TJJ Learning Journal | Dividend Investing for FIRE

When we think of a "courageous" investor, we usually picture the Speculator—the person making a huge, leveraged bet, the one who bravely calls a market top and sells everything, the one who waited for a market crash to purchase huge positions. It’s a path of bold, decisive moments and high-stakes gambles. But there is another kind of courage, one that I've chosen to build my entire philosophy around: the Steward's Courage . This isn't the courage of a single, dramatic action. It's the quiet, persistent courage to relentlessly follow a simple system. It's the discipline to be "boring" while others are chasing excitement. This post is about why I've chosen this path. The Courage to Trust The System It's easy to react to the market. It takes no courage at all to get caught up in FOMO and buy at an all-time high, or to get swept up in fear and panic-sell during a crash. Reacting is easy; it's an emotional reflex.   The hard part is havin...

 I recently finished reading "The Psychology of Money" by Morgan Housel. It's a really practical book which doesn't crunch numbers and run different formulas, but rather provides a new lens through which to see your own financial life. The core idea I took away is that financial success is less about what you know, and more about how you behave. The book was a powerful read for me because so many of its lessons resonated with my focus on simple dividend investing that keeps my peace of mind. Here are the three biggest takeaways that stuck with me. Takeaway #1: Being Reasonable, Not Rationally Cold My dividend investing strategy is meant to be  Reasonable . It might not provide the biggest returns compared to other investing strategies, but the constant stream of dividends provides flexibility, peace of mind, and the ability to stay vested for decades without losing sleep over it.  Few other investment instruments provide the same quality of risk-reward as our local S...

In our series so far, we’ve built a solid financial foundation, from creating a savings surplus to setting aside an emergency fund. That money, sitting safely in a high-yield savings account, is our safety net: reliable, accessible, and crucial for peace of mind. But while it’s safe, it’s also idle. To grow real, long-term wealth, we need to move beyond saving and start investing. Stable and Predictable Bonds When you buy a bond, you’re lending money to a government or company in exchange for regular interest payments and the return of your principal at maturity. Bonds are typically less volatile than stocks and can provide a steady income stream. The Singapore Savings Bond is a great choice under this category, which let you park savings and earn a higher interest over a period of 10 years. Although interest rates have lowered significantly from a couple years ago, these bonds can always be redeemed early and "rolled" into higher rates when given the opportunity. Do note: ...

Someone mentioned to me recently that it could be better to build my "war chest" and avoid buying at market all-time highs. Indeed, market highs could leave some people worried and keeping cash on the sidelines, fearing a market correction. Do you invest your savings now to make sure your money is in the market? Or do you wait patiently on the sidelines, keeping your "dry powder" for a crash that might be just around the corner? This is often framed as a battle between two disciplines: the discipline of consistent, regular investing (a steady drip) versus the discipline of patient, opportunistic buying (the war chest). I will write about both of these for you to understand and decide for yourself. The "Steady Drip" (Dollar Cost Averaging) This investing approach is about investing regularly and consistently, deploying cash into investments once cash is available. For example, I plan to continue purchasing DBS in November and December this year, although ...