“The grass is always greener…” “Better the devil you know…” We’ve all heard those well-worn phrases thousands of times, right? People are funny. No matter how exceedingly spectacular your situation (e.g., David Beckham, Kanye, Sir Paul McCartney, Bill Gates, etc.) we always want mo’ better something. Humans have an insatiable desire for faster, stronger, wealthier, better-endowed, younger, or whatever. The bartender life is no different. I did two (count them) four-year stints in a particular venue where I was basically: The Man. Among a large bar staff, I could demand outright, any shift, had my choice of pretty much any uh… womenses, and made beaucoup duckets on the regular. The earnings at that particular gig, while not rivaling strip club bartending money, were significant and steady – bankable. That job allowed me to save enough fat stacks to buy a private house, and bang out two money-sucking black holes of darkness (read: kids), in one of the most expensive real estate markets in the world -New York City.

So why the hell would I actively choose to pack my bags and walk off the job with nary a promise of another bartending gig lined up? The answer is not so simple.

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