Permission to Not Know
A CEO with a successful history of leadership sat across from me, spreadsheets between us. She'd planned for everything—succession, investments, properties, even some travel. Then I asked: "When all this is in place, what will you look forward to on a day-to-day basis?"
Silence.
Finally: "I honestly don't know. I know how to run companies. But without the pressure, I don't know if I will get bored or come up against things I can't even imagine."
That was how we opened the door to a different kind of conversation. One that started with questions instead of answers.
The Surprising Truth
Here's what catches executives off guard: The very skills that built your career—strategic thinking, decisive action, always having answers—won't take you where you want to go now. In fact, they can get in your way.
The Shift That Changes Everything
The professionals who create the most meaningful retirements aren't the ones with the best plans. They're the ones who give themselves permission to not know for a while.
Think about that. People who built careers on having answers find their freedom by first taking time to figure out their important questions.
One former CFO put it perfectly: "I spent 30 years being the person with solutions. The gift of retirement was finally being allowed to be curious again, to be unsure for a while."
Why This Matters
Those questions stirring beneath your confidence? They're not problems. They're the beginning of everything that matters next.
People who really thrive at this point don't rush through this uncertain space. They explore it.
Ready to discover what questions you should be asking? Let's explore what's really stirring beneath your retirement planning. Schedule a conversation.
Ready to go further?
These resources offer valuable perspectives, but nothing replaces a thoughtful conversation about your specific situation.
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