Why the stumble is part of the swing — and how to start taking risks worth taking
We have failure backwards. We treat it as an ending, a verdict on our ability, our worth, our potential. We rehearse it in worst-case scenarios before we even begin. We fear it. We hide it. And in doing so, we confuse the raw material of success with the outcome.
Failure is not the wall. Failure is the door.
Success has always had a prerequisite
History’s most celebrated achievements sit on a foundation of spectacular, unglamorous failure. I’m sure you’ve heard of Edison finding 10,000 ways NOT to build a light bulb. That Michael Jordan was cut from his high school varsity team. Or that the first Harry Potter book collected twelve rejections before a publisher’s eight-year-old daughter begged her father to keep reading the manuscript. The pattern is not coincidental. It is structural.
Success does not visit those who avoid failure. It follows those who accumulate it, study it, and refuse to let it be the final word. Every expert in any discipline, whether sports, architecture, jazz, or entrepreneurship, arrived there by doing the thing badly first. Then less badly, then well. Competence is built from repeating failure, on repeat, then tweaking it.
“No one steps up to the plate for the first time and sends the ball over the fence. The homerun belongs to the person who has already swung and missed — a hundred times, in front of a crowd.” If you’re tired of the baseball metaphors, just bear with me. We are deep into baseball All Stars, mainly because my ten year old’s team didn’t let failure set them back. This season the most impressive skill they learned was resilience. Shake off the last strike out and swing again. This time smiling at the opposing pitcher the whole time. It’s a whole vibe.
No one hits a homerun their first time holding a bat.
There is a particular insanity in expecting mastery from a beginner. And yet we do it to ourselves constantly. A newbie picks up a bat, swings at a curveball, misses, and privately decides this means something about me. It does — but not what they think. It means they are exactly where every skilled hitter once stood. At the beginning.
Expertise researchers have a name for this: the learning curve. What they don’t always say loudly enough is that the curve is built from failures. Each miss recalibrates the nervous system, adjusts the grip, teaches the eye. The swing that connects and leads to a Grand Slam exists only because of the fifty swings that came before it and went nowhere. Failure is not the opposite of the homerun. It is, quite literally, the training data for it.
If you missed my brag about my ten-year-old hitting a grand slam, I’m just going to quietly put it here. It makes me so proud especially because I remember the first practice of the season when my son kept striking out and we had to have the real talk about “if you want to get better, you have to practice and put in the work.” Every missed swing gets you closer to the one that connects.
What if those around you aren’t as encouraging?
Anyone who makes you feel like a failure is not a leader, they are a liability. If you run an organization, listen closely.
There is a difference between honest feedback and shame. A good manager/coach/mentor points at the miss and asks: what do you notice? A poor one points at you. When someone in your life — a boss, a partner, a colleague — uses your stumbles as evidence of your inadequacy rather than as information you can use, they are not developing you. They are diminishing you.
Research pioneered by Harvard’s Amy Edmondson, is unambiguous: teams and individuals perform better when they have psychological safety (e.g. they have permission to fail). They take more creative risks, report errors faster, solve harder problems. When they feel safe to fail without ridicule. Leaders who weaponize failure don’t produce excellence. They produce silence, compliance, and people who stop trying. If someone makes you feel small for falling short, that tells you something about their capacity to lead, not your capacity to grow.
Five ways to reframe failure — starting today
- Run a “failure audit” on someone you admire. Before you attempt something new, spend 20 minutes researching the setbacks of someone who has done it well. Read the interview where they got honest. You’ll find the failures hiding behind the highlight reel — and the distance between their early stumbles and their current mastery will recalibrate your timeline expectations entirely. There is no such thing as an overnight success.
- Take one “low-stakes swing” today. Identify something you’ve been avoiding because you might not do it perfectly — send the email, pitch the idea, try the sketch, start the paragraph. Make the stakes deliberately small. The goal is not to succeed. The goal is to practice the muscle of beginning under uncertainty and surviving the outcome.
- Debrief instead of dwell. When something doesn’t land, give yourself a structured five minutes: what happened, what I’d change, what I’ll carry forward. Then let it go. Rumination turns a data point into a sentence. A debrief turns it into a tool.
- Reflect who you’re taking failure cues from. Spend one week noticing whose voice shows up when you stumble. Is it someone who has attempted hard things and grown — or someone who has played it safe and called it wisdom? Your inner critic has a source. Make sure it’s worth listening to. My favorite adage is “no one doing more than you will criticize what you are attempting.”
- Define your “worthy risk” for this month. Write down one risk you’ve been avoiding — one that, if it didn’t work, you’d survive, and if it did, would change something real. Commit to a date by which you’ll take it. Failure and success both require you to show up. Right now, only one of them is waiting for you to move. Do what Anna Mack calls “shoot your shot Wednesday.”
The Bottom Line
The homerun is not the reward for never missing. It is the reward for swinging anyway — enough times, in enough directions, with enough willingness to look foolish in the process. Failure is not what we think it is. It never was. It is simply the price of admission for everything worth doing.
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If you want some additional encouragement, here are some other “big failures” who used their experience to achieve even bigger:
Dave Limp
From leading Amazon’s biggest flop to becoming the CEO of an aerospace company
The Amazon Fire Phone — launched in 2014 under Limp’s watch as SVP of Devices — became one of the most publicly mocked product failures in tech history, generating a $170 million loss in a single quarter. Bezos didn’t fire him. He kept trusting him. Limp went on to build Echo, launch Alexa, and oversee Project Kuiper. In December 2023, he became CEO of Blue Origin — a space company with over $10 billion in customer orders — despite having no background in aerospace. The man behind the Fire Phone is now running rockets. That is not a punchline. That is a data point.
Jamie Kern Lima
Told she was the wrong body type to sell beauty products to billionaire and first woman CEO in L’Oreal’s history
A male investor told her he didn’t believe women would buy makeup from “someone with her body and weight.” He thought he was being kind. QVC said no for three years. Sephora said no for six. She built IT Cosmetics from her living room anyway — using models of all ages and sizes, going on live TV and showing her own rosacea — until her products sold out in minutes. L’Oréal bought the company for $1.2 billion in cash, and she became the first female CEO in L’Oréal’s 108-year history. The investor who told her she was the wrong kind of woman to sell beauty products was describing his own failure of imagination, not her ceiling. He later apologized to her directly when L’Oreal purchased her company.
Whitney Wolfe Herd
Forced out, publicly smeared Co-founder of Tinder to Youngest female self-made billionaire at Bumble
She helped build Tinder into a cultural phenomenon as VP of Marketing, then was forced out in 2014 amid a sexual harassment lawsuit and a media storm that painted her as a liar and opportunist. She founded Bumble the same year — a dating app built on the principle she had learned the hard way: women deserved to be in the driver’s seat. When Bumble went public in 2021, she became the youngest female self-made billionaire at 31 and the youngest woman to take a company public. The humiliation wasn’t the end, it was what fueled her success to show them just how wrong they were about her.
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Yvonne Lee-Hawkins is a Holistic Career & Burnout Coach supporting high-performing professionals through career transitions, leadership challenges, and burnout recovery.
She also helps recent graduates land their first career. You can find out more on her website, or follow her on LinkedIn, Medium, or Instagram.
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