I'd probably just travel most of the year but I'd like to have a reality show where I travel to every college football venue and showcase tailgating. That or the same kind of job but as a correspondant for High Times.
Bullpen Catcher
Golf on the European Tour
Equipment Manager for Barcelona or the Cubs
Pro Poker Player
Sports Bar/Brewery Owner
Golf Course Owner or Manager
Own my own radio station and be the sole content programmer (with no commercials, of course). Then only play music I like and finally force people to listen to quality programming so they could see how it contrasts with the lowest-common-denominator crap that is on 99% of the radio stations in the country.