Lighthouse keeper or possibly manager/caretaker (on site) of a cemetery. Actually my current gig(s) aren’t bad but either of those has often appealed to me. Ages ago some estate in England (I believe) was advertising for a hermit to live in a cave and abuse passerbys but my wife wouldn’t let me apply.
College faculty where I teach computer programming. After getting laid off/down-sized at my company, I didn’t want to go back to that. When a community college teaching job came up and I accepted it, one of my friends from my old workplace was in awe, and actually used the phrase “that’s my dream job!”
I concur - playing with computer programming, learning new technologies (I teach some web and Android classes for example), figuring out how to best explain how an algorithm works, watching students progress and learn and grow, and lots of free time when I’m not on campus, all make me think of this as the best job I could imagine for myself.
Something like a “guitar coach.” Not a teacher - I can’t read music and have no clue how to take a structured approach to Theory - but someone who can help you figure out the right guitar for you and help you get the best mindset and approach to staying with it. A guitar whisperer, if you will ;). With a glass of scotch as needed, hanging out, immersed in geekery and dispensing wisdom, such as it is.
And for this service the fees I could charge would be lavish, to keep me in the lifestyle to which I have grown accustomed. 
Enough to fund the room needed for me to do my work, with a broad selection of guitars and amps to allow me to apply my expertise.
I’ll be in my bunk.
Test subject in an experiment looking at the effects of providing an individual with $100,000.00 a week for life. No obligation to do anything other than write a paragraph titled “What I did this month” each month.
Writing that paragraph would soon grow old, however. I’d be bitching to my friends. “Fuck. The goddamn paragraph is due tomorrow”.
Here is somebody doing pretty much your dream job: http://guitarheadquarters.net/Guitar_Headquarters/Welcome.html
The head honcho hangs out in his funky coffee shop *cum *guitar store dispensing Yoda-like guitar wisdom all day.
Much to my amazement he’s still in business after 6 years. In what seems to me a very unlikely town for success. The funky old-but-functioning 1920s downtown is ideal; the specific town he’s in is not.
IANA musician but my wife is. We used to frequent a nearby diner and occasionally stopped in the guitar place for a yak. Give him a call. He’d probably be glad to bend your ear for awhile on how it’s working for him and might work for you.
That looks fun. Thanks!
[Warning! Purposefully vague.]
I’m officially retired, but I continue to work on a gig basis as an expert witness for attorneys engaged in civil actions. The work I do is actually fun, sort of like solving puzzles, and I would do it for free just for the entertainment value. But the attorneys point out that I won’t be taken seriously if I do, so I charge between $200 and $350 an hour.
I normally just provide a verbal report and then I’m disclosed to opposing counsel as a potential expert witness. The majority of civil cases that I work on are settled well in advance of going to trial. I usually have no idea what the terms are in the settlements. I’m deposed in only about 20% of the cases and actually give testimony in only about 5% of cases.
Basically, I work as much as I care to, work at home, work the hours I want to work, and get paid on time. (Most attorneys do not want to antagonize their experts.) The work is also surprisingly steady. I have virtually no overhead and, of course, all expenses are covered.
It’s hard to find faults with the arrangement.
I’d like to be the guy who comes up with names for products.
Not really, though a creative job with no stakes like that does sound cushy and yet satisfying.
I like the sound of Velocity’s idea:
When I imagine what I’d do with a lottery win, it’s something along these lines. A Production Studio where we get to arse about making movies, but I get to pick and choose what we produce, and stick my oar in where I like.
My ultimate dream job?
Be extremely rich (like 11 figures rich) and use the money to support concepts and ideas I believe in. Neuroscience research, global anti-poverty efforts, machine intelligence development, progressive politics, etc.
In the book ‘the dirt’ about motley crue, they compared being a rock star and going on tour with having an erection. At first its great, but it rapidly just becomes an annoyance. Of course they were kind of drama queens in general.
But yeah, rock star sounds cool in a lot of ways. However a lot of it is just sitting on the bus/plane, sitting in hotel rooms, sitting in green rooms, etc. and then going on stage and playing the same 30 songs over and over and over.
