It's definitely a massive leap.
And there are phases of it, especially starting out. It'll feel weird knowing everyone else is going to work and you're going to wonder what to do with yourself. Eventually you start adjusting after a year or so.
I'm 4 years in (this week) and I can't even imagine working again. I just kind of do whatever and the idea of being beholden to someone else's schedule sounds retarded. I still keep some stuff scheduled, like I workout 6 times a week and generally do it the same time of day. I try to play drums for about an hour daily (and I do drum lessons every other week). Usually I'll watch some TV with the wife between 6 and 9pm. Walk the dogs once a day.
I don't even know how you worker bees get up early, commute, go to meetings, and all that other retarded shit. I mean, I know I used to do it too, but it honestly just seems so foreign to me. Knowing what I know now, if I did for some reason go back to work, my tolerance for all that would be so low that I'd either get fired or quit pretty quickly I think.