5 Singaporeans Share The Most YOLO Things They’ve Ever Done, And Why It Was Worth It

Most YOLO things experienced by Singaporeans

The term “YOLO” has been used liberally among many over the past decade. It’s no surprise why – with mounting pressures of mugging through studies, finding a job, and settling down plaguing many millennials, the mantra of “you only live once, reminds us that we need to stop and smell the roses once in a while. 

But there’s also a misconception that being spontaneous comes with way too much risk. To debunk all that, these 5 Singaporeans share the most YOLO things they’ve ever done, and why it was worth it. 

1. Got an open-sea diving licence to surprise BF

Image credit: @chlobigail

Open-sea diving is something many wish to conquer, but truth be told, it’s easier said than done. Water that goes deeper than the eye can see, “breathing” underwater, and of course, the possibility of marine creatures that feel a little chompy – this puts diving high up on the “balls needed” portion of any bucket list. 

True enough, 24-year-old Content Strategist Chloe Chew’s heart was in her throat when she was about to plonk into the waters of the Great Barrier Reef in Australia for the very first time. “I get chills everytime I have to put on that heavy tank,” she shared. 

The mission? Get a diving licence to surprise her then-boyfriend who was a diving enthusiast. The task? Dive – on an impromptu solo trip to Cairns. “I was super scared because the boat looks low, but when you jump in it’s actually quite high up and you will sink quite far down.

“When u see the corals at the Great Barrier Reef – wah!” – Chloe.
Image credit: Ocean Safari

Image for illustration only.

Nevertheless, she said that the entire experience was life-changing – and not just because she got to surprise her ex later on with a diving trip. “It cost me $1,000 to do that, which was very painful for me at the age of 21, but it was at that point that I realised there was so much more to see out there in the world.” 

Chloe cited meeting folks from various backgrounds during her diving trip, giving her a different perspective that life needn’t be all about study, work, and settling down. “My diving instructor gave me a lot of advice on how to live as a 21-year-old, which is not just study. It was very different from an Asian perspective, which I appreciated,” she said. 

2. Moved out from parents’ home during Circuit Breaker

Moving out from our parents’ home is on the bucket list for most Singaporeans. But it only took 48 hours for Steph Leong, a 33-year-old Project Manager, to make the jump into pure independence. 48 hours into the infamous Circuit Breaker (CB), that is. 

Steph always had dreams to live independently from her parents, and after realising that the uncertainty of the CB could delay her goals indefinitely, she decided to “test the waters” by checking herself into a hostel first. After all, the CB would present her the ultimate test of independence.

Steph hopes to soon rent an entire apartment on her own.
Image for illustration only.

As she settled into her hostel room, one of the biggest fears nagging at her was money. As she’d have to scrape through in order to pay rent, she decided she’d do anything to make it work. 

Besides, she recalled, “My initial plan was to move back after CB, but decided to rent a room after staying on my own for 2 months. It was very transformative as I finally had my own time and space to think about a lot of the things I wanted in life. I also got to set my own standards in terms of housework and how I wanted to do things. 

The entire experience taught her how to prioritise her needs versus her wants, and Steph gleamed, saying it was the best decision she ever made. She quipped, “Initially I had a lot of doubts; a lot of people say paying rent is like throwing away money. My reply to them is, I see it as paying for my own therapy.” 

3. Went on a solo trip to North America & fell in love

Solo tripping is something Jonathan used to do on the regular.
Image credit: Jonathan See

27-year-old accountant Jonathan See has been no stranger to taking solo trips around the world. Bangkok? Kuala Lumpur? Australia? No problem. But it was on one of his random trips to North America that he ended up finding the love of his life, Kae. 

Jonathan had met Kae on a previous family trip to Vancouver, and ended up staying friends after. So when he headed back to the city on yet another solo trip to North America, he ended up crashing at Kae’s place. “I spent a week in Vancouver and got to know Kae a lot better because I didn’t want to pay for an AirBnB,” he said.

“When Kae dropped me off at the airport, I just sat there crying for 40 minutes. And I cried more at the gate. And I cried on the plane. I don’t know why I cried so much in my life,” Jonathan recalled. “I think it was because I didn’t know when we would see each other again. When I was in my next destination San Francisco, Kae said ‘I love you,’ and I was like, ‘same, baby, same’”

Vancouver has now become Jonathan’s second home.
Image credit: Jonathan See

The entire ordeal was unexpected for Jonathan, who ended up having a long-distance relationship with Kae for 4 years. Once VTL flights were announced, he spared no thought nor expense to head back over to Vancouver for a 6-month stay. “Now that travel is back, we’re making sure that our relationship can withstand the trials of domestic life together.” 

He laughed, “Who knew a YOLO trip – my most ambitious one ever – would end up with me finding my soulmate, and possibly my spouse?”

4. Went for a rock concert at 15 & became hooked

33-year-old graphic designer Amara admitted she was always a timid kid – a timid kid who happened to love rock music. So at the age of 15, when her favourite band Incubus was headed to her hometown of Kuala Lumpur, she wasn’t sure if she should ask her parents for permission to go for her very first rock concert. 

