Chapter 1: What Was I Thinking?

Hi Gwyn. I almost didn’t come back from San Juan, my first vacation since joining your team. While it came at the heels of my associate promotion, something anyone else in this office would’ve celebrated, I looked for any reason to stay, running away from another accomplishment. Less than twenty-four hours ago, I attended Sunday services with a girl named Valencia’s family and nearly reinvented myself as a lobster fisherman living in a bungalow. So yeah, I’m having a quarter-life crisis.

Thankfully, I realized escaping wouldn’t magically fix my problems before pulling anyone else into this disaster. I spent the majority of my return reflecting on how I ended up here – getting into banking and subsequently wanting to leave. I pretended to sleep, so the flight attendant wouldn’t ask if I wanted a Blood Mary.

Approaching the skyline, I directed the cabbie to our office instead of my apartment. I didn’t want to delay this conversation any longer, so I swarmed through the typical lunch stampede, feeling their eyes on my Caribbean-inspired attire. Interestingly, you don’t seem nearly as taken aback as the guys on our floor.

I’ll probably sound like a douchebag, but I’m tired of pretending; from the outside looking in, both literally and figuratively, I have no legitimate reasons to complain. My parents supported me growing up and paid for college. At twenty-five, I live by myself in a New York City apartment with a closet full of designer suits. I’ve only had one real girlfriend, but don’t seem to have any trouble finding someone to marry. I’m the definition of success by any objective metric and couldn’t feel more depressed if I tried.

Notwithstanding our personal relationship, I’m also risking my career with this conversation. I mean… you’ve just named me an associate, the only analyst from my class earning that distinction. But I don’t have anyone else to ask for advice. Nothing ever works out how I hoped because I’m either not talented enough or it doesn’t meet my expectations. From football to journalism to finance, I’ve put forth my best effort and received nothing in return.

And please don’t tell me to keep trying. I don’t care what anyone says – work ethic can’t overcome bad luck and mediocrity. I feel like an idiot, chasing something that doesn’t exist. I never would have strapped on pads or attended a Gazette meeting or followed the herd to New York had I known how it’d end, not to mention my failed relationships along the way. So if your answer entails some version of apathy or settling, stop me now and I’ll hop on the first plane back to Puerto Rico.

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