The Halloween Costume I Almost Missed: Why This Company Exists

Most leadership stories start with promotions and corner offices. Mine starts with a babysitter bringing my son to a restaurant so I could see his costume for five minutes before going back to work.

Halloween night, early '90s.

I couldn't leave my shift, so the babysitter brought my son to the restaurant. He was dressed as a little clown. I can still see that costume as if it were yesterday. Half of his face paint had already come off by the time they arrived, right before the dinner rush.

I posed with him for a quick picture. One picture. Then straight back to dinner prep.

That's what "making it work" looked like.

I was a single mom running a restaurant, living in the kind of survival mode where you wake up before the kids and come home long after bedtime. Where you piece your life together in the quiet hours in between day after day, night after night.

Every milestone many mothers experience without thinking—first words, first steps, first crawl—was handed to me secondhand by babysitters. The pain was unbearable some days. Most days, honestly. I felt lost, drowning in responsibilities that often kept me up at night.

The Things They Said to My Face

Back then, single mothers weren't seen as leadership material.

My bosses never missed an opportunity to tell me why.

They would share their "concerns" in those one-on-ones, always framed as reasonable, always delivered with that tone that made you feel like you should be grateful for their honesty.

"We need someone available who can be here no matter what," they'd say. "Being a single mother means if you have a sick kid or an emergency, you won't be able to leave your shift."

Translation: Your children make you unreliable. We can't trust you with authority.

Never mind that I was already one of the most responsible people there. Never mind that I showed up, worked harder than most, and figured out solutions when things went wrong.

The message was clear: people like you don't get to lead.

The Backstory Nobody Asked About

Here's what they didn't know or maybe didn't care to know:

I'd learned to be on my own long before I became a mother.

My childhood was one spent alone being raised by an alcoholic father and a mother who split when I was 14. I was often left to fend for myself as a young teenager, learning survival skills nobody should have to learn that young.

So when I had children of my own, I just did what I had to do. I never really gave much thought to it, things were just the way they were.

But I did want to support them. Give them a home. Buy them new clothes for school. Provide the stability I'd never had.

So I worked hard. And it was pretty devastating having my single mother status thrown in my face when I was already being pretty damn responsible.

The Breaking Point

I left that job seeking a better future for myself and the kids.

Five years later, I was back. Different bosses. Different times. Finally, it seemed like things might work.

Then came the phone call.

It was my son's birthday. My son, daughter and I were in the middle of his small celebration cutting cake, handing out his presents, surrounded by family…the one day that was supposed to be just for him—and my phone rang.

They needed me to come in. My sister rolled her eyes in dismay.

I was so mad I could barely speak. Furious that I couldn't even seem to have this one moment. That after everything, after years of proving myself, after building a life for these kids on my own…I still couldn't protect a single birthday from the relentless demand to be available "no matter what."

That night I made a decision. Enough is enough. We are done losing.

What Survival Mode Leadership Actually Looks Like

That phone call on my son's birthday became my line in the sand.

So, I continued working full time and managed to finish my business degree at night.

I bought my first house with borrowed money from my dad and others, then spent years scraping together every mortgage payment like my life depended on it. Because it did.

There were weeks I didn't know if I could pull it off.

But I did.

Something they don't tell you about working in restaurants: you get to eat. That helped a lot.

A decade later, I finally landed my first 9-5 with weekends off. It felt like oxygen. I could finally show up for my kids without checking the clock every five minutes.

From there, I kept climbing. Through challenges, pivots, and more than a few moments where quitting would've been easier.

I got married. (Twenty years this year.)

I made it all the way to COO in a $100M+ company—proof that the girl running a restaurant on fumes, the single mom they said couldn't handle leadership responsibility, could build a career on her own terms.

The Leadership Training Nobody Gave Me

Here's what I want you to understand:

There was no map. No playbook. No real training to speak of.

Every step I took, I figured out in the dark. Every leadership challenge, I navigated alone. Every impossible choice between my kids and my career, I made without guidance or support.

And when I finally reached positions of real authority—when I had the title, the team, the responsibility—I still felt like I was improvising. Still felt like everyone else had been handed a manual I never received.

The skills that got me promoted? They didn't prepare me for the psychological weight of leadership. For the conversations that keep you up at night. For the decisions where every option feels wrong.

Nobody teaches you how to lead when you're terrified of making the wrong call.

Nobody gives you frameworks for navigating team tension, addressing performance issues, or having conversations you don't want to have.

They just promote you and expect you to figure it out.

What This Taught Me About Leadership Identity

What I learned the hard way is this: leadership isn't about competence—it's about identity under pressure.

When you're managing impossible logistics while maintaining relationships, making decisions under extreme resource constraints, persisting through systemic discrimination—that's leadership identity in action.

