If you’re reading this… thanks already.

Yesterday someone proposed the question to me,

“When was the last time YOU did something for the first time?”

“Well, last week in fact”

Last week I jumped out of an airplane whilst flying 10,000 feet above the coast of Maui, HI. This experience, and the thought process that lead me to finally plummeting to Earth at 130mph, I believe, requires some internal and verbal processing: all of which I am prepared to share right here in the next few paragraphs. 

I’ve always been a thrill seeker: by 28 years of age I know damn well I’ve done more than most individuals on the last lag of their lives: I’ve bungeed the highest jump in Thailand, I became PADI scuba certified at 19 years old, I’ve free-fallen from the Las Vegas Stratosphere, downhill mountain biked at mock-speeds in Peru, I’ve zip-lined in Mexico, swam in the Amazon River next to Piraña and hiked the coastlines of Italy and Greece- and NOTHING was going to prepare me for the moment a strange man would open the door to a miniature piper airplane and told me it was time to jump out. That moment, and the 5 minutes that followed: well, life just can’t prepare you for something like that. 

Thrill seeker or not, this shit was scary. Not scary in the “BOO, IM SHOOK” kind of way: but scary in the “I am-overthinking-what-could-go-wrong-worried-about-my-LIFE” kind of way. This was a type of scary I’ve never experienced before. A type of scary that lasted all of 1 second once I made the decision to push my foot off the tiny airplane step that seemed to be my last tangible peice of reality. 

The “fall” itself: not scary 

The moments leading UP to the fall itself: life changing-ly, scary. 

For the last month I knew skydiving was in my near future. I purchased this excursion for my husband back at Christmas time with the intention of forcing HIM to do something crazy with his wife while on our Hawaiian vacation. We both so eagerly committed and put the experience in the “deal with it later” memory bank. Well, last week- “later” came. 

We woke up in the morning and hit the road (“The Road to Hana”, nonetheless). Our skydive was located across the island in “Hana” more specifically, “The Hana Airport”: (HARD quotations of sarcasm around the word Airport) which required a 2-3 hour drive along the Maui coastline on a single lane road with little to no passing lanes. This narrow and yet stunning 62 mile drive is accompanied by an average of 10 turns PER mile. Yikes. Now imagine that on your anxious AF stomach jitters. Zooming next to your 7-year-old husband as he twists and turns his red rental Camaro like he’s fresh out of NASCAR. 

You see, the thing with skydiving is that they can call it off at any minute. Weather, wind, clouds, mechanics, parachutes, ya know: some important shit when plummeting to your death: it ALL has to be given the green light to jump. This “Road to Hana” had no cellular service for the length of the drive- meaning, we wouldn’t be certain if our dive was a “GO” until we we reached our destination. Clouds rolled in and rain sprinkled us about halfway while I simultaneously noticed I had received a voicemail: which of course, we couldn’t check until our service returned. I spent the last hour of the drive convinced the skydive was a no-go and all my anxiousness started to subside. Thanks for the call, Scotiabank. 

When we arrived at the “Airport” a small desk with a big happy man welcomed us. “Welcome  to Maui Skydiving” he said: “got an appointment?”, he quickly reassured us that today was a green light for skydiving and that we could sign our lives away on the dotted lines. Robbie skimmed his 12 pages of paperwork, autographed the bottom and returned it to our new friend at the front desk within seconds. It took me a little longer to get through my contracts as I made the choice to actually read all the rights and responsibilities I was waiving: none of which helped to calm the nerves that had now resurfaced. Robbie looked at me quizzically like, “you’re jumping out of a plane babe, just sign it”: and so I did. 

And in the time it took me to remove my shoes, step on a scale and return my signed sheets: I was ready to skydive. That was it. No formal training. No parachute fittings. No pep talk. I was over 18, blessed enough to afford it, sober for the last few hours and still stupid enough to jump. Those things alone made me a qualified candidate. 

