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Why Smart Leaders Still Make Decisions They Regret

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Smart leaders still make decisions they regret.

Not because they lack experience.
Not because they didn’t think it through.
And not because they aren’t competent.

Regret in leadership rarely comes from ignorance.
And it rarely comes from pressure alone.

Pressure matters — but it mostly reveals what’s already happening beneath the surface.

Because two people can make the same choice and experience it very differently, depending on whether they decided from fear or from clarity, from pressure or from alignment.

One leader may live with lingering regret — even if the outcome looks successful on paper. Another may face real consequences and still feel grounded in the decision they made.

The difference isn’t intelligence or outcome.
It’s the internal state from which the decision was made.

When leadership decisions start to drift

Leadership decisions tend to drift when leaders lose touch with their internal reference point — when identity, awareness, or connection slip under pressure, complexity, or relational stakes.

That’s when decisions start getting made to:

  • Manage reactions and questions
  • Preserve relationship and avoid conflict
  • Protect reputation or desired outcome
  • Maximize efficiency in the overwhelm

They also drift due to: Iidentity diffusion under complexity and big change.

When leaders aren’t clear on:

  • Who they are apart from performance, outcome, and metrics
  • What values anchor them when priorities collide
  • Which “self” and motivation is leading in a given moment

decisions become inconsistent across contexts.

This is why a leader can feel decisive and confident in one arena and uncertain or self-erasing in another. The decision isn’t the problem. The internal reference point is unstable.

Pressure doesn’t cause this. It simply exposes it.

The practical shift that changes how leaders decide

Identity-first decision making doesn’t require perfect clarity. It offers decision-making orientation.

Instead of starting with what will work, pause long enough to ask:

  • Where am I centered — and where am I activated — as I consider this decision?
  • What am I trying to protect right now?
  • What part of me is leading in this moment?
  • What choice would I make if I trusted myself instead of managing expectations?

These questions don’t slow leadership down — they steady it. And decisions made from clarity tend to feel different afterward. Even when outcomes are hard, there is less shame or regret from self-as-leader betrayal and more capacity to stand behind what was chosen.

What regret is actually pointing to

This often raises a fair question: Do bad decisions still exist?

Of course some decisions carry real consequences. But regret, more often than not, is feedback about how the decision was made — not just what happened.

Leaders rarely regret decisions made from alignment. They tend to regret decisions made from urgency, fear, or disconnection.

That feedback is useful — if we’re willing to take the time to listen.

A steadier way forward

You don’t need perfect certainty to decide well.

You need:

  • Enough identity clarity to know what matters
  • Enough awareness to notice what’s being activated
  • Enough acceptance to stay present without rushing
  • Enough connection to consider impact

Leadership decisions will always involve uncertainty. What changes everything isn’t eliminating doubt — it’s deciding with steady alignment.

When leaders slow down long enough to reconnect with who they are, what matters, and how they want to show up, decisions stop being something they recover from and start becoming something they can stand behind.

You don’t need perfect clarity.
You need enough alignment to move forward with integrity.

That’s what identity-first decision making offers — not answers, but orientation.

If you want support strengthening how you decide under pressure, this is the work I do with leaders every day through coaching, speaking, or consulting, let’s connect.

Image by Слава Вольгин from Pixabay

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