A few weeks ago, I found myself buckled into a helicopter seat, headset on, lifting off above the ancient sandstone cliffs and winding waters of Katherine Gorge in Australia’s Northern Territory.

Beside me sat my 90-year-old dad.

“Dad, want to take a chopper ride over the Gorge?” I’d asked him earlier that morning.

“Sure, why not? I’m not getting any younger,” he said, slightly nervous.

But he didn’t dwell on the ‘what-ifs?’ He simply decided it was worth the ride.

And it was.

Yet how often do we let our fear of what might go wrong direct our decisions. Not fear of falling from the sky, but the subtler fears – of embarrassing ourselves, of being found out as not as smart as others think, of ruffling feathers or of stepping up but falling short.

In The Courage Gap, I write about how these fears—often unconscious and disguised in more socially acceptable clothes like perfectionism, people-pleasing, or the need for consensus—can hold us back from taking the very actions that would fuel our growth, advance our goals, and create greater value for others.

We tell ourselves we’re “waiting for the right time,” “protecting others’ feelings,” or “just doing more preparation.” But beneath it, what we’re really doing is avoiding the risk of failure, rationalizing our caution, or giving ourselves cover not to take the very step we know, deep down, would move us forward most.

And it’s costly.

Harvard researcher Amy Edmondson, who has studied psychological safety for over 20 years, has found that when people don’t feel safe to take interpersonal risks, they default to silence — withholding ideas, concerns, and questions that could spark innovation or prevent mistakes. Over time, this erodes not just performance, but confidence. 

We regret our excesses of caution far more than our excesses of courage.

Even when our brave actions don’t land with the ideal outcome, we walk away with learning, growth, and often, unexpected opportunities. But when we hold back, telling ourselves we’re just being ‘prudent’ it exacts what I call a hidden ’timidity tax’ that is rarely obvious in the moment. 

• We don’t just stay where we are — we shrink our own capacity to stretch.

• We gradually lose confidence in our ability to do hard things.

• We reinforce avoidance, making future acts of courage harder.

As I’ve witnessed many times in others:

Comfort doesn’t stay comfortable forever.

On the flip side, every time we take action that defies our doubts and fears, we grow a little braver in our own estimation. And research backs this up. Neuroscience tells us that every time we choose to act amid our fears  – even in a small way – we strengthen the neural pathways that make courage more accessible next time.

The reverse is also true: every time we avoid, we strengthen the habit of avoidance. And the cost of caution compounds. In a world moving at speed, that hidden “timidity tax” we pay for holding back and ‘playing not to lose’ can be easily underestimated.

My encouragement to you is this:

Don’t wait for the perfect moment. Don’t wait for perfect conditions or until you feel 100% confident. The conditions will never be perfect, and confidence is a result, not a prerequisite, of action. Rather, identify one action you’ve been putting off:

• The conversation you’ve been avoiding (we nearly all have at least one!)

• The idea you’ve sat on, waiting to refine it to perfection

• The decision you keep procrastinating on making, waiting for the ‘fog to clear’ 

Then take it.

Because whether it’s climbing into a helicopter at 90 or taking a leap in your career, courage compounds.

The sooner you start, the more it grows.

Promise.