“But are you absolutely positive that my chute will open?”

This wasn’t the first time that I’d asked the question, nor would it be the last. After a full day of first-time-jumper training, I’m extremely familiar with the scenarios most likely to kill me. As it turns out, there are at least a hundred ways for a parachute to fail, all of which come with a set of emergency procedures that must be executed within seconds.

“You’ve got a 50/50 chance,” Dylan, the Jump Master on my load, replies with a grin. “Fingers crossed!”

“Thanks for the encouragement,” I mutter under my breath.

My chances of survival have seen a steady decline since my first inquiry several hours earlier. Body trembling, I sit crossed legged on the dirty concrete floor, close my eyes, and try to still the waves of panic that have been, for the past few hours, breaking over me in increasingly frequent intervals.

The afternoon is hot and the air is stifling. I feel a bead of sweat make its way down the back of my neck as I sit in silence, trying to block out the bustle of activity that surrounds me.

Everything’s going to be OK, I tell myself. As Dylan said: Jumping out of an airplane is just like jumping out of bed… while flying thousands of feet above the ground… with nothing but a malfunction-prone bed sheet to save you…

I feel a sudden urge to laugh. Terrified though I may be, the absurdity of what I’m about to do seems almost comical. Why am I doing this again? I think grimly. Oh yes! Like an idiot, I added it to my bucket list!

From the safety of my ground-floor apartment in Cape Town, getting a skydiving license seemed like the obvious way for me to overcome my crippling fear of heights. Next, I think I’ll dip myself in fish essence and take a swim around Seal Island, I berate myself. That ought to help with my fear of sharks!

“Oi, Relax!” Startled, I look up into the beaming face of my fellow first-time jumper, Dave. Evidently, I appear to need a word of encouragement. “Even if the chute doesn’t open,” he says cheerfully, “you know exactly what to do, don’t you?” Still smiling, he sits silently on the ground beside me.

Do I, Dave? Do I? To my absolute horror, while practicing emergency procedures, I discovered that if I were to accidentally pull the left handle before the right one, I’d cause an irreversible malfunction that would likely result in death. From that moment on, I lost the ability to differentiate between right and left. Never shying away from an opportunity dish out encouragement, Dave had taken it upon himself to yell “you’re dead!” every time I made this error.

I peer over my shoulder at the large clock hanging silently above the manifest window. An involuntary shudder passes through my body as I take in the time: 12:47 p.m. At any moment, the door will swing open, and I’ll hear the words that I’ve been dreading since last night.

As if summoned by my thought, Mikhaela emerges from manifest, walkie-talkie in hand, and shouts “Next load, kit up!”

Though I’ve been expecting the call for the better part of the past half hour, the words have an immediate effect: time seems to slow, and the chatter that fills the hangar takes on a strangely distant quality as if suddenly submerged in water. I feel the blood drain from my face and the voice in my head screams so loudly that I half expect Dave to notice. “This is a mistake!” The voice booms. “You can’t go through with this. You have to get out of here!”

My pulse quickens and I force myself to breathe normally. What would you do if you weren’t afraid? I ask myself.

Terrified, I force myself to my feet and, together with Dave, I make my way across the busy hangar to the equipment rack. Slowly, I scan through the available rigs until I find the ancient-looking student parachute.

Rig nine. This is the one I’ll be jumping today.

With a heave, I remove it from its place on the rack, conduct a safety inspection, and clumsily fit it to my body. When I’m done, Dylan checks me out and confirms that I’ve managed to put it on the right way around. So far, so good.

Amy watches apprehensively from the hangar door. “Good luck!” she says, encouragingly, as I approach her. “Try not to make me a widow, OK?”

“I’ll do my best,” I reply with a smile, trying to keep the fear out of my voice. The thought is uncomfortably familiar; we spent most of last week getting my affairs in order just in case. I give her a reassuring hug. “I’ll see you soon,” I say with more confidence than I feel. Then it’s time.

Together with Dave, Dylan, and three other fun jumpers, I make my way across the hot tarmac towards the waiting Cessna 206. The tension in my stomach seems to increase exponentially with every step that I take as the reality of the situation starts to set in.

Yes. This is really happening.

The Robertson drop zone is situated in one of the most picturesque settings imaginable. Great expanses of farmland extend in every direction and, to my left, the majestic Langeberg Mountains. On any other day, I’d stop to take in the beauty of my surroundings. Today, however, I keep my eyes fixed firmly on my destination: the tiny plane that, from where I stand, appears to warp and shimmer as hot air rises around it.

I’ll be the first jumper out, which means that I’m the last person to squeeze into the cramped passenger hold. Will I still be considered a “jumper” if someone has to throw me out? I wonder.

Dylan closes the door behind me and, slowly, the plane ambles onto the runway. Seconds feel like hours as we sit on the tarmac waiting for the green light. Then, with an inaudible mutter into his headset, the pilot pulls a few levers and the engine roars to life. As we gather speed, I ball my hands into fists in a vain attempt to keep them from shaking. The plane rattles violently and then, with a sinking feeling in the pit of my stomach, I stare helplessly out the window as we leave the safety of the ground.

My fear climbs steadily with the aircraft. By the time we reach jumping altitude, almost 10 minutes later, the trembling that started in my hands has spread throughout my entire body. So this is what it means to be afraid? I think, bitterly.

“ON YOUR KNEES!” Dylan bellows over the deafening roar of the engine.

An icy wave of fear passes through me. No! I’m not ready! I need more time! I want to disappear. I want to evaporate. I’d rather be anywhere but here! Resisting the urge to curl into fetal position, I clamber awkwardly onto my knees.

