“Why are you doing this?” My manager ventured tentatively, her kind eyes widening with concern and slight incredulity as I explained my reason for requesting some time off from work.

“Because I want to feel alive.”

When I was six, I caused a minor commotion at the shopping mall as I refused to take the escalators up. From my vantage point, five storeys was five storeys too high and I was not budging. With my two tiny feet firmly planted on the ground, I took a big inhale and let out the loudest cry my little lungs could manage. Dad swiftly picked me up and draped me over his shoulder, willing me to hush, if only to avoid the nasty looks from bystanders.

“Close your eyes if you’re scared,” Dad pleaded, wishing that I’d stop bawling. I was too busy wailing to take heed but squeezed my eyes shut anyway.

When I was fifteen, I committed the rookie mistake of glancing down when I was three-quarters up a bouldering element at a high school camp. In front of the entire cohort, with all my teachers in tow, I let out a (in my honest opinion, involuntary) curse, “F***k. I want my Mama, I’m scared!”

My classmates roared with laughter as they reeled from my deafening scream, while our discipline master had his lips pressed into a tight, thin line. As a school councillor, I had displayed extremely unbecoming behaviour. Once I shakily made it down, I was made to sweep the bathroom floors as punishment.

At twenty-nine, with a stunning view of Queestown, New Zealand, I leapt (rather involuntarily) out of a plane flying at about 200kph from 15,000 ft above.

And I would do it again in a heartbeat.

Skydiving was an idea that I had flirted with for years.

It was first incepted in my mind during my semester abroad in Europe. My initial plan was to skydive in Prague. But, likely due to my apprehensiveness, I hemmed and hawed about signing up for a slot until it was well into November. To my immense relief, the skydive was cancelled due to expected bad weather given the impending winter.

I eagerly took the cancellation as a sign that it wasn’t meant to be and shoved it to the recesses of my mind as, among other things, graduating from law school, studying for the bar exam and traineeship consumed my life.

Occasionally, like the mysteriously alluring neighbour you have a mild crush on, the thought of skydiving would return.

As I scaled through my twenties, however, any ounce of foolhardy bravado I had during law school dissipated. You’re terrified of heights, I reaffirmed. Your friends make fun of your horrific screams on the roller coaster. You even had to drink to get liquid courage to sit on a roller coaster in Amsterdam. Surely you’re not built for “extreme” sports such as this.

For better or worse, my (irrational) fear of heights was eclipsed only by my fear of turning a decade older and living a life that I would come to regret. In an impulsive moment of introspection of my twenties, as 2023 drew to a close, I hastily booked the last slot of a tour around paradise – the South islands of New Zealand.

At the “add-ons” section of my booking, my mouse hovered over the dropdown menu of options. “F***k it”, I exclaimed and resolutely clicked on “Skydive in Queenstown“, paying extra for photos and a video of the “once in a lifetime” moment. I hope it’s not once in a lifetime because I don’t make it out after, I muttered.

I spent the next three months treading the tightrope of agony, fear and excitement, torturing myself, my family, my friends, and yes, even my poor co-workers. I Googled “skydiving accidents” and enumerated at least 10 different permutations where the parachute wouldn’t deploy, become tangled up, or how my tandem master would experience a sudden heart attack or stroke, and all of which I’d suffer a swift but fatal death. I also interrogated every friend I knew who’d skydived and asked for a blow-by-blow.

My anxiety got the better of me, and about once every two weeks I would suffer from insomnia from the anxiety of my impending skydive. A friend suggested that I simply walk away from this. “It’s just money. If you’re so scared, just don’t do it.”

Others were understandably shocked. “You were shivering up the London Eye. And it was just a Ferris wheel. You were also shaking in the hot air balloon at Cappadocia. Are you sure???”

I AM SURE, I would counter. I am a finisher.

Maybe it was residual grief from the twin traumas of the loss of my Dad and Gong Gong in quick succession. Or the fear of regret as I heralded a new decade of my life. And my self-esteem – I couldn’t NOT skydive after practically broadcasting it to anyone who would cross my path about my “before I turn thirty” bucket list.

If anything, my pride wouldn’t let me back out.

It was 22 February on the morning of. The weather was just right – cool breeze, clear skies and warm sun. At the drop zone, we were divided into numbered groups, briefed with safety instructions and suited up.

One of the staff members drew #1 on my hand. “So you board the right plane.” All the easier to identify me if I fall from the sky.

My skydive master’s name was Sean. Big, burly and no nonsense.

“How many times have you skydived?”

“Thousands.”

“Are you sure this is safe?”

“The more questions you ask, miss, the worse my answers will be.”

I gulped and shut up.

