Executive Transition: Designing a Purpose-Driven Retirement for the Carters

Current State of Finances

Mr. and Mrs. Carter, recent retirees in their early 60s, have stepped away from high-powered executive careers and are now focused on crafting a retirement life that aligns with their values. Mrs. Carter recently retired as CEO of a major national chain, while Mr. Carter built his career in finance. The couple has amassed a considerable portfolio, including approximately $20 million in cash savings and $15 million in invested assets.

Much of Mrs. Carter’s current holdings are tied up in individual company stock from her former employer. She is also receiving stock-based compensation through her new role on the board of another company. This has created a concentration risk, since a large portion of their wealth is tied to a single company that she no longer works for.

Now that they have acquired their dream estate as a permanent home, they are shifting away from the constant travel of their careers and choosing to build a retirement around rest, purpose, and giving back. With no children, philanthropy plays a central role in their long-term vision. They are currently deciding whether to expand their donor-advised fund (DAF) or launch a private foundation to have more influence over how and where their giving makes an impact.

Although financially secure, they are seeking clarity. They want to know how much they can sustainably give while still maintaining their lifestyle. They are also looking for guidance on how to simplify their portfolio and reduce their exposure to individual stocks, without triggering unnecessary taxes.

Financial Advisor Insights: What are we thinking about?

Charitable Strategy

Philanthropy is a major priority for the Carters. Choosing between a DAF and a private foundation involves weighing simplicity against control. A DAF offers ease and anonymity, while a private foundation allows them to build a legacy with more direct involvement. We are helping them evaluate the long-term impact of each path, align their giving strategy with their personal values, and model sustainable levels of annual support.

Real Estate

The Carters’ new home is a lifestyle investment but also has financial implications. We are evaluating how it can serve as a hedge against market downturns, especially if they choose to reduce market exposure in their investment portfolio. At the same time, we are modeling the long-term cost of ownership, including rising maintenance expenses, and ensuring these are accounted for in their retirement spending plan.

Portfolio Simplification and Risk Reduction

The Carters’ current portfolio contains highly concentrated stock positions, especially from Mrs. Carter’s former employer. We are developing a plan to gradually reduce this exposure using tax-efficient methods such as charitable stock gifting, tax-loss harvesting, and structured sales over time. This approach aims to lower volatility while preserving gains and minimizing tax impact.

Tax and Cash Flow Planning

Multiple income streams—including board compensation, dividends, and potential investment sales—require an integrated tax strategy. We are creating a long-term tax plan that smooths income, takes advantage of charitable deductions, and ensures efficient withdrawals. We are also designing a flexible cash flow strategy that supports both daily living and philanthropic commitments.

Emotional Clarity

Beyond the numbers, the Carters are looking for simplicity and peace of mind. Our planning is focused on helping them understand how much they can spend and give, how to transition away from financial complexity, and how to feel confident that they are protecting what they have built. With a plan that reflects their values and lifestyle, they can focus on what matters most—living well, giving generously, and enjoying the next chapter at home.