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Once a week, I take one idea and put it under the microscope. Sometimes it’s about business, sometimes it’s about how people think, and sometimes it’s simply an observation about the world around us. If it challenges the way you see the topic, then it has done exactly what it was meant to do.

Last week, my family and I spent a few days in Lisbon, Portugal.

The trip wasn’t just a vacation. We went there to get a feel for the city and see whether it might be a place we’d want to live. After spending a couple of years in Bulgaria, life here has become comfortable and predictable, and if I’m being honest, a little boring.

There isn’t much of an expat community where we live, so over time, daily life settles into a routine that feels a bit too familiar.

That’s why trips like this are refreshing. They shake things up a bit and remind you how much you enjoy being around interesting people.

One thing I always look forward to when we get back from traveling is reconnecting with friends.

After we returned from Portugal, we met up with a family we hadn’t seen in a couple of months. They had been traveling as well, so it felt like a bit of a reunion. They have two kids, and their older son—who’s about twelve now, roughly the same age as my daughter—has recently been going through something interesting.

Or maybe concerning is the better word.

His parents told me about an assignment he had for school. They’re doing remote schooling, which means the kids follow the same curriculum as a regular school, but they attend the lessons from home.

The assignment was simple. He had to record a short talk on a geography or history topic while his mom filmed him.

That should have taken fifteen minutes.

Instead, it turned into a two-hour ordeal.

Every time he stumbled on a word or lost his train of thought, he would stop and insist on starting over. He wanted a perfect take. No mistakes, no pauses, no imperfections.

After an hour or two of this, frustration took over. He threw a bit of a fit and went outside to cool off.

His parents told me this has been happening more and more lately. The older he gets, the more he struggles with making mistakes. Even small things feel personal to him, and the moment something doesn’t go perfectly, he shuts down.

We started talking about why that might be happening.

His parents thought it might just be part of his personality, something he was born with.

I disagreed.

To me, this looked like conditioning.

One thing before I continue…

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My mother was a music teacher for decades before budget cuts eliminated her position. My father was a mechanical engineer whose experience became irrelevant overnight.

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Back to what I was saying...

If you think about how the traditional school system works, perfection is the standard we’re trained to chase from a very early age. Students sit in a classroom, listen to the teacher, read the textbook, memorize the right answers, and repeat those answers during exams.

If the answer matches what the teacher expects, you get rewarded.

If it doesn’t, you get penalized.

Over time, that process quietly trains children to believe that mistakes are something to avoid at all costs.

Most kids don’t enjoy getting bad grades. They want approval from their teachers and their parents, and they quickly learn that perfection earns praise while mistakes bring disappointment.

So they adapt.

They become careful.

They become cautious.

And eventually, they become afraid of getting things wrong.

The problem is that life outside the classroom works very differently.

In school, memorizing the right answer is usually enough.

In real life, most learning happens through experience—and experience is rarely tidy. It involves trial, error, wrong turns, broken ideas, and the occasional embarrassing failure.

The people who move forward in life tend to be the ones who are willing to make those mistakes and learn from them.

The ones who stay comfortable rarely grow very far.

That’s why I found that moment with our friend’s son so interesting. He’s a bright kid, curious, thoughtful, and full of potential. But the more he absorbs the idea that everything must be perfect, the harder it becomes for him to take risks.

And risk is where growth lives.

Without risk, people stay in the same lane for years. Their income stays predictable, their relationships stay predictable, and their ambitions quietly shrink to match the boundaries of their comfort zone.

Occasionally, someone encounters a mentor or a life experience that flips that mindset completely. Something happens that shows them mistakes are not the enemy—they’re part of the process.

But for many people, that realization arrives very late.

Or not at all.

Watching that situation unfold reminded me of something I try to keep in mind when building a business, writing emails, or trying new ideas.

Progress almost always begins with imperfect attempts.

The first version of something rarely looks impressive. The first draft is rough. The first campaign underperforms. The first attempt feels awkward.

But each attempt teaches something.

Those lessons stack on top of each other until eventually the mistakes stop feeling like failures and start looking more like stepping stones.

Which is why perfection is such a dangerous standard to chase.

Perfection keeps people waiting.

Growth belongs to the people who are willing to begin before everything looks flawless.

A small thought I’ve been carrying with me this week.

P.S. If you enjoy these ideas, you’ll love the deeper conversations we have on the List Building Lifestyle podcast.