Using ChatGPT to Spot the Gaps in My Financial Plan
That's why I decided to run my financial plan through ChatGPT. I wanted a second opinion, something that could point out potential weaknesses without the bias of someone trying to sell a product.
My goal was to see how AI would approach analyzing real-life financial plan, given all the details I could provide. Would it validate my strategy? Would it flag risks I hadn't considered? Most importantly, could it help fine-tune my path to financial independence (FI)?
What was provided to ChatGPT
To make this review meaningful, I shared a full picture of my finances:
Age: 35
Income from work: XX
Annual expenses: XX
Assets and liabilities:
- HDB flat valued at 650k, with 415k outstanding loan
- CPF: 33k (OA), 241k (SA), 75.5k (MA)
- Cash: 165k
- Investment: 720k (mostly in global and US ETFs/funds)
Investment approach: DCA monthly into
- S&P500 ETF (cash, 1.5k/month)
- All world ETF (cash, 4.5k/month)
- US small cap ETF (cash, 1k/month)
- Dimensional US Core Fund (SRS, 1.5k/month)
- Amundi World Fund (CPF OA, 1.5k/month)
Insurance: Term life, living care, disability income, class A hospitalization plan.
Goal: Reach FI by 45 with combined $2.5m across cash, investment and CPF, with HDB flat fully paid off. From there, work at a slower pace in something more aligned with personal interest until early 50s. CPF Life from age 65 will form a safety net.
Strengths identified by ChatGPT
Disciplined investing approach
The plan is anchored on consistent DCA into low-cost, diversified ETFs and funds across multiple accounts (cash, SRS, CPF OA). DCA has the advantage of removing emotions from investing decisions, especially during volatile periods. Over the long term, it smooths out entry prices and allows the compounding effect to work without disruption. By committing fixed amounts monthly, this approach also enforces savings discipline and ensures capital is always being deployed toward productive assets rather than left idle.
Intentional US-heavy equity allocation
The portfolio is deliberately tilted towards 80% US exposure, drawing from the investment philosophies of Warren Buffet and John Bogle, who both argued for the strength of the US market over the long run. The US market benefits from deep capital markets, global-leading companies, strong corporate governance standards, and historical resilience through economic cycles. While this concentration increases exposure to a single economy, it positions the portfolio to capture the growth potential of the largest and most innovative companies in the world.
Strong CPF foundation as a safety net
The early maximization of the CPF SA locks in a guaranteed 4% return that compounds over decades. Given the current trajectory, the SA is projected to reach at least 3x the BRS by age 55. Under the CPF LIFE standard plan, this will translate to a lifelong monthly payout of at least $1.9k in today's dollars starting from age 65. This income stream provides a reliable baseline for essential living expenses, ensuring that even in a worst-case investment scenario, basic financial security in retirement is maintained.
Clear and measurable FI target
Having a defined FI target of $2.5m brings clarity and focus to financial decisions. It allows progress tracking and enables scenario planning, such as retiring earlier if ahead of schedule or choosing to increase lifestyle spending with confidence. ChatGPT's projection showed that with the current investment rate and growth assumptions, this target is likely to be exceeded. This surplus creates flexibility: the option to retire earlier, weather prolonged market downturns without stress, or fund additional personal goals.
Downside risk protection
The insurance portfolio is well-structured to shield against major financial shocks. Term life coverage ensures dependents would be financially supported in the event of death, while critical illness coverage protects against income disruption from serious medical conditions. Disability income insurance provides a steady stream of replacement income if unable to work, and comprehensive hospitalization cover limits the out-of-pocket burden of medical treatment. These protections ensure the investment strategy can remain intact even in the face of health crises.
Blind Spots Identified by ChatGPT
Potential cash drags
While cash reserves are important for liquidity and peace of mind, holding too much can dilute long-term returns, especially in an inflationary environment. Given the stability of income, relatively low living expenses compared to earnings, and strong insurance coverage, ChatGPT assessed that the current cash buffer may be larger than necessary. Redirecting a portion of this idle cash toward productive assets could help accelerate capital growth without meaningfully compromising financial security.
Concentration risk despite global exposure
Although the portfolio includes global ETFs, the heavy US tilt means performance is still closely tied to the US economy and market sentiment. ChatGPT suggested that adding more exposure to Asia-Pacific and European markets could reduce volatility and capture opportunities from diverse growth drivers. Beyond equities, expanding into other asset classes, such as bonds, real estate investment trusts (REITs), commodities, or infrastructure could provide income streams and act as a counterbalance during equity market downturns.
Limited stress testing for sequence-of-returns risk
The projections rely on average historical returns, albeit a conservative one, but markets don’t deliver returns evenly year after year. A poor sequence of returns early in retirement e.g. a severe bear market in the first few years could reduce the portfolio’s longevity even if long-term averages remain the same. ChatGPT recommended modelling adverse market sequences to evaluate how spending might need to adjust or how withdrawals could be restructured (e.g., drawing from bonds or cash buffers first) to safeguard against early-retirement depletion.
Long-term volatility risk from high equity allocation
Remaining heavily invested in equities throughout retirement maximizes growth potential but also increases exposure to large drawdowns later in life, when recovery time is shorter. ChatGPT suggested considering a dynamic asset allocation e.g. a rising equity glidepath in the early retirement years followed by gradual de-risking to balance growth and capital preservation. While 100% equity can work for some high-tolerance investors, a more balanced allocation could reduce stress and volatility in later years.
Takeaways
ChatGPT’s review largely validated the financial strategy but highlighted areas worth further exploration: redeploying excess cash, broadening diversification, and testing for adverse return scenarios. These adjustments could make the plan more resilient without fundamentally altering its structure.
The exercise also offered a glimpse into the evolving role of AI in personal finance. ChatGPT has no commission-based incentives, so it avoids the conflicts of interest sometimes present with human advisors or insurance agents. However, its effectiveness still depends on the quality of the user’s inputs. Without asking the right questions or sharing complete details, important risks could be missed. And while it can offer strategic guidance, it cannot replace deep product knowledge in areas like insurance.
Used well, ChatGPT can act as a neutral, second-opinion sounding board, helping to challenge assumptions, surface blind spots, and reinforce strong financial habits. Paired with sound financial knowledge, it can make a good plan even stronger.
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