Travel writer. Novelist.
Politician.
Landscape Photographer
I would like to be a mystic. Wander around the earth and let the universe provide.
Frontman for the biggest rock band in the world, with a side of oscar winning actor - “Why no, I don’t crave the attention, why do you ask”?
Newspaper copy-editor
Romance or Fantasy novel/short-story editor
Professional video-game tester
Extreme couch potato
I’d like to work at a think tank or major university dealing with Latin American politics/cross border issues and being paid to travel there.
And do some stand up on the side (I’m not funny on the Dope, but I am funny IRL!).
But if not that, then this:
[QUOTE=Cat Whisperer]
Surf the web for a living. Seriously. Runner-up would be reading for a living.
[/QUOTE]
I would love to own and manage a pool hall. Would also love to be a professional pool player.
Hmm - Philosopher? Pondering Guy? Can that be a job?
While your conditions above give us some free range, there is still the hard work of the job - for instance, I would say guitarist, but I do that now in a semi-pro way and, unless you are a fantasy 1-in-a-million rockstar, the lifestyle is very hard, regardless of income. Groupies and never-ending bus rides get old fast. (although it is cool and interesting to see how many Dopers have mentioned music and guitar in their posts so far).
I am kinda in the “fuck you” category in that I love my job, and it is a dream job in a way. Framing the strategy of a company and ensuring it gets implemented is very fun in a mental-problem-solving way, offers very clear feedback (you achieve your desired strategy, add value for your customers, and make your numbers or you don’t), and, if you want the burden of leadership, well, there it is - you better be the adult in the room.
But I got here through a combination of right place, right time. I was trying to get off the Management Consulting track for a lot of reasons, and this small company was looking to fill a Marketing role, but really wanted someone who had Strat Planning skills because they were trying to figure out What’s Next. I got a random tip about the company (which is why it pays to network), met the CEO, we clicked, and I got hired. By following a bunch of the rules in this thread about 3 Nuggets of Business Widsom, I have ended up on the leadership team of the company.
But it would be really cool to achieve real success - grow or sell the business in a big way - and end up, I dunno, teaching at a University or something. It would be the culmination of a lot of things and would mean I could share something worth learning about (hey, if I want a gritty view of the life of a working musican, but an idealized view of academia, it’s my call for this fantasy, right? ;))
I’m about to start working at something that fairly closely resembles my dream job, at least in theory (we’ll see how that goes once I’m actually working there). I’ll be working as a game developer (some kind of haphazard combination of a programmer and a designer/creative).
I got to this point by getting a job as a programmer at a game development house for two and a half years and saving money, then being made redundant shortly before the company folded. Savings plus redundancy pay plus frugal living plus industry experience as a programmer allowed me to spend a year and a bit making a game on my own. Recently I was travelling in the US and happened to show my game to someone I spoke to who is a director at a small development house, and he said he liked it and would like to help me publish. Visa application is underway right now…
Don’t do it! It’s a trap!
Writer for a string of successful sitcoms.
Nothing. I would relax. I would sit on my ass all day. I would do nothing.
Pretty much what I am doing: I love teaching, and the subjects I teach–AP Rhetoric and AP Economics–are pretty much the two I would pick out of the all the ones in the world.
In my dream job version, I have fancy things like a projector mounted in the ceiling and less paperwork.
Oooo, my “how I would spend my time if I won the biggest lottery ever” daydream. 
I would be a jazz singer. Which is something I’m working toward right now anyway, but I’d be able to network more and take more classes and go hear more live music and take advantage of more opportunities to sing. I’d be a working jazz singer instead of just a wannabe/sort-of-working jazz singer. grin
And, since that would leave me with many free afternoons, I’d also volunteer at a few places. I did a lot of volunteer work in my 20s/early 30s, and I miss it. I wouldn’t try to fill a 40-hour week or anything, because I’d want to use many of those free afternoons to hang out with my dog, but I’d definitely do a few hours a week here and there.
(I actually do enjoy my day job, which involves nonfiction writing and editing, but I’d focus on music over that in a heartbeat – though I’d probably look for a volunteer opportunity that involved writing/editing.)
I’d write and illustrate kids’ books and be a potter.
I’d do these things part time, of course, so that I could be a layabout the rest of the time.
I’d invent the space elevator and accompanying technology.
BTW, this is why I never make small wishes. I’d hate to get one granted right when I was wishing for some guy to shut up or that I had a roast beef sandwich.
I would manage the Pittsburgh Pirates
I’ve always wanted to be a baseball player, specifically, a pitcher. I have M.D., however, and it’s an impossibility.
Joe
International restaurant reviewer and film editor!
I’d play piano and sing in a bar.
Absolutely no talent what-so-ever.