get me shivering violently for up to 20 minutes after. But when your body’s able to finally calm down, the sensation changes from fight-or-flight to ecstasy—fiery sensations that run all over your body, mental clarity, the high of surviving ‘near death’.

I made it a habit to find quiet moments without any kind of stimulation where I could. You find you grow more in tune with your intuition, start to feel when things are off and that change may be needed. The swims, quiet dinners, even music-free gym sessions—all served the same purpose: to escape distraction and tune into my intuition. These rituals had trained me to recognize when something was off, which brought me to that evening…

Staring off into the distance, the sun setting on the horizon, symbolic of what was to come. On the one hand, I had found my lucky ticket to an exciting future, one uniquely my own, with the potential to impact many South Africans in a meaningful way, and still a whole lifetime ahead of me. This was the dream, precisely what I had sought after entering university. Would I ever get this again? I mean, for all I know, come graduation, I’ll be stuck in a cookie-cutter 9-5, around the same people, with little to no exposure to new ventures. On the other hand, I was starting to see the cracks. It wasn’t what it seemed: immediate business needs took priority, the work environment was deteriorating, I was growing isolated. But above all else, I was sacrificing some of the most valuable time of my life—complete freedom—for a mission I was no longer on board with.

Twilight had arrived with the gold giving way to deep blues and magenta, and it was starting to get cold. I knew what I needed to do.

As I got home, I wrote some notes on what to say, knowing I’d likely go blank. I called my boss to give the news; each ring feeling unusually loud and slow. He answers, and just as I anticipate: blank. I read off the script awkwardly, like a teenager trying to confess their love for someone for the first time, measuring each word. Then it goes silent. He’s taken aback, clearly. This is the most critical stage of the company’s history, and we’ve already lost some people. It feels as though it’s hanging by a thread. And now I’m leaving them for dead. But he understands, doesn’t fight it. We come to an agreement on a handover, and end the conversation cordially. I sit in the silence for a moment, process the full extent of what I'd just done. The dream that once was, of stardom, was set to rest. Again, I was on the path of mediocrity, of no consequence. But at least it was true to me.

Rediscovery

With the newfound freedom, I knew not to take it for granted. The time was short, and valuable. So I chose to use it for rediscovery. Now, instead of saying yes to work-related things, I chose to say yes to everything else. Gymnastics, outdoor climbing, dance… I was making up for lost time. And in spite of it being my final year, I was ironically meeting more people than I had in the previous years combined. The new activities naturally put me in different circles, and I was actively seeking out novelty—new faces, new conversations, new experiences. I dyed my hair blonde, changed up my style, got my ears pierced. My mom argued that this preoccupation with my image was rooted in some deep-seated insecurity, or something was troubling me. I suppose she wasn’t all too wrong. But at the core of it, I desperately wanted to be and feel free: from commitment, expectations, and a set image. I was rewriting my own story: no longer the geeky, scrawny computer guy, but someone adventurous, athletic, spontaneous.

I’d wake up, with no deadlines looming, actually attend classes for a change, finish up at 11 (oh, how lucky I was), and then cruise to the beach, exercise out in the sun, finish off with a cold swim in the ocean, and grab a hot coffee on the way back. In my spare time, I didn’t write a single line of code (unless you count the university work). If you had asked me a couple years prior how I would feel about having that amount of freedom, and no ‘productive’ hobby, I would’ve cringed. No ways I could sit still, not feel complete dread at not doing anything ‘meaningful’ with my time. And yet here I was, perfectly content with its absence.

As the mid-year break approached, I had no intention of changing my course. But there was a little bit of anxiety building as I started thinking about what awaited me beyond graduation. I don’t know if I could say that I would happily accept a life of coasting. Leaving Loop in a sense felt to me like abandoning my one lottery ticket to glory. Would there ever be something like that again? My roommate had started working on a new project—he got drawn into the startup life, but was lagging a couple months behind me, which created some amount of dissonance: he was incredibly eager, while I was jaded. For many months, he tried hard to convince me to get involved in his project. The idea, which my roommate called Gather was a recommendation system for events, activities, places, whose intention was to address the glaring gap of the third place. It’d be marketed as “The IRL Social App”. I had always felt iffy about social media, but could see a world where something like this provided genuine value. But nevertheless, I couldn’t be dissuaded, and was firm in my stance. I no longer felt pressured to work for the sake of it—I had paid my dues, and now could afford the luxury of choice.

