Last week, iLumn8 B2B partner Ed Gurowitz and I were filming a short video to introduce a new program we’re launching next week. Somewhere in the middle of it — as happens often with us — we veered off-script into a debate.
The question?
Do we learn more from failure or from success?
What followed was a lively back-and-forth (the kind that usually makes an editor sigh and roll their eyes).
It was an off-the-cuff moment — the kind Ed and I are good at — but it stuck with me.
Ed argued that failure is our best teacher — that it’s in the sting of getting it wrong that we really reflect, adjust, and grow.
I countered that success is underrated — that if we only ever learn through pain, we miss half the curriculum life offers.
It was playful, but it got me thinking.
The idea that failure is our greatest teacher is so deeply woven into our culture it rarely gets questioned. In fact, it’s become one of those thought-terminating clichés — phrases that sound wise but shut down curiosity.
You know them:
- “Failure is the best teacher.”
- “What doesn’t kill you makes you stronger.”
- “Every failure is a stepping stone to success.”
- “No pain, no gain.”
Of course, there’s truth there. But when we glorify failure, we risk assuming that only suffering produces wisdom — and that success is just the quiet space between our “real” lessons.
So why is this story so sticky?
Partly because failure hurts. It brings embarrassment, shame, guilt — feelings our minds want to tidy up quickly. “Finding the lesson” in failure gives us back a sense of control, and control feels soothing when life feels uncertain. It also fits neatly with the “100% responsibility” myth — the comforting illusion that if we just learn hard enough from our mistakes, we can prevent pain next time.
There’s nothing wrong with reflection. But somewhere along the way, we built a culture that equates pain with progress — a kind of emotional capitalism where only hardship counts as currency for growth. And that’s expensive and exhausting.
When we glorify failure as our only teacher, we create a loop that keeps us chasing struggle and bypassing joy. It stunts our emotional range and cuts us off from something equally vital: learning from what goes right.
In my own work — and with coaching clients lately — I’ve started asking a different kind of question:
- “What worked?”
- “What can you celebrate?”
- “What can this success teach you about how you thrive?”
Interestingly, elite athletes and artists do this naturally — they study their wins as closely as their losses. They replay moments of excellence to understand flow, focus, and alignment.Why don’t we do that in our personal and professional lives?
Maybe it’s time we did.
We hear it all the time: failure is the best teacher.
But what if success is a teacher too — just one we rarely sit still long enough to listen to?
Failure demands reflection; success invites it.
Yet most of us rush past our moments of success, scanning for the next problem or bracing for when it all might fall apart.
Success has its own curriculum — lessons in joy, gratitude, confidence, collaboration, and the quiet satisfaction that comes when effort aligns with purpose. It reminds us that learning can be steady rather than punishing, expansive rather than corrective.
So maybe Ed and I were both right (but let’s be honest — I was a little more right 😉). Maybe it’s not about which teacher is better, but whether we’re willing to let both teach us — differently.
A practice:
Take a few minutes each day to notice one thing you did well.
Ask yourself:
- What did this success reveal about my strengths or values?
- How did it feel? In your heart and in your body?
- What can I repeat — not to control the outcome, but to understand and create the conditions where I flourish?
Because learning isn’t only born from pain.Sometimes, success itself is the whisper saying: This way, you got this, keep going.