Retirement Timing – Relax, It's Retirement Podcast

Don’t Let “One More Year” Steal Your Retirement (Ep. 106)

By Relax, It's Retirement | February 17, 2026

What if “just one more year” at work costs you more than it gives you?

In this episode, Josh Leonard challenges one of the most common retirement assumptions, the idea that working one more year is always the safer choice. While extra income can feel reassuring, delaying retirement can quietly take time, health, energy, and meaningful experiences you may never get back.

Josh walks through real client stories and practical planning scenarios that show why one more year is often an emotional decision, not a financial one. He introduces a simple trade-off filter to help listeners evaluate whether delaying retirement truly improves their plan or simply postpones living the life they’ve already earned.

Josh discusses:

Why being financially ready does not always make retiring emotionally easy
How taxes, required distributions, and healthcare can change the math
The hidden cost of delaying retirement when time and health are limited
A three-question framework to evaluate if one more year actually helps
How intentional income planning creates confidence to retire sooner
And more!