Ep. 180 - Why Messy Is the Best Medicine for Perfectionism and Procrastination

You only do something for the first time once. Every expert was once a beginner who was willing to step into the unknown and learn through the messy middle. In this episode, we’re talking about why waiting for “perfect” only keeps us stuck and how progress always begins with willingness, not perfection. Whether it’s a new habit, a creative project, or a goal you’ve been putting off, this is your reminder that messy starts still count—and that momentum is built one imperfect action at a time. 

Transcript

Recently, I got to be a co-host for two award luncheons. This took place over two days in New York City. I’ve hosted plenty of events before, but this awards format was new to me. Two hundred-plus people had to get in and get out of a ballroom in about two hours, and there were 20+ categories, each with multiple nominees. 

My co-host had done these ceremonies before and, thankfully, had a 56-page script to keep us on track–yea 56 pages. Even with that, on the first day, I stumbled in several places. At one point, I started announcing the next category while a previous winner was still walking up to the stage. I laughed and adjusted, clearly claimed my beginner status. By the second day, though, it was much more smooth. I was much more confident - after all, I wasn’t a first-time awards host anymore.

The Bottom Line on Top of this episode is that you only do something for the first time once.

The writer Anne Lamott says this better than almost anyone. She wrote this: 

“Almost all good writing begins with terrible first efforts. You need to start somewhere. Start by getting something, anything, down on paper.”

And she also warned:

“Perfectionism is the voice of the oppressor … it will keep you cramped and insane your whole life, and it is the main obstacle between you and a shitty first draft.”

That phrase, shitty first drafts, has become a mantra for many writers and creators, but it applies to life, too. Every time we try something new, we’re drafting. And drafts are supposed to be messy.

I saw this same truth years ago when my son spent a year in high school at an intense golf academy, he was training with a series of elite coaches. One afternoon, after taking a bad swing and feeling frustrated, his coach walked over to him and said, “Celebrate getting the bad shots out. Every swing teaches you about your own game.” 

Brain science backs this up: when we stretch into something new, our brains actually rewire faster. That discomfort you feel is neuroplasticity in action - your brain literally building new pathways.

So go ahead and get the bad swings out so you can start to learn your own rhythm.

Here’s the psychology of why this matters. 

Most of us hesitate to raise our hands, literally and figuratively. Studies show we overestimate how badly others will judge us. Psychologists call this the spotlight effect. We think everyone is scrutinizing us, when in reality most people barely notice. And many are just relieved it isn’t them up there–that’s the human part of us humans.

We also are likely to underestimate how willing people are to help or make room for us. Researchers at Stanford university found that people are much more likely to say yes to a request than we expect. And they’re also far less critical of us than our inner narrator predicts. 

When we raise our hand, something important flips. People are often silently grateful that we spoke up first, that we asked that question or that we were willing to try. Authenticity and effort connect more than perfection. Messy doesn’t push people away; messy makes us human. And more willing to be messy again. 

About a  week after the awards shows, I saw a post online about an invite-only event for women podcasters, entrepreneurs, and content creators. My first thought was, wow, I wonder how they found all those cool people. And then I realized, hey wait a minute, I could be one of those people. My business coach, Dave, has a great nudge when it comes to being bold. He’ll say: It’s always worth the question. 

So I decided to raise my hand and I sent a note to the organizer (who doesn’t know me) asking if I could be considered, if not this year then maybe next. Within half an hour, I got an enthusiastic yes. 

So next month, I’ll walk into a room where I don’t know anyone. But I will do that only once; because after that first walk, they won’t be strangers anymore.

So this is your nudge this episode. Where can you be new at something? If not new, where are you willing to be messy? Is there an opportunity to raise your hand? It doesn’t have to be dramatic. Share an idea. Ask to be included. Send a note to someone you admire.

How many chances are you willing to take? And where can you give yourself the gift of a first time, knowing that you only have to do it once?

Because once you do, you’ve already moved the bar. And whether it’s in front of hundreds of people or just within the quiet of your own space, what matters most is that you showed up. Each time you do, you build that muscle, find a rhythm, and get one step closer to the next Next.

Perfectionism and procrastination lead us up lonely staircases that never seem to end. I’ve climbed enough stairs.

Messy is a playground for first-timers, for those willing to raise a hand and give it a try. And the beauty of a playground is this: once you step onto it, you’re no longer new. And I bet you’ll find yourself in pretty good company.