A Money Confession: How I Built My Personal Investing System

Morgan Housel wrote in The Psychology of Money:

So here’s my money confession.

Five years ago, I had $0 in investments and zero clue about money. Today, my financial assets have grown 4x — not through crypto luck or stock-picking genius, but through surviving real life: layoffs, family cancer treatment, two Kawasaki disease diagnoses, home renovation, and a second baby.

Here’s exactly how I built a financial system that survived the sandwich generation reality.

🎯 Investment Foundations – My Portfolio and Financial Goals

In a reading notes: Profoundly Simple Investment Strategies, I shared an investment philosophy I strongly agree with. My current portfolio is basically built on top of that idea.

🍕 Current Portfolio Allocation

• Low risk: CPF
• Medium risk (high dividends, no FX risk): STI / S-REITs
• High risk (high expected return, high volatility, FX risk): Equities – Total World Index / MSCI Index / S&P 500 Index / Vanguard Funds / Dimensional Funds

Why include CPF in the overall portfolio?

My investment goal isn’t early retirement. With kids to raise and genuine interest in my career, I’m comfortable with CPF being illiquid until age 55. My portfolio target is roughly a 60:40 stock-bond split, and I treat CPF as a bond substitute.

At the moment, CPF makes up about 50% of my total financial investments, which is higher than my original target. Because of that, I haven’t added any additional bond investments.

Why is CPF still such a large portion and not closer to 60:40?

It wasn’t due to intentionally topping it up aggressively:

• Annual tax-deductible contributions
• Transferring OA to SA
• Refunding early OA housing withdrawals and paying the mortgage without OA

Over time, long-term accumulation plus compounding grew CPF to a meaningful size. Given my low risk tolerance, I’ve been very cautious with medium-to-high-risk investments, mostly doing small, slow DCA. On top of that, my husband has much higher equity exposure, so I intentionally keep my own risk level lower to balance our household portfolio.

Do I invest in individual stocks?

A very small portion — but honestly, it’s not a great fit for me. I don’t enjoy spending time on stock analysis. I’m far more interested in policy, macroeconomics, market structure, and asset allocation theory. I strongly believe in using basic financial instruments to earn average market returns.

Why no property investment?

I didn’t choose the HDB path early on, which meant missing out on a very attractive investment opportunity. Now, my concerns around property investing include policy restrictions, high prices, and large upfront capital requirements. If the right opportunity comes along, I’ll consider it — but it would only make up a small portion of total household assets. I previously wrote in detail about this in Should I Include Singapore Property in My Investment Portfolio?

Why no gold or crypto?

Currently, I hold none.

I previously held a small crypto position. After experiencing extreme volatility, including frozen funds during the LUNA collapse, I decided it was too stressful. Once funds were unlocked and slightly profitable, I exited. I also had small gold exposure through robo-advisors, which I later sold. Both assets went on to rise significantly — but that’s irrelevant to me.

For me, timing the market and obsessing over volatility make it very hard to hold alternative assets long term. In the future, I may add a small allocation to gold or crypto purely for diversification and risk hedging, but only if I’m confident I can hold them long term.

🎯 Investment Goals

Short-Term

• Gradually increase equity exposure to improve the stock-bond ratio
• Increase medium-risk, local-currency, high-dividend investments
• Add small allocations to crypto and gold for hedging

Long-Term

• Maintain a high savings rate over the next 6–7 years
• Keep a 60:40 stock-bond allocation
• Gradually increase high-dividend equity exposure so passive income can replace active income

📈 Portfolio Evolution – Five Years of Net Worth Growth

The above shows my current portfolio and future plan. But how did I get here step by step?

Tracking my personal net worth gave me a strong sense of control — both over life’s uncertainties and over disciplined saving and investing.

I started tracking net worth in 2021. Household consumption and property are shared with my husband, while personal consumption and investments are tracked separately here.

2021 – Starting from Zero

At the beginning, I knew almost nothing about investing. I slowly built foundational knowledge through books and online resources, learning about stocks, bonds, and index funds.

After comparing different options, I realized CPF’s risk-free returns were extremely attractive. I prioritized paying down OA housing loans, reduced interest costs, and transferred excess funds into SA for higher yields.

Because most of my assets were in cash and CPF, I felt comfortable experimenting with small amounts in high-risk investments. I tried robo-advisors, US tech stocks, China stocks, trendy funds, niche thematic funds, and crypto. I made plenty of mistakes but gained invaluable real-world experience.

2022 – Market Volatility and Staying Calm

At the start of the year, I quit my job without another offer lined up. Living entirely off savings, I felt the psychological pressure as monthly expenses steadily drained my account. That period taught me just how critical cash flow is when income disappears.

After a few months, I found a new job with significantly higher pay. Unfortunately, spending crept up too, driven by a compensation mindset. Income rose, but savings didn’t increase as much as expected.

