2025 Privacy Reboot: Six Month Check-In
Six months ago, I wrote about my privacy reboot — a gradual shift toward tools that take both privacy and security seriously. It was never about perfection or digital purity, but about intentionality. About understanding which tools serve me, rather than the other way around.
Here’s how it’s actually gone.
The Wins
Ente continues to impress. The family photo migration is complete, and the service has been rock solid. The facial recognition quirks I mentioned on Android have largely sorted themselves out, and the peace of mind knowing our family memories aren’t feeding Google’s advertising machine feels worth the subscription cost.
Signal has been the biggest success story. I’m now at about 95% Signal for personal messaging — a number I genuinely didn’t think was achievable. The automated WhatsApp replies did their quiet work, and most people made the jump without much fuss. There’s still a handful of contacts who simply can’t or won’t switch, but that’s reality, not failure.
Migadu has the entire family migrated and running smoothly. Moving away from Gmail’s tentacles felt daunting, but the transition was surprisingly painless thanks to imapsync. We own our email again, which feels both quaint and radical in 2025.
Mullvad VPN remains my travel companion, now with multi-hop enabled for that extra layer of paranoia that may or may not be justified. The fact that I can pay for it anonymously still feels like digital rebellion.
The Pragmatic Compromises
DuckDuckGo Browser works brilliantly for personal use, but I’ve had to switch back to Chrome for work. The reality is that some enterprise extensions simply don’t exist in DuckDuckGo’s ecosystem, and I’m not going to handicap my productivity to make a privacy point that only I care about. Work browser for work things, private browser for everything else.
Standard Notes didn’t stick. Despite liking the interface and the privacy-first approach, I found myself gravitating back to Obsidian. The tipping point was building a Granola-to-Obsidian plugin that automatically imports my work meeting notes. When your knowledge management system updates itself, convenience wins — even in a privacy-focused setup.
The Learning Curve
Bitwarden for 2FA has been excellent, and I’ve now gone full circle by self-hosting my own Vaultwarden instance. Access is limited to my Tailscale network for that belt-and-braces security approach. There’s something satisfying about controlling your own authentication infrastructure, even if it requires more weekend tinkering than most people would tolerate.
The email situation has one minor wrinkle: I’ve noticed periodic latency spikes with Migadu’s SMTP servers. Nothing broken, just the occasional sluggish send. It’s the kind of small friction that reminds you why Gmail’s infrastructure is so seductive. But it’s manageable, and the trade-off still feels worth it.
The Social Reality
Perhaps the most interesting observation has been about human behaviour. Some contacts would rather message me on Instagram than install Signal — a perfect illustration of how convenience trumps privacy in most people’s mental calculus. This isn’t a judgment; it’s just the reality of how digital habits form and persist.
The success of the automated WhatsApp responses proved something important: people will adapt to your digital boundaries if you make the friction low enough. Most friends didn’t mind installing Signal once the path was clear and frictionless.
What I’ve Learned
Six months in, this privacy reboot feels less like a radical departure and more like a gentle course correction. The tools I use now are more intentional, more aligned with my values, but they’re not perfect. They’re just better.
The biggest insight? Privacy-focused doesn’t have to mean productivity-hostile. Most of these changes improved my digital life in ways that had nothing to do with privacy — better focus, fewer distractions, more control over my own data. The privacy benefits were almost a bonus.
It’s also clarified where I’m willing to compromise. Work tools live in a different ecosystem than personal ones, and that’s fine. Perfect is the enemy of good, and good is far better than surveillance-as-default.
This might all look different in another six months. Maybe I’ll discover new tools, encounter new constraints, or decide that some trade-offs aren’t worth it. But right now, this feels sustainable. It feels intentional. And in a world where digital convenience often comes with hidden costs, that intentionality might be the most important thing of all.
The question isn’t whether you can achieve perfect privacy — you can’t, and probably shouldn’t try. The question is whether you can build a digital life that serves your values while still functioning in the world as it actually exists. Six months in, I think the answer is yes.