The Long View Emily Guy Birken: What to Do in the Five Years Before You Retire
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Mar 17, 2026 Emily Guy Birken, a personal finance author who writes about retirement and Social Security, walks through what matters in the five years before you stop working. She covers assessing if you have enough, the levers to pull if savings fall short, why delaying Social Security can help, health insurance and HSA/Roth strategies pre‑Medicare, budgeting for lumpy expenses, and mortgage vs investing choices.
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Expectations Drive Retirement Happiness
- Expectations shape retirement happiness more than objective wealth; unmet expectations drive dissatisfaction even when circumstances are good.
- Being open to what retirement brings, rather than rigid plans, increases contentment.
If You Might Run Out Of Money Take Concrete Steps
- If your nest egg falls short, pull levers: scale spending, work longer even one year, delay Social Security, or find part-time income to let savings grow.
- Consider cost-of-living moves like retiring abroad as a last-resort scaling option.
Delay Social Security If You Can
- Delay Social Security if you can afford it because benefits increase about 8% per year and provide longevity insurance; taking early usually loses long-term income.
- Social Security is highly likely to exist for current retirees; Congress will likely fix shortfalls before benefits stop.
