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The Benchmarking Trap: Why Macro Data is Ruining Your Peace of Mind

Every few months, it happens like clockwork. The government or employment agencies drops its latest reports. Suddenly, your social media feed is flooded with infographics breaking down Singapore’s latest median household income, or average earnings segmented by age, gender, education level, and sector. At first glance, this feels like helpful, transparent data. But if we are being completely honest with ourselves, clicking into those charts rarely makes anyone feel better. Instead, it triggers an immediate, involuntary defensive response. You instantly zone in on your age bracket or your industry. You look at the number, look at your own bank account, and the internal monologue begins: “Am I falling behind? Why is the median for my age group so high? What are these people doing that I’m not?” Suddenly, a routine government data release transforms into an existential crisis. But here is the truth we need to remind ourselves of: looking at macro data to measure your personal success is n...
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The "Freedom" You Think a Business Will Give You Doesn't Exist Yet

Every week, someone tells me they're done with their 9-to-5 and ready to "start a business for the freedom." I understand the impulse. I've felt it myself. But there's a costly misunderstanding hiding inside that sentence, and it's worth naming before anyone quits their job over it. The story people tell themselves The logic usually goes like this: my job controls my time, so removing the job will give my time back. It's a clean story. It puts the blame on the employer, not on the nature of work itself, and it makes the solution feel obvious, become your own boss, and freedom follows automatically. It's also, for almost everyone, wrong. What a paycheck actually buys you When you're employed, you trade a fixed number of hours for a fixed paycheck. It's not a great deal in a lot of ways, but it has one underrated feature: a boundary. Outside your working hours, the job , mostly, leaves you alone. Start a business and that boundary is...
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Why Do I Want to Give My Sons a Lump Sum at 21 and 23 in 2046

Some people have asked why I'm planning to let my sons access their investment portfolios when they're 21 and 23. The answer is simple: it's their money, not mine. As parents, we won't be around forever. Our job isn't just to provide for our children while they're young, but also to prepare them to stand on their own two feet. Based on the AI simulation I shared previously, if everything goes reasonably well, each of them could have a portfolio worth around S$130,000 by the time they're adults. I already know what some people will say: "S$130,000 won't be worth much in 2046." They're not wrong. Inflation is real. But if we use Singapore's historical inflation rate as a guide, S$130,000 in 2046 could have purchasing power similar to about S$70,000 today . That's still a meaningful amount of money. Ask yourself this: if your parents had handed you S$70,000 when you turned 21, would it have changed the choices available to you? For ma...
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I Used AI to Model My 2 Kid's Portfolio : Here's What I Learned

A father's attempt to turn baby bonus cash and ang bao money into a real investing plan, with a little help from AI. When my sons were born, like most Singaporean parents, I got a pile of well-meaning cash: the Baby Bonus, and stacks of ang bao from grandparents and relatives. The usual advice is "put it in a savings account" or "buy some insurance plan." I wanted to do something different, I wanted to actually invest it, and watch it grow alongside them. The problem was, I had no idea what the numbers would actually look like 10, even 20 years down the road. So I decided to try something: I asked Claude (an AI assistant) to help me model it out, year by year, using real STI ETF data. Here's what happened. Setting the Rules Before any modelling, I needed to lay out my actual plan in plain terms: Baby Bonus : I estimated I'd be able to invest about $1,600 a year until the elder son turns 6.5, then $800 a year until younger son turns 6.5 — roughl...
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My 20-Year Investment Plan for My Two Sons

For a little background, I've never touched my sons' Baby Bonus cash gifts or their ang bao money. Instead, I've invested everything for their future. In the beginning, I kept things very conservative by putting the money into T-bills and bonds. Looking back, I think I was being a little too cautious. While those are safe instruments, my sons have an investment horizon of well over a decade, so taking on more equity exposure makes sense. Many people would immediately choose the S&P 500, and I agree it's an excellent long-term investment. However, after weighing the pros and cons, I believe that, as a Singaporean, investing in the STI ETF is a sensible choice for my children's core portfolio. The S&P 500 has historically delivered stronger returns, but investing in companies listed in our home market and denominated in Singapore dollars gives me greater peace of mind. These are businesses I'm more familiar with, and there's no currency risk to worry a...
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Why I Bought SpaceX (And Why I Don't Care What It's Worth Tomorrow)

I recently bought shares of SpaceX, and interestingly, the first question almost everyone asks isn't why I bought it, but whether I bought it at too high a valuation. My answer is always the same: I genuinely don't care what the market thinks the company is worth today. This wasn't a purchase driven by the hope of making a quick profit, nor was it based on trying to predict where the valuation will be in the next year or two. It was made with a much longer horizon in mind. I'm fully aware that SpaceX is already one of the most valuable private companies in the world. In fact, for my investment to grow tenfold from here, it would likely require SpaceX to become more valuable than any company has ever been. That sounds almost unbelievable, and statistically, it is an incredibly high hurdle. But investing in truly exceptional businesses has never been about betting on what is most probable. It has always been about identifying what is possible. The world's biggest winn...
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Covered Call / Cash Covered Put vs Dividends : I Chose Growth (For Now)

Is selling covered puts/calls better than earning dividends? It depends, mainly on your goals and how much effort you’re willing to put in. If I had continued my dividend investing journey, the path would have been straightforward. Buy REITs and blue chips, hold them long term, and let the dividends compound over time. The problem? Growth is slow. After running my own calculations and simulations, I realised it would take a very long time to reach the level of income I’m aiming for. So I changed my approach. In the past, I made a mistake, selling long-dated covered calls and treating them like dividends. It felt passive, but it wasn’t efficient. Now, I focus only on short-term (weekly) covered puts and calls. The difference is significant. For example, with around $30,000 USD deployed in cash-secured puts, I’m generating roughly $300 USD per week on average. If I can sustain that over a full year (52 weeks), that’s about $15,000 USD, effectively a 50% return on capital. Of course, this...
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