I'd probably do #2 in that situation. Cool tech stacks are at lots of places. You can always find a new place with that stack to join in a year or two if you wa

I'd probably do #2 in that situation. Cool tech stacks are at lots of places. You can always find a new place with that stack to join in a year or two if you want. Also those places with the cool tech stacks will probably be places with outdated tech stacks in 4-5 years, anyway. You can also work on a side project a couple hours a week in the relevant tech stack to keep you up to date for when you're ready to jump ship again. I took a job as a video game producer for a year and a half at a company where I had to speak Japanese (not much, just a few phrases) and sit in on meetings conducted entirely in Japanese, and picked some up along the way (could have done more if I tried a lot harder). I wasn't programming at all for that job, it was all playtesting game builds, evaluating Japanese games to see if we wanted to bring them to the US, going over Excel files for localization, capturing and editing trailers and gameplay videos with Adobe Premiere and After Effects, designing game covers, websites, and advertisements, handling paperwork for localization, on calls with developers and QA to communicate what we needed, etc. so it definitely wasn't "with a relevant tech stack". A year and a half later we got some less-than-stellar reviews for a couple games, missed our sales targets, and the company folded, and then I switched back to a technical job programming again. I've since switched tech stacks completely two more times over the past decade (Objective-C -> C#/.Net/Angular -> React/AWS). So yeah, do the fun cultural job, expand your life in that direction. You don't get that at too many companies. I haven't gotten that at any company I've joined since, they're pretty few and far between (at least those that also pay well). Also, in my opinion, a stressful startup job is pretty overrated. If it's stressful, it's probably not managed that well, and so it'll probably crash and burn and you won't see anything for your efforts anyway, other than some better skills. Crashing and burning can happen at the fun jobs too (see my experience), but at least you don't have like, PTSD from being overworked at the end of it.