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Season 2, Episode 3: Navigating Transitions: When to Take Action and When to Let Go

Writer: Kristina Wiltsee
Kristina Wiltsee
4 hours ago
3 min read

Fred sorts transitions into three kinds: the ones you plan, the ones that blindside you (surprise and delight, or surprise and the other thing), and the ones that get delayed right before they go live. Kristina adds a fourth: the delay you cause yourself, because you know a change is coming and you're avoiding it.

What do you take in the boat?

Kristina's universal example of an unplanned transition is parenthood. You get nine months to plan, and none of it prepares you. For someone who had always moved around and lived "off in the ethers," becoming a mother meant becoming stable and putting all her attention in one place. Fred's summary: the fairy got her wings clipped.

She returns to the folk song "The Water Is Wide." Crossing from one shore to the other, you're in a boat with limited room. Some of your old life doesn't fit. Without a map of what motherhood was supposed to look like, she says she dropped so much on the way across that she could barely function, and recovering took a long time.

Fred's lens is responsibility as the ability to respond. When something hits suddenly, look at three things: the circumstances, the conditions you were living in, and the choices available now. He just finished six months as interim CEO of Chip City, a role that came up unexpectedly after a trip to India. As a consultant, he'd always advised. Now he made every decision himself. That gave him a new respect for his clients, and he leaned on the same mental models he'd been teaching to get through what he calls a marathon run at sprint pace.

Are you waiting for permission to leave?

Kristina's self-induced delay was staying at a company after a merger had erased everything she had liked about it. She was already doing coaching full time in her head. She waited for layoffs, severance, any outside event to make the decision for her. Fred calls it waiting for deus ex machina.

Looking back, she sees the lesson. Easy exits do happen. But when the same pattern keeps coming back, the lesson is usually to step into the resistance. For her, that meant trusting she was valuable enough to go out on her own. For someone like Fred, who works hard to make everything happen, the lesson runs the other way: let go and let the current carry you.

Fred maps it to coherence. Her head and gut agreed. Her heart was scared. When we stall, it's usually because one of the three is holding out. Kristina compares procrastination to waiting for the pressure cooker. We tolerate a slowly heating pot until it forces the decision. Fred's version: people change when the pain of staying the same outweighs the pain of change.

Can a delay be a gift?

External delays hurt in a business sense. Fred knows the feeling of a scoped and agreed project being pushed two months, leaving a hole in his calendar. Kristina's view is that internal delays are often our shadow, and external delays are often gifts. The project waited for Fred until India was done. Things line up.

The key, Fred says, is not to catastrophize. The worst case is a scenario, not the scenario. Kristina describes walking the razor's edge between sliding effortlessly across a frozen lake and forcing your own destiny through the swamp. Sometimes you lead. Sometimes you follow. Fred's metaphor is sailing: you don't control the wind, only your sail and rudder.

What did you ask for?

Fred reads a poem that is often shared without a clear author. It begins, "I asked for strength, and God gave me difficulties to make me strong," and ends with receiving nothing you wanted and everything you needed.

Kristina closes with fishing. You can know where the fish bite and bring the right bait and still not control the catch. Fred adds a third outcome: you catch nothing and it was a beautiful day on the water.

Listen to the full episode of The Executive and the Mystic on Apple Podcasts or wherever you get your podcasts.

 
 
 

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