When people ask me about the biggest retirement mistake, they expect me to point to something financial — not saving enough, claiming Social Security too early, investing too aggressively. But after 25 years of helping people retire, I've noticed something surprising: some of the most financially prepared people I've worked with struggled the most in retirement. The reason is that they treated retirement itself as the goal. When you retire, you don't just leave work — you lose the routine, identity, relationships, and structure that work quietly provided. Retirement doesn't remove your need for purpose; it simply removes the thing that had been supplying it.
That's why I believe everyone needs two retirement plans: a financial plan and what I call a daily retirement plan. One answers the question "Will I have enough?" The other answers a question that's just as important: "What am I going to do with this next chapter of my life?" You don't just need a plan for your money — you need a plan for your Monday. And this isn't only about happiness. The retirees who don't replace that sense of purpose often find the financial side of retirement gets harder, not easier. When there's nothing else going on, the portfolio becomes the most interesting thing in the day. Every market dip feels bigger, accounts get checked constantly, and a plan that was working just fine starts getting second-guessed. In short, when work is gone and nothing meaningful replaces it, your investments can quietly become your new job.
In my latest video, I walk through what a daily retirement plan actually looks like — the simple, mostly inexpensive things I've watched bring purpose to my clients' retirements — and why retiring to something matters far more than retiring from something. If you're approaching this next chapter and want help building both plans, not just the financial one, I'd welcome the conversation.
