Emily Guy Birken: What to Do in the Five Years Before You Retire - The Long View Recap

Podcast: The Long View

Published: 2026-03-17

Guests: Emily Guy Birken

What Happened

Emily Guy Birken delves into the importance of the five-year period before retirement, emphasizing the need for tangible financial adjustments. She points out that this timeframe is crucial for assessing if an individual's nest egg is sufficient, advising that envisioning both ideal and minimal retirement scenarios can guide necessary lifestyle changes.

Emily shares a story of a woman content with a modest lifestyle in Greece, illustrating that happiness in retirement isn't solely dependent on financial abundance. This anecdote supports her argument that expectations significantly impact retirement satisfaction, and managing them can prevent dissatisfaction.

For those approaching retirement without sufficient funds, Emily suggests options such as scaling down lifestyle, extending working years, delaying Social Security, or relocating to lower-cost areas. She reassures that Social Security is as reliable as possible, despite concerns about future solvency, and encourages delaying benefits for increased payouts if financially feasible.

Emily advises younger individuals not to rely on Social Security as a primary retirement strategy due to potential legislative changes. She also highlights the importance of budgeting for increased leisure and travel expenses in retirement while accounting for decreased work-related costs.

Healthcare costs pose a significant challenge for early retirees, particularly those under 65 who no longer benefit from Affordable Care Act subsidies. Emily recommends exploring alternative options like healthcare sharing ministries and health savings accounts (HSAs) for managing these expenses.

Long-term care insurance has become prohibitively expensive, with a study showing it is beneficial only for those with a nest egg between $400,000 and $2 million. Those with less than $400,000 might depend on Medicaid, while those with over $2 million are better off self-insuring.

Emily discusses the decision of paying off a mortgage versus investing for retirement, suggesting that the choice depends on the comparison between mortgage interest rates and potential investment returns. Historically, market returns average 8-10% annually, which can influence the decision to invest if mortgage rates are low.

Emily's personal experience with retirement planning has led her to prioritize aggressive savings and asset allocation. Initially focusing on her children's 529 accounts, she now balances both educational savings and personal retirement contributions, demonstrating a shift in financial strategy.

Key Insights

• The five-year period before retirement is critical for assessing financial readiness and making necessary adjustments. Individuals should consider both ideal and minimal retirement scenarios to guide their financial planning.
• Managing expectations is key to retirement happiness. An anecdote of a woman living contentedly in Greece with minimal resources highlights that financial abundance isn't the sole determinant of retirement satisfaction.
• Healthcare costs are a significant concern for early retirees, especially those under 65. Alternative options like healthcare sharing ministries and health savings accounts (HSAs) can help manage these expenses effectively.
• Long-term care insurance is only beneficial for individuals with a nest egg between $400,000 and $2 million. Those with less should consider Medicaid, while those with more may be better off self-insuring.