Caitlin Messerschmidt

Be willing to take the risk. Be brave enough to follow your instincts!

Growing up in Wisconsin, there was an assumed path that everyone seemed to follow without question. I tried hard to follow it too. But something in me always knew there was more. More to life and who I knew I could become. The more I listened to that quiet inner voice, the louder it got. Until one day, I found myself driving 12 hours for a job interview that led to me boarding a ship months later. And nothing has been the same since.

The butterfly effect of that one decision is something I still can't fully put into words. One risk led me to places that don't show up on maps. It introduced me to people who permanently changed the way I see the world. It cracked open a perspective I never could have found by staying comfortable.

My greatest advice: be brave enough to travel and see the world. The world will do the rest.

Listen to understand, not to respond.

Early in my career, I thought being heard meant talking more. Speaking first. Having the answer ready before the other person finished their sentence. What I didn't realize was that I was missing everything. The context behind the question. The frustration underneath the feedback. The real ask buried inside the surface one.

When you are leading people and , you learn quickly that communication is never just about the words. A nod means something different in one culture than it does in another. Silence isn't always agreement. And the person who speaks the loudest in the room is rarely the one with the most to say.

The moment I stopped preparing my response and started actually listening, everything shifted. I became a better leader. A better collaborator. A better entrepreneur. Because when you truly listen, people tell you exactly what they need. And that information is everything.

Travel! Whatever that looks like for you. Volunteer abroad, teach English in another country, take a gap year and immerse yourself in a culture completely different from your own. However you do it, do it. I promise you it will change you in ways you cannot anticipate and cannot fully explain once it happens. It made me a better version of myself, not just for my own sake, but for every person I have led, collaborated with, and built alongside since. That is not an exaggeration. It is a ten out of ten recommendation with zero exceptions.

Never ignore your gut instincts! I have spent years now living outside the expected script, and it has made me the happiest and most aligned version of myself I have ever been. So if something inside you is pulling you toward a goal that sounds too big, too unconventional, or too hard to explain to the people around you, that means it's the right path for you. It is showing you that there are options out there that most people are too afraid to consider.

One of my most personal challenges right now is building the right community around me. A lot of people in my circle are evolving, growing, moving in new directions, and that means constantly finding the next room to be in. It sounds simple, but finding your people at every new level is something most people don't talk about enough. It is one of the quieter challenges of growth.

In hospitality and real estate investing, the challenge takes a different shape. The space has exploded in popularity, and with that comes a lot of noise. Not everyone who shows up is serious, and that creates a bad reputation around certain strategies and paths that are actually solid when executed with integrity. So you have to earn your credibility the old fashioned way. Through consistency. Through results. Through building a reputation where people can point to your track record and say, without hesitation, that she knows what she is doing.

On the entertainment and guest experience perspective, the challenge is attention. We live in a world where no one has to leave their couch, or even look up from their phone, to be entertained. You are not just competing with other venues and productions anymore. You are competing with every single creator on the internet, all vying for only seconds of someone's day. That is a real and evolving pressure.

But here is what I find interesting about it. That same landscape that makes competition fierce also opens the door for collaboration and creativity in ways that did not exist before. When you stop seeing other creators as competition and start tapping into each other's perspectives, everyone expands. The challenge and the opportunity are the same thing. It just depends on how you choose to look at it.

Integrity is non-negotiable for me. It is the foundation everything else is built on. When the space gets noisy and people start cutting corners to get ahead, integrity is what separates the people who build something lasting from the ones who just make noise. 

And then there is fun. I know that might sound simple, but I mean it deeply. I built a career around the belief that fun is not frivolous. It is fuel. It is the thing that kept me going through 4:30 am alarms, high pressure moments, and years of sacrificing holidays and milestones. If I cannot find the joy in it, it is probably not the right room for me to be in.