Taken literally, my “dream job” is much worse than any job in the waking world. It’s the school dream (an important exam and you can’t even remember which classroom you were supposed to be for all those missed classes), only transferred to the workplace. Typically, a goldbrick job where you’ve been getting away with doing nothing for so long, your dream consists of looking busy.
In a way, what would seem to be a wonderful job wouldn’t be so great – having nothing to do except creatively looking busy until age 65. Which has to be done convincingly, all day every day, to avoid being fired. While everyone arouhd you except your boss knows that you are doing sweet fuck all, and giving you commensurte respect.
I’ve just retired from my dream job.
I taught chess, roleplaying and computer games at a private school. 
As a bonus it was well-paid and included quality free lunches…
One of the co founders of REI just passed away at 107, so the job may come with longevity benefits. http://www.seattletimes.com/business/retail/outdoors-enthusiast-mary-anderson-who-co-founded-rei-dies-at-107/
My dream job is doing what I already do, writing for children, but more successfully–although I’ve honestly done better than I ever expected to. So let’s throw in no writer’s block as well.
Enough work to keep me busy, but not more than I can handle.
Enough pay so I feel I’m valued.
Full-time, PTO, benefits, some overtime if you want it.
No Office-Diva politics.
Bosses who have their employee’s backs.
Someone else handles the Wealthy Over-Entitled clients. “Lorelei Gilmore? Oh no, you’re account is being handled by our ‘Special’ team. Here, let me transfer you…”
The goods or services are important, but not life or death (and anyone who says they Are life or death stands out instantly as an asshole drama-queen).
“No Civility, No Service”
I’d like to be an international currency trader.
Start with some dollars, buy pounds, sell them to buy euros, sell them to buy yen, sell the to buy dollars, ending up with more than I started with.
It’s the only way I can think of to literally make money out of thin air.
This sounds great.
"Lack of clean drinking in water in Burkina Faso - writes $3 billion check "
"Mosquito-eradication program - writes $15 billion check "
"Building schools in Laos - writes $12 billion check "
"Many people stuck with $60,000 medical bills in America they can’t pay - writes $44 billion check to cover all of them "
Is “emperor of the world who must be obeyed at all times” a valid job? I promise to treat the position responsibly… I mean, I’d try, for a while.
My dream job is to be the administrator of my own privately-funded charity.
How it would work is this:
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I win the Powerball Jackpot tonight. Lump-sum value: $90,600,000.
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I donate 10% of it to a 501©3 charity, leaving $81,540,000.
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I pay 39.6% federal income tax on the jackpot, leaving me with $49,250,160.
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I take a $5,000,000 slice for my own personal savings, and an additional $5,000,000 for kaylasmom’s personal savings, leaving the tally at $39,250,160.
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I set aside one million dollars each into three accounts: to buy a house; to put towards Kayls’s education; and to finance medical and surgical procedures we might
need. The pot now stands at $36,250,160. -
I take $18,000,000, and divide it into 90 chunks of $200,000 to present as gifts to my and kaylasmom immediate family members and their spouses, children and grandchildren. This leaves me with $18,250,160. (N.B.: the gifts are structured with a provision that I will pay the federal gift tax out of the $200K)
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I take $9,100,000 and invest in tax-free municipal bonds at a 4% rate of return. ENTIRELY AS A MATTER OF CIVIC PRINCIPLE, I donate 40% of the proceeds to my city, state, and U.S. treasuries. This should leave me with $4200/week to run my household. And the rest of the windfall now stands at $9,150,160.
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Now, $9,100,000 gets invested, also in tax-free municipal bonds at 4%. The proceeds from this investment should amount to $7000/week. My job, as the administrator of the charity, will be to choose an organization each week to which to donate the $7000.
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And the residual of the jackpot will be $50,160. I use that to have a party.
I consider the above plan to be well-thought out, generous, and responsible. So make sure you all vote to me to win the Powerball jackpot tonight.
Design and build sailboats.
I actually made about a months income in a few weeks doing that for just a few minutes a day, taking advantage of a bank’s failure to keep up to date on communications.