Every so often, you have a conversation that reminds you why learning matters.
Recently, I had the opportunity to sit down with Kristen Reynolds, President & CEO of Choose Chicago, for an episode of the Business Class podcast. While many people know Kristen as the leader of one of the world's most recognized destination organizations, our conversation focused on something deeper: how she got there.
Her story isn't one of checking every box on a job description.
It's a story about curiosity, resilience, and believing in yourself long before everyone else does.
Throughout our conversation, Kristen shared a theme that appeared again and again in her career journey: she was often told she wasn't qualified for the next opportunity.
She had never worked at a resort before becoming a resort communications leader. She had never been a lobbyist before becoming a tourism advocate. She had never worked at a destination organization before becoming a DMO CEO. She had limited convention experience before stepping into one of the industry's most prominent leadership roles.
Yet she kept moving forward.
Not because she had all the answers, but because she was willing to learn.
That willingness to embrace uncertainty and grow into new challenges is a lesson every tourism professional can benefit from, regardless of where they are in their career.
One of the qualities I admire most about Kristen is her curiosity.
When I asked about her approach to leadership, she spoke about constantly wanting to learn, explore new ideas, and understand the communities she serves.
That mindset resonated deeply with me.
At Learn Tourism, we often say that learning isn't something you finish. It's something you practice. The most successful leaders I've met in tourism aren't necessarily the ones with the most experience. They're the ones who remain curious, ask thoughtful questions, and continue growing long after others have become comfortable.
Kristen embodies that philosophy.
Even after achieving what many would consider the pinnacle of destination leadership, she is still focused on learning more about Chicago, strengthening her expertise in convention sales, and finding new ways to serve her community.
Another theme that stood out was Kristen's belief that destination organizations exist first and foremost to serve their communities.
Too often, tourism conversations focus exclusively on visitor numbers, hotel occupancy, or convention bookings. While those metrics matter, Kristen spoke passionately about creating places where residents are proud to live and businesses can thrive.
Her philosophy is simple: build a stronger community first, and visitors will be drawn to it naturally.
That perspective aligns closely with what we're seeing across the industry. The destinations finding long-term success are increasingly focused on community alignment, stewardship, resident engagement, and creating meaningful experiences that reflect local values.
Tourism works best when it benefits everyone.
Toward the end of our conversation, Kristen shared the four principles that guide her life and career:
She believes these four elements create the foundation for sustainable success and personal fulfillment.
It's difficult to argue with the results.
From Arizona to Long Island to Chicago, Kristen has consistently embraced new challenges, built strong relationships, and left a positive impact on the communities she has served.
Perhaps the most powerful takeaway from our conversation was this:
You don't need permission to grow.
Too many talented professionals hold themselves back because they don't meet every qualification, haven't followed a traditional path, or worry they aren't ready.
Kristen's career demonstrates that growth often happens when you step into opportunities before you feel fully prepared.
Learning fills the gap.
Confidence grows through action.
And leadership is developed through experience, not perfection.
For students, emerging professionals, and anyone considering their next career move, this episode serves as a reminder that the future belongs to those willing to take the leap.
Our conversation with Kristen Reynolds explores career transitions, leadership, lifelong learning, community impact, and the future of destination organizations.
Whether you're an aspiring tourism professional or a seasoned industry leader, you'll find valuable insights and inspiration in her journey.
As Kristen reminded us, success isn't about never being afraid. It's about continuing to move forward despite the uncertainty.
That's a lesson worth learning.