Considering it was my first ever game jam, it went surprisingly well, even if a bit stressful. I did as much as I could before the theme was revealed, created the git repo, discord channel, wrote out a schedule (that was vaguely followed), and got some of my friends to agree to help playtest ahead of time. We scheduled the playtest for Wednesday night so we still had time to make some somewhat serious changes if the playtest went really bad.
On Friday night we did wide brainstorming, where we just threw ideas at the wall, and then Saturday morning we picked some of the best ideas we had and pitted them against each other. Then our goal was to get the main gameplay loop done by Sunday night, which we actually did ahead of schedule. Then we spent the week iterating, slowly adding mechanics as we thought was feasible, shooting to be pretty much done by Wednesday night. The play test definitely showed we had some difficulty issues, but there was so much variation between players it was hard to make it engaging while still being doable. I think we did an okay job in the end. The final game ended up being MUCH easier than the playtest, and I still think it may have been a bit too difficult.
We had originally planned on a lot more jokes and wacky mechanics to be in the game, but in the end we realized that if each mechanic introduction added 2-4 minutes to the game, we would be looking at a 20-30 minute game, which was WAY beyond what we were shooting for, which was 10 minutes. In the end we realized that even under perfect play the game was still 10 minutes minimum, so we made sure to add cheats so if you hit a wall you could still see the rest of the game.
We made sure to get the itch page together a couple hours before the deadline, which was good because only when I uploaded the web version did I learn that Godot handles sound differently between executable and embedded, which caused a lot of weird audio issues I had to debug. I am glad I had time to fix them because I really didn't want to scrap the browser version.
So all that being said, key takeaway for next year, upload to itch periodically and test the game there, even if it is a pain in the ass to do so.