As I was pacing in the parking lot awaiting our turn to jump, an elderly couple arrived: whether on purpose or on accident through their scenic tour of the island, I am unsure- but we sparked conversation with them. In a few short moments, the older woman was certainly getting the sense I was shitting my pants with nervousness.

Once her husband turned to start his trek towards their car and as my husband eagerly watched the hang gliders above, she came closer to me, she put her hand on my shoulder and she whispered with authority: 

“Cover the Earth girl, before the Earth covers you. Go get it!” 

My eyes welled up behind my heart-shaped giant sunglasses and I thanked her for the encouragement. 

She was right. 

This was a blessing. This was a privilege. After the last few months from hell my appreciation factor for life and it’s unpredictable nature was at an all-time high. What better time to put it all on the line. “Live Like You Were Dying”– am I right, Tim McGraw? 

So, it was time. Time to meet my instructor whom I was told was named “Robbie”. He was blonde, and nice, and named Robbie. I felt like I could trust him. 

We walked into a large tent next to the airport runway to find our 2 skydiving instructors, and believe it or not, the ONLY instructors employed by Maui Skydiving. I was beginning to get the feel this was a very small business. They were rolling our parachutes like sleeping bags into large backpacks at the end of the tent. Those would be saving our lives. 

My instructor started mumbling out-loud, “my car didn’t start this morning” he stated, “of all days, today was the day it didn’t start” he looked up and made eye contact with me “if something is bound to go out of the ordinary any day… it is definitely today”, he smirked. 

I stared back intently, straight faced. I wasn’t playing around. 

He then pulled the rope used to secure the now parachute-containing backpack and… SNAP. The rope broke. He chuckled. “damn”, he started “the only other one I have is in my car”. By this time my stomach was doing somersaults. He quickly retrieved a new rope from inside. 

“You can joke around with me once the jump is over” I said with hesitation and sweaty palms. “Any sense of security you can provide me, even if it’s false, would be much appreciated”

He refrained from over-doing the sarcasm and got the hint that I was all-business. 

After hand shaking and proper intros I was asked to step comfortably into a harness held by Robbie (the instructor one, not my husband). “I like that” he said, as he pointed to the chemistry tattoo located on my left forearm- “and that one, too” he said, tightening the buckle on my right side and pointing to the fresh ECG heartbeat of my stepfathers I recently had tattooed. “Thank you” I said with a tight smile “that’s for my step dad Stu, he passed away 9 weeks ago, and he was only 49” I explained that my mom and 3 other siblings also have this tattoo. Words spilled out my mouth as emotions and pure terror began to pour from my eyes- this time, unprotected by my heart-shaped glasses. Vulnerability began. 

Within seconds our pilot arrived, his name: Bob. Again, close enough to “Rob” that it also brought a sense of comfort. He gave the instructors the thumbs-up as he opened the ONE door on the right side of the plane. One door, one window, one seat- that’s it. This plane was made for Barbie dolls. 

My husband and his instructor Kai entered in first: this meant, Robbie (my instructor) and I would be the first to jump out the plane once we reached our desired altitude (just above 10,000 feet). I was in pure terror as all the masculine energy loaded the plane. Robbie (my instructor) looked at me with the “pound it” sign in front of him, awaiting my “pound it back” and he nodded his head minimally as he squinted and mouthed to me “FOR STU”. 

Fuckin’ rights, for Stu. I got in the plane. 

Squished like a sardine amongst 4 adrenaline seeking males, we took off. A little rocky takeoff was the least of my worries as our altitude gradually escalated over the beautiful North end of Maui. I was doing this. 

My body language, lack of words, and shallow breathing were solid indicators I was losing my shit internally. The 20 minutes of anticipation leading up to the jump was certainly the “scariest” part of the day. As the plane coasted over the island, Robbie (the guy I was now harnessed to) explained to me in full detail all of the topography and history of the land below. I peered out a window the size of my head and attempted to process what he was saying. 

