What I Learned About Tech (and Myself)

Originally published on Substack — May 2025

Hitting Walls

Thirty days ago, I did something that would’ve felt unthinkable just months before: I switched from an iPhone to a Pixel.

This wasn’t some impulsive reset. The decision built slowly, over years. Little things kept piling up—frustrations, contradictions, blind spots I couldn’t ignore forever.

It started when we began building a digital wallet for art. From day one, we committed to supporting both iOS and Android. I assumed the hard part would be finding users. Turns out, the hard part was getting through Apple.

Apple’s app reviewers had no interest in nuance. Anything touching blockchain or NFTs was flagged. Google mostly copied their rules. Getting approved took nearly six months and became a full-time job. We eventually got through, but it came at a cost: constant compromise and delay.

Then, earlier this year, we launched a more experimental initiative—something closer to how I actually think and work. That’s when it hit me: a lot of our artists and alpha testers were using Android. They ran into weird bugs and friction I had never seen. I couldn’t help them. I didn’t even understand what they were talking about.

Inside our company, 70% of us were on iOS. We weren’t even testing our Android app seriously. And I realized: if I didn’t live with this thing myself—day in, day out—how could I lead the team? How could I see the rough edges, the missed potential, the quiet frustrations others were just learning to work around?

Cracks in the Promise

Around the same time, I started getting increasingly fed up with Siri. It wasn’t just the usual “she doesn’t understand me” stuff—it felt like Apple had quietly given up. Siri hadn't evolved. She still struggled with simple things. I’d ask her to set a reminder or change my calendar, and I’d get that familiar pause, that robotic tone, that awkward fallback into Safari. It felt like a ghost of what could’ve been.

Apple kept insisting this was all part of their “privacy-first” approach. But over time, that line started to sound more like an excuse than a principle. Their take on the cloud seemed especially conflicted. The phone itself had solid privacy controls. But iCloud? It relied entirely on trust. Not the kind of trust you earn, but the kind you assume: “Don’t worry—we’ve got you.” Personally, I prefer setups where nobody has to ask for that kind of trust in the first place.

Meanwhile, Gemini—Google’s AI—was starting to change. At first, I thought it was a mess. But something shifted. Week after week, it got better. Faster. More helpful. I started to wonder if Google might actually pull off what I’d always hoped was possible: not just AI tacked onto a phone, but something deeper. A kind of intelligence woven into how the phone worked—not just to answer questions, but to anticipate needs, simplify complexity, and get out of the way when it should.

A Familiar Kind of Lock-In

It’s strange how quickly old memories surface when the right questions get triggered.

Back in 2007, I was working on OpenMoko. We were trying to build something radical: a fully open-source phone. No locked-down firmware, no black boxes—just a device you could understand, rebuild, and trust from the ground up.

We believed deeply in that idea. But believing wasn’t enough.

The moment we tried to scale, the walls came into view. Carriers wanted control. Manufacturers wouldn’t supply parts unless we hit certain volumes. And when we tried to go around them, we hit dead ends. In theory, everything was possible. In practice, everything was bottlenecked by decisions we didn’t get to make.

Years later, working with HTC, I saw a different version of the same trap. On paper, Android was open. But if you wanted access to the Play Store—or even basic services like maps or messaging—you had to integrate Google’s proprietary stack. It wasn’t a suggestion. It was a requirement. You could see the shape of the cage if you looked closely enough.

And yet, we still called it “open.”

That’s what made this recent moment feel so complicated. I wasn’t just switching phones. I was returning to an old question I’d left unresolved: could any of these systems—Apple, Google, whoever—actually support something closer to what we originally imagined? Or had the shape of control simply evolved, becoming sleeker and more polite?

I didn’t know the answer. But it felt like the kind of question worth living with for a while.

Relearning Everyday Life

The switch wasn’t smooth.

Everything felt a little off—keyboard responsiveness, calendar behavior, even the fonts. Not broken, just unfamiliar. Like waking up in your own house and realizing someone had moved all the light switches.

Apple’s polish runs deep. You don’t notice it until it’s gone. They’ve shaped everything down to the tiniest decisions—how text renders, how menus bounce. On Android, things just felt… louder. Less edited. Less choreographed.

But that disorientation gave way to something else.

Moving thousands of notes out of Apple Notes and into Obsidian—just plain text Markdown files—felt like dragging boxes out of a storage unit and lining them up in daylight. They were mine again. I could see everything. Nothing hidden. Nothing proprietary. Just files I could read, back up, or even print, if I had to.

Bitwarden was like that too. It took a bit more setup—YubiKey, password exports—but once it was in place, I stopped wondering if my passwords were stuck behind some invisible wall. It was all transparent. All understandable. There was a kind of mental quiet that came with that.

Small, Quiet Wins

Then there were the little upgrades I hadn’t expected.

Brave Browser felt like someone had taken Chrome, stripped out the noise, and handed it back to me lean and quiet. Safari had grown stale. Chrome always came with that uneasy feeling of being watched. Brave just worked—and left me alone.

NextDNS did something similar, quietly sweeping up all the tracking junk I’d been living with for years. I hadn’t realized how much digital dust had settled on everything. Then it was gone. The web felt clean again.

And Google’s version of CarPlay? Honestly, it blew me away. Music, maps, voice commands—it all worked without fuss. It felt modern. Thoughtful. Apple’s version, by comparison, felt frozen in time.

Even my Meta Ray-Ban glasses worked the way they were supposed to. On iOS, they’d never quite connected right—Bluetooth always flaking out. On Android, they paired instantly. No fight. No explanation. Just on.

Frustrations and Disconnections

Not everything felt like progress.

I missed iMessage. And FaceTime. Not the apps themselves so much as the people behind them—family chats that no longer showed up, friends who assumed I'd gone silent. There’s no clean replacement for being part of the same invisible network.

Gemini, for all its promise, often felt like a prototype. It nailed some things—setting reminders, summarizing documents. But then I’d try to send a message, and it would respond with something like: Sorry, I don’t have access to your contacts. That kind of half-finished experience breaks the spell. It’s like talking to someone brilliant who keeps forgetting your name.

Shaking Loose

But the bigger surprise wasn’t in the software. It was in me.

In my twenties, I chased complexity for fun. I broke systems just to see how they worked. Somewhere along the way, I stopped doing that. I got comfortable. Not in a bad way—just in the slow, quiet way that sneaks up on you.

Had I found the perfect setup? Probably not. More likely, I just stopped noticing the compromises.

Switching to Android shook something loose. It reminded me that the routines I build—the platforms I rely on—aren’t fixed. They’re choices. And if I’m not careful, they become invisible ones.

After the Switch

Will I stick with Android? I’m not sure yet.

But that feels less important now. What mattered most wasn’t which ecosystem I landed in—it was the act of switching. The decision to start noticing again. To ask better questions about the tools I use and the assumptions I’ve stopped challenging.

This month reminded me that habits have gravity. That the smallest decisions—what phone to use, what browser to open, where my notes live—quietly shape the way I think, what I notice, and who I stay connected to.

None of this was really about Apple or Google.

It was about waking up.