Moonlighting as a Professional Wingman

If any of you guys have watched HBO’s new series, Bored to Death, then you’ll know what I’m talking about. For those who don’t, Jason Schwartzman stars as Jonathan Ames, an uninspired writer who needs to write a second novel but has zero direction. His love of wine and his ability to fail at life caused his girlfriend, Suzanne, to leave him. Not knowing what else to do with himself, he went on Craigslist and offered his services as an unlicensed Private Detective. Much to his surprise, someone emailed him asking for helping finding her missing sister. The rest has been an entertaining history. You have to check it out.

But watching this show reminds me of a year ago, when I didn’t exactly know what I was doing. I recently came off a break up and I wanted to create a video game. I sought guidance from many people, looking for direction and still not truly knowing what I should be doing with my life. Then, one night, I decided to put up a blog saying I was a dating and lifestyle coach, making it clear I wasn’t an expert whatsoever. And everything started from one person emailing me. I remember running around excited about my first client but not knowing exactly what to do or what to expect. Every client has a story and proposes a new adventure. It’s always fun and you never know what you’re going to get yourself into. It’s a learning experience for everyone involved and I love every minute of it.

It also brings me back to the point where we all start as rookies at whatever we want to do. Some of our jobs require preparation and education. Others require only experience. Others can get along well with just passion (to a certain point.). But we all start with nothing. Putting yourself in the trenches will always be the only way to truly be great at what you want to accomplish or make of yourself. So, yes, I definitely moonlighted as a professional wingman for several months before The Professional Wingman was born. Now it’s crazy to think that people would call me Boston’s Dating Coach (or Hitch, for that matter). I personally will always feel like I am moonlighting. It just seems more fun and adventurous that way.

Watch the show to know what I mean.

(See this week's episode referencing a backup Russian wingman for more details)

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