“6000 feet” I heard Bob say as we were now coasting through clouds with nothing but Pacific Ocean beneath us, “All right” Robbie said with conviction “we’re about 1/3 of the way there”- I nearly shit myself. I grabbed Robbie (the one I’m married to) by the forearm with wide eyes and tight lips. I looked at him sternly: “BABE, were only 1/3 of the way there” – Robbie (my instructor) chuckled behind me. He was fucking with me again. It was at 6000 feet above Earth, in a Piper airplane the size of a small car, where I was finally given the instructions of the jump that was about to happen. 

“So, I am going to open this door right here in a few minutes” he explained as he tapped the door that was currently pushed up against my left quad and shoulder. “When the door opens,  I need you to take your left foot and just dangle it outside the plane for me”- my heart was going to explode hearing this. “THEN, he continued, when I tell you it’s time, you need to take your RIGHT foot and bring it around to meet the left foot on the outside of the plane. Once both feet are outside the plane, you need to put your hands on your harness and let go- and whatever you do, do not hold onto the plane, onto the pilot, or onto your husband”. 

You see, the fact that I could so easily hold onto the plane, my husband and the pilot all within arms reach is a pretty good indicator of the size of this plane. “It will feel like driving on the highway with the windows down” he went on. 

Close, but not quite. 

“And one last thing that is VERY important” he continued sentimentally, “Stu is up here with you, you need to keep your eyes open and look around for him, don’t look down, look around” – that sentence alone made my eyes well up with tears: an easy task when you’re on the verge of a panic attack. “This door right here” his spiritual side went on, “this is a door to the third dimension”, “what I mean by that, is when you’re free falling, it is a meditative state: your conscious, your subconscious, they meet: you’re not possibly thinking about the past or the future- for the 30 seconds we are free falling: all you’re going to think about is that exact moment- people live their whole lives and never experience that”. He continued talking as my replies were minimal, “this door is an analogy for life Ashlyn, there will be lots of doors that will open in life, and you won’t know what’s on the other side, but it’s a shame not to find out” at the time I nervously nodded repeatedly at everything he was saying, but processing it now, I really appreciate the time he took to make me feel comfortable and connected to this experience. 

“All-right, Ashlyn- I am going to open the door now”: he braced me. I again, continued to nod at everything he said.

Then, BOOM: reality hit. The airplane door opened and there we were, flying through the air at 10,000 feet in a toy airplane, with the door open, clouds spilling out in every direction. My left foot dangled out the side. My right foot awaited his cue. 

The cue didn’t come. 

“Damn” Robbie yelled (it was loud AF at this point) “I was a little premature on opening the door, we need just a few minutes”

So there I was, for two whole minutes, half hanging out the aircraft, half gravitating inwards towards the safety of my husband, waiting to plummet towards the Earth at 130mph. 

Then it was time. He tapped my shoulders to indicate that my right foot needed to meet my left. My husband cranked his head around from the back of the plane and mouthed “I LOVE YOU”- and with puppy dog eyes I responded back “I LOVE YOU, TOO” 

And within seconds, my right foot came around to meet the left: and we were off.

It was like the drop-of-boom, ring-of-fire and carnival teacups all fell through me at once.

We were free falling for all of 30 seconds before pulling the chute. Start counting in your head in real time for me would ya?

1 Mississippi, 2 Mississippi, 3... and tell me 30 seconds of falling to Earth without a chute isn’t a LONG ASS time. 

Those 30 seconds we’re long enough for me to process WTF was going on and long enough for me to think, “holy shit… has this guy pulled the chute yet?” and within moments of that thought, “SHHHWWOOP” I could feel the elevation rise again as the parachute opened. Our 5 minute descent WITH the chute had now begun. A tad more relaxing than the free fall we had just experienced. 

“So the parachute is good?” I confirmed with instructor Robbie, and he replied, “Were good” and instantaneously I asked, “Is my husbands parachute open?” He giggled “Yes, he’s safe behind us, but I am not turning you towards him yet cause the sun will be in your eyes”: thank you kind man, I‘m just happy were both alive. 

