The choices you carry

Photo by Kalen Emsley

A few years ago, I was working on a change project at a family business. The operations director knew the organization inside out — more than ten years of experience, every process, every decision.

For me, everything was new. I asked questions. Why does this work this way? What was the thinking behind it? How did this come about?

One day he said: "I envy the questions you get to ask. When I ask those same questions, people look at me like I'm crazy. I was there when we came up with this, wasn't I?"

The insider's dilemma

When you've been somewhere a long time, you're part of the system. You helped build what's there now. The processes, the structures, the way things work — your fingerprints are all over them.

And then change comes. A new strategy that demands something different. Suddenly, choices you made in the past are up for debate. Sometimes years ago, with the best intentions, based on what you knew at the time.

How do you deal with that?

Two responses

Some leaders defend the choices they made. They explain why it made sense, why it worked at the time. They look outward: the circumstances, the pressure, the constraints of that moment.

Other leaders do something different. They acknowledge that they were part of how things became what they are. They take responsibility.

That second response takes courage. But it also carries a risk.

When responsibility tips over

Taking responsibility can easily tip into self-condemnation. The step from "I was part of this" to "I got it wrong" is smaller than you think.

And once you're there, letting go becomes impossible. You stay stuck in what you should have done differently. You keep defending yourself — no longer to others, but to yourself. And that keeps you anchored to the very thing you're trying to change.

The antidote

What helps is a different stance toward yourself. Acknowledging that you're fallible — without condemning yourself for it. Accepting that you did what you could with what you knew. And that now you know more.

Psychologists call it self-compassion. It might sound soft, but it's the opposite of letting yourself off the hook. It's what you need to look honestly without becoming paralyzed.

That balance — responsible and fallible — might be the hardest art of leadership in change. Not because you have to get everything right. But because you have to live with what you did, while trying to build something new.