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.
Thanks for the advice! After re-reading my comment, I should have articulated the thought differently. I've already been taking the path you and the sibling commenter described, all the variables are already more or less in-place, and I already have a strong love of the outdoors, long day hikes with sketchy scrambles, many wall climbers met, invitations received, etc.. So what I meant was, "One of the things I'd like to do is outdoor climbing, but I have a pretty clear path with no particular hurdles in the way of going for it, it's not as abstract as not getting fired or laid off from a job"
That said, I appreciate the sentiment nonetheless; more encouragement to get out and do hard, rewarding things, especially social things, should never be frowned upon.
Motivation and prioritization can be hard!
Personally, I love hiking. I like getting out in nature, seeing all the things I can observe along the way, and getting good exercise. That being said, I don't get up and go on my own as often as I'd like. My wife OTOH, also loves hiking but is adamant about going once or twice every weekend if at all possible. So, I take advantage of that extrinsic motivation and am the better for it.