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

Morningstar
MorningstarMar 18, 2026

Why It Matters

Understanding and acting on the five‑year retirement window helps individuals avoid financial shortfalls and align expectations, ultimately securing a more stable and satisfying retirement.

Key Takeaways

  • Focus on five-year window to shape retirement outcomes.
  • Dream big, then define minimal contentment baseline for budgeting.
  • Adjust expectations to avoid unhappiness from unmet retirement ideals.
  • Leverage delayed Social Security for higher guaranteed income.
  • Consider extending work, cutting costs, or relocating abroad if shortfall.

Summary

The Long View podcast features Emily Guy Birken, author of *The Five Years Before You Retire*, who argues that the five‑year horizon before retirement is the sweet spot for making meaningful financial adjustments. She explains that this period is close enough to feel real yet far enough to influence savings, investment choices, and lifestyle plans.

Birken’s framework starts with two exercises: first, imagine an ideal, no‑budget retirement day‑by‑day; second, define the minimal “contentment” baseline that would still feel satisfactory. By comparing the two, readers can budget for the gap, prioritize experiences, and avoid over‑optimistic expectations that often lead to disappointment. She also stresses the power of delayed Social Security—waiting even a year can boost benefits by roughly 8% annually—while warning that early claims usually only pay off for those with significantly shorter lifespans.

Illustrative anecdotes include a widowed woman who, after losing everything in the housing crash, found happiness with a roof, meals, and library access, underscoring that expectations, not dollars, drive satisfaction. Birken also critiques the common break‑even analysis for early Social Security claims, noting that the real tragedy is outliving one’s nest egg, not dying young.

For pre‑retirees, the takeaway is actionable: refine expectations, align spending with realistic goals, consider extending work, cutting costs, or even relocating to lower‑cost regions, and delay Social Security when possible. These steps can transform a precarious retirement outlook into a sustainable, fulfilling chapter.

Original Description

The author and retirement expert shares a punch list for near-retirees, how to play catch-up on retirement savings, and why she has changed her mind about long-term-care insurance.
Episode Highlights
00:00:00 Emily Guy Birken’s Path to Money and Retirement Writing
00:04:26 Why the Five Years Before Retirement Are Crucial and How Much Is “Enough” Savings
00:10:31 How Expectations Can Shape Happiness in Retirement
00:13:14 Key Moves for Preretirees to Cover Retirement Savings Shortfalls
00:15:58 Social Security: Benefits of Delaying and Advice for Young Workers
00:27:06 Budgets in Retirement and Irregular Expenses on a Fixed Income
00:33:14 Why Long‑Term‑Care Insurance Rarely Pays Off Today
00:36:10 Pre-Medicare Health Insurance Options
00:40:17 Early Mortgage Payoff vs. Investing in Retirement
00:42:26 How Writing About Retirement Changed Guy Birken’s Own Planning

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