You seem to have used this thread as an outlet -- outlets are good -- but maybe I can give you some advice anyways. The nice thing about the internet and anonymity is that you can take it or leave it and it doesn't matter.
Anyways, I can relate to bits of what you seem to be going through. Like me, you like to plan things out, and you like to know what you're getting into before you do it. The problem is that you'll never know enough.
Most people have no idea what they want to do either; I can't tell you how many times I've heard from successful speakers who, when asked how they managed to get where they are today basically just said they have no idea because they just did one thing they liked doing, which lead to an opportunity doing something else they wanted to try, which lead to further opportunities, until they ended up running some company.
Understand this: You will NEVER be 100% certain that what you're doing is the best thing for you or ultimately what you should be doing. What you are requiring of yourself is to be able to 100% accurately predict the future. That's an impossible standard to meet, and you're doing yourself a disservice by doing so. Telling you to just do something isn't bad advice, but like me, you probably need a little context to understand why.
Things will never be perfect -- don't expect yourself to wake up one day with a perfect vision of what your life will be like. Some people are blessed in that they know exactly what they want to do and how to go about doing that from an early age, but most aren't (a friend of mine knew he wanted to be a CPA when he was like 12, and so it's no surprise that he's well on his way on that very defined process). Instead, just make it your mission to find things that you like doing. If you don't know what you like doing, TRY NEW THINGS. Volunteer for various organizations, go take night classes in weird subjects, play sports, meet people and talk to them about what they like doing to see if it's something you may enjoy as well. The point is that without any experiences to fall back on, all that sitting around and thinking you're doing is just going to bring up how much you hate your boring job because you haven't experienced anything else.
You need to live, you need to eat. Most people's feeling of self-worth is tied to what they feel they've accomplished, and being out of work for 2 years probably doesn't help. I have no idea what your background is, so if it's just job-hunting tips you need I suggest reading "What Color is Your Parachute" by Richard Bolles, otherwise you may be stuck with those boring entry level jobs (for now) just so you can keep going. Then while you're working, start exploring other things (aforementioned volunteering, education, sports, anything that is even remotely interesting to you and that gets you meeting people that can further help you find out what you like). I can't imagine that you don't have any interests at all, so there should be at least something you like doing. Hell you're on neogaf, so you probably at least like videogames-- go work for a videogame company.
The point is that you just need to start, it doesn't matter what. Don't worry about picking the wrong thing and having to start over: first of all, learning what you don't like to do is valuable, and chances are you'll gain some knowledge/transferable skills that you can use doing something else (even if it's totally unrelated). Once you are doing things, and involved in all sorts of areas outside of work, you'll find things start to happen. One of the guys on the board of the charity you're working for that you start getting along great with happens to also run a business and he has a job for you because he's impressed with your work ethic. Or you play basketball at nights with a chef for a fancy restaurant and the more you guys talk, the more you realize how much you love to cook food. Or WHATEVER. It doesn't fucking matter what it is, just realize that the more you get yourself out there, meeting people, doing new things, the more likely it is that you'll find what you want to be doing with your life. And surprise, you'll also find that because of all this stuff you've been doing you're so much more than just an entry-level data entry guy because you have all this other experience and knowledge, and because of that you get the job.
Ultimately, it's up to you. Your situation WILL NOT CHANGE unless you own up and take complete responsibility for it, and that's not something I or anyone can force you to do. But you may want to consider that obviously what you're doing right now isn't working, and so considering what other people have to say may be a good idea. And if you decide to ignore everything I've said, do me a favour, pick up reading as a hobby. Mix it up between classics, non-fiction, and quality fiction covering all kinds of topics. It's not the same as experiencing, but at least you'll still be exposed to a multitude of new perspectives and eventually something may stick with you. Gaf's monthly 'what are you reading' thread is a pretty good place to get recommendations from people with (probably) similar tastes to you, or just browse amazon in interesting categories. Make a goal to read one book a week and stick to it.
