The first post on my Tumblr is dated May 15, 2011. It’s one line. I have a heart that flashed from heart to stone from heart to stone. I have no idea whether I wrote it or reblogged it.

That was me at 20. The blog tagline was a table-flipping ASCII guy: ┻━┻ ︵ヽ(`□´)ﾉ︵ ┻━┻. Most of what I posted after that was reblogs. Other people’s lines, other people’s images, occasionally something that sounded like me but I couldn’t be sure even then.

Looking at it now I can laugh at the earnestness. The kid who set that account up was doing something honest, though. He was looking for a corner of the internet that felt like home. He thought if he reposted enough of the right things, the right people would find him. That was the deal social media was offering, and he bought in.

By then I’d lived in three countries. Born in the US, raised in Malaysia, moved to Canada as a teenager and stayed there through university. The address kept changing but the question didn’t. Where are the people I belong with, and how do I find them.

Social media looked like the answer. Friendster came first, the platform that lasted longer in Malaysia than it did anywhere else. Even after I’d moved to Canada I kept getting friend requests from old high school classmates I didn’t really relate to anymore. Then Myspace. Then Tumblr.

I spent the better part of a decade pouring hope into that loop, and the loop never quite returned what I was looking for.

The disconnection happened slowly enough that I didn’t notice it for years. I’d post something. A few people would like it. I’d scroll past a hundred other things people I knew had posted. I’d close the app and feel slightly worse than when I opened it, but not by much, not enough to question the habit.

Most of what I posted was still reblogs. Echoes of things other people had said that I wished I’d said myself. I was telling myself I was curating a vibe. I didn’t have my own voice yet and didn’t know how to build one, so I was assembling a version of myself out of other people’s pieces and hoping it would feel like home.

It didn’t feel like home. It felt like standing in a crowded room where everyone was holding up signs and nobody was talking to each other. The friends I actually cared about, I spoke to in messages, or in person, or on the phone. Everything else was theater.

In 2019 I deleted everything. Tumblr, Facebook, Instagram, Twitter. I didn’t ramp down or take a break. I nuked the accounts and walked away. It felt clean. The last thing I’d done on any of them was scroll through someone else’s vacation photos, and I remember thinking that I’d rather not know whether they were having a good time.

Then COVID hit. Within a few months the friends I’d been seeing in person became squares on a video call, and the only social fabric anyone had left was the platforms I’d just walked away from. I considered going back but didn’t. Some stubbornness about not wanting the relapse to be the thing the lockdown was remembered for.

Over the next two years I rebuilt the muscle for belonging without the scaffold. I was in Montreal then. Long walks with friends, weekend hikes with the person I was with, bike rides of fifty to a hundred kilometers on most Saturdays. These were slow, specific, low-bandwidth versions of what I’d been trying to get from the feed, and they worked better than the feed ever had. The loneliness got quieter.

By the time lockdown ended I didn’t miss social media. The muscle was real. The friendships were real. But something else was off, and it took me a while to put words to it.

There’s a thing in pop psychology about generational trauma, the idea that one generation overcorrects against the wounds of the previous one and ends up creating new wounds in the process. The kid of an absent parent becomes a smothering parent. The kid of a strict parent becomes a permissive one. The correction is bigger than the problem, and the problem comes back in a different shape.

I’d done a version of that with technology. I’d quit social media to get away from the parts of being online that were hurting me. But I’d also quit the part of being online that I’d actually loved, which was the early-internet promise of finding strangers who would become friends. I’m a software engineer. The whole reason I got into this work was that I wanted to build things that helped people connect. I had thrown that out with the algorithmic feed, and I hadn’t noticed.

The frame that gave me language for it was Simon Sinek’s Start With Why. The book is mostly aimed at companies, but the framework is human-scale. Most people and organizations know what they do and how they do it, but very few know why, and the why is what makes anything they make worth caring about.

My why, when I sat with it long enough, was the same thing 20-year-old me had been reaching for when he set up the Tumblr account. Build things that help people find each other, on terms that respect both ends of the connection. The reason all the social media stuff had gone sour was that the business models underneath required the opposite of what the products promised. The product was sold as a way to stay close to the people you cared about. The business behind it needed you to stay on the app whether or not anyone you cared about was on the other end. Those two things were in tension from the start, and the tension eventually broke through.

I’m building two things in that direction right now. The first is fikastay, a tool for groups of friends planning a trip together. The thing it’s solving is the seven-thread group chat where four people are trying to agree on dates and a house and a budget, and the trip dies in the chat. If fikastay does its job, the friends spend the weekend together. The product is in service of that weekend, and that’s the whole job.

The second is this blog. Three countries became six over the years that followed (Japan, France, back to Canada, now back in the US in New York), and through all of it the thing I’ve kept circling is what 20-year-old me wanted from Tumblr. A corner of the internet I can carve out for myself, where the people whose ideas resonate with mine can find their way to me, and we can build whatever the next thing is together.

Fifteen years after that first Tumblr post, that line is still there. I still don’t know if I wrote it. What I do know is that this post, on this site, is mine, and if any of what I write here resonates with you, I’d love to hear from you. That’s the part 20-year-old me on Tumblr never quite got to do, which was actually talk to the person on the other end.