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The Messy Middle: How to survive the ugly stage without drowning in self-doubt

I’ve been an artist for a long time, and if there’s one lesson that’s stuck with me through every project, every painting, every brand I’ve built—it’s this: Everything goes through an ugly stage. Art. Business. Healing. Life. There’s always that part in the middle where everything looks like a mess, you feel like you're going in reverse, and your inner critic starts whispering (or yelling), “What are you even doing?” I know the feeling. In that stage, it’s tempting to stop. To quit. To convince yourself you're not good enough.


But really.. you're just a work in progress.


Here’s what I’ve learned about the messy middle:


  • The first pancake is always bad. It’s okay if your first draft, design, pitch, or launch isn’t perfect. That’s not failure.. It's practice.. A learning opportunity!

  • You don’t have to be good at everything. You just have to be willing to learn, reflect, and pivot. That’s how growth happens.

  • It’s okay to pause. Step back. Take a breath. Look at the bigger picture. Sometimes walking away for a bit gives your brain the space it needs to work through the problem in the background. That’s not quitting.. You're just regrouping and letting your brain work.

  • Your inner critic doesn’t get the final word. We all have an inner Karen. Sometimes she starts getting loud, mouthy, and nasty. At those times I tell her (sometimes out loud) to F OFF. Then I remind myself of all the things I’ve done in spite of her voice.

My husband—who’s always my biggest cheerleader—loves to joke that there have been plenty of times when he’s looked at one of my art pieces in progress and thought, “What the heck is she doing?”


And honestly? Fair. It usually does look like chaos at first.


But then he watches me keep going—layer by layer, color by color—until suddenly it all comes together. And every time, he's so impressed by how it all comes together.



That moment doesn’t happen unless you’re willing to sit in the mess and keep going — even when it looks like nothing’s working.


We don’t talk enough about how uncomfortable the in-between can be. The part where things feel half-formed and full of doubt.


But the truth is.. that's where the good stuff happens!


It’s where your voice gets stronger. Your brand gets clearer. Your confidence starts to grow—not because you nailed it on the first try, but because you kept showing up.


So if you’re in the thick of it right now, especially with your brand, I see you. Maybe you’re feeling behind. Maybe you’re questioning everything. Maybe you’re convinced you’re not ready.


But.. readiness isn’t a feeling. It’s a decision. And momentum is what actually builds confidence.


If you wait for perfect, you’ll find a hundred reasons to stall. (Trust me—I know.)


So post the post. Launch the thing. Do it messy. What’s the worst that could happen?


You might just get feedback. Or clarity. Or a little momentum. And that’s how progress starts;

You don’t have to figure it all out on your own.


Sometimes, just talking things through with someone outside your own head is the thing that helps everything click into place.


If you’re in the messy middle of your brand and not sure what comes next, let’s talk.


Schedule a free connection call


We’ll chat about what’s feeling unclear, explore what kind of support might help, and see if something like a Brand Audit or Brand Storey Guide could be the right next step.


No pressure. No perfection required.





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