How One Introvert Overcame their Inner Critic to go Skydiving in Waikiki

Last updated: 30 July 2023

Originally published March 2013. Updated in May 2023. Retrospective writing. 

Have you ever felt alone? Like truly lonely?  I have. 

This is the story of an introvert finding her voice, shaking off the cloak of shyness, finding the courage to make a friend, and eventually making the decision to go skydiving in Waikiki. Once upon a time, I was young, and single. After a hideous period in my life I was sad, heartbroken, and lonely. 

Have you ever dragged yourself to work every day just for something to do? That was me. Daydreaming as I sat in my office, starring out of my mediocre car-park-view window in Sydney, I knew deep in my soul that the daily grind was taking its toll. I just had to go. Somewhere, ANYWHERE. Minutes later I find myself browsing the website of Jetstar, a budget carrier in Australia. It was having one of their epic sales, and Hawaii on the list. I whipped out my credit card without a second thought, and it was done. Booked. I was on my way to the sunny shores of Hawaii in just a few weeks. 

I finally had something to look forward to, and a glimmer of a smile came across my tear-streaked face. 

Beach views in Waikiki Hawaii


Was Hawaii the right holiday destination?

It turns out Hawaii isn’t the ideal destination for a heartbroken 20-something. As a popular honeymoon destination it’s frequented by loved-up couples, and families seeking a sandy beach holiday at all-inclusive resorts. I’d picked wrong, and it didn’t take long for me to realise it. 

I had travelled solo before, but never under these circumstances. This was the first time I’d really felt lonely when travelling. I spent the next three days by myself. Surrounded by newlyweds who were arm in arm, feeding each other ice cream at sunset, laughing together as they twirled and danced the night away on the beachfront bars. Those three days were tough, where I wrestled with my inner critics, yes plural. I didn’t talk to anyone, I spent every moment alone, I ate alone, and I trudged my way around Waikiki feeling very isolated and depressed. 

Under a palm tree, with glorious cloudless blue skies and sunshine above me that should put a smile on most faces, I  considered changing my flights and going home early. I wasn’t enjoying my time and felt like I’d made a huge mistake. Fortunately, one of those inner critic voices took hold. It reminded me that I hadn’t even tried to talk to anyone. I was lonely because I hadn’t tried.  

At that moment I told myself every excuse possible. I’m too shy. I’m not that interesting.  What if they don’t like me. Well sure, they’re all possibilities, but not certainties. 

What if I fall? But what if you fly?!

The courage came from somewhere that day. I made it my mission to make a friend. 

In the days before Meet Up, and other social media apps (other than Facebook?) I gathered activity brochures from the hotel and ventured out to seek out my new friend.


Shopping fixes everything

On the outskirts of Waikiki is the Waikele Premium Outlet mallA place where you can buy brand name items on sale. fortunately for Aussies, our seasons are in reverse to the Northern Hemisphere, so items on sale in the USA are in-season in Aus. (There’s a traveller tip for all you antipodeans out there!)

Armed with a paper map, (remember those?) I hopped on a bus like a local, and hoped I’d gotten the directions correct. Glancing out the window, watching Waikiki pass by the bus windows my ears pricked up to an accent I recognised emanating from the back of a bus. They were Aussies! 

I got up the courage to approach this young couple on the bus. We quickly developed a rapport reminiscing about the interesting characters we’d met, and found we had common interests. I’d done it, I’d made a friend! Or two as it seemed! That day I shopped my heart out spending more money than I had, and found myself at the bus stop at the end of the day waiting to return to Waikiki. The couple from the bus approached the bus stop, laden with more bags than I had. Yet another spontaneous decision, we ditched the bus and splurged on a cab chatting the whole way about our shopping extravaganza. 

My trip to Hawaii had just improved 10-fold and there was no way I was going home early now!

Sunset view of a beach in Hawaii


Finally Feeling Positive, Did I Dare to Go Skydiving in Waikiki?

