The Truth About Perfection

What it really takes to win

November 7, 2022
min read

Greetings, Chief Storytelling Officers.

I'm finishing up this edition while watching Game 6 of the World Series. As a lifelong Astros fan, it's been an amazing run the past few years with 4 World Series appearances. Here's hoping I'll be celebrating later tonight with some champagne.

This week I want to hit on an idea around perfection.

Back when I was a trial lawyer, I learned that in every closing argument I would have moments of perfection but never be perfect.

This idea helped me announce ready for trial when other prosecutors would ask for a continuance to delay the trial. By the end of each year I'd try 3x-5x more cases than most prosecutors because I knew I would never try the perfect case. I just got into the courtroom and went after moments of perfection.

That idea has always stayed with me and today let's get into what that means for you as a storyteller, founder, and high performer.


DEEP DIVE: Perfect isn't Perfection

This summer, I watched track and field star Sydney McLaughlin OBLITERATE the women’s 400 meter hurdles record at the World Athletics Championships. Previously, no woman had ever attained a sub-51 second time, and Sydney clocked in at 50.68.

As I watched it, my jaw was on the floor. I got chills and my eyes filled with tears. The level of greatness and talent being displayed was so incredibly beautiful and moving. I was witnessing a perfect moment.

After Sydney accepted her gold medal, I listened to how she talked about her win. When asked how it felt, she shrugged. “We thought we’d be a little faster,” she said.

(A side note: the “we” she’s referring to there is both her and her coach. Because even though she’s the one running, they’re a team, and they train, gameplan, and execute together.)

How crazy is that? You just set a MASSIVE world record and your answer is “we thought we’d be a little faster?”

I see this all the time in people at all stages of their craft—they’re chasing perfection.

Back when I was a trial lawyer, I’d go into the courtroom and argue before a judge every day. Many times it was a probation revocation, sometimes it was a hearing or a motion, and other times it was a full-blown trial.

When I’d speak to the judge or the jury, there were times I knew I had them, that they were with me and picking up what I was putting down. But I also knew that I got something a little bit wrong. Maybe I’d forgotten something, or phrased something in an awkward way. In other words, I wasn’t perfect. And sometimes, that would eat me up—even if I got the verdict I wanted.

Perfectionism is a very normal thing to desire. Psychology Today states that it’s driven primarily by internal pressures, such as the desire to avoid failure or harsh judgment, “There is likely a social component as well, because perfectionistic tendencies have increased substantially among young people over the past 30 years, regardless of gender or culture. Greater academic and professional competition is thought to play a role, along with the pervasive presence of social media and the harmful social comparison it elicits.”

The article goes on to say that striving for perfection can lead to negative outcomes like procrastination or a tendency to avoid tough challenges. It’s known to contribute to depression, anxiety, and obsessive-compulsive behavior.

We’ve been conditioned to think about seeking perfection as a flaw, but I’d argue it’s not only a good thing—it’s something that you SHOULD aim for.

Here’s why:

Perfection is Rocket Fuel

Let me get something out of the way right off the bat: Perfection is an abstraction. It CANNOT be attained because it does not exist.

And while we all logically understand that achieving perfection is impossible, our lizard brain still seeks it. That’s okay—you can’t fight nature—but WHY you seek it matters a lot.

There are two types of perfectionists: positive perfectionists and negative perfectionists. Positive perfectionists are achievement-oriented, while negative perfectionists are failure-oriented. Positive perfectionists want to win, negative perfectionists want to not lose.

That’s a HUGE difference, and if you fall into the latter category, it’s something you need to switch in your brain right away. Because when we tell ourselves “don’t fail, don’t fail,” what our brain hears is FAIL. We’re not capable of processing the “don’t” part.

Negative perfectionists are the ones who attract all of the nasty side effects—the anxiety and depression. Positive perfectionists, on the other hand, have learned to harness their desire for perfection and use it like rocket fuel.

I know you were worried that I might make it through a newsletter without mentioning Kobe Bryant, but allow me to assuage your fears. Mamba hungered for perfection like few others did, and he channeled that hunger into motivation.  “What I’m doing right now, I’m chasing perfection,” he said. “And if I don’t get it, I’m going to get this close.”

Kobe wanted to master every aspect of his game, which is why he spent countless hours in the gym. He was a positive perfectionist, taking pleasure in facing the next challenge.

This is helpful not just on the basketball court but in all life domains. When you seek perfection in a positive way, it allows you to become more reflective and proactive. You respond to failure by examining your process, analyzing the results, and making adjustments to improve them in the future.

