Overcoming Fear: How I Almost Cried At My Bachelor Party

Over the years, I’ve taken some calculated business risks that usually turned out okay. So you’d think I’d have some good strategies for overcoming fear. But I never anticipated how my idiot friends would surprise me on my bachelor party.

On the day of my party, my best man convinced me we were going golfing. We were in Las Vegas. And if you’ve never been, there is a nice golf course a few miles south of the strip, in front of a small airport. And it wasn’t until we drove past the golf course that I realized there would be no golf…

“Just kidding. We’re going sky diving.”

My friends didn’t seem the least bit concerned that I had a fear of heights. Or that the absolute last thing I ever wanted to do IN MY LIFE was jump out of a perfectly good airplane.

overcoming fear

The Truth About Skydiving (And Overcoming Fear)

Now if you’ve never entered a skydiving facility before, the first thing you do is watch some terrible video that tells you literally, the top 10 ways you will most likely die. Then they make you get on a table, lift your legs to your chest and pretend you’re falling. That’s it. That’s the whole training. A video and a leg exercise.

Then the skydiving place makes you sign a waiver, which once again assures you that your parachute will probably fail and you will plummet 18,000 feet to your doom. All of which filled my mind with horrific imaginings of how my beautiful bride would be left alone, crying at the alter.

At this point, I was pissed. Any strategy for overcoming fear was replaced by an irrepressible desire to punch my best man in his stupid, idiot face. And while the memory is still a little fuzzy, I remember YELLING within earshot of a dozen other prospective skydivers.


Another buddy sort of pushed me outside and assured me that he also thought the idea of falling from an airplane was stupid. He said that him and I should just go back inside and wait it out.

But back inside, he was like: “Just kidding.”

Think about it. Those guys had months and months to mentally prepare for the jump. And I had like fifteen minutes to decide. At that moment, I had two choices:

— I could wait on the sidelines and miss out on a life changing, memorable experience.

— I could DECIDE to overcome fear and go for it.

The skydiving facility had already pegged me as “the terrified wimp” so when I turned in my fully executed waiver, they put me in tandem with the ex-special forces guy named Demetrius who I’m sure could pass as Jason Statham’s stunt double.

“Do not worry. I will not let you die today.”

Next thing you know we are 18,000 feet above the earth and Demetrius is telling me to put my legs out the door. Before I had a chance to protest, I was free falling.


Free falling to the earth (at approximately 120 miles per hour), I realized  three important lessons about overcoming fear:

1. Once you “go for it” crying and complaining (and screaming) is not going to help.

2. Time is limited. So find some way to enjoy the process.

3. When you achieve the goal, you wonder why you waited.

I would love to tell you that some aspect of my life profoundly changed that day. But I mostly realized that my friends are jerks who cannot be trusted. The good news is, there are more dude trips in our future and I’m already thinking up ways I can trick help my friends find new strategies for overcoming fear.

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