My business has handed me 99 problems over the years, and honestly, at least 100 of those were my own doing.
Now stay with me, because this is not going to turn into a self-blame thing. I refuse to beat myself up over it, and I don’t want you doing that to yourself either. I do want us to get honest, though.
If you run a business and you spend half your week putting out fires and wondering how things got this complicated, hear me. You’re probably not failing. It feels like failing, I know. But most of the time, what you’re actually dealing with are the after-effects of decisions you made while the business was growing, and that’s a completely different thing. These are business growing pains, and almost nobody talks about them honestly.
And that extra problem, the 100th one? That’s the one you don’t even know exists yet. Someone out there is probably annoyed about something you did months ago, and you may never even hear about it. That’s part of the deal when you’re a woman in business.
The Myth of the Smooth-Running Business
At some point, someone convinced all of us that a successful business eventually runs itself.
You’ll never catch me glamorizing entrepreneurship. A lot of us are waiting for the stage where things finally settle down and run on their own, and I waited for it too. It never showed up. It doesn’t exist.
Most of what goes wrong in our businesses starts inside the business. Think about the system you never quite finished setting up because clients kept coming, and you had to keep moving. Or the process that worked fine at one size and quietly fell apart at the next. Maybe you assumed everyone understood a boundary you never actually said out loud. (Spoiler alert: they didn’t.) I’ve watched offers go live before the back end was ready to hold them, mine included, and I’ve watched growth outrun the foundation underneath it.
None of that means you’re careless. It means you’re a builder.
What Business Growing Pains Actually Are
Business growing pains are the friction that shows up when a company gets built in real time, while the rest of your life keeps happening around it.
You build your business while you’re serving clients, managing people, getting dinner on the table, and trying to hold your own nervous system together. Some decisions got made fast because they had to be. Some things worked great for a year and then stopped working, and you didn’t notice right away because you were busy.
Almost every decision you’ve made has made sense when you made it. You used what you knew at the time, and you trusted your gut because momentum mattered more than perfection that day. The stuff you know now? That knowledge didn’t exist yet, at least not for you.
So yes, you probably said yes to a few things that deserved a pause. You kept a workaround running long past the point where it should have become a real system, mostly because it was fine. And fine felt like enough at the time. I get it.
That’s what building in motion looks like.
Problem Number 100: The One You Didn’t Know You Created
A business built in motion will always need refinement later. Always.
Which brings me to problem number 100, the one with a delay on it. Sometimes it’s a bottleneck nobody saw forming. Sometimes the team gets confused, one tiny miscommunication at a time, or the client experience drifts somewhere along the way, and you can’t point to when. And sometimes it’s resentment, the quiet kind that builds when everyone’s role has changed except yours on paper.
Finding it is discouraging, and I won’t pretend otherwise. You start wondering why there’s always one more thing when you’ve already fixed so many things.
This right here is where leadership maturity shows up: in how you respond when you find a problem, because creating zero problems was never on the table for any of us.
Founder Math: Why Business Mistakes Are Part of Scaling
I have a name for this cycle. I call it founder math. You build something, you learn what it can’t do, you fix it, you refine it, and then you do the whole thing over again.
A healthy business was never one long streak of perfect decisions. It’s a track record of responsible corrections. The business mistakes you’re untangling right now are evidence that you built something real enough to outgrow its first design. That’s worth sitting with for a minute.
So if you’re cleaning up a mess you accidentally made, you are not behind. You’re scaling. It’s the same shift I talk about in winning versus learning: every founder creates problems. The difference shows up in what happens after you spot one.
What This Looked Like at Leading Lady
I want to give you a real example from my own business, because I never want you to think I’m preaching from some problem-free mountaintop.
As the Leading Lady Ambassador program expanded, I started noticing blind spots I’d created myself without ever meaning to. Some roles were fuzzier than I’d realized. Our communication had gaps I hadn’t seen. Honestly, parts of it were still in the workshop phase, and I was the one who’d left them there.
So I went back to basics. I sat with my core values, looked hard at the commitments I’d made, started some clarifying conversations, asked for honest feedback, and made changes. Nothing was broken, exactly. It needed clarity, and providing clarity is my job.
Was that process comfortable? No. But I wasn’t going to quit over the uncomfortable. I recalibrated and kept moving. Some of the best lessons I’ve learned came from leading and learning alongside other women who were brave enough to admit they were still figuring it out, too.
How to Respond When You Find Problem Number 100
So what do you actually do when you spot a problem? Here’s my process, pulled apart so you can borrow it.
Start with your core values. Before you touch a single system, ask whether the thing you built still lines up with what you said matters. Then review your commitments. What did you actually promise, and to whom? Half the confusion in a growing business comes from promises nobody wrote down.
From there, have the clarifying conversations. Yes, even the awkward ones (especially the awkward ones). Ask the people inside the mess for feedback, because they can see things you can’t.
And then make adjustments. Small ones count. You don’t have to overhaul your whole business by Friday. You just have to start designing on purpose.
Stop Pushing Harder. Start Designing Better.
If this hit home, pause and ask yourself: which problem in your business has been quietly asking for a structural fix while you kept throwing effort at it? Don’t rush the answer. It tends to show up once you stop firefighting long enough to listen.
More effort won’t fix a structural problem. Better design will.
You’re not alone in this, and you’re braver than you give yourself credit for. What you’re building matters, and it’s going to keep needing refinement. Now you know that doesn’t mean anything is wrong.
Ready to Refine What You’ve Built?
If you’re staring down your own problem number 100, start with my free Strategic Planning Wheel. It helps you step back and look at your whole business so you can spot structural gaps rather than just patching the loudest one.
Then come join us in the Leading Ladies Facebook Group. Nearly 7,000 women entrepreneurs are in there telling the truth about building businesses in motion, and I’d love for you to be one of them.
And when you’re ready for ongoing support, The Hub gives you weekly live coaching calls, access to our Ambassador network, and a community of women who get it. You were never meant to do this part alone.
