I was sitting on the floor in the back of an old single engine propeller-powered plane which was flying straight up toward the sky like a rocket ship. I was just a few feet away from the back door which was left open the entire ride. There were no seatbelts so I was not attached to the plane in any way nor was I attached to a parachute. One tiny hiccup of turbulence and that’s where my life’s story would have ended. I should mention that I was afraid of heights. Scratch that. I was terrified of heights. Needless to say, just 3 minutes into our climb my clothes were already drenched with sweat. In case you’re wondering, I did indeed inquire as to why the back door was left ajar, given our vulnerable seating arrangement in the aircraft. The matter-of-fact response I received was that it was a slight inconvenience to open it midflight. An “inconvenience”? I’d call my being spit out the back of a plane and falling at terminal velocity toward the earth a slightly bigger inconvenience. But I could tell nobody was particularly interested in hearing what I had to say on this matter so I just kept my opinion to myself, closed my eyes and prayed. [It’s uncanny how quickly atheists can become God-fearing in the face of imminent death.]
We finally reached our destination at 14,000 feet when the instructor announced that we had just 60 seconds to prepare for our jumps or we would miss the landing zone. Before I had a moment to process any of this, my tandem partner was already finished connecting our harnesses together. [It’s one level of nervousness when your survival depends upon your deploying a thin piece of fabric and having it inflate at exactly the right time but it’s an entirely different level when it depends upon your tandem partner doing so. You don’t know the meaning of trust until you trust a complete stranger with your life.] “Are you ready to jump?” he asked. “Are you sure we’re attached?” I responded while double and triple checking each connection point. “Yes, we’re good to go,” he assured me. “And you’re absolutely certain this chute is going to open and support the two of us?” I responded nervously. “Don’t worry. We always have the reserve chute just in case,” he countered. Just in case? That wasn’t exactly the kind of reassurance I had in mind. “One more question…” I started to ask but got cut off. “No more time for questions. Here we go. 1, 2, 3, jump!” And with that we were airborne.
I’m a pretty analytical thinker so I was well aware going into it that the fatality rate for skydiving was a miniscule one per hundred thousand jumps. Roughly speaking, that’s about the same likelihood as keeling over dead at a dance party (no joke, I looked it up). But while my dance moves have a lot to be desired, I’m still way more comfortable trying to shake it up on the dance floor than jumping out of a perfectly good airplane. Yes, one out of a hundred thousand are very low odds indeed. But here’s the troubling part about statistics. If 100,000 people are all about to jump out of a plane thinking that they’re safe because of those favorable odds, one of them will in fact be wrong.
So at this juncture in the story, you might be wondering what I was thinking doing this jump. Why was I so determined to knock a skydive off my bucket list? With my lifelong fear of heights and anxiety about the risk of fatality, why do it? What was the point of this stunt? The point was to prove to someone I knew that I could do it. To show that person that I could overcome my deepest, most ingrained fears. To convince that individual that I could do anything in the world, no matter the perceived risks or obstacles along the way, if I was just determined enough. And that individual was me.
I was a recent Silicon Valley transplant at the time, fresh out of business school. My plan was to join a couple startups to get the feel of it and then launch my own venture. I had played it safe my entire life up until that time and I needed to shake things up. I needed to test my limits. To push myself harder than I had ever been pushed by anyone else. And to face my fears. I had always excelled in academic settings where there were clearly defined rules of engagement. Learn material, write paper, take exam. Rinse and repeat. But in the world of startups, there would be no rules. There would be no safety net. The failure rate for tech startups was over 95% which is a pretty daunting figure if you think about it. But before I could convince investors to write a check, employees to quit their jobs and join our cause, strategic partners to work with us and customers to try us, I had to convince myself that I was up to the task. So I felt I had to first get myself into the right mindset.
I’ve had a pretty severe case of acrophobia since as long as I can remember. I don’t just get the increased heart rate, rapid breathing and sweaty palms when I’m standing near the edge of a building, I get these symptoms even if I’ve got 3 sturdy layers of glass separating me from the outside world. Heck, I get nervous just watching other people peak over the edge. Truth be told, even watching someone precariously high up in a movie can make me uncomfortable. I don’t know that phobias are all that rational but they feel pretty real when you’ve got one, that’s for sure. So when it came time to consider some activity that would be the ultimate test of courage, I didn’t have to think too hard. Given my terrifying fear of heights, I had no business even contemplating a pointless adventure like skydiving. Which is exactly why I knew I had no other choice but to do it.
If you want to run a marathon, you’ve got to get your physical self into tip-top condition. A startup, in many respects, is also a marathon but a mental one. Any rational person could see that the odds are heavily stacked in favor of the house. Whatever your market, whatever your product, there will always be established companies more well known, more heavily capitalized and more organizationally sound with real customers, real revenue and real profits. The hurdles appear practically insurmountable. And if you eventually succeed, it will most likely be after years and years of restless days and sleepless nights. It will take superhuman levels of mental toughness. Just as the marathoner needs to continue to push their physical limits, so too must the entrepreneur push their mental limits. Stepping off that plane was my first such test for me. There would be many more to come.
I wasn’t so naïve as to think that I simply jump out of a plane and presto, I’ll be a successful entrepreneur. I realize there’s probably no correlation between skydiving and entrepreneurial success. But what jumping off that plane does is it builds confidence. It helps to placate the nerves. It gives you reassurance that you will not succumb to your fear but rather, you will be able to face your fear head on with inner strength and courage. It reminds you of the old but reliable adage that you can do anything you want in life that you set your mind to.