John G. Youngs,
Partner, CEO

For our clients, retirement planning is about more than financial security, it’s about navigating unique challenges and opportunities.

With the right strategies in place, you can help sustain the life you’ve built, shape a meaningful multigenerational legacy, and enjoy the years ahead with clarity and confidence.

Here’s a guide to retirement planning that truly goes beyond wealth.

Q&A

Q: Why is longevity such a significant factor in retirement planning?
A: We’re living longer than ever, which means your assets may need to support you for anywhere from 20 to 40 years. Planning for healthcare, inflation, market shifts, and long-term care helps ensure your wealth lasts a lifetime while still leaving a legacy.

Q: Do I really need multiple advisors involved?
A: Yes. Retirement planning for high net worth involves investments, tax law, and estate law. By coordinating your financial advisor, tax specialist, and estate attorney, you’ll get a plan that works from every angle—helping you enjoy today while protecting tomorrow.

1. Preserving Lifestyle Through Strategic Planning

Retirement is your time to focus on living your best life. For affluent families, however, maintaining that lifestyle takes more than steady income; it calls for strategic, forward-looking planning. With your advisory team, you’ll want to:

• Optimize your portfolio: Position assets across taxable, tax-deferred, and tax-free accounts, prioritizing long-term holdings to enhance growth and reduce tax drag.
• Plan for healthcare: Many affluent families turn to private or concierge care. Health Savings Accounts (HSAs) offer triple tax advantages: deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.
• Manage liquidity: Well-timed capital gains, Roth conversions, and distributions can limit tax surprises while keeping funds available for travel, philanthropy, and other priorities.
• Leverage business strategies: 1031 exchanges and qualified opportunity zone investments can defer (or even eliminate) capital gains.

2. Protecting and Transferring Multigenerational Wealth

For many retirees, leaving a legacy for children, grandchildren, and charitable causes is just as important as enjoying their wealth today. Thoughtful planning can help ensure taxes and other obstacles don’t reduce what you pass on. You may want to:

• Prioritize charitable giving: Donor-advised funds, charitable trusts, private foundations, and qualified charitable distributions (QCDs) can help you support causes you care about in a tax-efficient manner.
• Align retirement and estate planning: Converting traditional IRAs to Roth IRAs during favorable tax periods can help minimize long-term tax exposure. Holding these assets in irrevocable trusts for heirs may also help protect against creditors and unnecessary taxation.²
• Embrace irrevocable trusts: Intentionally defective grantor trusts (IDGTs), spousal lifetime access trusts (SLATs), and dynasty trusts enable tax-efficient transfers to your heirs while maintaining family control. In some cases, non-grantor trusts may enable you to divide ownership of a home and fully utilize the enhanced $40,000 SALT deduction (subject to income limits).³
• Plan for business succession: If you own a family business, consider tools such as recapitalizations, buy-sell agreements, or family limited partnerships (FLPs) to help make the handoff to the next generation smoother and more secure.⁴
• Make the most of exemptions: The OBBBA made the higher lifetime federal estate tax exemption permanent, increasing it to $15 million per person starting in 2026.⁵ You and your spouse may gift up to $19,000 per recipient (or $38,000 jointly) in 2025 to further reduce the taxable estate without reducing your lifetime exclusion.⁶

3. Planning for Longevity and Risk Management

Today’s retirees are healthier and living longer than ever before. That’s a gift, but it also means your wealth needs to work harder and last longer. Talk to your advisor about:

• Smart investment management: A well-diversified portfolio should balance growth to outpace inflation while aiming to protect against market downturns. Tools like Tax-loss harvesting, rebalancing, and select alternative investments can help build resilience.
• Funding long-term care: Hybrid life and long-term care policies, along with customized insurance solutions, can help cover rising care costs while preserving family assets.
• Asset protection: Trusts, comprehensive insurance, and thoughtful ownership structures can help shield family wealth from lawsuits, creditors, and divorce.
• Creative gifting approaches: Although complex, “upstream gifting” to an older family member (rather than directly to a younger heir) can potentially limit estate tax exposure while preserving a step-up in cost basis.⁷
• Purpose and legacy: Longevity isn’t only financial, it’s also about staying engaged with family, community, and causes you value. For example, you might “superfund” a 529 plan, front-loading five years of contributions at once to a grandchild’s education without triggering gift taxes.

Planning for Every Dimension of Retirement

Affluent retirees need strategies to help maintain their lifestyle, protect and transfer multigenerational wealth, and plan for longer lifespans.

We can collaborate with your attorneys and tax specialists to design a retirement plan that integrates lifestyle, legacy, and longevity—tailored to your specific needs and goals.

Schedule a consultation today to get started.

Sources
¹www.irs.gov
² www.fidelity.com
³www.cpajournal.com
⁴taxfoundation.org
⁵ www.irs.gov
⁶ www.fidelity.com

The views expressed represent the opinions of Tiller Private Wealth as of the date noted and are subject to change. These views are not intended as a forecast, a guarantee of future results, investment recommendation, or an offer to buy or sell any securities. The information provided is of a general nature and should not be construed as investment advice or to provide any investment, tax, financial or legal advice or service to any person. The information contained has been compiled from sources deemed reliable, yet accuracy is not guaranteed.

Additional information, including management fees and expenses, is provided on our Form ADV Part 2 available upon request or at the SEC’s Investment Adviser Public Disclosure website, here. Past performance is not a guarantee of future results.