Her 4th Incubus concert.
Image credit: Amara

“I told them I’d save up my allowance – RM100 (~S$33) was a lot back then, and I sort of made excuses in my mind if I should just not go because I was afraid that it would be rabak,” she shared. But once she found out some of her friends were going, she dug out those precious angbaos, went to her local music store and bought a ticket. 

“I don’t know how, but I ended up standing right smack in the middle of the mosh pit. A girlfriend and I got separated from the rest of our group, so we were two tiny 15-year-olds cowering there, shoulder-to-shoulder with huge, sweaty guys,” Amara recalls. “And then Incubus came on and started playing. Everyone started moshing. It was terrifying.”

Amara and her friend did the next best thing – they joined in, and thankfully, the folks around them were conscientious enough to not get out of hand. Following that experience, Amara says she was hooked to live concerts. “When you’re surrounded by fellow music lovers, you don’t feel the need to hold back.” 

Foo Fighters in Singapore and Phoenix in Genting Highlands.
Image credit: Amara

She would later spend a huge chunk of her adult life forking out cash for concerts and music festivals, no holds barred. “For me, it’s really about creating memories of my youth, and not regretting having missed seeing a good artist in person, and that feeling of freedom that comes with live music.” 

5. Solo-travelled to Bangkok with a baby

Having declared Bangkok her “second home”, it was only natural for 30-year-old Kimberly to revisit her favourite city after her first child was born. At the age of 26, she hauled a then 4-month-old Ellie onto her first mother-daughter solo trip to Bangkok

Image credit: Kimberly

“I refused to think that a baby would stop me from travelling and exploring like I used to,” Kimberly said, recounting that she used to plan spontaneous trips with friends 3-4 times a year. “I thought, you know, I’ll just bring my baby along. I was comfortable taking care of her on my own, so I figured travelling with her wouldn’t be too hard.” 

Kimberly also didn’t want to miss out on making memorable experiences with her child. She added, “Travelling with her on my own showed me that I was stronger and capable of so much, and that while motherhood wasn’t easy, it definitely was manageable and I could have fun along the way.”

Kimberly and Ellie in New Zealand.

She has since brought Ellie with her on 10 trips around Asia and Australasia, before giving birth to her second child during the Circuit Breaker. In a couple of months, she and her family will be moving to Pattaya, Thailand after leaving it in the backburner for many years. 

“My husband does a lot of business in Thailand, so it only seems natural that we’d find ourselves going over eventually,” she explained. “For us, it’s the need to slow down and just enjoy being alive and in nature. I’m looking forward to camping, road trips and even having our own mini farm in our yard.”

Being spontaneous and “YOLO” in life

They say life is too short to hide in the shadows, and as these Singaporeans share, being spontaneous has led them to chalk up experiences they’d neither forget nor regret. 

Being “YOLO” and flexible doesn’t have to apply only to life experiences. While many might think it’s impossible to save without being “rigid”, there are ways to allow ourselves to just do it, while safeguarding our futures. 

You can live spontaneously and save for your dream lifestyle with a flexible insurance savings plan such as Gro Cash Flex from NTUC Income. It allows you to grow your funds through a plan that suits your lifestyle needs while helping you reach your savings goals.

From the end of the 2nd policy year, you can enjoy yearly cash payouts^ and spend it on anything you fancy – be it getting that diving licence or going for that rock concert. There’s also the option of accumulating them to receive interest. 

You can also have a flexible choice of premium and policy term. Choose from a premium term of 5, 10, 15, 20, 25 or 30 years, with a policy term of 10, 15, 20, 25, 30 years or till the age of 120 depending on the selected premium term. 

Needless to say, safeguarding your future doesn’t need to put an end to all things fun and liberating.

Find out more about Income’s Gro Cash Flex

This post was brought to you by NTUC Income.
Some names have been changed for anonymity.
Cover image adapted from: Kimberly Lauren Wong, @chlobigail

^Policy T&Cs apply.

All opinions expressed in this article are solely those of and do not reflect the opinions of NTUC Income Insurance Co-operative Limited (“Income”). Income is not responsible nor liable to any party in any manner whatsoever for such opinions, and is solely responsible for any opinion and the accuracy and completeness of any information and intellectual property used in this article. The information contained in this article pertaining to any insurance product or plan is provided and meant for general information only and do not constitute an offer, recommendation, solicitation or advice by Income or to buy or sell any product(s), plan(s) or investment product(s). It is not and should not be relied on as financial advice and has no regards for any person’s investment and financial needs. If you are unsure whether this product or plan is suitable for you, you may seek personalised financial advice from a qualified insurance advisor. Otherwise, you may end up buying a product or plan that does not meet your expectations or needs. As a result, you may not be able to afford the premiums or get the insurance protection you want. Precise terms, conditions and exclusions of the product are found in the policy contract.

For customised advice to suit your specific needs, consult an Income insurance advisor. 

Protected up to specified limits by SDIC (applicable for Income products that fall under the Policy Owners’ Protection Scheme).

This advertisement has not been reviewed by the Monetary Authority of Singapore.

Information is correct as at 12 May 2022.

Jessica Fang

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