In this Office Hours Live, I dug into a question I get constantly: can you actually escape Google Calendar without wrecking your day-to-day workflow? I broke down why calendars are way more sensitive than people realize (events, locations, patterns, who you meet with), and why Google’s model is fundamentally different from privacy-first options. From there, I compared the two “ideal” paths: end-to-end encrypted hosted calendars (like Proton and Tuta) versus self-hosting (where you control access and don’t need E2EE in the same way). The problem, as always, is usability—widgets, notifications, and friction that can genuinely make you miss meetings. I also talked about the “middle path” people forget: services that aren’t end-to-end encrypted but are still a meaningful step up from Google because they’re not ad-driven and have stronger privacy commitments (Fastmail is the big example I brought up). I touched on Apple Calendar too, including the important caveat that even with Advanced Data Protection, Apple excludes calendar/mail/contacts from E2EE. Beyond calendars, we covered practical file sharing (why Proton Drive expiring links are often totally reasonable), my go-to Mac storage tool (DaisyDisk), and some Android tracker-blocking nuance—especially how browser traffic can complicate “app tracker protection” approaches.