Climbing the Crooked Ladder

Momentum, Imperfection, and the Work of Change

I saw an image recently: two ladders leaning against a wall.

One is crooked, uneven, imperfect, a little wobbly, but it reaches the top.
The other is beautifully designed, straight, and polished, but it stops well below the ledge.

The image stayed with me because it captures something I’ve been feeling as this year draws to a close, a time when life picks up speed in many directions at once: new projects moving, courses to finish, family visiting, teenagers navigating their own paths, festive plans taking shape, and that familiar urge to pause and reset before the new year begins.

In the middle of all this, the temptation of the “perfect ladder” is strong.
The perfect plan.
The perfect timing.
The perfect conditions for the “right moment.”

Waiting feels sensible.
Finishing the plan feels responsible.
Clarity feels like something I should have before taking a step.

But the truth is this: learning, improvement, and impact don’t come from waiting.

So what do we do when waiting feels safer than taking the first imperfect step?
When does the desire for clarity become the very thing that slows us down?

I’ll say this openly: I naturally seek clarity… maybe a little too much. It has helped me in many seasons, yet sometimes it quietly keeps me still.

Michael Fullan often reminds us that clarity is rarely a starting point; it develops because we begin.

So another question arises: If clarity grows through movement, what do I lose when I hesitate?

The perfect ladder, half-built, is the plan that never leaves the page.
And haven’t we all been there?
The elegant document, beautifully structured, refined again and again… instead of being climbed.

Why imperfect steps matter

Educational research helps explain why the crooked ladder often leads to bigger, more meaningful change:

• We uncover things that planning can’t show us.
  Real action — even messy action — reveals hidden assumptions and details we couldn’t see on paper.

• We create feedback that helps us grow.
  Early movement, even small movement, gives us something real to respond to.

• We build a sense of “we can do this.”
  Collective teacher efficacy grows when teams see small wins, not perfect plans.

• We make room for coaching and learning.
  Adults learn best through conversation, shared practice, and trying things together. Real work creates space for this; theoretical work rarely does.

In this way, the crooked ladder becomes a symbol of learning in motion.

Psychological safety and the first climber

There’s a reason many people wait at the bottom of the ladder before stepping on.

Amy Edmondson’s research on psychological safety shows that people take risks — asking questions, trying something new, exposing their thinking — only when they feel safe enough to do so.

The first person to climb the crooked ladder takes a reputational risk.
If the ladder wobbles or creaks, everyone notices.

Leaders don’t just design ladders; they climb them.
They invite colleagues into guided experimentation.
They treat missteps as information.
They protect the space for learning.

They hold the balance of high expectations and high compassion: committed to quality, while knowing that excellence usually comes through many rounds of refinement.

Perhaps the crooked ladder is not irresponsible at all. It is scaffolded bravery.

In busy, uncertain, or demanding seasons, professionally and personally, people look for signals of safety and direction. Someone stepping first matters.

Sometimes the first step is like switching on a light in a dark room.
Nothing is fully solved, but suddenly everyone can see enough to move.

A small action changes the emotional landscape. It says:

We’re not stuck.
We’re learning.
We’re in this together.

Progress — a quiet driver of joy

Harvard researchers Amabile and Kramer found something striking in their study of 12,000 diary entries. On days when people made even a small amount of progress toward a meaningful goal:

• motivation rose

• mood improved

• creativity strengthened

• performance lifted

Another reason the crooked ladder matters: imperfect progress still moves us, as long as we’re climbing in the direction of purpose.

A gentler intention for the new year

As I move through this busy stretch of the year, the visitors, the travel, the work I care about, the parenting, the celebrations, and the early shape of next year, I am learning to hold a softer intention.

Not to perfect the ladder, but to step onto it sooner.
Not to let go of high standards, but to remember that excellence grows through iteration, not immaculate beginnings.

And perhaps most importantly: to move with enough humility to learn, enough courage to begin, and enough compassion to allow the work, and myself, to unfold in real time.

Some ladders are crooked.
Some seasons are messy.
But movement creates meaning and sometimes even a little magic.

Here’s to imperfect starts, adaptive journeys, and the courage to climb the ladders that actually reach the wall.

A question to carry forward

Where in your life or work are you still waiting for the perfect ladder, and what small step might help you see just enough to move?