After working with over a hundred retirees, I’ve noticed a consistent pattern. The biggest regrets people share aren’t about investments, account balances, or tax brackets. They’re about the things money can’t buy back: time, health, energy, and missed experiences. Again and again, I hear the same three words: “I wish I had…”
In this video, I share the three most common retirement regrets I hear and the lessons behind them:
“I wish I had taken care of my health sooner.” Too often, people spend decades focused on work and finances while their health slips away. By the time retirement arrives, energy and mobility aren’t what they used to be, making it harder to enjoy the very years they saved for.
“I wish I had lived with less fear.” Many retirees hoard their savings, not out of greed, but out of fear: fear of market crashes, unexpected expenses, or outliving their money. That fear often masquerades as responsibility, but in reality it keeps them from fully enjoying life.
“I wish I had retired earlier.” Retirement isn’t one long chapter. It comes in phases: the go go years, the slow go years, and the no go years. Too many people delay retiring or spending on experiences, only to find the healthiest and most active years have passed.
The word that keeps coming up is delay. Delaying the trip, delaying the decision, delaying the joy until the opportunity is gone.
My hope in sharing these stories is simple: to help you prioritize what truly matters before it’s too late. Yes, your retirement savings and income plan are important. But so is your health, your time, and your ability to create meaningful experiences now, not just someday.
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