It started with a water taxi.
I was working with a client on their presence at a major industry conference. The kind of event where everyone shows up in business casual, grabs a lanyard, and blends into a sea of blazers and massive booths. My client had booked a water taxi for an evening event on the water. A fun idea. A good idea. There was just one problem. One of the other big players had booked a yacht.
A yacht.
So, there we were, staring down the reality that our scrappy little water taxi was going to be floating in the same harbor as someone else’s luxury vessel. And somewhere between panic and creative direction, I said:
“That’s OK. We just need to go all in on the pirate theme.”
Because in Tampa? Water taxis are also called pirate taxis. And suddenly the whole thing made sense. (To me! 🤣) We didn’t need a yacht. We needed a story.
So, I built a 24-page strategic deck. Theme integration. Messaging. Visual identity. Booth presence. And one recommendation that would come back to haunt me: the whole team should dress as pirates. A full pattern interrupt. Not a cute nod to the theme. The real thing. Which meant I had to do it first.
Two Suitcases and Zero Confidence
I shopped for about four weeks. Thrift stores, Etsy, Ebay, Poshmark. And then packed two oversized suitcases full of clothes with a pirate vibe. Nothing was an actual outfit yet. Just pieces. Flowy things. Leather things. Linen things. And one perfect pirate hat.
Side note: If you’ve never shopped for pirate attire as a woman, let me save you the trouble. Almost every option is designed to be “party city” rather than “pirate ship.” I wasn’t going for that. I wanted a working pirate. A Northwest pirate. Sturdy boots, flowing tans and browns, a lacy white sleeves. Someone who looked like she’d actually sailed something. Not someone selling rum on a billboard.
The morning of day one, my roommate helped me put it all together. (Which took an hour.) Puffy pants. No! This flowy skirt. No, these pants. Wait. Take this very long belt. The hat. And then I stood at the hotel room door and thought about what I was about to do.
I tell people all the time to be bold. Be different. Stand out. Break the pattern.
Walking out that door? I felt like I was walking around with my fly open.
The Silence, the Stares, and the Coffee Line
The first person I saw was someone I know well. She said nothing. She was with new colleagues from a new job, and I think she just wanted to sidestep the whole Sheri-in-costume situation and keep moving. Fair enough. But when you’re already feeling exposed, silence is louder than laughter.
Then came the coffee line.
A woman looked at me with something I can only describe as irritation. Not curiosity. Not amusement. Irritation. “WHY are you wearing that?” she asked. Not in a playful way. In a way that made it clear she found the whole thing unnecessary. Maybe even offensive to the seriousness of the event. I don’t know what her deal was. Honestly, I was more curious than bothered. What is it about someone else’s choice to be different that makes certain people so uncomfortable? But here’s the part nobody warns you about.
The Explaining Never Stops
All day long, I explained myself. Every conversation started the same way. People were curious. They’d seen the pirates-for-hire at the booth. They know I’m creative, aka “weird.” But this was beyond weird; they needed the back story. The WHY. And that required me to walk through the whole thing, from the water taxi to the strategic deck to the recommendation that the team go all in. Which meant that I had to demonstrate what “all in” actually looks like.
You can’t tell someone to commit fully and then show up in pants and a blazer.
Yes. I wore the hat. And the hat made me hot. Uncomfortably, distractingly hot. And I wasn’t even sure it was working. There were moments where I genuinely wondered: do I look like a pirate? Or do I just look like Sheri with a different hat?
One of my friends, when I told her how far outside my comfort zone this was, said she was surprised I even had a “zone!” That line stuck with me. Because it’s the whole point.
Day Two: Deeper In
The next morning, I went further. A vest. Flowy pantaloons. Sturdy boots. I leaned into it harder because I’d survived day one and realized something. The discomfort doesn’t kill you. It just follows you around like a shadow, tapping you on the shoulder every few minutes to remind you that you’re the only one in the room who looks like this.
And it worked.
More people showed up to the evening event (now a real pirate ship!). More people stopped by the booth. More conversations happened. More energy. In the far back corner of the exhibit hall, we stood out. Not because we were louder. Because we were different.
But what made it worth it, what really mattered, was the team. These were people who had never done anything like this before. And by the end of it, they were smiling. They were proud. They saw how creativity and a willingness to break the mold can actually move the needle. I watched them start to believe that showing up differently isn’t reckless. It’s strategic.
That’s what I care about most. Helping the next generation of this industry see that they can bring more of themselves to the work. That creativity isn’t a liability. That bold can be smart.
Here’s What I Want You to Know
I preach this stuff. Be unmistakable. Be unconventional. Break the pattern. Stand out. And I’m telling you right now: it is so much harder than it sounds.
Standing out by yourself is lonely. It’s hot under the hat. It’s the woman in the coffee line who thinks you’re ridiculous. It’s the friend who looks the other way. It’s explaining your choices on repeat to people who aren’t sure if you’re brilliant or unhinged. It’s wondering, halfway through the day, if you should just go change.
I didn’t go change. But I understand why people do.
Consider This Your Invitation from a Fellow Renegade
I wore the hat. I sweated through it. I explained myself a hundred times. I stared down the coffee line lady. And I’d do it all again. But next time? I want you in the room.
Join us at SWAY | LIVE Boulder. August 2–4, 2026.
Register now: https://swaylive.sherifitts.com/swayliveboulder
SWAY | LIVE is where financial professionals stop wondering if they’re too much and start building the personal brand that only they can build. Not alone. Not guessing. Together, in a room where being different is the whole point.
FAQ
1. Why is standing out so difficult professionally?
Standing out is difficult because it often creates discomfort before it creates results. Being different can attract attention, questions, and even criticism, which makes many people want to retreat back to what feels safe.
2. Is being bold in branding worth the risk?
Yes—when it is strategic. Bold branding works best when it is tied to a clear message, a consistent theme, and a business goal. It is not about being different for shock value; it is about being memorable and meaningful.
3. How can professionals stand out without feeling inauthentic?
Start with what is already true about you. The goal is not to become a character. The goal is to express your perspective, voice, strengths, and values more clearly so people remember you for the right reasons.
4. What does “pattern interrupt” mean in branding?
A pattern interrupt is anything that breaks expectations and gets people to pay attention. In branding, this could be visual identity, messaging, storytelling, wardrobe, booth experience, or content that feels distinct from the norm.
5. What makes standing out strategic instead of risky?
Standing out becomes strategic when it supports visibility, conversation, trust, and differentiation. If it helps the right people notice you and remember what you do, it is serving the brand—not distracting from it.