09/25/2012 11:53 am ET Updated Nov 25, 2012

Finding Yourself and Your Pants

I remember crying for days.

Tissues, a tub of ice cream, sappy love movies and my best friend -- a true cliché of young heartbreak -- kept me company when I thought I was going to die. I had never felt so sick, so lost, so alone and rejected.

Maybe it was puppy love... but I was 14 and in true teenage turmoil, it was the end of the world.

After picking myself up from the (let's say hypothetical) floor, my older (15) and wiser comrade reminded me, "You broke up with him..."

Oh, the pain. It hurt to see him with another -- very pretty -- girl.

It was then I was intelligently informed, "Boys are like pants..." A shopping analogy? Please continue, I begged Pam. "No matter how good this pair of pants looks in the catalog (on paper) -- or on someone else (my ravishing replacement) -- they just didn't fit you."

I sobbed another 20-something hours, and I was over it. Magically, this insight cured me from catastrophic to calm, and today, my 20-something self applies this mantra to many other aspects of my life.

Making big decisions -- moving to a new city, pursuing a new career and changing dry cleaners (okay, maybe not so much the latter) -- are tough. They come with a lot of back and forth, doubt and ultimately the dangerous question: "What if I did this differently?"

For me, this query pops up pretty infrequently, but always in the month of January, when friends in my South Florida hometown are laying on the beach in 70-degree weather. It is then I question starting my career in a place with snow shovels vs. sunscreen. Why did I move to New York?

In this moment of insecurity (when my boots replace my Havaianas, I miss my car, and my once-sun-kissed-skin channels albinism), the important thing to remember is that my pants (or in this case, shorts) have been outgrown.

While I enjoy reminiscing about my former high school wardrobe (we'll save that for another post), it's important to not second guess the choices we make once we're submerged in different circumstances. Situations change, and we forget the tiny details that solidified our ultimate resolutions.

The truth: My Abercrombie & Fitch (aka high school) days are over. While South Florida is a great place to visit my past, parents and the pool, my life at the moment is centered in the city. The bottom line: When I made the decision to move, I realized the Sunshine State was not sufficient for my success, so I keep this in mind while slugging through snow, pacing the stairs to catch a subway and surviving schools of swarming tourists in Times Square.

Perhaps New York isn't forever, and I'll migrate south sometime in my 60s. But for now, I'm enjoying my digs and gigs, and I'm content with my dry cleaner.

Like my former favorite pair of cut-off jean shorts, it's best leaving the (sometimes questionable) choices of our past in the past. I think my 14-year-old self would agree the healthy thing to do (besides putting down the ice cream) is continue to let our lives evolve, much like our closets.

For more by Hilary Sheinbaum, click here.

For more on emotional wellness, click here.

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