Helping the Sandwich Generation Navigate Care and Legacy with Financial Clarity

Over half of Americans in their 40s are part of the “sandwich generation,” simultaneously caring for aging parents and dependent children. At The Private Bank, we are knowledgeable in multigenerational financial planning—helping families prepare for these complex responsibilities by proactively protecting their wishes and securing their financial future.

In Hawaii, caring for our kupuna is more than a financial obligation—it’s an expression of kuleana rooted in love, respect, and tradition. Yet, for those in the middle, this role can feel overwhelming without a clear financial plan. Conversations around aging, legacy, and care are often delayed out of reverence. But initiating them early—while your parents are healthy and mentally sharp—can transform a time of stress into one of grace and preparedness.

Planning for Elder Care—Before the Urgency Arrives

Hawaii has the highest life expectancy in the United States, with an average of 80.7 years. Factor in our high cost of living and the financial considerations can be substantial. By engaging in proactive, collaborative planning with your parents, you create the opportunity for greater flexibility, sustained control, and peace of mind—ensuring your family is prepared with intention rather than reacting in urgency.

Anticipating Costs in Advance

Where will your parents be most comfortable? Who will care for them—and how will their care be paid for? Answers to these questions go beyond the typical estate plan or trust. Without thoughtful planning, the rising costs of assisted living can quietly erode even substantial family wealth—assets often intended for future generations, education, or philanthropy.

In Hawaii, long-term care averages $586 per day—over $213,000 annually. Premier senior communities with continuity of care may require a $1 million buy-in, plus monthly fees of $4,000 to $10,000. Even home care, at $30 per hour, can exceed $260,000 per year for round-the-clock support—before factoring in home modifications like ramps, lifts, or accessible bathrooms.

Proactive planning matters. Implementing strategies like the ones below to not only fund care—but also protect your legacy, honor your parents’ wishes, and preserve what matters most.

• Establishing dedicated care reserves through long-term investment strategies aligned with your family’s timeline
• Utilizing hybrid life insurance policies with long-term care riders to fund future needs or pass on wealth tax-efficiently
• Creating irrevocable trusts to protect real estate and other assets while preserving eligibility for premium care

Preparing for the Rising Cost of Education and Beyond

If you're investing in elite education—from private school to postgraduate studies— the total cost of tuition, travel, and housing could rival retirement-level expenses. Annual costs for Hawaii private schools are up to $30,000 per year while top-tier colleges can exceed $90,000 per student.

Further, with the high cost of living in Hawaii, many families with wealth also provide financial support to adult children to help them achieve major life milestones such as purchasing a home, starting a business or getting married.

It’s essential to treat education funding and financial support not as standalone expenses, but as strategic components of your broader wealth management and estate planning. By integrating these costs into your long-term financial strategy, you can empower your children’s futures—without compromising your own financial independence or legacy goals.

You and your family may benefit from:

• Designing 529 plans or education trusts that align with your long-term wealth transfer goals
• Structuring family gifting vehicles, such as a Family Limited Liability Company (LLC) or Family Limited Partnership (FLP), to support education while reducing estate tax exposure
• Leveraging portfolio drawdown strategies to maintain liquidity across generations

Protecting Your Retirement and Lifestyle

Amid the complexity of competing financial priorities, it can be tempting to postpone planning for your own retirement. Yet your financial independence is not just important—it’s the cornerstone that empowers you to support others with clarity, confidence, and resilience.

Annual planning sessions with a relationship manager can help ensure your retirement goals remain on track, even as your family’s needs evolve.

• Running retirement stress tests that account for elder care costs, tuition, other financial support, market shifts, and inflation
• Creating multigenerational investment strategies that balance current income with long-term preservation

Preserving Multigenerational Wealth

Today’s financial decisions can have lasting impacts—echoing across generations and shaping futures well beyond your own. These choices are often as emotional as they are rational, reflecting a blend of family values, cultural perspectives, and generational priorities. Because of this complexity, it’s often wise to engage a neutral third party—professionals who can facilitate thoughtful conversations, keep discussions focused, and help craft solutions tailored to the unique needs and circumstances of your ohana.

Some long-term approaches to consider:

• Investing with a multigenerational horizon tailored to your family’s goals
• Planning strategic gifting and estate planning to maximize gift exclusions and minimize tax exposure
• Developing succession plans and preparing subsequent generations for responsible stewardship
• Building a collaborative team of financial advisors, tax professionals, and estate planning attorneys to ensure decisions are aligned

Senior Care Resources

Where to start? Below are some helpful resources for you and your loved ones to consider as you start your journey.

AARP: In-Home Care: Helping Loved Ones Age in Place

AARP Care Connect: AARP Care Connect - Simplifying Your Caregiving Journey

US Health News: A Checklist For Finding the Best Assisted Living Facility

National Council on Aging: A Checklist for Moving to Assisted Living

State of Hawaii: Hawaii Aging and Disability Resource Center (ADRC)

Honolulu Magazine: 2025 Kupuna Resource Guide

Creating a Safe, Strategic Space for Conversations

One of the most powerful steps you can take is to create a respectful, neutral space for family conversations—before urgency dictates the terms. Four tips for communicating with family members are:

1. Outline and organize your thoughts in writing ahead of time;
2. Think about who should be there and choose a location that will not be overwhelming;
3. Make sure that everyone present is heard. Employ active listening skills and pay attention to keep your tone and body language;
4. Recap key takeaways and agreements and end the conversation on a positive note.

If you are a member of the sandwich generation, you know how difficult it is to manage your busy life. Your relationship manager in The Private Bank can be a key member of your team that helps you simplify your life, understand your prioritized goals, and help build your overall financial strategy and action plan. To learn how we can help you take the next step, please contact your relationship manager or a member of our team.