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What 300 Skydives Taught Me About Fear, Risk-Taking, And Flow States

Mitchell Wilson


Mitchell Wilson


Feb 9, 2023

What 300 Skydives Taught Me About Fear, Risk-Taking, And Flow States

We all get nervous. We all want to do amazing things. We all want to be good at something.

It doesn’t matter what thing you choose to do. You need to have multiple incentives to commit to it or else your skills won’t advance very far.

If you want to be on a path to mastery, you’ll have to be consistently dropping into flow states. This is the surefire way to go beyond your comfort zone in a sustainable way. You couldn’t skip to expert mode immediately. You have to start small, as a beginner, and gradually increase your skill & the difficulty of the task at hand.

I wanted to get really good at something, something that reliably had me in flow. So, I chose skydiving, but it took a long time for it to ‘click’. 

Skydiving probably isn’t your thing, but that’s not the point. The point is to extract the lessons here and apply them to your own craft & calling. Even for me, skydiving isn’t a part of my life now, but I certainly use the lessons learned every day.

Realize that fear is normal 

You're born afraid of everything. 

That’s okay, that makes sense. Humanity wouldn’t have even reached this point if we hadn’t been afraid as a default. We’re fragile and not as strong as many other animals out there in the wild. We just want to get 80 years in with a smile on our face.

Fear is a useful feeling and it’d behoove you to work with it rather than against it. 

It’s always there no matter what kind of training, experience, etc. you may have. It’ll just take on new worries and concerns. Your experience will inform the fear in higher detail as you go. Sure, you may be less afraid of certain basic things, but you’ll be more afraid of other advanced aspects now that you know more.

You learn to be brave, but the fear always remains. 

In skydiving, we practice emergency procedures constantly. Once you know the worst-case scenario, bravery naturally begins to kick in.

You get brave by knowing what to do if things go awry.

Bravery is confidence as it relates to fear. The more you are trained on what to do in a fearful situation, the braver you’re going to be.

It’s useful to rehearse and ingrain the IF-THEN behavior you’ll turn on if it’s needed. Think through the worst-case scenario so that you can at least find a bit of peace knowing that you’re well prepared.

The last thing you’re going to want to do is to wait until it’s actually happening to think it through or know what to do. Especially in something like skydiving, where the risks are huge.

Do dangerous things carefully

True adventure has danger woven in. 

You want your life to be a little dangerous. It wakes up your nervous system, keeps you alert, and keeps you sharp. Without danger present in our lives, we may get too arrogant, too naive, too soft. Doing something dangerous, carefully though, is the perfect way to lean into an adventurous life. 

The key is to prepare, to think through, and to trust what you know.

Take the time to be safe, leaving little to chance

You might imagine skydivers to be crazy, wide-eyed adrenaline junkies, but more often than not, they are PhDs, business owners, and advanced military types. The majority of them seek calculated, incremental progress - constantly looking for mentors and training. (Don’t get me wrong though, there are definitely some absolute crazy people too.)

Before every single jump, actually, before you even get on the plane, there are several checks you make on your gear and have a friend make that ensure a high standard of safety. 

You make sure your straps are routed correctly so that the gear doesn’t slip off your body when the parachute opens. You make sure your AAD is turned on so that if you get knocked out unconscious, the reserve parachute will fire automatically to save your life. You make sure the drough is cocked so that when you pitch at opening altitude your parachute is going to get pulled out above you. All of these checks become routine, ingrained into the sport. 

Some try to claim that safety is cool, but it’s not. 

What’s cool is not dying. What’s cool is being able to do it again and again.

For my first several jumps, I was terrified. 

I couldn't wrap my head around why all my peers were dedicating every weekend (if not their lives) to jump out of planes as much as possible. 

They would drive for hours just to get to the dropzone, they go all out jumping as long as the plane was flying, party at night, and stay until the last possible moment on Sunday before they had to return to the world of the muggles.

But, around jump 30, it clicked for me.

Once I had the basics of freefall down, the emergency procedures memorized, and some experience under my belt, I started dropping into flow states every time I jumped.

Flow states: the greatest part of being human

Time distorts, awareness & action merge, and your entire brain is devoted to the present moment.

Everything feels magical, telepathic, and flawless. There's no better high. 

You're not thinking about your problems, your to-do list, your lover, or your hunger. You're ALIVE and you don't want it to end.

Most of a skydive's freefall lasts 60 seconds before you're under a parachute. As you gain experience, flow states make it feel like minutes, 5+ minutes long. Some of my friends with 10k+ jumps can describe how shoes are tied while in freefall. It's THAT slow for them.

It's amazing what the dance of fear & flow will teach you. 

It's not as scary as it seems if you're willing to be careful with your risks, prepare for the worst-case, and keep going to experience flow. Once you're in flow, you're on the path to mastery. 

It becomes addictive. You’re intrinsically motivated to repeat it over and over again while making tiny improvements each time. 

It’s been said that around a 4% stretch of your comfort zone is optimal for dropping into flow.

Not too much to break you and be ineffective, not too little to make you bored. The sweet spot, the goldilocks zone.

Persevere long enough to experience the ecstasy of getting good at something

You want to be able to improve your skills in a tangible way. In a way that’s clear if you’re getting better or not.

This would happen with skydiving often. Landing closer and closer to the spot on the ground I wanted, despite the wind conditions. Learning how to exit the aircraft clean & smooth. Keeping up (speed-wise) with friends in the air. Learning how to fly vertical vs horizontal. 

All of this and friends would notice, they would point out what went right & what didn’t. Gradually, over time, I upgraded to better and better problems. This is all thanks to deliberate practice.

We would ‘dirt dive’ the jump before we got on the plane. We’d plan the exit of the plane, the freefall plan & how to execute, and at what point we’re breaking off from one another to go pull our parachute. Mentally rehearsing all the time. 

The real treat was simply focusing on each jump on its own. Ensuring that each one meant something.

The thing you learn along the way in any discipline is that there’s always the next level up. No matter how good you get, there’s something even more advanced to be doing. Some may find that disappointing, like climbing to the top of a huge mountain only to realize the bigger ones not yet climbed.

I find it inspiring. Even relieving to some degree because that means there’s more to do. More to the path of mastery. More craftwork to be done.

Feet on the ground

It’s been a few years since I was consistently jumping out of planes, but the lessons still stick with me. (I mean, how could my nervous system ever forget that?!)

My relationship to fear has evolved so much because of skydiving. When I go into a situation that triggers fearfulness, I know to trust it. It likely has my best interest and I need to do my part to calm my nerves and be prepared.

At the same time, after having experienced fear that was true & worthwhile to listen to (such as falling out of planes from 14,000 feet up), it’s super easy to spot fake fear and illusory fear.

I see risk-taking in a much different light too. A calculated and careful approach, one where you’ve done all you can to ensure upside and minimize downside. 

This is key.

When you prepare in this way, you are reframing the risk. Oftentimes, it’s not as daunting and scary as you initially imagined.

To my surprise, dropping into flow states has become easier. I would have assumed that it would now require an incredibly high bar to get me into flow, but now that I understand how flow states work, I can reliably pull the lever any day I want if I’m intentional enough about it.

You have to do something that demands your full attention and do everything in your power to give your attention to the task at hand. Play with the levels of skill and challenge involved, increase the risk factor if needed, and get out of your own way.

Falling out of the sky at 120mph isn’t for everyone, but the insights discussed here can be applied no matter what hobby, craft, art, or passion you find yourself obsessed with.

“Once you have tasted flight, you will forever walk the earth with your eyes turned skyward, for there you have been, and there you will always long to return.”  - Leonardo da Vinci

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