Steven Legg
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May 2026 Update

May 2026

I'm doing well. There's a lot going on, some of it hard, a lot of it good, and writing it out feels like the right thing to do.

Work and What Comes Next

EF Boston is closing. I'm going to be honest — I really love my job here, and I'm not sure it's fully hit me yet that everyone is getting laid off. The people I work with are genuinely wonderful, and watching a community like that come apart is its own kind of loss separate from the practical situation of needing to find something new.

I'm looking for work starting in August. What I'm really hoping for is to relocate with EF — specifically to Germany, Switzerland, or Austria. That would be ideal, and I'd love it if it worked out. Nothing is confirmed yet and I'm trying not to build too much on it before it's real. But it's what I'm hoping for.

The support I've gotten from colleagues has been genuinely moving. A coworker said something really kind to me recently that I've been holding onto. I got a text the other day that warmed my heart in a way I didn't expect. It's been a difficult couple of years in a lot of ways, and I am so grateful for the people I have around me. I have a lot to be thankful for.

I'm also taking a bit of a break from dating for now. The timing just feels right for focusing on the other things in motion.

Umbra

My cat Umbra got out of her harness at the park about a month or two ago. I've been trying to get her back — I set up a Have-a-Heart trap in the area with permission from some of the people in the neighborhood, but so far no luck. I miss her a lot. She's so shy, and tiny, and fast, and genuinely excellent at hiding, so I really don't know when or how she might turn up. But she's chipped, so if she ends up at a shelter there's a way back to me. I still have a lot of hope for that. I have to keep going with my own life in the meantime, but I haven't stopped thinking about her.

Once I've relocated in August, I'll probably adopt another cat. Not as a replacement — there's no replacing Umbra — but because having a cat around is something I really want in my life.

ClaudeCowork and Language Learning

I've been using ClaudeCowork a lot lately and it's genuinely incredible. Not just for coding — I've been using it for studying, language learning, regular office tasks, anything where I get stuck and need help pushing through. I'm learning a lot through vibe coding too, just trying things and seeing what happens and using ClaudeCowork to help me through the moments where I'd otherwise stall. I'd honestly recommend it to anyone, not just developers.

I'm planning to try getting it to make some Anki flashcards for Cantonese and Mandarin. Accuracy is always a concern with AI-generated language content, which is worth keeping in mind. But for my main 2026 decks — the ones I'm taking seriously — I'm sticking to making the cards myself. There's something about the process of building a card by hand, deciding what to include, writing it out yourself, that does part of the learning before you've even hit the review queue. AI can be useful for supplemental material, but for the stuff that needs to really stick, I think the manual approach is still better.

Getting Off the Cloud

I've been methodically moving away from cloud storage — iCloud, Google Photos, OneDrive, Dropbox, all of it. I requested my data from each and archived everything locally. I bought two 5TB external drives last year and they were great investments. Mostly I'm using them for .mp4 files from DVDs I've ripped, plus photos and general archives.

I don't miss Google Photos as much as I expected to. What I don't miss is being shown memories I didn't ask for — a random screenshot from three years ago, a photo from a hard period resurfaced as a "memory" because it happened to be taken on this date. The algorithmic surfacing of your own past is something I find draining rather than comforting, and getting away from it has been genuinely good. I have plenty of things I want to remember. I don't need an app deciding which ones to surface and when.

Social Media

I haven't had Instagram, Facebook, Snapchat, or TikTok since January. The first few weeks were strange — a real sense of social isolation, reaching for apps that weren't there anymore. That passed. What's on the other side of it is quieter and, honestly, better. I don't regret it at all.

I'm still on Bluesky and Mastodon. Those feel different — smaller, less engineered to keep you in them, more like places where conversations actually happen.

WhatsApp is the one I genuinely don't know what to do with. I really wish Meta had never bought it. It's the only Meta product I'm not sure I could leave, purely because of who I need to stay in contact with. It makes me uncomfortable. I don't have a resolution for it yet.

My screen time is still higher than I'd like, and it's mostly YouTube Shorts. Getting sucked into them randomly is the one habit I haven't managed to break yet. I really dislike how much the YouTube app pushes Shorts over everything else. It's something I try to reduce my non-human notifications generally but plenty still get through. Work in progress.

Generally

There's a lot up in the air right now — work, location, various things still unresolved. I'm trying to hold that lightly rather than anxiously. Some things just take time. I'm doing well, and I have good people around me, and that's a lot.