Why Messy and Imperfect Still Wins in Business

I just finished a quick 12.5 miles on my Peloton and nearly tripped over my own bike shoes running to my laptop, because I had something to tell you that could save you six figures in wasted courses and coaches.

Just start. That’s it. That’s the advice.

Obvious? Yes. Something you actually do? That’s the harder question.

As a business owner, you’re going to get hit from every direction with messaging about the “right” way, the “best” way, the newest hack. It changes faster than the algorithms everyone’s chasing. But the truth is simpler than any of it: the only way you actually learn is by doing.

And the early days of doing are messy.

I Built a 220,000 Download Podcast Without a Plan

In 2021, I started my podcast without researching how to structure a good episode. I recorded on a $60 microphone. I crossed 100,000 downloads with that same cheap mic.

“Do you ever listen to your own episodes?” a friend asked me early on.

“Nope,” I told her. “Because then I’d stop recording.”

I’m sure those early episodes weren’t great. I still don’t know, because I’ve never gone back to listen. I just kept recording. Kept publishing. Got the reps in.

Five years later, I still carry that same attitude, in my business and everywhere else.

Recently, I hit play on one of my own episodes while heading to the gym, one of the most vulnerable ones I’ve ever recorded, about how grief has reshaped the way I run my business. I almost thought about pulling it before it published. I felt like I could have done it better.

But by now I know: publishing teaches me something listening never will. So I let it play, and I listened as an observer instead of a critic.

I heard twelve things I’d do differently. The intro needed to be tighter, for one.

Here’s the thing, though. If I’d waited for the perfect intro, or gone back and picked apart my 2021 episodes, I would have quit by episode eight, if I made it that far. I never would have reached 290+ episodes and 220,000 downloads. I still see plenty of room to improve. That never fully goes away, and that’s the point.

The Same Thing Happened With a Newsletter

I had a similar moment recently with one of my email newsletters. I read it back and immediately spotted everything I’d done “wrong.” The story ran long. It meandered. I struggled to stick to just one idea, something I’m actively working on.

Here’s a trick I use now: before hitting send, I ask myself, “What is the main point of this email?” Then I reread what I wrote to see where I drifted off course. That one email alone probably had enough material to be split into three or four separate newsletters.

But even with all of that, the stats told a different story. That email performed incredibly well.

My strategy with it wasn’t perfection. It was showing up as a cheerleader that day. Some days I bring tough love. Other days, I’m the coach on the sidelines, cheering because I know you can do it, and somewhere underneath it, you know it too.

Those “cheerleader” emails consistently perform well for me. I think it’s because people want to feel seen. Sometimes what someone needs most isn’t a flawless strategy breakdown. It’s a pep talk.

Drop the Idea That This Will Be Easy or Fast

Whether it’s your business, a podcast, a YouTube channel, or a brand-new hobby you just picked up: embrace the messy beginning. Even four years in, there’s still messiness in learning something new, and that’s exactly how it’s supposed to work.

You don’t need the polished version to make an impact. You need the version you were actually willing to publish.