Come the mid-year break, I was visiting my brother in a quaint town called Cirencester where he used to live. It was a week day and he was away for work. I decided to go exploring a bit, get myself a coffee and read in the historic town centre, the imposing abbey just across the road from me. I’m flipping through the pages of Aldous Huxley’s Doors of Perception, but am admittedly far more preoccupied with the surroundings. A group of friends at a nearby table keeps catching my attention—I occassionally tune into their conversation, hear them laughing at some jokes I’m not privy to. I can’t help thinking how great it’d be to be able to join in with them, share in the laughter. Maybe that’s what I was missing—genuine connection, the kind of spontaneous social moments that Gather was supposed to facilitate. I get a call from my roommate. Huh, talk about good timing. He brings up the project again, and I almost reflexively say no, but this time there’s a bit of hesitation in my response. Are you really sure that you want to be passing on this opportunity? Your time’s ticking, 6 months to go. Remember, come graduation, you’re cursed to a life of mediocrity. Rather rashly, the words came out before I’d fully decided: “Actually, you know what? I think I’ll join on the project.”

Déjà Vu

Fast forward a couple weeks, I’m back home in Cape Town, and we’re planning for the long road ahead. My roommate is a real go-getter, and at this point has a pretty vast network of investors from his previous startup. He reaches out to one of them and arranges a meeting. We rehearse our pitch-deck, make sure that we’re on the same page, and are able to communicate clearly this grand vision of “trying to connect people in real life; to fix the eroding third place.” Though, I couldn’t quite shake off the feeling that the true underlying motivation was the glamour of it all. Still, I pushed the doubts aside. We had a meeting to nail.

It was a hazy, crisp day, towards the end of Winter—something out of a dream. If anything, I was glad to be doing the drive. I recall vividly listening to Angie Stone’s “Wish I Didn’t Miss You” as we left the car, the song left half finished. Again, the song plays in the cafe. Funny coincidence I think. This meeting again proved that if there was one thing we could do well, it was leave an effective impression. The sort of narrative that we were constructing was of the “genius precocious visionaries” and it worked pretty well. We left on a promising note, that we would get a cash injection as soon as we launched, and had his full support. We had a bright future ahead of ourselves. We get back in the car and finish off the song on the way back. My roommate’s enthused, emboldened. But something just feels off. Instead of excitement like I would expect from a situation like this, I feel deep inexplicable melancholy. The song in the background feels poetic, almost deliberately chosen for this occasion. Am I making the exact same mistake I made before?

Working with a roommate sounds exciting: sleepless nights hacking away together, positive reinforcement cycles—their excitement feeding into your own which in turn bolsters them—, tight feedback loops. That is, if you’re both on the same page. But the reality looks quite different: dishes left dirty by the sink, dry laundry not collected, guilt for leaving the apartment to see friends, go to the gym, y’know, life things. For my roommate, this was his dream. Nothing else mattered. To found a startup meant to sacrifice one’s life for the mission. I respected his clarity of thought and priorities. Though through trial and error, I had come to understand the age-old adage “It’s a marathon, not a sprint” earnestly.

Being the only technical person, I was bogged down in the work while my roommate was the visionary, ideating, getting feedback from people, iterating. I’d on the odd occasion provide some feedback, but would largely get shut down, or at least challenged. In truth, I didn’t even have it in me to fight. It’s not really my vision anyways. The order of command was clearly starting to take shape as being one-directional. One too many times we had a conversation around commitment. We were 50:50 in this, and for that reason, it was all or nothing. I would always fight this point, argue that it’s much better to do this sustainably, for fear of burnout, only to be met with the response “I just don’t get it?” Maybe I was wrong. As an equal cofounder, it’s hard to argue otherwise. And his conviction only seemed to grow stronger as the project progressed.

