I'm a bartender at a fairly low key bar though we have our super busy days, most nights it's just me by myself. My bosses are awesome, though, partially because they're usually gone 6-8 months out of the year (our owner/GM is a famous musician and his road manager) and also because they're just so relaxed. There aren't many rules to follow other than serve correct pours, charge correct prices and keep the place clean. We're free to drink on the job, bring dogs into the bar, think up specials on the fly and all kinds of stuff. It's also a really interesting staff (one of our bartenders is a drummer for another pretty famous national act) and the regulars are always super awesome while newcomers often walk away giving me compliments.
Before this job I was slumming it in kitchens making minimum wage, sweating my ass off and being unable to afford anything resembling an interesting lifestyle whereas now I can go out for nice dinners, drink nice liquor and wear nice clothes. I feel like a proper adult for the first time in my life and it's done wonders for my self-esteem and past anger issues, I am essentially a zen master right now and I love it.
For the previous seven years I was also a music critic for PopMatters.com, a fairly large website and one of the original internet pop culture magazines (it used to be bigger than, and when I started was on par with, Pitchfork if you can believe it). But their policy was always that you were paid in exposure, CDs, interviews with artists you love and press access to any local shows in your area whether you planned to cover them or not. And I did at first get a ton of CDs I loved, go to a ton of shows I loved and got to talk to some really amazing people like Big Boi, Method Man, Curren$y, Slug and Big K.R.I.T. But as the "how do I get into games writing" questions began pouring into various Giant Bomb Tumblr's and Bombcasts over the past year and the staff remained adamant that you not work for free - again, I'd been working for free for nearly a decade and written over a thousand high-traffic reviews - while the industry shifted more and more towards YouSendIt files and Soundcloud streams rather than shipped promo discs I lost my love for it. I haven't written a review since mid-April and I really miss constantly talking about music, but at some point I had to put getting paid ahead of that, and it's been nice to just listen to music without pretense these past six months.
Edit: As for how I got into those jobs, PopMatters usually posts an open call for writers of all kinds of media every 3-4 months as writers come and go, so I just sort of went for it when I started college and realized I was never going to finish but I really enjoyed doing reviews on RateYourMusic.com. And with the bartending gig (fuck it, I have no shame - it's Pageturner's in Omaha and Patrick really ought to bring his wife's family in over some holiday. They should also try Mula for some truly great midwestern Mexican food and tequila cocktails) I simply was a regular there until one night one of the bartenders asked if I wanted to work the door on weekends, which eventually led to being a bar back (though I was essentially just her personal assistant five nights a week) and then out of pure necessity when she left I assumed all her shifts. It was pure American Dream personified, promotion from the bottom up. I started as a drunk and now I stand on the other side of the wood.
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