What is it about The Wizard of Oz that remains so enduring?

Part of it is surely the surface-level spectacle: the yellow brick road, the songs, the flying monkeys, the witches, Emerald City. But like all great works of art, its real power sits beneath the surface. There is the longing for home, and the strange childhood mixture of fear and fascination that comes from being stranded in a beautiful, terrifying place “somewhere over the rainbow.”

Watching it as an adult, you realise something else. At some point, the familiar terrain of home ceases to exist in the way it once did. Life’s challenges have to be faced. But you can ask friends to help you. And when you look back, you may discover that the scary terrain has already been crossed in small ways.

Dorothy is the protagonist. She is swept up, carried into a frightening place, and has to find her way home. But the more interesting story, at least for my purposes, belongs to the companions she meets along the road, each of whom depends on her for help.

The Tin Man, the Scarecrow, and the Cowardly Lion arrive in the story with familiar aches. They are adrift, uncertain, somehow incomplete. Each believes an essential part of themselves is missing. The Tin Man longs for a heart. The Scarecrow wants a brain. The Lion wants courage. Perhaps they are projections of childhood fears: Am I too stupid? Too unlovable? Too scared?

Their hope is that somewhere, someone possesses what they lack. The Great and Powerful Oz will bestow these missing qualities upon them. So they set off toward Emerald City in search of the thing they believe they do not have.

Like most enduring stories, however, the destination turns out not to be the point. It is the journey itself that matters. Along the way, the Tin Man repeatedly shows tenderness and care. The Scarecrow thinks, reasons and improvises. The Lion repeatedly acts in spite of fear. The irony is that they spend the entire film searching for qualities they are already practicing.

But it was their doubt that sends them searching. The road reveals what was there all along.

Perhaps doubt works in a similar way.

We tend to think of doubt as evidence that something is wrong. We treat it as a problem to solve or an obstacle to overcome. Doubt feels uncomfortable and so our instinct is to get rid of it as quickly as possible.

Yet Viktor Frankl argued against the idea that questioning meaning was a symptom of sickness. He believed that doubt and questioning could provoke a search for meaning. Rather than being a defect, uncertainty could become a kind of invitation.

The important thing may not be the answer itself but the question. Questions have a way of expanding us. Consider someone who asks, "How can I become more courageous?" The answer rarely arrives neatly. Courage is not a destination that one reaches and permanently occupies. There is no graduation ceremony after which one becomes Courageous Person forever.

Instead, the question begins to work quietly in the background. It influences choices in ways too small to notice at first. You speak up once when you normally would remain silent. You volunteer for something uncomfortable. You have a difficult conversation. Over time, these actions accumulate.

Questions shape identity long before answers arrive.

This may be why fixed ideas about ourselves become dangerous. Once we decide what kind of person we are, we stop listening. We premeditate our identity. We close ourselves to possibilities that might otherwise call us forward.

Doubt, however, rarely arrives alone. It often arrives carrying fear.

Fear has a narrowing quality to it. It turns our attention toward safety and certainty. It persuades us to postpone difficult things. It sends us toward distractions and what's comfortable. A night of Netflix. Endless scrolling. Another day spent gathering information before beginning.

Fear rarely says, "Do not go." It usually sounds more reasonable than that. Maybe later. You are not ready yet. You need more clarity first.

This is where vulnerability enters the picture.

Brené Brown defines vulnerability as uncertainty, risk, and emotional exposure. Her definition captures something important because vulnerability is often misunderstood. The traditional meaning suggests exposure to attack. If you are entering battle, hardening yourself makes sense. You train. You put on armour. You raise a shield.

Battles with ourselves may require something different.

Rather than hardening, we may need to soften. To expose the soft underbelly first to ourselves and then to others. To admit uncomfortable truths: I do want this. I am frightened. I do not know what I am doing. This matters more than I pretend it does.

Perhaps the way through doubt is not certainty. Perhaps it is vulnerability.

In 1947, George Dantzig was working on military planning problems. Resources were limited and choices were complex. He developed what became known as the simplex algorithm, a method for finding solutions without having to search every possibility.

The insight was that rather than attempting to evaluate every conceivable option, you move from one promising position to a slightly better nearby position. Then again. Then again. Eventually clarity emerges through movement. The key word there is movement.

During periods of doubt, we often assume that clarity must arrive before action. We imagine that we need to solve the entire problem of our lives before taking the first step. Should I quit? Should I stay? Should I become an entrepreneur? Should I start the not-for-profit?

But life does not ask for complete certainty. Perhaps it only asks for the next adjacent move. One conversation. One application. One experiment. One small act of courage.

Evidence often arrives through action. Small actions create information. Information creates confidence. Confidence creates momentum.

We rarely think our way out of fog. We move our way through it.

While writing this essay, I happened to come across an interview with Conan O'Brien where someone asked him when the nervousness and self-doubt finally disappeared. After decades of success, after television shows, awards, audiences and recognition, his answer was that It never really goes away.

There was something comforting in his honesty. We often imagine confidence as a destination. We think one day we will finally become the person who no longer doubts. Yet Conan suggested something different. The doubt remains. The task is learning how to continue alongside it.

Which brings us back to the Cowardly Lion.

The Lion believed courage meant becoming a different kind of creature altogether, one no longer governed by fear. He thought it was a possession waiting for him somewhere in Emerald City. By the end of the journey, the revelation was that he was not cured by fear. But he has acted, again and again, in situations where fear would have given him a perfectly good excuse to retreat. Perhaps doubt works the same way. We spend much of life waiting for certainty before acting. Waiting for the fog to lift. Waiting to feel ready. Waiting for the wizard to tell us we already possess what we need.

Meanwhile the yellow brick road waits beneath our feet.

_{*This section is adapted from Jim Collins’ wonderful book What to Make of a Life}

A quick note before you go.

I’m running the next Finding Meaning in Work workshop on Saturday 30 May.

This is for people who are doing fine on paper, but know something in their work needs proper attention. Maybe the work is going well enough, but no longer feels fully yours.

Maybe you’ve become good at something without stopping to ask whether you still want it. Maybe Sunday night keeps telling you something your calendar keeps drowning out.

These questions rarely answer themselves while you’re moving from meeting to meeting.

That’s what the workshop is for.

Four hours. A small room. Guided prompts, writing exercises, reflection and discussion.

You’ll leave with a workbook, a personal manifesto, and clearer language for what has been sitting in the background.

When: Saturday 30 May, 11am–3pm
Where: Sanders Place, Richmond
Lunch: included

If you’re unsure whether it’s a fit, reply with a line about where you’re at with work right now and I’ll tell you honestly.

If you’d like to join, you can book below. Use DBN2026 at checkout..