I began regular fund DCA to fight inflation, but 2022 markets performed poorly, leaving my investments in the red. Still, I stuck with monthly investing and learned to stay calm during market drawdowns.

2023 – Life Gets Hard

The first half of the year was consumed by caring for a sick family member, frequent hospital visits, and emotional exhaustion. I paused my financial tracking during this period.

Work also became unstable. Layoffs hit, and my company’s Singapore office shut down. Facing medical expenses (thankfully covered by insurance) and preparing for a home upgrade, I tightened spending and built cash buffers. Severance pay provided temporary relief.

By year-end, we completed the home purchase. Down payment, taxes, and renovation caused major cash outflows. This period reinforced the importance of emergency funds and insurance.

2024 – Big Expenses

Major home renovation led to sustained cash outflows early in the year.

After reassessing asset allocation, I increased high-risk investments and monthly equity DCA. Markets performed well in 2024, and investments made during earlier downturns started paying off.

2025 – Consistency Pays Off

I continued disciplined monthly index investing and periodic portfolio reviews. 2025 was a steady year so I saw double digit rate of returns.

From 2021 to now, my financial assets have grown fourfold. The journey wasn’t linear — it included volatility, pauses, and reallocations. Along the way, I went through the full sandwich generation experience:

• 🥪 Child’s Kawasaki disease and year-long cardiac treatment
• 🥪 Burnout and a four-month career break
• 🥪 Caring for family during cancer treatment
• 🥪 Layoffs and another three-month work gap
• 🥪 Second Kawasaki diagnosis, thankfully without long-term effects
• 🥪 Home upgrade and sale
• 🥪 Renovation
• 🥪 Second child

Each life event impacted our finances. After every phase, I adjusted, reflected, and strengthened our family’s risk resilience. Life isn’t smooth, but tracking money gave me a stronger sense of control.

⛑️ Risk Management – Our Family Insurance Setup

Real-life experience has made me certain of one thing: risk management always comes before all other household spending decisions. I previously shared our family insurance setup in My Approach to Family Insurance Planning. The overall logic hasn’t changed, but I’ve made some adjustments as our family structure and lifestyle have evolved.

Dropping Accident Insurance

I’ve mentioned before that once you have medical insurance with outpatient coverage, accident insurance for kids feels redundant, so we’ve paused it for now.

For our parents, comprehensive hospital coverage is already in place, and accident insurance is just a nice-to-have. In recent years, they’ve found life in Singapore a bit boring and spend a lot of time traveling and living in different cities. The accident policies required them to stay in Singapore for at least six months each year, which they didn’t meet last year. So we cancelled those policies altogether.

Adding Basic Coverage for the Younger Child

Same setup as his older brother: just two policies — hospitalization and critical illness. Honestly, there aren’t many good consumer-type CI options for kids anyway.

Some people have suggested that whole life plus a CI rider is the most cost-effective option for children. My FA said the same thing, especially if you’re thinking in terms of “lifetime coverage.” That may be true on paper, but I really don’t like whole life insurance. I wouldn’t buy it even for myself. I already own one policy from years ago that’s neither useful nor worth surrendering, so I’m definitely not buying it for a child who doesn’t even have income-replacement needs.

More importantly, the numbers don’t work for me. The quote I got was over $6k per year for ten years for a whole life policy with similar CI coverage to our current term plan.

Adding Company Group Insurance

I’m genuinely grateful for how comprehensive our company benefits are. Beyond the very practical family medical coverage, what matters most to me are the three core protections: life, critical illness, and accident insurance.

I’ve always believed in buying term coverage based on actual needs and keeping it flexible. When active income is high, you need higher life and CI coverage. As you gradually rely more on passive income, the need for income-replacement insurance naturally decreases. Our company insurance fits this logic perfectly. The term coverage amount tapers with age, moving through different stages from peak earning years through 60, 65, 70, and eventually 85.

Adding General Insurance

Home insurance and helper insurance were added after we upgraded our home and hired a domestic helper. These are also part of our overall household insurance spending.

Monthly Insurance Spend

Total monthly spend: $2,446

• Pure protection (term/health): $2,063 ($1,578 cash + $485 CPF)
• Policies with cash value: $383

Coverage for: 2 adults + 2 kids + 2 parents = 6 people Average per person: ~$400/month

🛒 Spending and Budget – Monthly Household Expenses

Spending Breakdown

Household structure: 2 adults + 2 kids + 2 retired parents + 1 live-in helper = 7 people

Our family setup means balancing the needs of very different age groups. We’re thinking about kids’ education and growth, parents’ health and quality of life, and day-to-day household operations, all while keeping things running smoothly.

