Character vs Reputation: The True Measure of Success

I recently listened to an episode of Freakonomics Radio titled “If You’re Not Cheating, You’re Not Trying,” featuring an interview with disgraced cyclist Floyd Landis. The conversation eventually turned to John Wooden’s famous maxim: “Be more concerned with your character than your reputation, because your character is what you really are, while your reputation is merely what others think you are.”

Landis, perhaps unsurprisingly for a man whose career was defined by a massive deception, rejected Wooden’s idealism. He argued that in the “real world,” reputation is the only thing that functions. It’s the currency that buys you the contract, the sponsorship, and the adoration. To Landis, character is just a consolation prize you cling to once your reputation has been torched.

I understand his cynicism. But I fundamentally disagree with it.

Landis views reputation and character as two separate assets you can trade, like stocks. But Wooden’s point was deeper: Reputation is merely the shadow cast by character. You can manipulate the shadow for a while – stand in the right light, distort the angle, make yourself look larger than you are – but eventually, the sun moves. The shadow always snaps back to the reality of the object casting it.

In my media career, I’ve seen this physics play out repeatedly. We live in an industry obsessed with the “shadow” – the ratings, the viral potential, the race to be first. I’m certainly not perfect; I’ve made mistakes in my career. But I’ve learned that the “reputation” of a news organization isn’t built on its speed; it’s built on its credibility. It’s built on the boring, invisible machinery of character: fact-checking, sourcing, and the refusal to cut corners when no one is watching.

A journalist can fake their way to a scoop once. They can build a reputation for being “first.” But if that reputation isn’t grounded in the character trait of accuracy, the fall is inevitable. When the correction comes – and it always does – the reputation doesn’t just dip; it evaporates.

Consider the case of Janet Cooke, a Washington Post writer whose heartbreaking profile of an 8-year-old heroin addict won a Pulitzer Prize. The unraveling of her reputation began, ironically, with a celebration of it.

Her former employer, the Toledo Blade, initially rushed to publish a tribute to their former staffer. But the tone shifted when editors compared the Associated Press biography—based on Cooke’s own resume—against their internal personnel files. While Cooke claimed to be a magna cum laude Vassar graduate with a master’s degree, the Blade’s records told the truth: she had only attended Vassar for a year and held a standard bachelor’s degree. Because the character didn’t match the reputation, the entire structure collapsed. Her prize-winning article, “Jimmy’s World,” was exposed as a complete lie, and the Pulitzer was returned.

I’m seeing a similar tension now as I study the business strategy and ethics of Artificial Intelligence. The temptation in the AI space is to let the “reputation” of the technology—the hype, the valuation, the promise of an AI future—outpace the “character” of the build (safety, bias, alignment).

Landis would argue that we should ride the hype wave because “that’s how the world treats you.” But history suggests that tech bubbles built on reputation without underlying substance always burst. The companies that last are the ones where the internal reality matches the external promise.

Warren Buffett famously said, “It takes 20 years to build a reputation and five minutes to ruin it.” Unlike Landis, Buffett doesn’t see reputation as a mask to wear; he sees it as a fragile byproduct of integrity.

Bob Iger, the retiring CEO of Disney, reinforces this in his memoir, The Ride of a Lifetime: “True authority and true leadership come from knowing who you are and not pretending to be anything else.” For Iger, character and decency are not merely “soft skills,” but strategic advantages that define a company’s success.

Floyd Landis believes he was punished for playing the game. I would argue he was punished for mistaking the shadow for the man. Ultimately, the spotlight always falls on a person’s character, not their reputation.