Sean helped me with the rest of my safety suit and I, along with about 10-ish passengers, skydive masters and skydive photographers, were herded into a barren sardine can-like tin they called our orange plane. I think this is what budget airlines have in mind if not for consumer standards and aviation regulations, I mused.

In the plane were two strips coated in bright blue laid side by side. We were to slide in this order – skydive master, passenger, skydive photographer. Like the inventory cost method you study in business school, the first in were last out.

As luck would have it, of course I’d be the first in. Sean glided in with ease and signalled for me to follow. Once all of us were in, tightly packed like actual sardines, the plane took off without much fanfare.

My stomach was churning. I couldn’t back out now. And the only way out was to jump out of the plane.

I tried praying.

My heart was thumping furiously.

I couldn’t decide if I needed to cry or wet my pants.

Amidst my fear, I was able to appreciate the professionalism of the skydive masters. Like clockwork, as the plane steadily climbed in altitude, they sprung into action in harmony like sychronised swimmers at the Olympics.

Sean would regularly check his watch for the rising altitude and progress preparations for our dive while in the plane. I scarcely remember the exact figures now, but for the purposes of recounting this story, we’ll make increments of more or less per 5,000 ft.

At 5,000 ft he had his gear fully on.

At 10,000 ft he secured my safety straps to him and triple checked for security, while my skydive photographer had a GoPro in front of my petrified face and quizzed me with a few interview-like questions. Barely coherent, I cursed my vain self for signing up for extra behind-the-scenes footage.

At 12,000 ft Sean and all the other masters put our oxygen masks on. I was so nervous the oxygen mask didn’t really help with easing my breathing.

I tried to soak in the beautiful views while holding in my pee and my hammering heart.

At 15,000 ft the orange sardine tin can paused. With a buzz, the light in the top corner of the plane flashed from red to green and the door to my right burst open as a gust of wind blew in.

The first skydiver leapt out, causing our tin bucket to tilt to the right and almost immediately disappeared from view.

One by one, the skydivers exited.

Sean started inching forwards. As I was strapped with him, I had no choice but to follow suit. Whatever you do, don’t grab onto the plane, he warned, reading my mind and pre-empting my last-ditch plan to save myself. I suppose many have attempted to cling onto the plane.

Soon, I was the last passenger in the plane. My skydive photographer had nimbly crept to the side of the plane and held onto it like Spider-Man, with his GoPro capturing my every pore. (How are these pros so fearless??? I’m truly in awe.)

I was on the edge of the plane, with my knees and feet tucked in as instructed. The entire world, including the clouds, in all of its majesty, was beneath my feet.

Sean tilted my head back towards him.

“Smile”, he gestured for me to look up to my left at the camera.

It’s go time.

Sean snapped his helmet shut and with the finesse of a pro who’d been skydiving almost everyday for years, tumbled us out of the plane.

If you’ve ever sat on a roller coaster, you’ll viscerally understand what I mean when I refer to the “heart drop”. Skydiving is significantly more overwhelming than that. I barely have words to describe it.

For the first 20-30 seconds, my stomach was in my mouth as we hit terminal velocity. I think I screamed, but I was overpowered by the wind slapping against my face. All my senses were heightened. I was tearing and had snot dribbling down my nose.

We were free falling!

Into the beautiful, vast nothingness!!!

And it was the most exhilarating, freeing feeling on earth!!!

About a minute in, Sean tapped my shoulder and we got into a banana like position. It was then that I was finally able to register the phenomenal view.

I’ll never forget what I saw. Nature in its tremendous, breathtaking beauty.

It was a sight to behold; I was humbled.

All too soon, Sean deployed the parachute and we were snapped into a vertical stance. He piloted us in a few dramatic swirls, allowing me to enjoy the view before us. Before long, Sean commanded “Knees up”.

We soon touched the glorious, sweet, sweet ground. Never had I been so grateful to touch grass.

I had tears in my eyes. I profusely thanked Sean. We high-fived and he had the biggest grin on his face. Sean was readying for his next ride but I was still reeling from the high of my skydive.

In that brief moment, all my worries and anxieties melted away. Relative to the beauty before me, I felt so, so special yet so, so insignificant all at once.

I had an emotional high that lasted for a good week and to date, is one of MY FAVOURITE MOMENTS to recall.

I’ve severally takeaways from this. Apart from confirming that I’m overly dramatic (no surprises there), I was again reminded of how I’d worried for nothing. My anxieties were blessedly unfounded. The other was that my problems will too come to pass (or are trivial in the grand scheme of life).

If this is any indicator of how fun and exciting my 30s would be, I’m here for it!

To my future self, and my dear readers – don’t let fear hold you back from living a life that’s too small. As NZone Skydive puts it, EMBRACE THE FEAR.

With all my love

Pearls 🩷