Comment by brailsafe
There's a few that come to mind, but none that feel actually as daunting intellectually as much as they are qualified by other factors.
I'd like to go from indoor bouldering to rock climbing, but coordinating with a belayer doesn't seem super interesting and otherwise it's just a matter of expense, gear, and a slight pivot in my leisure time to start going at it.
Otherwise, the skill that seems most out of reach is keeping a job for longer than a year. I'm in a decent spot now, after a year and a half prior of being unemployed, and I feel like this might be my last real shot at a career of any kind. Other people seem to handle it fine, but this is the thing that seems most out of reach. Unlike engineering problems that are made up of abstractions with ways to break them down and piece together systems, keeping a job is as opaque of an abstraction as I'm aware of, that doesn't necessarily depend on a measurable skill or even on anything within one's control. I've never once felt stability or been able to bet on money coming in next year, and if I had the money for a mortgage, I'd be stopped by the knowledge I can't count on an income flow at any time in the future. I'm thankful for what I have and what I've learned nonetheless.
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 need to find people you like hanging out with and you can trust. (If you don't find them at your gym, try another or ask around at outdoor stores, your local university rec department, etc.)
About jobs, I can't help you. I tend to stay too long if anything.