It's a surprisingly common position to be in: You finally achieve the impossible (or at least what seemed impossible for a long time) and become debt-free, but instead of feeling financially empowered, you have a deer-in-the-headlights episode. You're so accustomed to being in debt that you don't quite know what to do without it.
Here's the problem: Once you get paid, your money has to go several places at once. Bills need to be paid, credit card balances need to be settled, groceries need to be bought, perhaps even some nonessentials, too -- and, in all the shuffle, the money that you should be saving becomes your discretionary income.
Later this year, at the age of 32, I plan to quit my full-time job as a software developer and don't intend to look for another one. By then, I expect my portfolio will be large enough to fund my essential expenses for at least the next 30 years, if not indefinitely, so that getting another 9-to-5 job becomes an option rather than a necessity.