You’ve spent decades building a career, saving diligently, and dreaming of a comfortable retirement. You’re so close. But lately, you feel a familiar squeeze. Your aging parents require more support, both financially and physically. At the same time, your adult children, navigating a competitive job market and the high cost of living, still lean on you for help.
Welcome to the “Sandwich Generation.” You are caught in the middle, caring for two generations simultaneously. It’s a role born out of love and filial piety, but it comes with immense financial and emotional pressure.
The decisions you make in this pre-retiree phase are critical. Mismanaging this squeeze can unravel decades of careful planning, forcing you to delay retirement, downsize your dreams, or worse, become financially dependent on your own children later. But with a strategic and compassionate approach, you can navigate these challenges, support your loved ones, and safeguard the golden years you’ve worked so hard for. This article will provide a practical framework to help you do just that.
Have the ‘Money Talk’ – Sooner Rather Than Later
In many Singaporean families, money is a taboo topic. We’re taught to respect our elders and not pry into their finances. However, having open conversations about money with both your parents and children is no longer just advisable—it’s essential.
With Your Parents: Frame the conversation around their well-being and ensuring their wishes are met. The goal isn’t to scrutinise their spending, but to understand the full picture. Key questions to gently explore include:
With Your Adult Children: The conversation here is about fostering independence while understanding their goals. Discuss their career path, savings habits, and any significant financial goals like getting married or buying their first HDB flat. It’s crucial to manage expectations about the level of financial support you can provide for these milestones.
Having these conversations can be awkward, but ignorance is not bliss. A clear understanding allows you to plan effectively, preventing surprises and financial emergencies down the road.
Set Clear Boundaries: You Can’t Pour from an Empty Cup
Filial piety is a core value, but it shouldn’t mean sacrificing your own financial security. Your ability to help your family tomorrow depends on you being financially stable today. This is where boundaries become your most important tool.
Financial Boundaries: First, review your own retirement plan. How much do you need to set aside each month to reach your goal? Once this amount is earmarked, you can determine what you can sustainably afford to give to your parents and children. This isn’t about being ungenerous; it’s about being realistic.
Differentiate Needs from Wants: Are you funding a parent’s essential medical treatment or a discretionary expense? Are you helping a child with a downpayment for a BTO flat or funding a lavish wedding beyond their means? Prioritising needs over wants ensures your support has the greatest impact without derailing your own finances. Setting these boundaries early helps manage expectations and prevents resentment from building up on all sides.
Don’t Forget Your Own Oxygen Mask: Prioritise Your Retirement
The airline safety briefing has it right: you must put on your own oxygen mask before helping others. Your retirement security is paramount. If you are not secure, you cannot be a safety net for anyone else.
1. Stress-Test Your Plan: This is a comprehensive cash flow projection. Map all your assets—cash savings, investments, CPF balances, and properties—against all your liabilities and projected retirement expenses. Then stress-test this complete picture against the “what-ifs”:
This “stress-test” moves you from hoping you have enough to knowing you have a resilient plan that can withstand real-life pressures (see example below).


Above example of “Stress-Testing” your plan.
2. Build Your “Second Engine” with Private Investments: Your CPF is your stable foundation, but you need a “second engine” for growth, inflation-proofing, and liquidity.
Essentially, we need to ensure you have robust, independent financial pillars that stand strong, even as you generously support your family.
Take Control of Your Future
Navigating the financial and emotional demands of the Sandwich Generation is one of the most complex challenges you will face. It requires a delicate balance of love, responsibility, and unwavering focus on your own future. Open communication, firm boundaries, and smart strategies are your keys to success.
You don’t have to figure this out alone. As a financial advisor specialising in retirement planning for pre-retirees, I host a complimentary bi-weekly online workshop designed for individuals like you.
In this hands-on workshop, you get to stress-test your retirement plan against your family’s needs, and build a clear roadmap that allows you to care for your loved ones without compromising the secure and fulfilling retirement you deserve.
Important: The information and opinions in this article are for general information purposes only. They should not be relied on as professional financial advice. Readers should seek unbiased financial advice that is customised to their specific financial objectives, situations & needs. This advertisement or publication has not been reviewed by the Monetary Authority of Singapore.
Ri’an’s mission to elevate financial well-being often begins in the boardrooms and town halls of Singapore’s leading companies. His work promoting financial literacy across the workforce has given him a unique insight: the years leading up to retirement are when people need more than just information—they need a dedicated, trusted strategist.
This conviction is deeply personal. A family loss, which could have been mitigated with proper planning, inspired Ri’an’s career and is the reason he is so passionate about ensuring financial and estate plans provide genuine peace of mind during this critical life stage.
Ri’an understands the specific concerns that can keep you up at night. He specialises in simplifying the complex questions you now face: how to protect your hard-earned nest egg from market volatility, structure a reliable retirement income that outpaces inflation, and plan for future healthcare costs without becoming a burden on your loved ones. He helps clients confidently balance the responsibility of supporting their family with the absolute necessity of securing their own future.
His mission is to provide you with a well-researched, stress-tested roadmap that transforms retirement anxiety into a clear, actionable plan. Building lasting relationships on a foundation of trust and clear communication, Ri’an ensures you can feel secure and make informed choices for the future you’ve worked so hard to build.
Ready to navigate your retirement with confidence? Connect with Ri’an for a meaningful conversation.
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In compliance with the Personal Data Protection Act, Financial Alliance Pte Ltd (“FAPL”) seek your consent to collect and use your personal data (e.g. name, NRIC, contact numbers, mailing addresses, email addresses and photograph) for the purposes of and in accordance with FAPL’s Data Protection Policy, which can be found on FAPL’s website at https://fa.com.sg/data-protection-policy/.
根据《个人数据保护法》,鑫盟理财私人有限公司征求您的同意向您收集并使用您的个人信息。鑫盟理财将根据公司的个人数据保护政策所阐述的用途使用您的个人资料(例如姓名,证件号码,联系电话,邮寄地址,电邮地址和照片)。 该政策可在本公司网站上查寻,网址为 https://fa.com.sg/data-protection-policy/.
By submitting this form, you are deemed to have read and understood FAPL’s Personal Data Policy.
提交此表格,即表示您已阅读并理解鑫盟理财私人有限公司的个人数据政策