Daddy Knows Best

6 Dec

When I was young, I once told my Dad that if I was ever going to bet on sports, I would put money on the team I didn’t want to win. That way, either my team would win, and I would be happy — or if they lost, at least I would win some money — and still be happy! It was a no-lose situation!

My decision-making for the rest of my life would be shaped by his response.

“What’s the point in that?” He said to me in the car, shaking his head. “That’s like half-assing your life.”

He probably didn’t say ‘half-ass’. To this day, neither my mother nor father really curse in front of me, unless they’ve had a few glasses of pinot grigio or Jameson, respectively. But you get the idea.

What he meant was, when all of your eggs are spread out in multiple baskets, you don’t win big.  You’d be playing it safe, sure. You’d never be left wondering if that last chip was going to fall to the right or the left; you would know your routine, day to day, you would probably get married early, have a tolerable career and two-point-four kids. White picket fence sold separately.

But by living big .. dreaming, big – that’s where the yacht comes in. That’s how you end up winning on the poker table. That is how you end up driving twenty-four hours straight to Chicago at three am with your three bestfriends sleeping in the backseat. This may not be true for everyone, I realize. But for me … being so fully invested in something – anything ! – and then seeing it pay off is what true happiness stems from.

That is not to say that I have not made my fair share of mistakes. All your eggs in one basket often means that, on many occasions, shit will hit the fan. Hell, I’d say the mistakes I’ve made in the past twenty years might outnumber the ‘outrageous successes’ 3:1 easily.

There was the mistake I made hitting the bar a bit too much in my undergraduate courses. I once put a kiddie pool in my sophomore-year housing that could have expelled me. I picked Wino-Wednesdays over Writing-My-Thesis-Wednesdays on several occasions … but, through all of this, I made some of the best friends in the world – true kindred spirits, people I would do just about anything for during these debacles.

I drove to see the play of a boy I barely knew – twice in one weekend – only one of which he knew about. I licked rum-punch out of a boy’s mouth … a boy I did not know very well, for that matter. I puked rainbow jello shots in the living room of a boy I liked very, very much. But over four years, I learned what I was worth; and what kind of guy I deserved to wait for.

I went out drinking so much the night before Mother’s Day with my best friend that we had to pull over so she could puke out the side of my car at a gas station. I frequented Happy Hour in New York City, befriending the cute bartender, during my Master’s program rather than applying to Medical Schools for the following year. One Christmas, because I insisted on wearing high-heeled boots instead of snow-boots, I slipped on the ice and squished every dessert from the expensive bakery for our Christmas Eve Party that evening. But I learned the love of family; and the bonds of friends who become family.

The really big wins … those happen when you’re fully invested. When you’ve thrown your heart and soul and every damn egg you’ve got into the baskets, you’ve made sacrifices. This is worth something.

And, for me, that means everything.


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