The Personal Finance Podcast The Biggest Retirement Mistakes People Make (Avoid These!) Jesse Cramer
Mar 28, 2026
Jesse Cramer, financial planner and author who focuses on retirement planning and tax-smart moves. He discusses why Social Security is longevity insurance, when delaying benefits helps, Roth conversions and common timing mistakes, the pitfalls of unrealistic return assumptions, and how to measure true retirement spending. Short, practical topics to rethink retirement timing and taxes.
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Coordinate Claims For Couples
- For married couples, claim timing should coordinate: lower earner may claim earlier while higher earner delays.
- Delaying the higher earner protects the survivor because the higher record passes to the surviving spouse.
Don’t Claim Early Just To Invest
- Avoid claiming Social Security early solely to invest the checks; the delayed benefit is a guaranteed ~7–8% return.
- Investing early checks assumes higher, volatile returns; guaranteed increase often beats risk-adjusted market odds.
Roth Conversions Are Timing Plays
- Roth conversions shift taxable income from later high-tax years into lower-tax years early in retirement.
- They work best in early retirement years when income is low before Social Security, pensions, and RMDs increase taxable income.