I've tried a variety of tools over the years and always end up going back to a low tech approach: spreadsheets. I set up my credit cards to email me after every transaction, which I then manually copy over to my spreadsheet with additional category information. Pivot tables give me a breakdown by category / month.
The added friction of having to manually copy everything over is a nice incentive to buy less stuff.
If you're interviewing for staff level positions and above, you'll be discussing long term planning and some pretty tactical stuff where an NDA makes perfect sense. Might be a bit overkill for senior and below but meh.
I’m in Pittsburgh but didn't end up applying anywhere local. I was looking for remote-friendly positions to keep things flexible due to an upcoming move, which definitely limited my options. Out of the 50 or so companies I looked into, barely a third turned out to be remote friendly, with some only pretending to be (e.g. Meta seems to have gone out of their way to make remote suck for everyone involved by limiting it to staff+ on top of manager discretion).
I was definitely nervous about the time off being an issue. The usual stream of recruiter emails had pretty much dried up by the time I started looking for work, and I was fully expecting the search to take forever. It wasn’t an issue at all in the end - no one brought up the gap during interviews. I mentioned it in passing a few times when talking about why I left my previous job and mostly just got “dang that sounds like fun” from people. That being said, I have no idea if I would have gotten more responses to my initial inquiries without the gap on my resume.
I can't help but feel like I lucked into easy mode given the general consensus that everything sucks right now. Applied to 10 places (mix of FAANG and small startups) after taking a year off from work. Heard back from 5, somehow got offers from all 5 and am starting at one of them next month.
It took a fair bit of prep to get back into things - especially when it comes to system design interviews - but otherwise everything went fine. Really enjoyed how some companies are trying non-leetcode approaches lately like code review and debugging sessions.
Another vote for Pocket Casts. The only thing I dislike about it is that the search feature can be janky at times, especially when it comes to non-English languages. No complaints other than that.
I suppose this is a bit of a special case but the US and Canadian governments both require you to provide the full list of trips from the last ten years when applying for citizenship and permanent residency. Timeline is incredibly helpful there.
You wouldn't necessarily need to retrain that frequently. If your model outputs hashes / vectors that can be used for searching, you just need to run inference on your new data as it comes in.