As a solo traveller who had spent all their funds on a shopping extravaganza, the next few days were beach days.  I spent my days between beach-facing resort sunbeds. I’d stay for half an hour and then get moved on by the hotel attendant, because unless you staying in the hotel, you can’t use their sun loungers.

It seemed to be the trip of new beginnings.  Feeling brave, confident by my success of making friends, I was overdue for yet another spontaneous decision. Was it time time to try my hand at  skydiving in Waikiki? Like most spontaneous decisions, throwing myself out of a plane at 16,000ft seemed like a good idea at the time.

Skydivers over Hawaiian waters
Hawaii inspired me to try something daring…it was time to fly

What does it feel like to jump out of a plane?

My bus pick-up was scheduled for 8am so I spent the hour-long ride trying to calm the nerves and convince myself that I’d made the decision to skydive for a reason and that there was no sense in pulling out now. It turns out I was the first jump of the day so after attending the safety briefing I was suited up where I met my tandem-jumper (Steve) and we chatted mindlessly as we climbed into the plane. We were strapped together closer than a horse and saddle. As the plane took off I thought to myself there was no backing out now!

It wasn’t until we started to scoot to the edge of the open door that I realised what I was about to do. Steve was great, he’d obviously had a nervous jumper before, and without giving me time to think, we jumped out the door of the plane……

Everything they tell you in the safety briefing left my mind the second we jumped. As we jumped, I reached out as if to grab something, and then we started to free-fall.

I remember screamed. I screamed like I’d never screamed before. Then I forgot how to breathe. The air is hitting your face with such force you need to consciously breathe through your nose, but you forget that too!

Roma on a tandem skydive over Waikiki Hawaii
A life-changing experience I’ll never forget

Steve, showed me the Oahu coastline from 10,000 ft and also showed me that rainbows aren’t semi circle that we’ve come to know, but are in fact full circles! Apparently it’s the Earth that cuts them in half. And with that, we soared like a bird straight through one!

Eventually you will relax into it.  It won’t be like lying on a sunbed in the sun and you’ll have so much adrenaline coursing through your veins but eventually there’ll be a moment of acceptance where whatever happens, will happen. I never expected to have a philosophical moment whilst plummeting through the air!   

As we were coming into land, Steve said “legs up” which meant raise your knees so you don’t break your leg and so you can assist the landing, which was the time I realised I was literally legless! I couldn’t lift my legs, I had no strength in them. We landed safely, albeit me on my bum and after a few minutes the feeling came back and I was pumped full of adrenaline.

It was a rush like I’d never felt before. I remember having the shakes and feeling cold.  Almost like you’re in a state of shock. The whole experience is still all a bit of a blur and is over before you know it.  I thank the cocktails the night before for the Dutch courage that obviously helped me out of that plane. 

My trip came to an end not long after that, what a way to end my time in Hawaii. 


Final Thoughts

The couple from the bus are still together, and we still remain friends. I use this story to remind myself that rarely nothing happens unless you MAKE it happen. I could have gone home after sitting under that tree.  If I had I would have never met some wonderful people or thrown myself out of a very fine functioning plane! 

If you’re contemplating expat life, or moving broad, or taking the next step in your career, but perhaps riddled with fear. May I suggest you reflect on your own mindset and ask yourself is it fixed or a growth mindset? One will see you take opportunities and make changes, the other won’t. Step outside your shell, go out on a limb, and embrace the short life you have. You just might fly. 


Read More: Roma currently lives in London and is busy exploring the UK and Europe once city at a time with her husband, Russ. You can read more about their travels here on Roaming Required or watch their travel videos on YouTube


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Roma was raised on the white sandy beaches of Australia's East Coast, and she has called London home since 2012. With an adventurous spirit, a love of regional travel and anything food related, Roma looks to encourage working professionals to follow their dreams to travel the world one adventure and short break at a time. Don't let a full-time career stop you from seeing the world. Come roam with us!

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