Why Even the Best Retirement Calculator is Wrong

From Retirement Answer Man by Roger Whitney, CFP®, CIMA®, RMA, CPWA®

March 25, 2026 · 60 min · Episode 636

About this episode

Roger Whitney discusses the limitations of retirement calculators and the importance of understanding their results.

Roger Whitney explores why retirement planning software—especially Monte Carlo simulations—can give a false sense of confidence if misunderstood. He explains what these tools actually measure, the hidden assumptions behind them, and why retirement is a complex problem that requires judgment, flexibility, and resilience—not just a high “success rate.” Roger shares how to properly interpret results, avoid common traps, and use software as a guide rather than a decision-maker so you can build a retirement plan that supports a great life. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN (00:00) This show is dedicated to helping you not just survive retirement, but have the confidence to lean in and rock it. (00:30) Roger introduces the episode topic—why your retirement calculator’s success rate can be misleading. PRACTICAL PLANNING SEGMENT (02:50) Roger explains his perspective as a long-time practitioner and outlines his experience using Monte Carlo-based retirement tools. (05:05) Complicated vs. complex problems: why retirement can’t be “solved” like a math equation and must instead be managed over time. (09:30) Concerns about overreliance on software—from advisors scaling…

People in this episode

Host: Roger Whitney

Topics covered

retirement planning
Monte Carlo simulations
financial software
success rates
complex problems
judgment in planning

Keywords

retirement calculator
Monte Carlo simulations
financial planning
success rate
software interpretation
retirement strategy

Mentioned in this episode

Organizations: Monte Carlo