In the horizon, now about 4000 feet above the island of Maui, I could see a HUGE rainbow appearing, just as reality began to register. “Oh my gosh, a rainbow” I yelled as I gained the nerve to unfasten my right hand for a split second, pointing excitingly to the prominent red, oranges and yellows that appeared before us. “thats Stu” my spiritual gangster of an instructor clarified. 

Fuckin’ rights, that’s Stu.

Instructor Robbie must’ve thought my anxiety had settled completely as he calmly attempted to hand me the two handles that were controlling our parachute decent. “take these” he said, “I am just going to loosen up your harness”. He handed me two yellow ropes that would guide us safely to Earth. 

“I am perfectly comfortable” I told him. Unwilling to have my harnessed fucked with whilst controlling my own parachute thousands of feet above Earth. 

He loosened it anyways and I began steering the chute with his instruction. “pull the right handle tight towards your hip, OK, good… now pull the left handle, tight towards your hip…” 

Across the way and through the clouds I could see my husbands orange parachute zooming back and forth at mock speeds. I knew he must’ve been controlling his own chute too: likely with a lot more grace, excitement and speed than I was. I SCREAMED at him across the way- “HEYYYY BABE!” 

Robbie (my husband) and instructor Kai jumped 10 seconds behind us… and landed about 10 seconds before us- leave it to the daredevils to one-up my life’s most terrifying experiences. 

Robbie instructed me to lift my legs and turn over the control of the parachute back to him. We landed gracefully on our asses on a plot of grass, in the middle of the “airport” about 3 feet from my husband. I jumped up, kissed Robbie (… NOT the instructor), and then proceeded to kiss the ground for the video that was filming from Kai’s Go-Pro. This is something I saw my Dad do on an old-school 1992 home video after he bungee jumped with my mom as I sat below in a stroller admiring their bravery. Great role models if you ask me. 

So, that was it. We did it. We fuckin’ did it. We checked off an item on the bucket list that according to Google, only 1-2% of people will EVER do: and that’s pretty fuckin’ sweet if you ask me. 

I did it with my best friend. I did it for myself. And, let’s be honest, I did it so I could share it on the ‘gram and forever be able to say, “I’ve done that”- a reason why I do many things. 

We then proceeded to make our way back to the small desk and big man that initially greeted us and my hands vibrated slightly as a handed over my credit card. 

“I definitely want the pictures AND video, and we need 2 tee-shirts, and good tips for those guys” I proclaimed with a proud chest as I pointed back to my new friends and skydiving gurus. I was drinking all the kool-aid. 

We paid our $1000 USD bill without hesitation (totally worth it) and headed back to our red Camaro as if we were so casually exiting the grocery store. 

Just like that, the nerves were gone and the euphoria of accomplishment had set in. 

We decided to take the scenic tour of the island back to our Air BNB (as recommended to my husband by his instructor during their decent)- 4 whole hours of breathtaking beauty and the best decision we made all trip. Although the “Road TO Hana” was great, the “Road FROM Hana” just couldn’t be beat. 

Palm Trees, mountains and Hawaiian hills to our right, unlimited and infinite ocean to our left, red Camero, the man I love, and two phones that both lost all service and charge for the entire length of the drive back. 

This meant: no music, no distractions, no photographs, no post-skydive Instagram updates, no text messages, no GPS. Maybe THIS was the third dimension Instructor Robbie spoke about. THIS was peace. 

After going through some really hard times this past year, days like this remind me more and more of the beauty of this world, the love I have for my husband and the desire I have for growth: both through spirituality and through physical experience. 

Days like this don’t come by often: which is why taking the time to write this in full concrete detail is so utterly important to me. This is a day full of memories and lessons I will cherish for a lifetime.

So, if you enjoyed my storytelling and want to read more, please leave me your email address and be notified when I share the next blog. 

And if you found joy in my writing and want to share it with your friends: hey, I wouldn’t oblige- my goal to become a one-day author can only be improved with your support. 

And if you’d like to see this whole story displayed in 3:53, take a look at my official “Maui Skydiving” video at this link:

Mahalo, Friends!