Why Retirees Struggle & How to Avoid Common Pitfalls

Retirement should feel like a reward—so why does it so often feel like a loss?

For many high-achieving professionals, retirement is both anticipated and underestimated. You’ve spent decades with a calendar full of meetings, goals to achieve, and a clear sense of responsibility. And then… it all stops.

Here’s the hard truth: nearly one-third of retirees report feelings of depression and regret within two years of retirement. Why? Because retirement is a major life transition, and like any transition, it requires more than just a financial plan—it needs a life plan.

Here are some common pitfalls—and how to avoid them:

• Lack of Structure
  Going from full-time work to no schedule can feel liberating… for about three weeks. After that, many feel lost. The fix? Create a new rhythm of life—one that includes purpose, contribution, and growth.
• Undefined Purpose
  Retirement without direction can feel like a boat without a rudder. Clarify your why before you walk away from work. What do you want to contribute? Who do you want to become?
• Underestimating the Emotional Shift
  Retirement can trigger a true identity crisis. Prepare for that shift by investing in relationships, setting goals, and exploring new roles that align with your values.

Retirement can be rich and rewarding—but not if it’s approached passively. A successful retirement doesn’t just happen. It’s designed.