Back in secondary school, I remember one hot afternoon in March 2007. We were in physics class, under a ceiling fan that wobbled more than it spun. My desk was covered in vandalism—profanities, names of crushes, simple greetings. Some old and faded, others fresh enough to feel rough under your palm. Each one a small story of someone who’d sat here.
The table next to me was empty.
My friend had called in sick that day.
We were pretty close. He was one of my few classmates who actually gave a damn about school. A few weeks earlier, we’d visited Junior Colleges and Polytechnics together—partly to collect goodie bags, mostly to figure out what came next. We were both taking the O-level exams that year, and we’d spent hours talking about goals, plans, futures.
I figured he’d eaten too much bak kwa during Chinese New Year. That sweet-savory pork jerky is considered “heaty” in Chinese medicine—the kind of thing that gives you a sore throat if you overdo it during the festive season. Normal stuff.
The next day, I saw him and we started chatting. He didn’t sound sick at all.
“So what happened?” I asked.
He looked away, like he’d been caught doing something wrong.
“Actually… something huge happened.”
He told me slowly, almost reluctantly. His dad’s boss had given his father a red packet for Lunar New Year—a pretty standard gesture in Singapore. Bosses give employees red packets during the festive season as a bonus, usually cash.
Sometimes, though, they don’t give cash.
Sometimes they give hope.
In his dad’s case, his boss had given him a lottery ticket—the Singapore Sweep, with a top prize of over $2 million.
His dad won.
My jaw dropped. My teenage brain couldn’t comprehend that level of luck.
Over $2 million. The boss had fought to get the ticket back—or at least demanded a portion of it. I never learned exactly how it ended, but his dad quit his job not long after, so I assumed he kept everything. The family became estranged from relatives who’d expected generosity with the windfall, who’d wanted their own slice.
My friend and his siblings each received a tidy six-figure sum from their dad.
His family became millionaires overnight.
Looking back now, I realize that the Chinese New Year was probably their last normal one as a family. The last time money was just money, not a test of relationships. The last time people showed up because they wanted to, not because they wanted something.
Weeks later, my friend was gone from school. Then his younger brother. Both citing health reasons—the kind of vague explanation that doesn’t really explain anything.
I was confused at first. My friend seemed fine. He’d always been healthy.
But looking back, I think I understand now. When you’re seventeen and suddenly receive that kind of windfall, grinding through another year of school probably feels pointless. What’s the point of studying for exams when you’ve already won?
While his world was exploding with possibility, mine was narrowing to a single point.
I needed a scholarship for my polytechnic education.
My family couldn’t afford the tuition fees, and I wasn’t willing to start my adult life carrying debt. That fear of owing money before I’d even begun kept me awake some nights. So I stayed laser-focused on the O-levels. Every practice paper, every past-year exam, every weak topic I drilled until it wasn’t weak anymore.
I ended up topping the O-levels in my stream.
My friend enrolled in a private diploma program. We’d still meet up occasionally—less frequently as time went on, but we kept in touch.
One afternoon, we met for lunch at The Cathay, a shopping mall in town. The kind of air-conditioned refuge you seek out during a sweltering Singapore afternoon. I asked him what private education was like, curious about a world I’d never considered.
He told me about the modules he was studying—accounting principles, Maslow’s hierarchy of needs, and marketing fundamentals. The usual business school fare. Then, almost as an afterthought, he shared: “My lecturer keeps pushing these two books on us. Says they’ll change our lives if we read them.”
“Which ones?”
“The 80/20 Principle and Rich Dad, Poor Dad.”
“Have you read them?”
He shook his head. “Nah. Not really my thing.”
That weekend, I went to the library and checked them both out.
The 80/20 Principle was the first one I finished.
The core idea is simple: 20% of your actions drive 80% of your results. It sounds obvious when you say it like that, but when you really internalize it—when you start looking at everything through that lens—it changes how you operate.
I stopped trying to manage everything. Started hunting for leverage instead. What’s the 20% that actually matters? What gives me disproportionate returns? And just as important: what’s giving me 80% of my problems that I should just stop doing?
Even today, I’m constantly asking myself those questions.
Rich Dad, Poor Dad sent me down a different rabbit hole entirely. The book is about assets versus liabilities, about making money work for you instead of trading time for money. It made investing feel less like some distant adult thing and more like something I could start learning right now.
I read everything I could find about investing. Spent hours in the library, then online, absorbing everything—stocks, bonds, how markets work, what compounding means. When it came time to choose my polytechnic course, I enrolled in banking and financial services at Ngee Ann Polytechnic. It was the closest thing to investing I could find.
The day I turned eighteen, I went to a local brokerage firm to open my first account. I remember sitting across from the agent, filling out forms, answering questions about my investment objectives. I felt very adult—like I was doing something real, something that mattered.
My friend and I lost touch after that. Just the natural drift that happens when lives move in different directions.
