What I Learned About Startups from Falling Out of Planes

The first thing that hit me was the noise. I could barely hear myself think. I hadn’t expected it to be so loud but I guess it makes sense when you open the door of an airplane traveling 100+MPH with the engine running full out.

The instructor pointed at me, then out the door underneath the wing. It’s too loud to talk so all he could do was hand gestures. My heart was pounding. It felt like that “forgetting something” feeling I sometimes get when I first leave home and enter the car at the beginning of a long trip. Only multiplied by 1000 because if I was forgetting something I could literally die.

I knew if I just stayed in the plane no one would ever know. It was just me, an instructor and a pilot — two strangers I’d probably never see again. But I made a commitment to learn what this was like, and I wanted to see it through.

The plane’s cabin was too short to stand up, so I scooted feet-first towards the door and stuck my legs into wind. It was strikingly powerful, even violent. My unprepared chicken legs flailed like rag dolls.

In an effort to calm my nerves, I took in a deep, slow breath. I studied the strut brace running from the underbelly of the plane up to the underside of the wing. As the instructor told me in training, I was supposed to grab that thing, swing my body out of the plane, and hang below in the wind. Sounded simple down on the runway, but absolutely ludicrous now.

I took in another breath, leaned out the door, and went for it.

From that moment, there was only one way down.

I paused and hung there for what felt like an eternity. It was surreal. Hanging under the wing of an airplane. Looking down between my shoes at farm fields rolling by a mile below, back up at the mountains in the distance, even further up at my hands gripping the strut, back down at the farm fields again. I could literally feel my heart pushing blood through the veins in my forehead.

My mind was racing.

I thought about the absurdity — being hurled laterally through this thin slice of atmosphere wrapped around a giant ball of rock, which itself is flying through space at 70,000 MPH.

I thought about the pre-jump class I had taken the weekend before where they teach you about all the ways your parachute can malfunction (there are a lot).

I though about my family and my friends, about how much I liked my life, about everything I was looking forward to accomplishing, and how shitty it would be if it all ended here because of some stupid thing I signed up for to get an adrenaline rush.

“Breathe,” I told myself, and turned my attention towards the sensations my body was feeling. There was so much fear and tension in my muscles, like nothing I’d ever experienced before. I was keenly aware of the tiniest internal movements, like my body was telling me I’d better enjoy them because they might be my last.

It was fight-or-flight in pure form.

At the same time, this extreme awareness brought to mind an unexpected parallel to the way I feel during meditation, and I began to focus in more and more on that. Something interesting started to happen. It all went quiet. The roar of the engine and the wind fell to a static hum. Time slowed down. Like way down. Like each of my breaths was as long as a sunset. The adrenaline fell into a strange calmness. The fear began to release from my muscles. My grip relaxed.

For a few seconds, I was truly 100% present.

And I realized I had already let go.

Later that night as I was thinking back on the experience, I made a commitment to myself to do that or something equally terror-inducing at least once a year for the rest of my life. I’ve been two more times since.

That feeling of 100% presence is something I‘ve never quite been able to shake. My animal brain was so focused on the intensity of the current experience. But simultaneously, I felt like I could perceive the motion of the entire universe. It was zen, impermanence, oneness, and sheer adrenaline-to-the-max terror all at once. And it was perspective-changing.

Weirdly enough, I run into constant parallels between skydiving and my daily life and daily work in a startup, and reflecting on those lessons continues to add value to my life. Here’s what I learned…

You’re never going to be fully prepared.

If there’s one thing I took away from skydiving it’s this: no matter how ready you think you are and how much preparation you’ve done, when the door of that plane opens and it’s time for you to jump out, you’re going to be shitting your pants.

Your brain says “Dude. NO. Are you kidding me?! STAY IN THIS F***ING PLANE”.

A similar thing holds true across many facets of life, and business. The moment before you walk into that meeting to ask your boss for a raise, or tell your investors you’re going to pivot your company in a new direction, or walk up to that sexy girl sitting across the bar, that same part of your brain starts telling you “What if this goes horribly wrong? Maybe we should just stay in the f***ing plane”.

