Being able to retire earlier is a common aspiration these days, and a central topic among the (Financial Independence, Retire Early) FIRE crowd. Gavin (not his real name) was well on his way with this financial goal, where the plan was to retire by 45, and start his own apparel line. But despite doing everything right, and an initial run of good luck, it was a family tragedy that also cost him his dreams. But Gavin doesn’t regret it too much, and has an optimistic take:
A dreamer from an early age

Gavin says the roots of his FIRE journey started before he had even started thinking about personal finance. The dream for independence began as early as Primary to Secondary school:
“I was interested in drawing from a young age,” Gavin says, “And I started from drawing my favourite manga characters; other people’s heroes were soccer players or pop stars, mine were all mangaka*.
By the time I was in Secondary school, I had moved on to drawing my own characters, and from there I developed an interest in fashion. This was bad for my schooling, because I was frustrated at being told what to do all the time, and I couldn’t devote myself to what I really wanted to do.
From that young age I developed this fear of living a very controlled life, where my life might be like schooling, with people telling me when and what to do, for every hour of my day.”
Gavin also realised that avenues to pursue fashion were limited in Singapore; and given his family’s financial situation, which he described as squarely middle-class, his prospects were limited.
“By the time I finished my O-levels, I was actively looking for ways to escape,” Gavin says, “And I was lucky in that I had a good mentor. My partner at the time had a dad who worked in a family planning office, and I learned a lot from him about long-term, low cost investing, as well as concepts like Fat FIRE.”
*Comic book artists in Japan
Side-hustles and going beyond budgeting

Gavin says the main lesson he learned was:
“There’s an ultimate limit to budgeting, so FIRE, especially Fat FIRE, isn’t really possible if all you’re doing is tightening your belt. I was definitely careful with saving, and I was setting aside around 60% of my earnings. But that wasn’t going to cut it, I had to earn more, not just save a lot.”
As Gavin had limited time, he opted not to be reliant on part-time jobs:
“I used investments like tracker funds, and I put a small percentage, about 5%, into high risk alternatives, including crypto. Honestly I was not lucky most of the time with alternatives, but the losses were capped because I was disciplined in limiting my exposure – the few times they did well made up for it.”
One of Gavin’s smarter moves was to take on a part-time job as a security guard in an office building, which allowed him to monetise his design sessions:
“Since I was going to spend time drawing, I may as well get paid for it right? So I signed up with this security company, and on Saturdays and Sundays I would work. It was near Raffles Place which is deadtown on weekends, so there’s nothing to do but check the place now and then, the rest of the time I could draw.”
Once he had risen up the ladder in his job, which he declined to describe for privacy, Gavin took on side projects instead. These ranged from illustrating Primary school assessment books, to technical drawings in instruction leaflets.
Coupled with his investing and saving, Gavin was consistently ahead of his financial targets for almost 10 consecutive years.
A death in the family

Gavin’s father was uninsurable, and had been for most his life. He says that:
“My dad was not very well educated, even though he did well given his circumstances. So he didn’t really think about buying insurance and so forth, for most of his adult life. He had prostate cancer when he was in his early-thirties, and he couldn’t be covered for it.
When I myself reached my 31st birthday, his cancer was back, and he would battle it for the next four years. But there was no critical illness or any such thing to help, and even his life insurance was very basic.”
Gavin and his family ended up spending a huge sum on treatment bills; and part of the reason was also alternative treatment that the family sought overseas. This had to be paid out of pocket, with Gavin and his brother splitting the cost.
By the time it was over, the death benefits from his father’s life insurance was a pittance compared to the expenditure. Gavin described it as covering perhaps a tenth of the total costs involved.
Worse still, the expenses were so huge, Gavin lost several years worth of accumulated wealth:
“The worst part is I’m also older now, I have more responsibilities, I can’t do as many side hustles as in the days after uni,” Gavin says, “So I have to make a choice. Either I give up on my apparel line, or I push my retirement date further back.”
After some discussion with his partner, Gavin settled on the latter:
“We agreed that I wouldn’t be happy if I retired early, but then my main passion, my big dream, remains unfulfilled. That’s not a very happy retirement anyway. As the saying goes, better late than never. So I have pushed back my timeline, and I’m hoping by 55, I can retire and really live the way I want, putting my work out there in stores and on shelves.”
No regrets over the tragedy

Gavin is quite optimistic about the setback, and says that:
“It hurt at first of course, but I am content that I was in a position to help my dad as much as possible. And I definitely don’t regret anything. If I hadn’t saved up such a sum, then not only I couldn’t help him, my dream might be dead altogether.
So I don’t feel that my efforts were a waste. Rather, I see myself as being rewarded, because by aiming high and saving more than I need, it allows me to absorb the damage and keep going forward.”
That said, Gavin does have a bit of advice for others on the FIRE path:
“We tend to look at our finances a lot, but take a look at your family’s finances as well. If it’s someone close to you, then any gaps in their savings or insurance is also a gap in your own. You’re all in the same boat together, so don’t just focus on patching holes in your part of the boat. If someone else isn’t dealing with a leak, you’re going down with them, no matter how good a job you do on your part.”
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