Tuesday Email: Failures

Read time: ~3.25 minutes

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

We are failing if we don’t share our failures.

From an early age, we learn that failure is bad. It’s something to avoid, something to hide. When we fail, our instinct is to conceal it from others, protecting ourselves from judgment, disappointment, or rejection.

But what if our reluctance to share these failures isn’t shielding us—it’s actually holding us back?

My heart was racing, and my palms were sweaty as I picked up my iPhone to make the call I’d been avoiding for months.

I paced back and forth, staring at the screen, rehearsing my lines like an anxious actor moments before the curtain rises. I wasn’t just afraid of delivering bad news—I was terrified of losing respect, credibility, and trust. An investor with decades more experience than me in wealth management had backed my wealth-tech startup. Now, after months of struggling, we were out of cash and out of time, and I needed to let him know it was over.

As the phone rang, I considered hanging up. But before I could, he answered, his voice warm but unsuspecting.

With a dry mouth and trembling hands, I delivered my carefully rehearsed message: “We’re out of money. We’re shutting down. I’m so sorry.”

Silence hung between us—only a few seconds, but long enough for dread to fill my chest.

Then he spoke, softly and deliberately: “I appreciate your honesty. I’ve been exactly where you are right now. It’s brutal.

But know this: it won’t define you.” In that five-second pause before he responded—my self-worth suspended in the balance—I realized something profound. I had been so afraid of admitting failure that I missed opportunities to ask for help, to share my struggles, and to learn from someone who knew exactly what it felt like to stumble.

By avoiding failure, I hadn’t protected myself. I’d isolated myself.

We often worry about how others will perceive us, believing they’ll judge harshly, lose respect, or distance themselves. But that phone call taught me an important lesson: People are far more understanding of our failures than we imagine because everyone fails.

Our fear of sharing failures stems from a miscalculation. We assume others are always watching, always remembering, always judging. The truth is, no one thinks about us nearly as much as we believe. Each of us is consumed with our own story—an endless, looping movie reel of our successes, anxieties, hopes, and disappointments. If we’re so busy watching our own film, how much mental space do we really have for the daily details of someone else’s?

We also create unrealistic expectations by comparing our uncertain journeys to others’ finished stories. By the time we hear about someone’s success, their failures have been neatly edited out. We see only the tree at its tallest, unaware of the years it spent fighting gravity, storms, and drought to get there. This skewed perspective convinces us our setbacks are abnormal rather than entirely ordinary.

What happens if we start viewing failure differently—not as shameful setbacks but as vital data points, valuable chapters in the ongoing narrative of our lives? When a book offers a profound insight, we’re quick to share it. Why, then, do we conceal our own hard-earned insights just because they originated in our own missteps?

Holding failure inside is like trapping an echo—it gets louder and more distorted each time it reverberates through our minds. Shame and self-doubt grow stronger in isolation. But when we share these failures, we replace echoes with dialogue. Others reach out, grateful for permission to reveal their struggles. Vulnerability breeds connection, empathy, and, ultimately, resilience.

Our industry needs innovation and progress—both of which come at the cost of inevitable failures. If we hide those failures, we deny ourselves and others critical opportunities for learning. We stunt our growth. We limit our possibilities. If we genuinely want to move forward—to build something better for ourselves, our teams, and the families we serve—we must redefine failure. It isn’t a permanent stain on our reputation; it’s proof we’re daring to push boundaries. Sharing our failures openly gives others permission to do the same, forging paths of growth that no single success story could ever achieve alone.

Because the only true failure—the only one we can’t learn from—is the one we refuse to share.

The best is ahead!

-Matt