Jun 26, 2025

When Experience Stops Working

This feels good.

Chanelle leaned back in her office chair, closed her eyes, and savoured the moment.

Last night’s gala dinner was electric. One speaker after another praised her brilliance, poise, and “grace under fire.” Someone even called her “the rare leader who combines genius with warmth.”

She smiled, unsure what tasted better—the champagne or the sense of achievement.

Success?

  • Education.

  • Home in the suburbs.

  • Salary.

  • Peer respect.

  • Loyal team.

But then—Frank and Jasmine.

Two millennials.
Two headaches.

Yesterday, Frank strolled into a meeting ten minutes late—like he ran the place. Jasmine? Smart, but always armed with a fresh excuse: her partner, her pet mongoose, her ingrown toenail.

Chanelle—used to negotiating million-dollar deals—felt powerless.

Her best instincts didn’t work. Her leadership presence didn’t land. Nothing that worked in the past seemed effective now.

She felt:

  • Frustrated

  • Confused

  • Resentful

And worst of all… like screaming.

When What Worked… Stops Working

What would you tell Chanelle?

Be more patient? Be more assertive?

But here’s the real question:

What do you do when your best intentions and trusted methods stop working?

The Seduction of Experience

We lean on experience like a crutch.

“If it worked before, it’ll work again,” we say.
But change isn’t baking. Even then, the same ingredients don’t always yield the same cake.

We forget:

  • Success is context-sensitive.

  • What worked then may not work now.

  • Sometimes, we confuse short-term results for long-term transformation.

Worse still?
The same methods that brought past success may now be fueling current failure.

The Trap of Default Response

You:

  • Still talk to your kids like they’re children.

  • Lead every team the same way.

  • Speak to your current partner like your ex.

  • Treat all donors, clients, or colleagues as one-size-fits-all.

We do what we’ve always done—not because it works, but because it’s easy.

We’d rather reuse the past than face the complexity of the present.

Why We Default

  • Thinking deeply takes effort.

  • New problems are complex.

  • The brain hates confusion, so it uses shortcuts from the past.

  • We’d rather feel confident than be right.

But in doing so, we often miss what the moment is actually asking of us.

The Universal Rule of Change

There are no universal rules. Only universal adaptation.

The right action is the one that fits the situation.

Some moments need:

  • Patience

  • Others, urgency

  • Some need control

  • Others, trust

There is no habit, no strategy, no tone that works everywhere.

The best leaders are those who keep adjusting their approach until the situation aligns.

Action Point

Think of one persistent challenge in your life or work.

  • How might this situation differ from those you’ve faced before?

  • Are you leaning on patterns that no longer apply?

  • What might this moment truly demand?

Ben Ajayi