I look back in time to see a malevolent grin dance across Dylan’s face. “ARE YOU READY TO SKYDIVE?” he yells.

No. I’m not! I’m definitely not ready to skydive. One day of training? ONE DAY? Are you out of your mind? I don’t know what I’m doing! What is the emergency procedure, again? Is it “right left,” or “left right?” If I jump, I’m going to die! It’s a certainty! Panicked thoughts tear through my mind in a barely comprehensible blur.


“DOOR!” Dylan shouts, ignoring the question, and, with a heave, he removes the only thing separating me from thousands of feet of empty space. Adrenalin explodes through my body as wind thunders into the small aircraft.

Trying not to be sick, I look away from the gaping hole to my right into the smiling face of the pilot. Would these people stop smiling? I rage inwardly. A memory floats into my mind; I have spoken to this pilot before… Meat bombs,” I remember. That’s what he calls us. Turning away, I steel my nerves and focus all of my attention on the task at hand.

“CLIMB OUT!” Dylan shouts.

“RIGHT FOOT!” I yell, almost automatically, as I thrust my right leg out of the relative safety of the aircraft. The wind rips at my limb, and I fight to place my foot on the small step just outside the door. Just like we practiced on the ground, I reassure myself. The memory of Dave shouting, “You’re dead!” pops into my mind, and I feel a renewed sense of dread.

“RIGHT HAND!” I bellow, leaning out and taking hold of the strut beneath the wing. I grip the thin metal support with all my might, as I feel the full force of the wind hit my unshielded body.

“LEFT FOOT!” The words are instantly snatched away by howling gale. “Be aggressive,” I remember Pam, my ground school instructor, advising me. “Move with purpose. Don’t hesitate in the door.”

“LEFT HAND!” I shout as if my life depended on it.

Then, I slide my hands to the end of the strut and allow my feet to slide off of the step.

The wind is deafening and I’m dangling from the wing of an airplane thousands of feet above the ground. This is, quite possibly, my greatest fear. Yet, unexpectedly, I feel a sudden sense of calm. This isn’t that bad, is it?

I glance over my left shoulder and see Dylan crouching in the doorway. I force a smile and wait for the command. It doesn’t take long:


I see Dylan’s lips moving, but his voice is lost. I look up at the smiley face sticker below the strut, take a deep breath, and release my grip.

The sense of calm evaporates instantly. Not calm! Not calm! I’m going to die! I’m being pulled in every direction! Adrenaline is coursing through my veins! Which way is up? What do I do? And then, I feel a forceful deceleration that can only mean one thing. I look up, and relief floods my body as I take in the glorious sight of a purple canopy flapping merrily above my head.

My body goes limp, my vision blurs, and I have to fight to stay awake. I reach up clumsily and release my toggles for the first time. Then, after conducting a series of control tests, begin my slow descent. Breathing deeply, I manage to relax and take in the view. The colors seem somehow brighter and my surroundings more beautiful. The fear that filled my body moments earlier is replaced by an equal measure of joy. I’m alive. More alive, in fact, than I can ever remember being.

“What would you do if you weren’t afraid?” I whisper to myself, as my smile threatens to breach the boundaries of my face. I’ve been told that this motto will be the death of me. From my vantage point, though, it seems far more likely that it will continue to show me what it truly means to be alive.

The Killer of Dreams

Growing up, I was plagued by countless deep-seated fears and insecurities and I went to great lengths to avoid anything that involved risk. While my fears changed slightly as I reached adulthood, I still worked hard to keep both feet firmly planted within my comfort zone.

Learn to dance? Hell no!

Speak in public? Never!

Jump out of a plane? Not a chance!

I didn’t realize it at the time, but almost every decision I made until the age of 25 was shaped by a fear-centric worldview. Ultimately, these decisions resulted in a one-dimensional existence in which income generation was my sole focus and anxiety was my constant companion. Were it not for my burnout and subsequent panic-inducing medical evaluation in 2014, I’d probably still be trying to win the rat race.

As many of you know, this burnout marked the start of my journey towards income automation and the “professional vagabond” lifestyle. For me, though, these external changes, however dramatic, were merely symptoms of a far greater internal decision: the decision to master my fear.

Fear kills more dreams than failure ever will. We all have an internal voice that pipes up the moment we consider attempting the extraordinary: What if I’m not good enough? What if they don’t like me? What if I lose my money? What if I lose my life? It doesn’t matter who you are; if you have a vision, you will, eventually, be forced to answer the voice in your head. The response that you give, more than anything else, will determine your future.

Fear may help you to survive life-threatening situations, but, if not mastered, it will just as surely prevent you from living in the first place. In reality, fear is an imaginary barrier that shatters the moment you decide to face it. The goal, therefore, is not to be fearless. Rather, the goal is to master your fear so that you can choose the new over the familiar, the extraordinary over the ordinary.

Why did I get a skydiving license? First of all, I desperately wanted to experience free-fall. More importantly, though, I saw it as an opportunity to exercise control over my fear; to give expression to my new-found worldview.

Getting a skydiving license was one of the most rewarding experiences of my life. Now, nearly 50 jumps later, skydiving has become an absolute passion. What a travesty it would have been if, like so many things in the past, I let the experience pass me by because I didn’t have the courage to grab hold of it.

Courage, I’ve found, is the cure to regret. Every one of your dreams can be achieved if only you will cross the “chicken line” and take the first step.

So, let me ask you the question that I ask myself morning: What would you do today if you weren’t afraid?

About The Author

My name is Ryan and I love adventure. I love it so much, in fact, that I spend around nine months out of every year traveling the world and working on my bucket list. The rest of my time is spent teaching others to do the same.

Click here to find out how.

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