Otherwise, the skill that seems most out of reach is keeping a job for longer than a year

I haven't done much climbing at all but I would encourage you to go for it. Being outside is a whole different level and a great excuse to spend time in nature. Start by talking to people at your bouldering gym. If you hear anyone discussing going out climbing, ask if you can tag along and just watch for a few times. Watch some videos about climbing basics to get an overall feel for it and some of the concepts and terminology. I'd say you should start out "top roping" on smaller walls. As for equipment for that you don't need much especially since your partner will probably have a rope and gear to build an anchor, etc. You'll need, shoes, a harness, and a helmet. Going from gym bouldering to outdoor climbing _does_ require being a little more social. It's a minimum 2-person sport usually. But going as a small group and rotating roles and just hanging out watching works too.) You just nee…

I would encourage you to speak to the wall first in case they run outdoor sessions or see if there are any clubs in your area. This assumes you live in an area with some outdoor climbing. Outdoor bouldering can be done with little equipment, but you need to start way easier than what you'd do at the wall. The ground is surprisingly hard and I've seen someone break their ankle right in front of me a few times and it does not look fun. Outdoor sport climbing is pretty easy to get into if you have bolted climbing in your area, but as you get higher the ground gets even harder so make sure you know what you're doing. Lots of good books and resources available. If you really want to get into trad climbing be prepared for a longer apprenticeship, take your time and start easy.