The gift of sitting in the messy middle (and why you shouldn’t skip it)

Being in the messy middle can sometimes feel (and look!) a lot like failing.

When I came back from maternity leave last fall, so much had changed. A company I'd been writing for consistently had laid off their entire marketing department. A proposal that felt like a sure thing fell through. I pursued a client I knew in my gut wasn't a good fit, and then got ghosted the moment I mentioned my pricing.

It would be easy to look at all of that and think: I'm failing. I'm going in the wrong direction. Time to panic.

And I won't pretend those thoughts didn't show up. They did. But here's the reality I kept coming back to: I had just had a baby. The economy had shifted. AI was doing its AI thing.

None of this happened in a vacuum, and very little of it was actually within my control. Of course things felt messy. That wasn't a signal I was doing something wrong. That was just reality.

I could acknowledge those truths, but the harder thing to sit with was what came next.

The urge to skip

When things feel messy, the instinct (especially for recovering perfectionists, which, hi 👋) is to treat the mess like a problem to solve. Get to the other side as fast as possible. Push through, pivot, find the answer, restore order, and come out the other side bigger and better.

I understand that instinct, and I've acted on it plenty of times. But what I've learned, and what I keep relearning, is that rushing through the messy middle means you miss out on opportunities for growth.

The mess is where we learn. Where we experiment. Where things don't work out or go how we planned, and we get data we can use to move forward. I know that's not what it feels like when you're in it — when you're in it, it just feels bad! But that's the thing about the messy middle: you can't skip it or rush it. You have to go through it. That's actually how you figure out what's on the other side.

Yes, it's uncomfortable. But it's also, if you can get some distance from it, kind of exciting. The mess is the work.

What sitting in the mess looks like

I want to be honest about what "sitting with the mess" looks like in practice, because it’s often not particularly graceful.

For me during this most recent transition, it looked like taking stock of what had fallen away and resisting the urge to immediately replace it with something new. It looked like noticing what I'd already been doing, what I actually loved, what left me feeling energized instead of depleted. It looked like recognizing what work, services, and audience I’ve outgrown and feel disconnected from.

It looked like asking myself, with more honesty than I'd allowed myself in a while: “What do I actually want my business to look like?”

Not what makes sense. Not what's safest. What do I actually want.

What came out of my messy middle

The clarity I found on the other side of that question surprised me a little, not because it was completely new, but because it had been there for a while and I hadn't quite named it yet.

For years, quietly, in the background, I’ve felt most energized by the conversations with self-employed coaches and consultants where I got to be a thinking partner, helping untangle something until we found something solid underneath. Like wading through the mud until we find a diamond, which is exactly how it feels.

Realizing this is what led me to step into this new (yet not new) professional identity. I am a thinking partner for self-employed coaches, consultants, and solopreneurs in the messy middle of building a business. That's what I do. That's what I've been doing. I just hadn't said it out loud as the whole thing.

I couldn't have gotten there by pushing through. I got there by staying in it long enough to see what was actually true.

If you're in your own messy middle right now

I know it's easier to say from the other side of a particular messy patch than it is to hear when you're in the thick of it, but if you can sit with it for a bit, the mess can be a gift.

If you're there right now — if things feel unclear, or like you've taken a few wrong turns, or like everyone else seems to have figured something out that you haven't — I want to offer you this: the discomfort isn't a sign you're doing it wrong. It might be a sign you're right in the middle of figuring something out.

You can't skip it. You have to go through it. That's actually how you find out what's on the other side.