It has been 15 years since I made my very first stock investment. When I first started in 2011, I had no idea where this journey would take me. My only aim was to build an "Investment Machine" that could generate passive income that could offset part of my daily expenses.
Like many beginners, I spent countless of hours reading books, blogs, financial news, annual reports and learning from experienced investors. I made mistakes, experienced market crashes, celebrated dividend payouts, rebalanced my portfolio and participated in corporate actions.
Today, as I look back at the past 15 years, I realise that my greatest achievement is not the size of my portfolio or the amount of dividends I have collected. Instead, it is the transformation in my mindset as an investor; the journey
Hence, I uploaded my transactions into AI and have it analyse how my strategy has evolved.
How My Investment Strategy Has Evolved
Phase 1: Building the Foundation (2011–2014)
My very first purchases were small, scattered, and honestly a little experimental. A REIT here, a blue chip there, roughly one or two counters a year. I did not have a strategy yet. I had a vague sense that dividends were a good idea.
Phase 2: Becoming a Dividend Investor (2015–2017)
This is where things started to take shape. Names like Keppel Corp, OCBC, ComfortDelGro, and Ascendas Reit entered the portfolio for the first time. I was diversifying deliberately across banks, industrials, healthcare, and telcos rather than committing to one style, laying the foundation before I understood exactly what the finished structure would look like.
Instead of constantly searching for new ideas, I became more comfortable averaging into businesses that had already earned my confidence. Looking back, this was probably the point where I truly became a long-term dividend investor. My focus shifted from chasing capital gains to building a reliable and growing stream of passive income.
Phase 3: Opportunistic Buying (2018–2019)
By this stage, my investment decisions became increasingly driven by valuation rather than simply adding new names to my portfolio. I accumulated more shares in companies that I believed were trading below their intrinsic value, including Ascendas Reit, Keppel DC REIT, OCBC and Keppel Corp.
Quality companies do not always need to be bought once. Sometimes, the best investment decision is simply buying more of a company you already understand when the market offers a better price.
I learnt that investing is not about owning many different stocks.
Phase 4: The COVID Opportunity (2020–2022)
The COVID-19 pandemic became the biggest test of my investment journey. When COVID-19 shook global markets, uncertainty was everywhere. Many investors reduced their exposure or waited on the sidelines.
During this period, I made 18 purchases in 2020 and another 22 purchases in 2022, making it the most active investing period since I started. I added new positions such as DBS, Mapletree Industrial Trust, Mapletree Logistics Trust and Ascott Trust, while increasing my investments in OCBC, Keppel Corp, Keppel DC REIT and Ascendas REIT.
It was uncomfortable at that time. In hindsight, it was the single highest-conviction period of my entire journey.
Looking back today, many of those purchases became some of the strongest contributors to my portfolio.
Phase 5: Refining the Portfolio (2023–2024)
The pace slowed. Instead of chasing new names, I mostly topped up conviction positions I already owned and introduced fixed-income investments through Astrea 7 and Astrea 8 Bonds. Fewer trades, same discipline.
This was the point where I realised that successful investing is not just about making money—it is also about protecting what you have built
Phase 6: Quality Over Quantity (2025–2026)
Recent investments such as Sembcorp Industries, Centurion Accommodation REIT, Keppel REIT, CapitaLand Investment and Astrea 9 Bonds reflect another subtle evolution.
I now make fewer purchases than before, but every investment decision is far more deliberate.
Today the portfolio sits at roughly 55% REITs, 40% individual stocks, and 4% bonds, with total dividends collected to date equal to almost 30% of what I have put in. It is slow. It is not glamorous. But it is compounding, brick by brick. It is slow, but I still believe it is the way.
Revisiting My Earlier Lessons
Back in 2023, I wrote a post titled "10 Learning Points in My Investment Journey." Looking back today, I am glad to say that those lessons have stood the test of time. If anything, my conviction has only grown stronger.
Time in the market continues to matter more than timing the market.
Patience remains one of the greatest competitive advantages an investor can have.
Market corrections still present opportunities rather than reasons to panic.
And perhaps most importantly, continuous learning remains essential because markets never stop changing.
Looking Ahead
Fifteen years sounds like a long time, but in investing, I believe it is still only the beginning.
I have achieved milestones that once felt distant, but I know there is still much to learn.
My portfolio will continue to evolve.
Markets will continue to change.
New opportunities will emerge.
My objective remains unchanged to become a better investor, continue growing a resilient portfolio and let time and compounding do their work.
Thank you to everyone who has followed my journey over the years.
The journey continues, and I look forward to sharing the next chapter with all of you.
What milestones or lessons have shaped your own investing journey? Let me know in the comments.
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