When You Don’t Feel Ready

Lloyd Dobler stands outside a window with a boom box in Say Anything.

Lester Bangs declares that truth matters more than cool in Almost Famous.

Will Hunting solves complex theorems while mopping the floor in Good Will Hunting.

Billy Beane rejects a century of baseball wisdom in Moneyball.

Jeffrey Wigand takes on the tobacco industry as a whistleblower in The Insider.

These are iconic images from my favorite movies, some based on real life stories, some fictitious. In each case, the central characters stand in a moment of truth.

I’ve always been drawn to underdogs and everyday heroes like the characters in these stories. I’ve celebrated them in this newsletter.

They’re not the coolest. They’re not the most polished, most powerful or most credentialed. To the outside world, they don’t look like heroes. People underestimate and even criticize them.

But, below the surface, these underdogs have a powerful inner drive, an unerring North Star.

They’re dreamers. They’re idealists. They’re imperfect people trying to stay true to themselves and make a difference in a sometimes-cynical world.

We relate to them because they seem a lot like us. They have an essential decency we admire. They commit themselves to doing what’s right.

In Say Anything, Lloyd Dobler represents every high school kid who didn’t quarterback the football team, didn’t take all the advanced classes and didn’t become class president.

In Project Hall Mary, Ryland Grace represents everyone who is thrust into a high-stakes situation but doesn’t feel like a hero.

In Almost Famous, Will Miller represents everyone who has felt awkward, nerdy and uncool.

In Erin Brockovich, Julia Roberts plays a character with little power but an unrelenting passion to make her community better.

The canonical example in music is my favorite band of all time, the Replacements.

They were unpolished. They hit wrong notes. They were ambitious but had deep reservations about the music industry. They were incapable of faking it.

They are the most unlikely rock and roll heroes. Yet they captured the essence of rock better than anyone before or since, even as they doubted themselves.

Their songs are timeless love letters to underdogs, outsiders and misfits: “I Will Dare,” “Unsatisfied,” “Aching to Be,” “Left of the Dial,” “Swinging Parties.”

There is a common theme across all these unlikely heroes. They feel unprepared for the task in front of them. They have deep qualms about the world and their ability to drive change. They’re imperfect.

We can relate to this. How many times in our lives have we felt unprepared or unequal to the opportunity or challenge in front of us?

I’ve had many times in my career and personal life where I thought: “I’m not ready.”

Digitizing a centuries old industry at Amazon to prepare for the Kindle.

Grappling with the cancer diagnosis of a loved one.

Taking on the chairperson role of a large non-profit board.

Climbing one of the world’s Seven Summits.

Taking the Chief People Office role at a big retailer, with no background in HR.

I’m not ready.

I need more time. I’m scared. I want more certainty. How did I get myself into this?

What separates these underdogs and everyday heroes is this: They act anyway, even if imperfectly. They overcome fear. They take the next step despite uncertainty and tall odds.

They recognize that a superhero is not coming to save them or their community. Their intense sense of purpose, their inner drive, outweighs their fears. They expand their ambition to the size of the challenge in front of them.

These are universal themes, especially in times of adversity.

When Lloyd Dobler holds his boom box over his head playing “In Your Eyes” in Say Anything, we relate. When Ryan Grace in Project Hail Mary declines a hero’s role at first, we understand.

My own theory is that these outsiders, underdogs and everyday people are not anomalies. They’re the primary vehicle of positive change in the world. They represent the best of who we are.

Billy Beane reinvents modern sports. The Replacements create the greatest rock music ever recorded. Jeffrey Wigand upturns the tobacco industry. Erin Brockovich helps save her community.

They’re imperfect. They’re scared. People underestimate them. But they don’t wait until they have all the answers. They don’t feel ready, but they try.

These stories inspire us to maintain hope in the face of cynicism. To care deeply when caring is risky. To be vulnerable even when the world is cruel. To remain steadfastly uncool when the truth requires it. To follow a powerful inner voice even when it is scary. To maintain decency in an indecent world.

And to ask ourselves, “Why not me?”

Maybe there’s a book you want to write. Maybe there’s an injustice in your community you care deeply about. Maybe there’s a business you want to start. Maybe there’s a career path that scares you.

Maybe you don’t feel ready. Maybe you aren’t.

Do it anyway. I’ll be cheering you on.