Total monthly spend: $9,800 (excluding mortgage and taxes)

💳 Fixed Expenses: $3,900/month (40% of budget)

🥘 Daily Living: $3,900/month (40% of budget)

🏖️ Discretionary: $2,000/month (20% of budget)

The Biggest Spending Categories

🏥 Medical + Insurance: $2,100/month (21% of total budget)

Medical costs are estimated based on post-claim cancer treatment expenses, plus occasional clinic visits for our parents. I’ve written about our insurance setup before. We’re well covered, and that naturally comes with a sizable cost.

🥯 Food: $2,700/month (28% of total budget) ← Biggest category!

Weekday dinners are mostly home-cooked. My mom takes food seriously and guides our helper almost daily to prepare proper meals. On weekends, my husband and I cook too, usually with better-quality ingredients. Even so, food spending is still high. Probably because everyone in the family loves food, and also because Singapore is just expensive. This is one area that’s really hard to cut further.

🏖️ Travel + Shopping: $2,000/month (20% of budget)

We don’t buy luxury goods anymore, but let’s be honest — the urge to spend doesn’t just disappear. Clothes, shoes, bags, home items — if I like something I’ll usually buy it as long as the price isn’t outrageous. Individually they’re not expensive, but together they add up to a few hundred dollars every month.

Areas Where We’re Relatively Frugal

👦🏻 Raising Kids

Public preschools are still great value for money. Fees have been coming down every year, and after subsidies, we’re now paying under $400 per month. We’re also pretty relaxed about enrichment classes, mostly choosing affordable sports and music options. The only expensive one is English class, which we only added recently. At home, it just wasn’t working, and I was honestly losing my mind. The moment he started classes, he became well-behaved, excited, and could clearly explain what he learned — and even told me the teacher teaches better than Mom.

Our second child is still a baby, so expenses are minimal for now. Government newborn benefits also help offset a big part of early childcare costs.

🚗 Transportation

My husband’s simple and environmentally friendly mindset has influenced us a lot here. If we can walk, we walk. If we can cycle, we cycle. If public transport works, we almost never take a taxi. I work from home, and my husband cycles to work daily. Honestly, the $300 transport budget might even be on the high side.

💳 Cash Flow Planning – Monthly Income Allocation

Whether a financial plan actually works comes down to daily execution. Above, I’ve broken down my investment portfolio, its evolution and goals, and our household spending budget. Once you’re clear on your financial position and goals, you can automate investing and parts of your spending based on your budget and target savings rate.

This monthly paycheck routine is something I’ve been practicing for years. The allocation changes depending on the stage we’re in, for example:

• Before upgrading our home, cash savings took priority and investments were much lower
• For a period, I transferred OA to SA monthly to optimize CPF returns, stopping once SA was mostly topped up
• Right now, the goal is to increase stock exposure, so I’ve deliberately increased my DCA amounts

Our joint family account covers daily living expenses and GIRO payments like utilities and management fees. My husband handles mortgage payments and travel-related big-ticket items. I cover education costs, helper expenses, and most insurance premiums. There isn’t a rigid split — the shared goal is to maintain a reasonable savings rate.

Investing and Saving

Automated — Transfers to brokerage accounts and DCA on fixed dates without market timing

Manual — Investing bonuses or extra income and CPF/SRS tax optimization

Spending

Automated — CDA transfers for childcare fees

Manual — Transfers to the joint family account and personal credit card payments

Automation

Investing is almost fully automated, so money gets saved and invested every month without much thought. Spending, aside from fixed GIRO payments, is still handled manually through transfers and credit card repayments. This helps in two ways: it makes it easier to spot unusual activity like fraud, and more importantly, it keeps me aware of how much I’m spending. Feeling a bit of pain when paying helps reinforce mindful spending.

💭 Final Thoughts

Facing money head-on started with a moment of self-reflection five years ago, when I realized I had both money blindness and money avoidance. I made learning personal finance my New Year’s resolution that year.

Investing and money management are never a straight line. They’re more like an ongoing conversation with life itself. Over these five years, I’ve gradually built a personal system that works for me: 🎯 financial goals → 📈 net worth tracking → ⛑️ risk management → 🛒 spending budget → 💳 cash flow planning. This system reflects both my plans for the future and the curveballs life has thrown along the way.

This is my honest record of five years of personal finance practice, and I hope it can serve as a practical reference for anyone navigating life in the sandwich generation.

🚀 Start Your Own Financial Journey

If this post resonated with you, I built a free tool to help you create your own financial tracking system.

What you can do with it:

• Visualize your portfolio allocation (like my CPF/stocks/cash breakdown)
• Consolidate the insurance policies and view the insurance matrix
• Budgeting and visulization
• Income planning and visulization
• Play around with the numbers to see the route to Financial Independence

Free Tool

My Financial Planner

Track your portfolio, budget, and income flow with interactive visualizations. Plan your path to financial independence.

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