Frequently my roommate would call friends to get their feedback on the app; the app and his identity becoming intertwined. No conversation could go without making mention of it. He was totally enamoured by the concept of going viral and launching something many would love. To be a successful founder: the modern-day rockstar. And he would go to whatever lengths necessary to make that a reality. This whole approach felt wrong to me, though I struggled to articulate why.

I recall a particular moment in my teenage years, walking down the aisles of a grocery store, the lure of bright-coloured plastic packets, filled with things I probably don’t need, almost screaming out at me: “pick me! pick me!” Something about it repulsed me so intensely that I forced myself to only look forward, to not fall victim to their gravity. This was the beginning, and most extreme period, of my anti-consumerist tendencies. But at its core, this feeling has stuck with me ever since. The way it felt was that we were creating demand for something that didn’t naturally exist. Well, obviously dumbo. That’s innovation. I mean, sure, but I just couldn’t craft a convincing enough case in my head where this has enduring value for people—instead it feels as though we’re trying to desperately capture people’s attention long enough that we’re able to make a decent exit.

For this reason, I would never speak about my involvement in the app. And also because I generally operate on the principle of showing over telling… Okay, and perhaps most importantly, I felt ashamed to be associated with a social app. But it would be naive to think that something like Gather would ever see the light of day without my roommate’s conviction, his audaciousness, and complete shamelessness in promoting it. So on one hand, you have a founder touting the app, totally unapologetic about it; and on the other, you have me, far removed from it, as though I was never involved at all. And yet, I was selling my soul for it.

We’d regularly circle back to the conversation about continuing the project together. It was palpable that I clearly was not feeling this as much as my roommate was. I expressed my misgivings earnestly each time, but I insisted that it was probably just a consequence of burnout, a short bout of intensity that would pass post-launch: “It’s fine. I’ll manage. It’ll pass,” became my usual words of reassurance. Though each morning I’d wake up, hear my roommate pacing the balcony (a habit of his when he was deep in thought) while listening to Drake (If I have to hear “Virginia Beach” one more time…), and muster up the patience to play it cool, act at least partially interested, enough to keep faith. We must’ve had that conversation about 5 times.

I remember getting some advice from my uncle sometime in this period. I mentioned that I was grappling with many potential paths, and was lost. He’s the kind of person that runs on pure logic. I often find it a bit heavy-handed, but think that for a change it would be appropriate, instead of the bullshit ums and aws and “Oh, I don’t know.” So I construct a decision matrix, with each outcome on one axis, and the weighted factors on the other (E.g. Financial security, growth potential, etc.). Lo and behold, Gather comes out on top.

But sometimes, you really just can’t logic your way through things.

We were at last nearing launch—what was feeling like something totally insurmountable until this point. Still, it would be naive to think that the efforts would reach a climax and suddenly drop off. Launching meant fully committing to the project for at least up to several months after. By this point, I no longer had any gas in the tank to even push through doubt. I had no pride in the work; I was just running on autopilot to see this thing to fruition, to not disappoint my roommate after having come so far. Nights running on red bull and nicotine pouches were no longer glamorous. What once was a funny story to recount became déjà vu. I knew I wanted out this time. But how could I break the news?

If there’s anything I can give my roommate the utmost respect for, it’s his unwavering ability to respect one’s autonomy. I knew that he would understand me choosing to step away. But it hurt deeply to have led him on until this point, to have reassured him that I could handle this. I had given him my word that I could be part of his vision—I had consented to it. And now I was going to flush it all down the shitter, when it mattered most. But I had also learnt to respect my own time. Sure, I was late to realize this, but better at that point than post-launch, when the stakes would be far greater. Just like the Loop incident, I wrote myself a rough script, and recited it. Instead of the conversation coming about organically, this time I initiated. The words start spilling out as though they’re not really mine, like watching myself speak from outside my body. The tension between us had also peaked at this point. Me in my almost totally dissociated, depressive state, and my roommate increasingly frustrated with my coldness. He verges on tears, his face falling into his hands. In truth, I had expected him to acquiesce. Instead, he begged me, earnestly, to see it through. “Please, please, please. Can we just launch.” It was a heavy decision to make, I knew that launching would mean remaining involved for a while longer. But seeing him like that, knowing how much this meant to him... I couldn't bring myself to walk away. So we agreed: we would launch, I would keep the lights on, but would eventually hand over to someone else.

