Lead with Levity

Ep.27. Spreading Happiness from Grand Cayman to the Hill Country of Texas (and everywhere in between)

If you want to know how to build a fun family culture then you’re in the right place. Today, we discuss the benefits of adopting and leading by values. I’m happy to say that I recently discovered that there are people out there in the world (not the multiverse, but here in our dimension) with the job title of ‘Chief Happiness Officer’ and ‘Director of Happiness’. I found one!


Today, I get to share a conversation with Kylie Rae Fitzgibbons, Director of Happiness and General Manager at JL Bar Ranch in Sonora, Texas. Kyle has traveled all over the world and picked up experiences that have all led to her passion to have fun and get work done.

“Everyone is influenceable, and everyone is an influencer even if you don’t have a bazillion followers on Instagram.”

Kylie Rae Fitzgibbons

In this episode, we cover:

  • How a small town in Texas wooed her away from Grand Cayman.
  • What it’s like to work in a family-owned business.
    • How they build shared values
    • How they approach confrontations or “collisions” within the team
  • Kylie’s experiences on the Grand Cayman islands and how that fed her perspective on hospitality
    • The “Cayman kind” approach taught her that “people taking care of people” is more than just a concept, it’s about creating a family feel.
  • Try this icebreaker from Kylie that’s guaranteed to improve the mood within a group:
    • (32:18) The Smile Game: One quick and easy way to bring joy to a meeting or change the energy in a group. A simple 30 second activity that you can do at the beginning of a meeting, with friends. Instead of sitting, you stand in a circle, make eye contact. Say: “I’m going to start” and smile at someone and make eye contact, and then that person turns to the left and smiles at their neighbor. Then do a few rounds and try to get faster.
  • Kylie’s leadership philosophy and maintenance tips:
    • Energy is contagious. Own your own energy.
    • Make sure that people are better after they meet you than when they first saw you
    • “As the leader of a team, it is important that I come with an enthusiastic energy and a positive ‘can do’ spirit with that attitude and showing resilience. That concept of having fun, it’s how I show up to be able to impact others.” – Quote by Kylie Rae
    • “Everyone is influenceable and everyone is an influencer even if you don’t have a bazillion followers on Instagram” – Quote by Kylie Rae
    • “The learning of service is a different perspective to consider. Everyone is in a service industry, whether you’re a mom with a young child. Whether you’re serving your neighbor when they need sugar…or if you’re in hospitality serving a customer.” – Quote by Kylie Rae
  • Activities that help team spirit and one-ness
    • Team photo and celebration
    • Team prayer
    • End of the day reflection and review of a value-based story or moment
    • Celebrate national pizza party day – “food is fuel”
    • Keep the team loved and well fed and listened to
Also available on iTunesGoogle, and other major podcast outlets.
woman smiling holding a sign that reads choose happiness

About Kylie Rae Fitzgibbons

Kylie Rae Fitzgibbons is a luxury hospitality executive leader who brings Service with a Smile workshops to other professionals with a focus on positive mindset and culture of kindness in the workplace. On a mission to share smiles and simple standards of service, acquired from 15 years of experience in the service industry, including The Ritz Carlton Hotel Company, LLC., and the Kimpton Seafire Resort & Spa in Grand Cayman. She currently holds the position of General Manager and Director of Happiness at The JL Bar Ranch Resort & Spa in Sonora, Texas.


The Lead with Levity podcast is a show for leaders who care deeply about what makes/breaks the employee experience. Our guests are dynamic researchers, practitioners, consultants, and business leaders. We cover foundational elements that are needed to avoid forcing the fun. We also invite lively managers who lead with levity to show us how it’s done. Thanks for joining us on this journey.