But organizations don't recognize it when it doesn't look conventional. And here's what made it worse: I personally kept my story close to the chest so others wouldn't know my struggle, wouldn't find out how I had been winging it. I was terrified that if anyone saw behind the curtain, they'd confirm what my bosses had already told me, that I didn't belong in leadership.

They promote people who already fit the mold. People who've had mentors, networks, room to make mistakes without consequences. People who've been told their whole lives that they belong in positions of authority.

The rest of us? We lead in survival mode. We prove ourselves ten times over. We carry the psychological weight alone.

And when we finally get the role, we're still figuring it out without support.

Why The Manager's Mind Mapping Company Exists

I started this company because I never want to see another single mom—or anyone for that matter—lead without a guide, without support, or without the tools to survive and succeed.

No one should have to figure leadership out in the dark.

Period.

End of story.

The managers I serve aren't the ones who glide effortlessly into leadership roles with built-in support systems and executive coaching. They're the ones navigating impossible terrain with no map.

The ones who care deeply about their teams but don't know how to have difficult conversations without rehearsing them at 6 AM in their kitchen.

The ones who were promoted for their skills but never taught how to handle the psychological weight of leadership.

The ones who feel like they're drowning but don't have permission to ask for help.

You're not failing. The system is failing you.

Leadership training acts like the hard part is learning frameworks. But frameworks don't help when you're standing in your kitchen at 6 AM practicing words you don't want to say.

Frameworks don't help when your team tension is eating trust alive and you don't know how to name it without making things worse.

Frameworks don't help when you're exhausted from trying to sound confident while feeling completely lost.

What You Actually Need

What you need is a map for the terrain nobody warns you about.

Tools that acknowledge the psychological weight of leadership, not just the tactical requirements.

Permission to admit that leadership is hard—not because you're doing it wrong, but because the work itself is complex, emotional, and lonely.

You need someone who's been there. Who knows what it costs to lead from survival mode. Who understands that the Halloween costume moments—the impossible choices, the missed milestones, the nights you wondered if you could keep going—don't make you weak.

They prove you're stronger than anyone realized.

The Map I Wish I'd Had

Every tool I create, every framework I design, every map I draw—it's the support system I never got.

The Manager's Mind Mapping Company isn't about teaching you to be a better leader. You're already leading. You're already doing the impossible every day.

What you need is structure for the messy moments. Language for the conversations that terrify you. Permission to acknowledge the weight without pretending it doesn't exist.

You need tools that meet you where you are—in crisis, in doubt, in the gap between the role you hold and the support you've been given.

Because the truth is: leadership capacity shows up in survival mode.

It shows up when you're making impossible choices with impossible resources.

It shows up when systems fail you and you keep going anyway.

It shows up in single moms running restaurants, in managers promoted without training, in anyone navigating authority without a map.

Your struggle isn't evidence of failure. It's evidence of leadership.

What I Want You to Know

If you're reading this and recognizing yourself—if you're the manager practicing conversations at 6 AM, if you're carrying weight nobody sees, if you're trying to hold it together while wondering if you're doing it all wrong—

You're not alone.

And you don't have to keep figuring it out in the dark.

That Halloween costume moment? The babysitter bringing my son to the restaurant for five minutes because I couldn't leave my shift?

That's not just my story. That's the reality for countless people leading from survival mode—doing the impossible, proving themselves constantly, receiving zero support.

I built this company for us.

For the managers who weren't handed the playbook. Who don't have executive coaches or leadership development programs. Who are navigating impossible terrain while everyone assumes they've got it figured out.

You deserve a map.

You deserve tools that acknowledge the real challenges, not just the tactical ones.

You deserve to stop carrying this weight alone.

Your Next Step

I can't give you back the Halloween costumes you missed. The milestones handed to you secondhand. The years you spent in survival mode.

But I can give you the map I wish I'd had.

Start here: Take the free Leadership Pathway Explorer to discover your leadership identity—the patterns, strengths, and challenges that shape how you lead under pressure.

Then explore: The Manager's Map Drawer delivers three new leadership tools every month—frameworks for the conversations, decisions, and moments that keep you up at night.

Here’s the truth: You're already strong enough. You're already capable. You're already leading through impossible circumstances.

You just need someone to acknowledge how hard it is—and give you the support you should've had from the beginning.

That picture at the top? Halloween night, early '90s. My son in his little clown costume, half the face paint already gone. The babysitter brought him to the restaurant so I could pose for one photo before the dinner rush.

That's what "making it work" looked like.

You don't have to lead like that anymore.

About Catherine Insler

Catherine Insler is the founder of The Manager's Mind Mapping Company and creator of Leadership Cartography™—a methodology for navigating the invisible terrain of leadership. After years of leading without support, she now builds the maps she wishes she'd had. Her work serves managers who are doing the impossible with no playbook, proving every day that leadership capacity shows up in survival mode. Learn more at YourLeadershipMap.com.