Why Messy and Useful Beats Simple and Pretty

You know how sometimes you come across a blog post, quote, or image, and it feels like it was made just for you, right now, in the exact mind space or situation you’re experiencing? Like, all those cheesy breakup movies suddenly don’t seem so dumb after you’ve just been dumped?

That happened to me last weekend.

Jason Cohen’s latest article, All pretty models are wrong, but some ugly models are useful, landed in my inbox, and it felt like a message meant for me. It hit me right in the middle of my ongoing struggle: how do I communicate complex ideas in a simple way without stripping out the nuance that makes them actually useful?

See, I love nuance. I love digging into the layers of a topic, exploring the details that make something tick, and questioning everything. But I also recognize that communicating ideas—especially in tech, Pilates, and startups—often requires simplicity. Being able to explain a complex topic in a simple way is a skill I admire.

So I try to make things simple.

And I fail.

Every blog post I’ve written so far has an unfinished diagram to go with it that I didn’t publish because I felt it was too simplistic. I’ll start sketching out a framework, trying to fit my thoughts into a clean, digestible format, and then—bam—I find an exception. Or another rule that needs explaining. Or a whole subtopic I hadn’t considered. Suddenly, I have five more blog post ideas and a model that no longer looks neat and tidy.

I’m caught in a cycle. If I simplify too much, it feels like I’m glossing over the important stuff. But if I keep all the nuance, it’s messy, hard to follow, and doesn’t fit into a pretty flowchart.

At the same time, I hate the marketing-driven simplicity that makes everything seem easy—because it’s not. There are a shit-ton of startup newsletters out there, loaded with big claims, big numbers, and binary advice: Do this. Don’t do that. This is the way.

“Running out of cash? Lay off staff.”
“Subscription churn creeping up? Do a customer survey.”
“Trying to land a big celebrity influencer? Get in touch with their agent.”

Sure, those are options. But the reality is always messier. Context matters. Execution matters. Timing matters. And an 800-word blog post that claims to have the answer to your problem is a fantasy.

Jason’s post was a breath of fresh air. It reminded me that useful models don’t have to be pretty. In fact, they usually aren’t. At the end of the day, I don’t care about making my ideas look polished—I care about making them work. And that means embracing the mess.

I want to build transformative technology in Pilates. That tech will only be as good as the model it’s built on. And a model that looks good but doesn’t actually function? Useless.

So my takeaway?

1. My Pilates model will not be pretty, almost ever. And that’s okay. The marketing model might be pretty, but the functional model that helps me build something meaningful will not be.

2. Trying to model the Pilates experience is useful—but probably not in the way I expect. And that’s okay too.

3. It’s possible to deliver value without having everything figured out or packaged into a perfect, binary piece of advice.

The act of creating the framework—even if it’s messy, even if it’s incomplete—is useful in itself. So I’m going to keep writing, keep mapping, and keep wrestling with the mess, knowing that the best ideas don’t come in neat little boxes. And maybe, just maybe, my ugly model will end up being the most useful thing I build.