There’s also the whole “shoot for the moon, land among the stars,” aspect of seeking perfection. “Perfection is not attainable, but if we chase perfection we can catch excellence,” legend Vince Lombardi told his players on his first day of coaching the Green Bay Packers in 1959. The team had gone 1-10 the season before, but Lombardi’s mindset had an immediate impact on the locker room. “Shortly after Lombardi’s speech, [quarterback Bart] Starr called his wife and told her the Packers were going to win lots of games,” reads an ESPN article.

I probably don’t have to tell you Lombardi went on to be considered the greatest coach in American sports history. He won five NFL championships in seven years, and the Super Bowl trophy now bears his name. He never quite achieved perfection, but looking at his career, I doubt anybody cares.

Perfect Moments, Not Perfection

Another important aspect of perfection is the remembering difference between perfection and perfect moments.

The reason I got goosebumps watching Sydney McLaughlin break the hurdles record was because I was witnessing a perfect moment—those times in life where everything feels beautiful and right. It’s the idea that a sunset can be perfect in that moment. Even though you know the world isn’t perfect and won’t be perfect moving forward, you can still FEEL the perfection for that moment in time.

And I think that mindset is why Sydney responded the way she did when the reporter asked her how she felt. She still celebrated the win and appreciated it, but she knew there was more.

This mind shift is what I did to get out of my head when I was in court. Rather than being down on myself for flubbing a line or forgetting a piece of my argument, I relished the fact that what my audience was experiencing was perfection. To remind myself of this, I adapted a mantra: There are moments of perfection, but I’m never perfect.

I saw it as a trial lawyer. You can see it as a founder, when you’re leading your team and you have that great insight, or the first customer pays for your product or service. It’s the reason businesses tape the first dollar they make to the wall—it commemorates that first moment of perfection, even though you know your product isn’t perfect.

Or maybe your moment of perfection comes when you’re talking to someone in your industry and they have no idea who you are. They talk about the tech they’re using and all of a sudden they drop YOUR name as someone they’re considering. Or maybe they show up wearing merch for your company that you never expected to see this soon out in the wild.

Or maybe it's the story you share in the boardroom that highlights why your company should adopt a new direction and every major player gives you the green light. They come to you after the meeting and tell you how that story made it so clear why your view was the right one. You probably know you could have done it better, but it created the perfect outcome.

Those are moments of perfection. But we always know there’s more. Every successful founder knows the product, the business, is never perfect. And to me, the beautiful thing about life is that we get to have these moments of perfection even though we’re never perfect. So we get to experience and feel it and know there’s always more.

That’s what keeps pushing the best. That’s what you’re after. As a founder, a speaker, a storyteller. That’s why Performative Speaking wants more founders to share their stories and develop into world-class storytellers.

Because you’re going to have that moment where someone comes up to you and says “aren’t you so and so building this?” or “your story showed me how I could be a founder just like you.”

You can inspire a generation—even if you don’t ever achieve perfection.

You can change the future in a massive way if you're ready to create those perfect moments and never give up on the journey towards perfection.

RESOURCES for Founders and Storytellers

What do Luke Skywalker, John McClane, and a lonely dog on Ho’okipa Beach have in common? Simply put, we care about them. In the book, Damn Fine Story: Mastering the Tools of a Powerful Narrative, author Chuck Wendig walks through how to get your audience to care about the story you’re telling. Wendig is great and snarky and, at times, a little crude. Using a mix of personal stories, pop fiction examples, and traditional storytelling terms, he helps you internalize the feel of powerful storytelling. If you want to up your storytelling game, pick this one up.

US VC deal value for female founders reached $32.4 billion through Q3 this year, but we need that number so much higher. There's still a huge issue in the venture ecosystem when it comes to funding disparities. The latest edition of Pitchbook’s All In Report breaks down the numbers by cities, sectors, and exit activity. Check it out here.

A lot of problems worth solving aren’t the ones that you can solve in a year or two or even 10. For founders and investors alike, such long timelines can seem daunting. But for Gene Berdichevsky, co-founder and CEO of batter tech startup Sila, hard tech problems are also some of the most tantalizing. This TechCrunch article explains why.


This week I'll be down in Brazil for some work with Latam founders and VCs. I'll also be at the event put on by Latitud and Jason Yeh in Sao Paulo.

If you're down that way, make sure to say hello.

One ask this week. If you've found this newsletter valuable this week or in past weeks, sharing it with other founders, investors, and storytellers would be amazing.

See you next week.

If you think that becoming a world-class storyteller and founder is something you want help with, that's what my consultancy at Performative Speaking does. We've helped founders raise rounds ranging from 2 million up to over 50 million. Talk with my team by applying here to see what that might look like for you.

Know someone who might enjoy this?

Read other issues: