From Imposter Syndrome to Confidence – A Leadership Secret

leadership, self-awareness, obstacles, imposter syndrome, self-care, communication, accountability, empathy, personal growth, coaching

Imposter Syndrome: A Sign You’re Ready to Grow

I’ve worked with thousands of store owners, and the truth is, leadership challenges often start from within, often fueled by imposter syndrome.

We second-guess ourselves. We power through burnout. And deep down, we wonder if we’re really cut out for this.

That’s why I couldn’t wait to sit down with Sherry Winn, a two-time Olympian and one of the most grounded leadership voices I know. We talked about imposter syndrome, leading through fear, and why self-care isn’t optional if you want to lead well.

Let’s start with the truth: nearly every retail leader looks around and wonders, “Who am I to be in charge?” or “Someone’s going to find out I have no idea what I’m doing.”

That feeling? In fact, it’s called imposter syndrome, and it’s far more common than you think.

“If you have self-doubt, you’re levelling up.” – Sherry Winn

Imposter syndrome doesn’t mean you’re failing, it means you’re growing. It shows up the moment you step outside your comfort zone and start expanding into your next level of leadership.

Personally, what I’ve learned: When that voice shows up, I pause… then I lead anyway.

Watched the full episode here:

Real Leadership Begins With Self-Awareness

It’s so easy to think leadership is about managing others, making the sale, or having all the answers. Ultimately, what Sherry and I talked about is this: before you can lead anyone else, you have to lead yourself.

That means being honest about your triggers. Knowing your strengths and blind spots. Taking responsibility without beating yourself up.

Try this: Ask yourself, “what am I avoiding or overcompensating for right now?” That’s where the growth begins.

Failures Are Part of the Deal

I can’t tell you how many mistakes I’ve made over the years running RETAILMavens. And every single one has taught me something valuable about my systems, my leadership, or myself.

“With every greatness, there are failures behind it. They’re not flaws, they’re fuel.” – Sherry

That’s not just inspirational fluff. It’s how real leadership is built.

What I’ve learned: If something goes wrong, I ask: What was my role in this? What can I take forward?

Self-Care Is a Leadership Skill

Yep. I said it. If you’re skipping sleep, skipping meals, and saying “I’ll rest when this is done,” you’re on a fast track to burnout.

For example, Sherry gets up every day at 5 a.m. just to give herself time to fuel up. And I loved this reminder she shared:

“You can’t give what you don’t have.”

Leadership requires energy, focus, empathy and those things don’t come from running on empty. Personally, I set three reminders on my phone every day. Each one says: Breathe. Believe. Begin again.

One small shift: Start with just 5 minutes of you-time. Every day.

Obstacles Are Adventures (Seriously)

This one made me laugh when she said it, but it’s so true. I used to see problems in my business as proof I wasn’t doing it right. Now I see them as invitations to level up.

“Obstacles are adventures. They take you to the next level of yourself.”

A difficult staff conversation? An inventory crisis? A customer complaint? All of it teaches you who you are becoming.

What I do now: I stop asking “Why is this happening to me?” and instead ask “What is this here to teach me?”

Listen to the full episode here:

You Don’t Have to Be Born a Leader, You Learn It

This might be the biggest myth I want to break for every store owner out there: you are not supposed to be perfect. Leadership is a learned skill.

The longer I’ve been in business, the more I realise that what makes someone a great leader isn’t charisma, it’s consistency, curiosity, and courage.

“You don’t need to be perfect. You just need to be willing to grow.”

It’s a skill that can be improved with practice. Better at asking for help. Better at letting go of control. These are all learnable things and if I can learn them, so can you.

You Millie Moment

This is your invitation to put what you’ve read into action:

  • Notice when imposter syndrome shows up and keep going anyway.
  • Reflect on a recent failure. What lesson is hiding in there?
  • Choose one self-care act today, no matter how small.
  • Reframe a current obstacle as a stepping stone.
  • Ask yourself: Who am I becoming right now?

Resources & Links

Don’t forget to join us in our Facebook community: Richer Retailer Facebook Group.

💚 Remember: If you’ve ever questioned whether you’re a “real” leader, I want you to know this: You already are. You’re just building the skills to lead with more clarity, strength, and heart. Imposter syndrome doesn’t mean you’re unqualified. It means you’re on the edge of something bigger. Let it be a sign, not a stop.