Because I did

A few years ago, I decided to leave a job I’d been at for six years. It was a great company and I had been doing well, but I was completely burned out. The company had been bought by private equity. We’d purchased a giant competitor, and we were in the throes of all the work that occurs when billion-dollar companies combine. No offense and no hard feelings, but it no longer felt or looked like the special company I had joined six years prior. That was fine - seasons change; everything has a lifecycle. I was happy to have been a part of it, but I am an all-in or all-out kinda guy, and I was finding it increasingly harder to be all-in. So I decided it was time to go.

What does a forty-something year old do after departing a billion-dollar company as a Senior Director? Become a professional skydiver, of course - isn’t that the obvious progression? With the support of my wife, I decided to take a sabbatical, do things that brought me joy, and just be. For 12 months, I would jump out of planes, fly planes, take the kids to jiu-jitsu and take lessons myself, do drop offs and pickups, make random Tuesday trips to Chuck-E-Cheese’s (shhh, don’t tell your mother!), recharge, and see where it took me. It ended up being one of the most amazing years of my adult life.

If you know me, you know that I love skydiving, but not like you might think. It’s not an adrenaline junkie thing. Sure, it’s adventurous and there is certainly an adrenaline rush when you jump out of a plane. But in a world of constant noise and connectivity, of workaholism, of likes and buzzes and tweets and distractions, skydiving brings me a zen-like respite. When you’re soaring through the sky, you must be present, in that exact moment. You must take the deliberate actions that will save your life. The closest I’ve come to a state of flow, if I’ve achieved it, is mid-skydive. Like the surf shop kid said in Point Break, “Surfing’s the source. It’ll change your life.” That is how I feel about skydiving because it has changed my life by giving me peace, perspective, and community. (Side note: if you tell me you can’t stand Keanu Reeves or don’t like Point Break, we will probably not be friends).

As a tandem and freefall instructor, I made real connections with people beyond the fact that they were often physically strapped to me. Some were dreadfully afraid and some excited beyond belief. More than a few burst into tears of joy after the canopy opened, not because it worked and they were going to live but because they felt the experience as one of true beauty. Everyone I jump with signs my logbook and leaves a little note of what the skydive meant to them. Sometimes when I’m feeling down, I leaf through it and am reminded of a real, lasting, human connection that I facilitated, and it makes me smile.

But my most meaningful and memorable jump occurred in the summer of 2019. My nephew Oso had been diagnosed with cancer (Ewing’s Sarcoma) at the age of 18. Over the course of several years, he’d had his leg amputated, had been through treatment, was in remission - and then the cancer reappeared with a vengeance. He was undergoing aggressive treatment and was even in experimental trials. It wasn’t looking good, and we all knew it. He had always said, “Hey, Uncle Dave, I’m going to jump with you one day,” but we hadn’t done it yet. I assumed he never would until my phone rang. “Yo. How soon can we do this? What do I need to bring, and where and when do I have to show up?” I gave him a date and time and told him all he had to do was get himself to the dropzone. I knew that this would be important. I didn’t know how much time he might have, but I was preparing for the likely outcome that the cancer would take his life. I wanted this jump to be special, not only for him, but for the family in the event this became one of a too-small number of treasured memories of Oso. I hired two trusted videographers I worked with, “Stache” and “DJ Ha-Mez,” to document the whole thing.

Oso tried hard to be cool, but like most, he was nervous and a bit scared. He did the “Wile E. Coyote running off a cliff” leg motion right out the door. IT. WAS. EPIC! After we landed, I gave him a giant hug and cried, holding on to the beauty and the meaning of this shared moment that no one could take away from either of us. I cried, knowing that it was possible he might not be with us next year. While I wish his illness had never happened, I am grateful it occurred in this stage of my life. Had I still been in the Army, I wouldn’t have been present. I am so happy that I was there for him – so happy that he was there for me!

When I left that company two years ago, I had several friends and colleagues look at me with the “confused dog head-tilt” and say, “Wait, you’re going to go do what?” after telling them I was going to jump out of airplanes for a living. In business, we talk about opportunity costs – what you forego in gain from Option A by having chosen Option B. Sure, there were opportunity costs to walking away from a traditional corporate career - salary, stability, conventional recognition and prestige. But what if I had stayed? What would I have lost? A moment of priceless joy, meaning, and connection that makes all of those things pale in comparison. The opportunity to create many more of those moments with people who started as strangers and became bonded to me in a way that can’t be measured in dollars.

This is not a call to “Jerry Maguire” your way out of the office tomorrow and throw all of your responsibilities to the wind. Rather, a reminder to think about what you are doing and why. To figure out what is important to you and move purposefully in that direction. You will never hear me say? “Man, I wish I made that one skydive with Oso.”

Because I did.