I plan on (semi?) retiring at the age of 48, in early 2015. Except for two years spent doing real estate (which I loved), I've been in the IT field for almost 30 years (I've been working with computers and IT in some form or fashion since I was about 17 years old), and I've grown jaded and bored. It simply doesn't interest me anymore, and in the grand scheme of things, I find the work I do boring and meaningless.
I tried to escape all that with my first career change (not just job change, but a career change) in 2005 when I got my license and started practicing real estate. I loved it. For the first time in my life, I was working for myself, with no boss, projects, or schedules hanging over me. I just couldn't make it last due to the economy. 2005 was probably the WORST year to get involved in real estate, and I lost every dollar I had.
If I'm blessed enough to walk away from where I'm at with a life-changing windfall in 2015, I am leaving the IT field forever, and never looking back. If I do choose to work again, it will definitely not be in IT, nor be for another person. I'll run my own business of some type. But I'm taking at least 2 or 3 years off to travel and enjoy the world before I even think of something like that. I want zero responsibilities for a couple years, with nobody to answer to but myself (I'm not married, and have no kids, so that makes it easier for me to do that than most people).
And even if I do start my own gig, be it real estate or anything else...the day it stops being "fun", or rewarding, is the day I'll shut the business down.
Regarding the OP's statement about management...when I had to give up the real estate thing and get back into IT, I decided I was going to try climbing the ladder a bit more, something I hadn't really done before, as I was content to be a worker bee. I assumed a management role for about 6 months when my boss got promoted, and I took over our team.
HATED IT. I detest office politics, and I didn't realize how much my manager shielded us from all the BS that went on at the executive level. All of a sudden, I had to deal with all that crap, and I hated it. I also hated dealing with interviewing, hiring, salary reviews, performance appraisals, and all that other paperwork BS crap that goes along with managing people. The final straw was realizing that when you're a manager, ALL your peoples' problems are YOUR problem.
No thanks. I lasted 6 months, and then went to a new company. I have no plans to pursue a "management" job again, unless it's me running the show at my own place, in which case I'll delegate all the junk I don't care to do to somebody else (it's good to be the king, right?)
My .02...