Lessons from 20 years of investing
October 3, 2025
By the end of this year, I’ll have been investing in the stock market for 21 years – and the journey is still going strong.
It’s been an incredible ride, filled with both highs and lows. Along the way, I’ve learned not only about investing, but also a great deal about myself.
Investing, after all, is a marathon, not a sprint.
The moment you put your first dollar into the market, you begin a long-term journey of learning, growth, and wealth-building.
Think of it like building a wall – laying one brick at a time. Each smart decision becomes part of the foundation for something greater.
With consistency and patience, you can construct the retirement nest egg you envision while generating a steady stream of passive income.
Over the past two decades, I’ve picked up some valuable lessons. I hope sharing them will help you on your own investment journey.
Many investors tend to monitor the stock market too closely and end up feeling frustrated when their portfolios underperform, or when they fall short of benchmarks like the Straits Times Index (SGX: ^STI).
But here’s the thing: stock prices are naturally volatile in the short term. They can swing wildly based on earnings reports, market sentiment, competition, and countless other factors.
What truly matters is this: over time, share prices tend to follow the performance of the underlying business.
Put simply – when the business does well, the stock price usually catches up.
If you’re able to stay invested through the ups and downs, and the companies you own continue to grow their revenue and profits, you’ll likely be rewarded over the long haul.
That’s why investment performance shouldn’t be measured in weeks or months. Instead, take a multi-year view.
A five-year period is often long enough to smooth out short-term noise caused by economic cycles or shifting investor sentiment.
Stretch that horizon to decades, and you gain a much clearer picture of your portfolio’s true quality.
Take Temasek Holdings as an example.
Renowned for its long-term mindset, Temasek consistently reports its total shareholder return (TSR) over 10 and 20-year periods. TSR includes both capital gains and dividends – providing a more complete view of investment performance.
Its most recent 20-year TSR came in at 7%, comfortably outpacing Singapore’s 20-year average core inflation rate of 1.9%.
When you extend your time frame, you free yourself from the pressure of short-term results, and start focusing on how well each business is creating lasting value.
A common question that investors often ask is: What’s your ultimate goal in investing?
Are you aiming to build a comfortable nest egg, generate steady dividend income, or perhaps a mix of both?
While it’s a valid question, the reality is that the answer varies widely from person to person.
When I was younger, I used to fixate on hitting a specific number – say, S$1 million, as my target for a secure retirement.
But over time, as life evolved and my circumstances changed, that number started to lose its meaning. What once felt like a clear goal eventually became irrelevant.
The key takeaway?
Don’t get too caught up chasing a fixed dollar amount. Your financial goals should be flexible, evolving alongside your needs, priorities, and stage of life.
And even if you do reach that magic number – what’s next?
Would you stop investing entirely? Sell off your entire portfolio?
Chances are, the answer is no.
That’s why it helps to view investing as an ongoing journey – not just a destination.
So, enjoy the process. Learn from it, grow with it, and take time to savour the rewards along the way.
When I first started investing, I was incredibly competitive.
I had a bad habit of constantly comparing my returns with those of my peers. Whenever someone seemed to be doing better, I’d beat myself up for doing worse.
I’d also try to pick up lessons from their approach – hoping to replicate their success.
While there were certainly useful insights, the constant comparison did more harm than good.
The truth is, every investor operates under different circumstances. The playing field isn’t level.
Some people are born into wealthy families and start with far more capital to invest. Others land high-paying jobs early in life, with generous bonuses that accelerate their portfolio growth.
Trying to measure your progress against theirs isn’t just unproductive – it’s a distraction.
What really matters is not how you’re doing compared to others, but how you’re improving compared to your past self.
Forget about trying to “beat” your friends or colleagues. Instead, focus on beating yesterday’s version of you.
Your real competition is your former self.
The goal is to become a smarter, more disciplined investor over time. Learn from your mistakes. Keep a journal of your buys and sells. Reflect on your decisions and refine your strategy.
As long as you’re improving, you’re moving toward better outcomes – like generating better long-term total shareholder returns (TSR).
And that’s what investing is really about: continuous growth, on your own terms.
It’s important to regularly take stock of your investment journey.
Think of it as an investment health check – just like how you’d go for routine medical tests to make sure your body is in good shape.
This is your chance to reassess your goals, celebrate milestones, and fine-tune your portfolio where needed.
Personally, I make it a habit to review my investments every year. I take a close look at each holding and ask myself: Am I still comfortable owning this stock?
At the same time, I track the dividends I’ve received to see if I’m making steady progress toward my goal of building a growing stream of passive income.
This annual review keeps me grounded, focused, and aligned with my long-term investment objectives.
Investing is often a solitary journey.
Each of us brings a unique set of goals, circumstances, and strategies – so your investment path will be one that only you truly understand.
Along the way, don’t forget to pause and enjoy the journey. Take time to appreciate the progress you’ve made and the fruits of your labour.
At its best, successful investing doesn’t just grow your wealth – it gives you the freedom and flexibility to live a better and more fulfilling life.
For me, investing is both a path to financial independence and an intellectually rewarding process.
It has the power to enrich your life in many ways – not just financially, but personally as well.
Whatever stage you’re at, I wish you continued success on your investment journey.
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Disclosure: Royston does not own shares in any of the companies mentioned.
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