The Iron Wall: Regret as Executive Distraction

I’ve always been especially vulnerable to regret.

My mind, especially on a quiet day, can replay decisions and missed opportunities with a kind of cinematic drama that’s more heavy than helpful. Even after years of studying practices such as mindfulness, regret was always the one voice I couldn’t quiet.

Until recently.

I was in conversation with a trusted advisor, the brilliant futurist Daniel Burrus, an author, speaker, and strategic thinker whose decades of work have helped organisations prepare for disruption before it arrives. (If you don’t follow him, you should.) We were speaking about kids and the stuff of life when he said something that stopped me cold:

“I never regret the past,” he said. “I just don’t go there.”

From my vantage point this seemed improbable.

“Never?” I asked.

“Never.” He said.

And I believed him.

It was as matter-of-fact as it was radical. Here was a man in his seventies, with a lifetime of experiences behind him, calmly stating that regret had no seat at his table. It made me realise how much of my own mental energy was being siphoned off by the pull of the past.

I left that conversation inspired. And out of it came a mental visual that’s helped me reclaim untold hours of focus and energy. I call it The Iron Wall.

A Practice for High-Demand Leadership

The Iron Wall is simple: when I feel myself drifting into regret, I imagine a hugely thick, infinitely wide slab of iron dropping down behind me, blocking all access to the past. I feel the incalculable weight of it, the thudding sound, and the puff of the earth as it lands. And then I say slowly to myself, “That was then. This is now.”

This realignment allows me to reclaim the most precious resource an executive has: attention.

What would it mean if leaders everywhere practiced the same discipline? Imagine a team that could acknowledge a mistake, extract the lesson, and then truly shut the door. In my work with executive teams, I see the opposite all the time—leaders subtly tethered to moments they can’t change. A bad hire. A missed opportunity. A product that launched too soon. We often mistake regret for reflection, but regret is not harmless. It is a thief. And when it lingers, it drains three core capacities required for leadership:

Clarity. The past fogs up the windshield, obscuring the road directly ahead.
Confidence. Regret erodes your belief in your ability to make the next call.
Presence. You might be in the boardroom, but your mind is lightyears away on a past misstep.

The Iron Wall, when applied at a leadership level, protects a company’s forward momentum. Which brings me to the mirror image of regret: future-tripping.

Regret and Future-Tripping: Twin Distractions

If regret is the distraction of the past, then future-tripping is the anxiety of the not-yet. It’s the mental rehearsal of a crisis that hasn’t happened. The “What if this deal doesn’t close?” “What if the numbers next quarter collapse?” “What if we’re too late to catch this trend?” spiral. (Need I mention the not-yet, coming soon recession that never comes?)

You also can’t strategise effectively for the future from a place of anxiety. So try a subtle shift on our mantra phrase. "That is then, this is now."

Both regret and future-tripping remove leaders from the present moment, and that’s the only time zone where leadership actually happens.

Learning Without Looping

But before we banish regret entirely, let’s acknowledge that it can offer value If it does not emotionally control you as mine did. That’s where the other Daniel enters the picture: Daniel Pink.

Daniel Pink’s book The Power of Regret is a strikingly beautiful and thoughtful exploration of how regret, handled with intention, becomes a powerful teacher. As Pink so eloquently puts it, “Regret reveals what we value.”

That means the executive who regrets not speaking up values integrity. The founder who regrets not taking a risk values growth.

The danger is when that teaching point turns into a loop. A moment of regret can give you clarity about your values; an ongoing cycle of regret will only sap the energy to act on them.

Let regret instruct you. Follow its clues and then drop the wall, and move on.

Executive Attention Is a Finite Resource

P.S. Regret is also expensive.

Regret and future-tripping both drain executive bandwidth. They clutter the mind with non-actionable noise. They contribute to the fog that many leaders describe when they say, “I can’t prioritise,” or “I can’t think clearly.”

Attention is your greatest resource and it must be fiercely protected.And that’s what the Iron Wall does. So next time you feel yourself drifting back into yesterday, try this:

Pause. Picture the wall. Say it slowly: That was then. This is now. And come back to the present.

Because if this is what you’ve built while carrying the weight of regret, imagine what’s possible without it.

See you on the other side of the wall.

This was also published on Juliet Funt's LinkedIn.

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