Permission to Not Know
A CEO with a long history of successful leadership sat across from me, spreadsheets between us. She had planned for everything. Succession, investments, properties, travel. Then I asked: "When all of this is in place, what will you look forward to on a day-to-day basis?"
She paused.
"I honestly don’t know," she said finally. "I know how to run companies. But without the pressure, I am not sure what I will do with myself. I can’t even quite imagine it."
That was how we opened the door to a different kind of conversation. We started with questions rather than answers.
It’s easy for accomplished professionals to be caught off guard at this stage. The skills that built your career, like strategic thinking, decisive action, or always having a solution ready, aren’t always the ones that will take you where you want to go now. In fact, they can get in the way. If everything is viewed as a problem to be solved, the more interesting questions never get asked.
The professionals who find the most meaning in transitions are rarely the ones with the most detailed plans. They are the ones who give themselves permission to not know for a while. People who built entire careers on having answers, can begin instead with their questions.
"I spent thirty years being the person with solutions," one former CFO told me. "The gift of retirement was finally being allowed to be curious again. To be genuinely unsure for a while and not treat it as a problem."
It is worth listening carefully to whatever is quietly stirring. Not rushing toward answers, but noticing the moments and places where something feels unexpectedly alive. Those are rarely random. They tend to be pointing somewhere worth following.
The uncertainty of this particular in-between time is not a gap to be filled as quickly as possible. Instead, we can consider uncertainty as a necessary pause, one where the most useful things begin to surface.
Ready to go further?
These resources offer valuable perspectives, but nothing replaces a thoughtful conversation about your specific situation.
Have a resource that's helped you? I'd love to hear about it. Drop me an EMAIL.
Photo courtesy of Skyler Ewing.