5-Minute Insight: Letting Go in 2026, Part 3 - Pain of Failure
“Would you like me to give you a formula for success? It's quite simple really. Double your rate of failure.”
— Thomas J. Watson, IBM Founder
In this four-part series, we're resolving to let go of four “P's” in 2026. To read Parts 1 and 2, click here. So far, we've released:
1. Perceived Limitations
2. Past Hurts
Today, we confront the third:
3. The Pain of Failure
Concerns about failure can dominate our thinking.
They whisper in advance (“What if I mess this up?”) and shout afterward (“How could you have done that?”).
Whether it's anticipatory regret or the aftermath of a mistake, the pain of failure can paralyze us — limiting our potential and robbing us of joy.
But failure is not the enemy. Unprocessed failure is.
Here are three powerful ways to cope with it.
1. Understand It
“Life is like baseball. A great hitter is only successful 3 out of every 10 times… Life, like baseball, is set up for you to fail. But it's not about how you fail… It's how you bounce back.” — Unknown
Baseball is a game of failure.
A .300 hitter fails 70% of the time — and is considered great.
So first ask:
• Were my expectations realistic?
Is this truly catastrophic — or is it part of the normal rhythm of trying hard things?
• Which part do I own?
If you're accountable for 50% of the outcome, own 100% of your 50%. When discussing a mistake, resist the urge to highlight what wasn't yours.
Acknowledge your role and outline the corrective steps you've taken.
• Am I keeping this in perspective?
Early in my career, I was promoted to CFO of a behavioral healthcare company.
A few months in, I mistakenly signed a contract obligating the organization to a long-term lease. (Yes, I still cringe typing that.)
I was mortified. When I confided in my brother, I was dramatic — maybe even apocalyptic. He calmly responded:
“You just haven't screwed up enough before.”
He was right.
It was my first big failure. It wasn't my last mistake — but it was the last of its kind.
A thoughtful postmortem doesn't deepen the pain. It transforms it. When you analyze expectations, accept responsibility, and regain perspective, failure becomes data — not identity.
It might sound counterintuitive, but repeated failure often predicts success.
Research on smoking cessation shows that most successful quitters try 6-10 times before it sticks. Those early attempts aren't wasted--they provide data. Each one reveals triggers, refines strategy and builds resilience.
Failure, when understood, becomes feedback--and feedback becomes progress.
2. Reframe It
Marcus Aurelius wrote, “The obstacle is the way.”
Modern leadership examples underscore this truth.
As a young reporter in Baltimore, Oprah Winfrey was promoted to news anchor. She was later demoted for being “too emotional” and “too involved in other people's business”.
That demotion redirected her to daytime television.
The obstacle became the way.
Failure often reveals how we're wired — what energizes us, what doesn't, and where we still need growth. A setback can prevent a larger misalignment later. When we view life as a series of experiments rather than verdicts, we gain freedom.
Sara Blakely, founder of Spanx and once the youngest self-made female billionaire, grew up with a father who asked nightly at dinner:
“What did you fail at today?”
Failure wasn't shameful in her home. It was evidence of courage.
She later said, “Once you redefine failure as not trying, life opens up in many ways.”
Reframing failure turns it from humiliation into information.
3. Celebrate It
I'm not kidding.
I once had a boss who was unexpectedly let go after eight years. On his last day, he invited 20 colleagues to a happy hour across the street. No bitterness. No drama. Just basking in the attention, affection and well wishes of his friends.
It was extraordinary.
Some organizations formalize this practice. Intuit — the maker of QuickBooks and TurboTax — has been known to celebrate failed projects to reinforce its culture of innovation and risk-taking.
Humor restores perspective. Even if you can't laugh yet, you can say:
“Whew! I survived.”
“Glad that's over.”
“I can handle hard things.”
That alone is worth celebrating.
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Failure is not a character flaw. It's a marker along the road to a fulfilling career and a well-lived life.
If you are stretching, risking, leading, building, reinventing — you will fail. And if you process it well, you will grow faster than those who play it safe.
In 2026, let's release the pain of failure — not by denying it, but by understanding it, reframing it, and even celebrating it.
Because the goal is not to avoid failure.
It's to double your times at bat.
If you're navigating a setback or standing at the edge of something new, I'd love to talk with you. You can book a complimentary introductory session here.
Warmly,
Sally