So we launched, and… nothing. Besides some friends that downloaded it, it was really quite underwhelming. In a sort of masochistic way, I desperately wanted to see that outcome—it meant I wouldn’t have more sleepless nights on call. But there was also satisfaction in seeing it come to fruition. The cruel irony was that it worked almost flawlessly, all its moving parts functioning near perfectly, despite being built by someone who'd checked out months ago.

Off to New Lands

After this whole journey, I can’t say that the answers were laid out neatly before me. But something had fundamentally shifted in how I saw ambition. That almost childish excitement to throw myself at anything promising—that was gone.

Part of it was simple saturation. After three years of being in the trenches, constantly programming, another project felt more like obligation than opportunity. I no longer saw the late red bull-fuelled nights, sucking on a vape or buzzing on nicotine pouches as virtuous or exciting.

But deeper than that, achievement itself had started to ring hollow. Coming into university, I had a very narrow perspective of the world. In my mind, having a wikipedia page, being at a prestigious university, with a long list of accolades—all that status signalling—was what people would care about most. But those 3 years gave me the added perspective that I needed to recalibrate. Sure, there’s a high that comes from achievement, from being appreciated and respected. And it works as a powerful incentive. Though after experiencing it several times over, you start to understand its fleeting nature. Life’s not a performance, one with a clear journey that has a natural end; when the audience erupts with applause and the curtains close, you remain in the darkness, only with your thoughts.

And yet there’s this strange contradiction: the very achievements I was chasing only had meaning through other people’s eyes. I needed to be seen, validated, appreciated. But in chasing recognition, I was systematically cutting myself off from the very people whose acknowledgement I craved. I’d sacrifice genuine connection for the possibility of external validation. It was this bizarre circular logic that I was only beginning to untangle.

See, the thing is, you are the only constant in your life. You can go to whatever lengths you feel necessary to construct a narrative about yourself, to have others admire you, and sometimes it really does serve you, but only you know if it feels true to you.

What felt true to me was that I’d been treating life like it was all about the main act—the career, the achievements, the story I could tell about my work. But I was starting to understand that the true richness in it all was in everything else: the friendships I’d let fade, the joy in self-discovery and adventure, the simple pleasure of a cold swim. I found that these things were enough to make me feel full, without existential dread of ‘making something of my life.’

The irony wasn’t lost on me that I’d spent months building an app designed to help people connect in real life, while systematically disconnecting from my own. I still cared about doing meaningful work—that hadn’t changed. But I was beginning to see it as one thread in a larger tapestry, not the whole fabric.

As my time in Cape Town was coming to an end, I took one last stroll through campus and up towards the Rhodes memorial further up the hill. This was the very same path I took the first week I got to university, and that I hadn’t done since. It’s quite a curious thing repeating an experience at very different stages of life. Kind of like returning back home after many years, in the kitchen alone, hearing the sound of that old clock that’s been there for as long as you can remember, ticking away. The environment’s much the same, but the lens through which you experience it is vastly different.

I had fallen in love with this place. Maybe it wasn’t even so much the city: it had become symbolic of a time in my life where I was free, bright-eyed, thriving. Would I ever find that again?

I got a lift from friends to the airport where we said our last goodbyes. Alexia and Maya, 2 of my closest friends, broke down into tears. I’d convinced myself I’d grown distant, let people down, and looked out only for myself. But in that moment, I felt a flicker of hope—maybe I hadn’t squandered everything.

Walking through security and to the boarding gates, I was fighting off tears. I recall staring out the terminal window and struggling to keep composure. In the bathroom stall I broke down crying… And again in the plane while everyone was asleep. Jeez, what a wimp.

So, then what’s the plan next? Honestly, I have no clue. But, for a change, I’m okay with that.

I'm actually writing this many months deep into my time in the UK, so I know what awaits :P. All I'll say for now is that it didn't quite go according to plan, but in a… good way. Maybe I'll write about the rest at some point.