And the thing I took away from my skydiving experience is that I need to change my perspective, and make these my favorite moments in life. You either embrace your inner FILDI (Fuck It Let’s Do It), take the plunge and walk away a stronger person, or you back down and walk away a smaller person. Growth or retreat. The entrepreneur’s ultimatum.

Trust yourself to figure it out before you hit the ground.

There’s a funny misconception about skydiving, which I shared, that most of the people who die do so because their parachute doesn’t open.

In reality, 95% of skydiving deaths actually happen simply because the person is bad at flying a parachute — runs into a tree/power line/river, etc., or simply turns too hard too close to the ground, which creates a momentary free fall. It makes sense if you think about it. There’s only one way to learn how to fly a parachute, and you don’t get a do-over.

In truth its not that hard, but the key is that you have no safety nets. No one is there to help you if you fuck up. Just you, a big piece of cloth, 5000 ft, and ~60 seconds to figure it out.

Every time I start to doubt myself, I think back on that experience of learning how to fly a parachute for the first time. Our instincts and our bodies are powerful — the product of millions of years of evolution. And there are so many stories of humans doing insane, seemingly impossible things in moments of extreme trying. You’ll always be surprised what you can pull off if you just throw yourself into something and trust yourself to figure it out.

It’s healthy to take big risks that really test you every once in a while to remind yourself of that innate resilience we all have.

Keep the learning curve steep.

Anyone who’s studied Einstein knows the amount of time you have on this earth is not a fixed quantity. Time is relative. If you’ve ever been in a bad car accident, you‘ve felt this too. When you realize what’s happening, your brain gets a rush of adrenaline and time literally slows down for you as you experience the crash.

Another way to frame the same concept is that your perception of time is inversely correlated to how much you are learning at any given time. When your car is crashing or you’re falling from an airplane for the first time, your brain is experiencing an extremely steep learning curve trying to figure out how not to die in this new situation. And as a result, your experience of time literally slows down. It’s the same effect that causes years to feel so long when you’re young, learning tons of new things every day, and shorter and each year as you get older and have fewer new experiences.

When you’re learning, your brain is coding so many more things to memory than when you’re just going through your day on autopilot — and this increased encoding has a very real impact on how vivid and vibrant your experience of life is. And the beautiful thing is you never have to stop. You can keep learning every hour of every day if you choose to, and your life can be as vivid and vibrant as you want it to be.

This principal holds true across nearly every area of life (new relationships, travel, new hobbies, etc), but it’s particularly important in your career where you spend the majority of your waking hours. If you don’t keep your learning curve steep, you’re going to get tired and burnt out. You’re going to feel old, even in your twenties. You’ll start looking forward to retirement or another distant exit plan, and letting the toxic paradigm of deferred-happiness creep into your life.

This is the allure of a startup. Some people think you join a startup and it’s all just going to be like an episode of the Silicon Valley and “we’re going to IPO and everyone’s going to be millionaires :D”. And then when it becomes clear that’s not how it actually works, these are the people that quit and go on rants in the comments section of TechCrunch articles.

But there’s another group of people that dive into a startup because they value keeping their learning curve steep, and the richer experience of life which flows out of that.

The reality in a startup is everything is on fire 24/7. You have no idea what you’re doing, but neither does anyone else, even the CEO. A startup is by definition uncharted waters, and the whole company is built on the premise that you can be the first to find the island that no one else knew existed. And it’s this uncertainty, daily challenge and chaos that make the low pay and long hours worth it, not the prospects of an IPO and millions for everyone, which seldom ever happens.

Those who understand the power of keeping their learning curve steep have the keys to an endless youth, and to a more fulfilling experience of life. There’s value there that no IPO or exit could ever bring.

Each day, you’re either learning, or you’re dying. The choice is yours entirely ;)

So, what have you done to terrify yourself lately? Get out there and go do something that scares the shit out of you. Life’s too short to rot behind your laptop screen. Embrace your FILDI baby!

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