Why 'What If I Had Done This?' Is The Worst Possible Question You Can Ask Yourself

The biggest mistake I’ve made in my 23 short years is not having taken a risk that could have changed my life. No, seriously, I regret it every day.

I sit at home, jobless, trying to imagine where I’d be and what I’d be doing had I followed the advice of the tattoo on my arm and seized the day.

When I sat down to write this, I thought, "What advice or motivational tip could I possibly glean from my unfortunate regret to bestow upon my peers?" Well, here it is: When you're presented with an opportunity, do yourself a favor and take it.

Eminem wasn’t lying, you guys — you only get one shot.

This past December, as a college senior, I was trying to figure out what to do in the next chapter of my life. I had applied for an internship at Esquire because I’m ambitious, a bit idealistic and a fan of the thought, “Why not?”

To my surprise, I heard back almost immediately. I interviewed with the publication, pitched some stories and pulled an all-nighter researching and writing a story as a test. They ended up liking my work (and apparently, me, too) and offered me the internship.

There was only one problem (there’s always one problem, right?): It had all moved so fast. They wanted me to go to New York at the start of the year and hit the ground running.

Now, you may be saying, “Problem? What’s the problem?” And if that’s what you’re thinking, you sound like every last one of my friends. However, it was very short notice and I didn’t necessarily anticipate getting the internship.

I would have had to put off graduating for a semester or more, found someone to sublease my apartment in just a few weeks’ time, renege on my job as editor-in-chief of the student newspaper (which also provided a full scholarship) and figure out how I would get to the Big Apple.

All of the decisions seemed insurmountable, while the time was still short. As you can probably guess, I ended up not going. I tried to position myself for an internship during the summer; I even showed up at the magazine's offices on a school trip to New York, but it didn’t do much good.

The moment, the opportunity and the life that could have been, had passed. Maybe that’s overly dramatic, but I want it more now than I did when the magazine initially offered the position to me. I’d go to school for three more semesters to get the chance again.

As I sit at home, every day, and apply to almost any publication that’s hiring, I’m sure I’ll find something eventually. And I’m sure I’ll enjoy it, move on and go about my life. But, it won’t be Esquire; it won’t be that opportunity.

I’ll never know what could have been, so do me a favor and don’t make my mistake. If Esquire — or whatever your personal “Esquire” is — offers you an internship, take it. Make it work, drop your things, pack your bags and go for it.

You’re young and you can afford to take risks. When you’re not having luck in the job hunt, you don’t want to find yourself wondering, “What if?”

So, take the risk, take the job, move to that city, go on that adventure and kiss the girl, because, well, you simply never know.

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