But I think about him sometimes. Specifically, I think about timing.
At seventeen, that kind of windfall looks like freedom. Looks like every door opening at once. No more worrying about tuition, about scholarships, about starting life in debt. Just pure possibility.
But freedom from what, exactly?
My friend hadn’t built anything yet. Hadn’t struggled for anything. Hadn’t earned the quiet confidence that comes from overcoming something you weren’t sure you could overcome. He hadn’t had the chance to discover what he was capable of when things got hard.
And here’s the thing about struggles: they don’t just test you. They build you.
The person who emerges after fighting through something difficult is not the same person who went in. That transformation—that forging—can’t be bought. It can’t be given. It has to be earned through the experience itself.
Confidence doesn’t come from having money in the bank. It comes from proving to yourself that you can handle what life throws at you. That you can work for something, fail at it, learn from it, and try again. That you can set a goal that scares you and then chase it down anyway.
A windfall at seventeen doesn’t give you that. If anything, it might rob you of it. Because why would you push through the hard stuff when you don’t have to? Why would you discover your limits when you never need to test them?
I think about what each of us received that year.
My friend received a life-changing sum—complete, ready to use, his the moment he got it. I received two book titles.
His gift required nothing of him. Mine demanded years.
Years of reading, applying, making mistakes, and learning from them. Years of figuring out what worked and what didn’t. Years of building something from nothing, one decision at a time. The recommendation itself was a gift—without it, I’d never have found those books. But the real gift was the work that followed.
Maybe my friend used that money wisely. Maybe he invested it, started a business, found his calling. I hope he did.
But I know which gift built me.
I know which one taught me that I could learn hard things, that I could change my own life through nothing but effort and attention. I know which one gave me the confidence that comes from earning your own wins.
Maybe struggles aren’t something to escape as quickly as possible.
Maybe wealth at the wrong time—especially wealth you didn’t earn—can do more harm than good. Not because money itself is bad, but because it removes the very friction that shapes you into someone capable of handling it.
Maybe the real gift isn’t getting what you want when you want it. Maybe it’s getting it exactly when you’re ready for it, which usually means later than you’d like, after you’ve built the person who deserves it.
The struggles I faced—the scholarship I needed, the debt I feared, the work I had to put in—those weren’t obstacles. They were what shaped me.
If you got something from this, share it with someone who’s grinding right now. Someone who might need the reminder that the struggle is building them, not breaking them.
And if you’ve got your own version of this story—the thing you didn’t get that turned out to be the best gift—I’d love to hear it.
Leave a comment below. I read everything.
P.S. Those two books my friend’s lecturer recommended? I’d still recommend them to any young person starting out today. Start with The 80/20 Principle—it’ll change how you think about everything.
Great article., Rich dad Poor dad was eye opening for me. And as you wrote, sometimes the thing you don’t get is what motivates you to keep going. If is handle in a silver platter, is not the same as sweating for it.
Reynaldo – Rich Dad Poor Dad hit different for you too, huh? That book has a way of flipping the script on how we think about money.
The sweating-for-it part you mentioned… that’s exactly it. I think about my friend sometimes and wonder if he ever got to experience that satisfaction during those formative teenage years – you know, when you’re figuring out who you are and what you’re capable of.
It’s not that he never struggled in life, but he missed that crucial window where struggle shapes you. There’s something about earning your first wins as a teenager – it builds a kind of confidence you can’t get any other way.
Curious if there were any other books or experiences in your life that were eye opening for you as well?
Your writing is brilliant. What should parents do. Leave something for their kids or not? Or only much later in life??
Abinash – appreciate that, man. And you’ve asked THE question that keeps parents up at night.
Here’s my take: Leave them tools, not just treasure. My friend got treasure at 17. I got two book titles. The difference? One required nothing of him, the other demanded years of work that shaped who I became.
I’d say: Leave enough to be helpful, not so much that it removes the struggle. And leave it when they’re ready – not when it’s convenient. The timing might matter more than the amount.
Wow…this piece was really impactful Thomas. If you’d asked me at 17 if I wanted a million dollars, I’d probably jump at the chance. Anyone would be crazy to turn it down right? But having gone through life and having to work hard to earn my keep, I think I just might tell my younger self to politely decline. Or maybe take it but put it right in an investment tool and don’t think about touching it until years down the road (and let compounding do its magic). You never truly appreciate the value of something that just falls in your lap than if you worked hard for it. I think your piece really crystallized that concept really well. And now I have 2 more book titles to add to my reading list the next time I visit the library 🙂
Thanks Christopher! Man, you really captured the paradox perfectly. At 17, turning down a million would seem insane. But you’re spot on – the investment approach would’ve been the smart play, letting time work its magic while you build character through the grind. There’s just no substitute for earning your way. Really glad this resonated with you, and enjoy those books!