Start small. Buy a decent tent, sleeping pad, and sleeping bag (if you like REI, their people are usually very good at helping you find what you need in your budget). Find a local car camping campground (such as a state park) and just go car camping. For those unfamiliar, car camping is where you go to a campground that you drive up to your campsite (and you are rarely very far from some sort of civilization). Before you go think of all the things you'd want with you (food, water, entertainment, etc.) and pack it up in your car (cold food in cooler with ice, of course). If things go wrong (which they probably will at first, and that's fine), you can always choose to drive to the store if you forgot something or go home if something else happens. Most of these campgrounds have small hiking trails as well. Start small (Do a few of these and try something new out every time. Maybe you want to work on building skills like fire making. Maybe you want to try out new equipment such as using a camping stove with dehydrated food instead of a fire. Or try out techniques like packing all of your stuff in a backpacking pack and take it on hikes to see how what you'd need (and possibly not need) go backpacking.
Once you feel comfortable start expanding out. Maybe try a day hike where you cover more ground (but don't overdo it at first, stay within what you know for a fact you are capable of). Do an out and back one where you start at your car, and end back up at your car. Maybe try going for one night of backpacking to "wilderness" camp sites at a local park. These sites are usually a short hike from where you'll park with no amenities. Practice your skills. Enjoy the nature.
From there figure out what you are enjoying and maximize that. Do you like the hiking? The camping? Just hanging out with friends around a campfire? Do that. It's not about how extreme you can make it, it's about what you like. If hiking makes you miserable and all you want to do is sleep outdoors for a few nights with a stable fire, then there is no shame in sticking to car camping. There will be purists who look down on it, but who cares?
Try new things, find what you enjoy, and don't push yourself more than you know you are capable of.