When I was in my late teens, I decided that one of my major goals was becoming an outdoors woman. For me, that meant being comfortable in the outdoors for an extended time, which meant being competent in outdoor skills. It took a few years but here are 5 steps that helped.
1. Gather information. Read Backpacker Magazine, any of the many books available, and talk to people whose experience you admire.
2. Join a local outing club. Almost all cities have some kind of club and starting with people who know more than you do is always helpful.
3. Take some specific skills classes. For example, REI has stores everywhere and they usually offer weekend clinics and programs throughout the year. See if you have a local outdoor store as they may offer the same. For example, Midwest Mountaineering in Minnesota is an excellent source. Practice the skills on your own. I guarantee that you won't learn how to use a map and compass in one clinic but it will give you a basis for practicing on your own.
4. Make a list of equipment and clothing that you know you will need, and then start looking at sales, Craigslist, discount website etc. Don't focus on gear but know what you need and get decent quality that will last a long time.
5. Once you have some basic competence, take an extended wilderness trip. It could be backpacking or canoeing or kayaking, but it should be at least 2 weeks, in the wilderness, and it should not be with a company like us. If you're not ready for that, then by all means go on a shorter trip with a company and hone those skills a bit more. But here's the thing - there is a common saying that good judgement comes from experience. And you can only really get experience when you are the one who has to make decisions, which won't happen if someone else is in charge. Yes, you will make mistakes. But that is how you will learn and those are the lessons you will never forget.
6. Ignore all these steps. Just get out there and do it.