The Enemy of Good

Hello,

My name is Heather, and I’m a recovering perfectionist.

For a long time, I believed perfectionism was a strength. It felt like a high standard, something worth striving toward. In practice, it did not give me joy. It gave me stress. It made me hesitate, question whether I should even begin something if I could not do it exactly right, and sometimes stop midway because I felt too far from where I thought I should be.

Perfectionism is deceptive in that way. It does not just show up at the finish line demanding excellence. It shows up at the starting line and quietly asks, “If you cannot do this perfectly, why start at all?” Even when I did begin, it lingered, reminding me how far away I was from the outcome I had imagined. This is how great becomes the enemy of good.

That tension led me to a question I could not ignore: how do we develop the will to do something when we do not yet have the skill to do it well? That question became much more real for me when I became a parent. I realized very quickly that I could not hold myself to perfection. It simply was not possible. If I could not hold myself to that standard, then I could not expect it from my children either. That realization forced me to rethink everything. It changed not only how I approached parenting, but how I understood growth, effort, and what it actually means to make progress.

What I began to notice is that we already understand progress better than we think we do. Consider a child learning to speak. A child does not begin with full words or sentences. The process starts with sounds, fragments, and approximations. When a child says “ma,” no one corrects them for not saying “mom” or “mommy.” People celebrate it. They record it. They encourage it. They create an environment where that imperfect attempt is recognized as meaningful progress.

That imperfect attempt is what I have come to understand as an approximation. It is not the final form, but it is moving in the right direction. Over time, something else happens. The child continues trying. The sounds become clearer. The words become more precise. “Ma” becomes “mom,” then “mommy,” and eventually full sentences. Each attempt builds on the last and creates a new version to grow into. That ongoing cycle, where one attempt leads to the next and creates a new target, is iteration.

Children live in both of these naturally. They approximate, and then they iterate. They try, adjust, and try again without expecting perfection at the outset. Adults celebrate them every step of the way. The question is why we do not offer ourselves the same grace.

At some point, many of us stop treating our own efforts like approximations and start treating them like final evaluations. Each attempt becomes something to judge rather than something to build from. That shift is where perfectionism takes hold.

There are examples of iteration and approximation all around us. The first iPhone is one of them. When version 1.0 was released, it was revolutionary. It was celebrated and widely adopted. At the same time, teams were likely already working on version 2.0. The goal was never to create something final. The goal was to create something that could improve. This is why the latest iPhone is the 17, but we all know there are many more to come.

That first version was also an approximation. Compared to what exists now, it was limited. It lacked features that are now considered essential. It was still necessary. Without it, none of the later versions would exist.

People understand this when it comes to products, innovation, and history. The first Model T or the first airplane carries value because they represent a beginning. That same level of appreciation is rarely extended to personal effort. Early attempts are often dismissed for not being what later versions might become.

This idea became more personal for me through running. When I first used the RunDouble (a couch to 5K app), I could not run a 5K. The program is structured around intervals, alternating between walking and running in manageable segments. The design is intentional. It builds endurance and confidence over time.

During my first attempt, I did not realize how many intervals there would be. I remember reaching the sixth run interval and thinking, “When is this going to end?” I stopped running at that point and walked the rest of the session, even though I later realized there were only 2 run intervals left. Even though I only ran for a total of 6 one-minute intervals. I still finished, but not in the way I had expected. That run was an approximation. It was not perfect, but it was not failure either. It was a step forward.

The program itself reinforces this approach. It does not expect someone to go from zero to running 3.1 miles without stopping on day one. It expects consistency. Three sessions a week. Ten weeks of gradual progression. Each session builds on the last. Each interval contributes to a larger goal.

Eventually, I was able to run a full 5K. That outcome did not mark the end of the process. It marked the beginning of a new one. I set a goal to run faster. After that, I set a goal to run farther. Each completed goal created the next one. That is iteration. At the same time, every run, whether strong or difficult, remained an approximation.

This is how iteration and approximation work together. Iteration provides direction by continually redefining what comes next. Approximation provides permission by allowing imperfect action within each step of that process.

Perfectionism disrupts both. Perfectionism tricks you into focusing on the final outcome rather than the first step, and that makes starting feel overwhelming. Perfectionism makes continuing feel discouraging because attention is fixed on the distance still remaining instead of the progress already made.

There is a concept in The Gap and the Gain that illustrates this clearly. Measuring success by the gap, the distance between the current state and the desired outcome, creates a constant sense of falling short. Measuring success by the gain, the distance traveled from the starting point, creates space for recognition and motivation. Perfectionism lives in the gap. Progress lives in the gain.

This brings me back to where I began. Hello, my name is Heather, and I’m a recovering perfectionist. The first step in that realization was acknowledging that perfection was not a sustainable or meaningful standard. I could not hold myself to it, and I could not hold others to it either. That acknowledgment did not solve everything, but it changed how I approached the process.

Each step since then has been an exercise in iteration and approximation. I set a goal, attempt it imperfectly, adjust, and continue forward. I am learning to accept what I cannot control, to find the courage to change what I can, and to develop the awareness to recognize the difference as I go.

The process is not perfect. It is progressive. Progress is not about arriving at a final version of yourself. It is about continuing to move, adjust, and grow. In that movement, there is something that perfection never provided. There is joy.

~Heather

P.S. The Olympics have a way of stretching our sense of what is possible. That is why my Catch of the Week this week is a short clip from Diana Kander that pairs perfectly with this idea.

In the video, she shows a gold medal winning vault from the 1956 Olympics next to what wins today. The difference is almost hard to believe. She jokes that there are probably people watching that old clip thinking, “What? I can do that.” But at the time, that was as good as it got.

Now we watch Simone Biles and think the same thing. This is the peak. This is the limit. But it is not. Why? Because somewhere, someone is watching Biles and thinking, “I can do that… and maybe even better.”

The thing is, progress always looks final until it is not. What feels like the ceiling today is often just the latest approximation of what is possible. So whether in sports, leadership, or our own growth, the question is not whether something is the best. It is whether we are willing to keep building on it. "We have to be able to imagine a future where things are better. That is how we will create it."

P.P.S. Please remember to...

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