For Starters, We Humans Were Never Meant To Be Optimistic

I’m done being an optimist. I’ve always looked at the world through rose colored glasses (metaphorically, of course. I’m not John Lennon or Shawn Michaels for Christ’s sake.) But no more! Here’s why being a constant sunny-side-upper can be detrimental to your health:

It blurs the line between right and wrong. Being a serial optimist can actually get you in trouble. Example: I’ve had friends go to supermarkets that installed the self checkout lane and protest. They believed it’s an evil piece of technology because it takes away from American jobs and money that could be going into the economy. I disagreed. I always thought you can take a bad situation, flip it on it’s head and make it a great one. I loved the self checkout lane – because it allowed me to ask myself this question: “Do I have to pay for all my stuff really?”

The answer is yes and no. Whenever I’d go to the supermarket – I’d grab ten carts worth of stuff. Everything I’ve ever wanted in my life. I’d bring the groceries up to the self checkout lane, put them on the counter, and weighed everything I got as if it were bananas. So, technically, I paid for everything I had…as if it were .99 cents a pound. (For you non-math majors – you can leave with $1,000 worth of goods for $9.99.)
My only word of warning: Don’t go to any store that has a voice automated self checkout lane. You’ll put your newly found bounty up on the counter, hit the banana button (which is 4011, if you must know) and a woman’s voice comes over the speaker yelling “Please place your BANANAS on the scale!” Everyone will look over to see you have nothing but red-glossy eyes and Pop-Tarts. Busted.

It masks the reality of a situation. On a balmy, August night in 2009, I was tired, broke and leaving New York City to move back home to Boston. Having $200 to my name, I did what anyone would do: I closed my bank account – asking for a single 20 dollar bill accompanied by 180 1’s– because that’s how you fake a serious stack of cash. If it were to be my last night in town I’d need one last hurrah – the strip club.

My friend and I took our ones, stuffed the pockets of our suits and headed down to an unnamed gentleman’s club on the West Side Highway. Seeing our duds, the bouncers let us right in free of charge, took a reserved sign off the front table and asked: “Would you fellas like a bottle?” After browsing a menu filled with overpriced vodkas and whiskeys – the cheapest of which was $300, I told the man: “We’ll have the 19 dollar Bud Light, my good sir. With two straws, please!”

While this was happening, a woman dressed in a cubic zirconia encrusted sling-shot bikini and clear heels took the stage in all her glory. Everyone started tossing money at the stage, but the dancer’s attention was on me.

She likes me! I thought. So I kept putting down more of the 180 Washington’s I had rolled in my pocket. I was throwing more one’s than a catcher looking for a fastball– and she kept making eye contact. At the end of her three songs she starts collecting the money – most of which are 20s, 10s and 5s– takes the scattered one’s (most of which are in front of me), crumples them up into a big ball, hands it to me and says: “You need this more than I do.” Do you understand what a life changing experience that should have been and wasn’t? What would have been anybody’s rock bottom had me exclaiming: “Jackpot! Shots on me!”

It makes you feel good when you shouldn’t. Recently, I was doing some shows at a casino in Baltimore, Maryland. Before the drive home, I wanted some breakfast and saw there was a Ken-Taco-Hut (KFC, Taco Bell and Pizza Hut combined into one sad shack) located in the parking lot of the Days Inn I was staying at. A realist looks at this situation and gets the hell out. An optimist thinks: “Cheap and easy food! Let’s do it!” So there I was – mowing Taco Bell at 9 AM in my car at a Day’s Inn parking lot in Baltimore, Maryland – happy as hell. Honestly, I was upset that I wasn’t upset.

Optimism can be a helpful tool to make bad situations seem bearable, but beware of constantly seeing the good in things. Thinking positively turned me into a thief, pitied by strippers, who’s okay with eating fast food in a car at 9 in the morning in the city that The Wire is based on. While it’s okay to look at the bright side – remember staring for too long will make you blind.