#73 | Wear the Hat (Even If They Talk)

What’s hanging in your closet right now that represents the version of you you’ve been too afraid to show the world?

In this powerful episode of Lead With Swagger, Jennifer Sukalo dives into the hidden ways we shrink ourselves to fit in, stay comfortable, and avoid judgment. What starts with a hat becomes a deeper conversation about confidence, identity, authenticity, and the invisible rules we follow without even realizing it. If you’ve ever held back, played small, or waited for permission to fully express yourself, this episode will challenge you to stop hiding and start showing up boldly, unapologetically, and fully as you.

Connect with me: leadwithswagger.com

Transcript

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You know what's wild? There are grown, successful, capable adults who are being held back in life by a hat. Not a job, not a relationship, not a lack of opportunity, a hat. Now stay with me here because this is about to get uncomfortably real. Welcome back to Lead with Swagger, the podcast where we get real, raw, and ridiculously honest about what it takes to lead with confidence, authenticity, and a whole lot of heart. I'm your host, Jennifer Sukalo, and today we're talking about something that might sound simple on the surface, but is actually exposing some very deep truths about how you're showing up in your life. Let me ask you something. How many times have you stood in your closet, picked something up, and then immediately put it back? Not because it didn't fit, not because it wasn't appropriate, but because you thought to yourself, oh, what will people think? Or this is way too much. Or I can't pull this off. Yeah, that's what I'm talking about. Now I was speaking with some of my clients recently, brilliant, successful women, and they were telling me how much they love getting dressed up. Love it, but they don't do it anymore. And when I asked why, they said, well, it's just not the vibe where I live. The environment doesn't really support it. To which I said, says who? So here's what I did. It was Kentucky Derby weekend, and I felt like getting dressed up. Not for a party, not for an event, just because. So I wore the hat. Not the safe hat, not the maybe no one will notice hat. The hat. The one that says, I love hats, and I'm not here to apologize for it. And then my husband and I went downtown, just walking around, popping into places, having a drink, chatting. And you know what happened? People loved it. Compliments everywhere. But more interesting than that was what people were saying. People kept saying to me, I wish I could do that. I've always wanted to wear something like that. I don't think I could pull that off. And here's where this gets deeper. Because there are two things happening here. One, you think your environment is dictating how you show up. And two, your fear is keeping you small. I mean, let's call it what it is. That environment story, it's not about your surroundings, it's about your discomfort with standing out. Because let's be real, you're not worried about the sidewalk judging you. You're worried about the people, about disrupting the norm, about not fitting in, about being seen. And somewhere along the way, you started following rules that no one ever actually gave you. What is this like the Stepford Wives Dress Code edition? Now, don't get me wrong, there are moments in life where dress codes matter. But most of the time, you're self-editing, you're shrinking, you're choosing acceptable over authentic. And here's what I would love for you to really pay attention to and to hear. I don't dress for other people. I dress for me. If I feel like wearing pearls and a hat, done. If I feel like wearing cowboy boots with a dress, absolutely. A full suit to run errands, let's go. Because it's not about the outfit, it's about what it represents: freedom, expression, ownership. And here's the ripple effect. When you show up boldly, you give other people permission to do the same. Women literally stopped me and said, You inspired me to wear my hats again. That's leadership, not the title, not the role, the energy. Now let's talk about the second piece. Fear. We met this man out the other night who absolutely loved my husband's hat. And he said, gosh, I would love to wear something like that, but I don't think I could pull it off. And to that, I replied, then you never will. Not to be harsh, but to be honest. Because that's how limiting beliefs work. They don't just sit quietly in your mind, they shape your behavior, they dictate your choices, they keep you stuck. If you believe you can't pull it off, you won't. If you believe you'll be judged, you'll keep playing small. If you believe you need permission, you'll stay stuck waiting. And here's the real question what are you trading for that? Belonging? Approval? Comfort? Because if you have to become someone else to get those things, is it really worth it? I mean, listen, fear is sneaky. Don't get me wrong. I mean, it convinces you that it's protecting you when it's actually limiting you. And life is way too short to keep parts of yourself locked away in your closet, literally and figuratively. So wear the hat, wear the thing, do the thing, say the thing. Not someday, not when it's appropriate, not when you feel ready now. Because when you honor what you feel called to do, even in small ways, you build self-trust, you build confidence, you remind yourself, I matter, I'm allowed to be seen, and that's powerful. Now, I'd like to say this before we wrap up. I am so proud of you for being here, for listening, for doing the work, because it's not always easy. It requires honesty, it requires courage, it requires you to look at parts of yourself you might have been avoiding, but you're doing it. And I fully believe in you. Now, here's your challenge for this week. This week, I would like for you to wear your version of the hat. And no, it doesn't have to be literal, it could be the outfit you've been avoiding, speaking up in a meeting, sharing your opinion, posting something maybe you've been holding back. Ask yourself this: where am I playing small to stay comfortable? And then do the opposite. Just once. Start there. Because the more you practice being unapologetically you, the more natural it becomes. And the more your life starts to reflect who you actually are. So go on. Wear the hat. And I'll see you next time.