WHEN PERFECTIONISM CONFUSES ITERATION FOR FAILURE
When I wrap up work each day, I shift into mom mode which often includes homework support. Recently, 11 year old had to write a short story about someone he considered a hero*. He worked hard on it, finished it, and felt done. I like seeing my kids through their school work and to offer support so I asked to read it. I wasn't trying to make it perfect, I genuinely enjoy seeing how my kids think, and I wanted to understand his approach and offer support if it was helpful. I asked one question to clarify some deatails and he panicked. While throwing his arms down at his side, he said 'I have to redo the whole thing!'
As far as a parenting moment - eek! That is a hard mindset to redirect. From a perfectionism standpoint, it made complete sense. In his mind, he’d started the project when everything felt clear. He had a plan. He executed it. And once he had finished, that meant the project was finished. Any suggestion to revisit it felt like proof that he had done it all wrong. That’s a familiar feeling for a lot of adults, too.
What he’d forgotten, until we slowed down, was the rubric. There were details he hadn’t looked at again after mapping the project in his head. He simply had a plan, and once the plan was in motion, he assumed it was complete. When we reviewed it together, it was clear he didn’t need to start over, scrap his idea or his work and redesign the entire assignment. He just needed to adjust a few things.
Perfectionism often confuses iteration with failure; with being wrong. The clarity my son needed wasn’t missing. It just hadn’t been available until something existed. This experience mirrors how perfectionism shows up in so many areas of adult life, especially in leadership, creativity, and innovative work. When perfectionism is in the driver’s seat, starting feels like a declaration: I have this figured out. And finishing feels final. So any feedback, adjustment, or new information can feel destabilizing, as if it invalidates the original effort. Most meaningful work doesn’t function that way.
Clarity rarely comes before you begin. It comes because you begin. Action brings information you couldn’t access from thinking alone; drafts reveal gaps and conversations surface assumptions. And yet, I see smart, capable people delay starting all the time because they’re waiting for a level of certainty that only comes through movement. They tell themselves they need: more time, more alignment, more confidence or more clarity. What they often really need is permission to let the first version be incomplete (ahem, not perfect). In situations like this, perfectionism becomes costly because it treats revision as evidence of being wrong rather than part of the process. Over time, this mindset slows down progress and erodes confidence. People begin to associate starting with stress. They avoid work that matters to them because the emotional cost feels too high.
Ironically, waiting for clarity can be the very thing that prevents it.
I see this often in leaders who are thoughtful and conscientious. They care deeply about doing things well. They don’t want to create unnecessary rework or confusion. They hold themselves to high standards that sometimes quietly turn into barriers. What would shift if iteration felt neutral instead of threatening? What would change if starting didn’t require certainty, only curiosity?
What I appreciated most about that moment with my son is that it reminded me how early these patterns form, and how gently they can be interrupted. Once he realized he didn’t need to redo everything, his calmed down and with support tackled it. The work felt manageable again and he didn’t feel alone in it. He could move forward. That’s true for adults, too. Progress doesn’t require having it all figured out. It requires being willing to begin, noticing what you learn, adjusting from there and sometimes accepting help.
So if you find yourself waiting…it may be worth asking a different question: Where might clarity be something you discover after you start, not before? And what might become possible if iteration didn’t feel like failure but simply part of the work? If you want to explore the answer together, please reach out!
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🚇 Proud to say he wrote about his paternal great-grandfather; who he shares a name with and who in 1978 saved a man from getting hit by a train! That's another story for another post though.