296: I’ve Got 99 Problems and I Created 100 of Them

Hi there. You’re listening to the Leading Lady Podcast. I’m your host, Allison Loftus, and I’m a certified professional coach specializing in leadership and work-life balance. I work with clients to shift their limiting beliefs, insecurities, and self-doubt. This podcast will be filled with tools and strategies to help high-achieving women like you feel connected, empowered, and in the lead of your life, both personally and professionally. Let’s transform your life starting now. Lead yourself. The rest will follow.

Hi there, leading ladies, and welcome to today’s episode. Today I want to start with a confession. I have 99 problems, and if I’m being honest, I created at least 100 of them. And before you assume this is a self-criticism or self-blame or self-deprecating episode, let me be clear right up front. This episode is not about beating myself up, and I hope that as you listen to it, you don’t beat yourself up either.

This episode is about telling the truth. Because if you’re an entrepreneur and you feel constantly overwhelmed—feeling like you’re fixing fires, untangling messes, or wondering how things got so complicated—there’s a really good chance that you’re not failing. Okay? Hear me.

If you’re doing all those things, I promise you it feels like you’re failing. But chances are you’re not failing. You’re just living inside decisions you made while growing and scaling your business. And that extra problem—that 100th problem—that’s the thing that you didn’t even realize you created yet.

The Entrepreneur Myth

There’s probably somebody out there in the universe that’s upset with you because of something that you did, and you don’t even know it. And that’s just a cold, hard truth of being a woman in business.

So the first thing I want to talk about is the entrepreneur myth. Somewhere along the way, we were sold this idea that successful businesses run smoothly. I will be the first to tell you that I will never glamorize entrepreneurship. If you think you’re going to hit this level where everything just runs smoothly—hunky-dory, 24/7—it’s just not true. It’s a myth.

You’re never going to get to that “figure-it-out” stage where the chaos just stops. It does not exist. The reality is, most of the problems entrepreneurs face are not external problems—they’re internal problems. And they come from systems we never finished building, processes that worked once but didn’t evolve, boundaries we assumed instead of clearly defining, offers we created before the infrastructure was ready, and growth that happened faster than the foundation could support.

None of this makes us irresponsible. It just makes us builders.

Decisions Made in Motion

You don’t build a business in a vacuum. You build it while serving clients, managing people, raising your family, and trying to keep your nervous system intact. So of course some decisions are made quickly. And of course some things work—until they don’t.

Here’s something I say often, and I want you to hear it clearly: most decisions make sense at the time. You’re using the information you have. You’re trusting your intuition. You’re moving with your gut. You’re making the decision you need in order to gain momentum.

At the time, you didn’t have the data you have now. You didn’t know what growth would actually require from you. So maybe you said yes when you should have paused. Maybe you built something manually that now needs automation. Maybe you kept a system because it was “fine.” Or maybe you avoided changing a process because it felt overwhelming.

That doesn’t mean you were careless. It means you were in motion.

Problem Number 100

Businesses built in motion are going to require refinement. And this brings us to problem number 100—the problem you didn’t know you created.

Problem number 100 is the unintended consequence. It’s the bottleneck that appears later. The team confusion that grows quietly. The client experience that starts to feel inconsistent. The resentment that builds because your role never clearly changed.

This is the part that can feel really discouraging. You think, “I fixed so much. Why is there still another issue? Why didn’t I see that coming?”

But this is where real leadership maturity shows up—not in avoiding problems, but in responding to them without shame.

Founder Math

Here’s what I call founder math: we build, we learn, we fix, we refine, and we repeat. Healthy businesses are not built by perfect decisions. They’re built by responsible corrections.

Leadership isn’t about never creating problems. It’s about recognizing them faster, addressing them sooner, and building systems that support the next level.

If you’re solving problems you accidentally created, you’re not behind. I promise you—this is part of scaling.

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Growing With Integrity

As Leading Lady has grown, we’ve added programs. We launched the Hub—with live coaching—and it didn’t explode overnight. We’re still growing. We’re still ironing out the kinks.

As we added more groups and expanded our ambassador program, I realized there were blind spots I unintentionally created. Roles weren’t always clear. Communication needed refinement. And the truth is, I was still workshopping it.

So I went back to my core values. I reviewed my commitments, had clarifying conversations, asked for feedback, and made adjustments. Not because something was broken—but because it needed clarity.

That process wasn’t easy. But leadership isn’t about quitting when things get uncomfortable. It’s about recalibrating and moving forward with integrity.

Leadership Is Design

Leadership isn’t about doing more. It’s about designing better.

If this episode resonated with you, pause and ask yourself: what problem in your business is asking for a structural solution—not more effort?

You’re not alone. You’re brave. You’re building something meaningful. And growth will always come with refinement.

Thanks for tuning in to another episode of the Leading Lady Podcast. Until next time—take the lead.