For me the secret was voluntary jobs. They are an amazing way to start working (again). You don't have this overwhelming feeling that you are constantly being judged or that you have to prove yourself. You are their by choice and any organisation would be happy to have you on board no matter what your qualities are.
Also think of what kind of work you'd like to do? What are you hobbies, interests? Animals shelters, for example, were for me the best choice because there were not many people around and I got to spend my days with cute animals.
I than started with part-time jobs in offices. Easy jobs through a temp agency. In time you'll notice that from gaining experience, you become less tense and find a way to get over the awkward & scarry moments.
I now have a fulltime job at an office as an assistant. I have bad days, I have worse days but working is amazing self-confidence booster. Earning your money, spending that money is really something that affected me deep down. (I was on disability for years)
You should never forget that NOW is never too late to start.