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Conversations with Becky Chidester

Today we’d like to introduce you to Becky Chidester.

Hi Becky, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
After spending nearly 20 years in corporate leadership roles across strategy, consulting, and analytics, I realized I wanted to build something of my own that would have a more direct, positive impact on people’s lives. As a 40-year-old woman with two young kids, my focus on health and fitness became less about looking good and more about feeling strong, managing stress, and showing up as my best self.

That perspective, combined with my passion for fitness, led me to JETSET Pilates, a rapidly growing franchise brand based in Miami that offers the energetic, high-intensity, low-impact workouts I fell in love with. With JETSET Pilates Arboretum, my goal is to build a community where people can prioritize themselves, get stronger, and leave feeling better than when they walked in.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Definitely not. I’ve been fortunate to have an incredible support system through JETSET, but no amount of preparation fully prepares you for the transition from corporate life to entrepreneurship. One day you’re making high-level strategic decisions, and the next you’re also handling marketing, hiring, operations, finance, and everything in between.

The biggest lesson has been learning to let go of the things I can’t control. Every day brings new wins and new challenges, and I’ve had to become much more comfortable with uncertainty. It’s been a roller coaster, but it’s also been one of the most rewarding experiences of my career.

Can you tell our readers more about what you do and what you think sets you apart from others?
Throughout my career, I’ve been known as someone who combines analytical thinking with execution. I enjoy solving complex problems, building relationships, and turning ideas into action. Whether I was leading teams in the corporate world or now building my own business, I’ve always been someone who likes to roll up my sleeves and make things happen.

Today, I’m applying those same skills to launching JETSET Pilates Arboretum—from strategy and operations to marketing, hiring, and community partnerships. I’m most proud of taking the leap from a successful corporate career to entrepreneurship while raising two young kids. It’s definitely stretched me in new ways, but it’s also reinforced that growth comes from being willing to bet on yourself.

Is there any advice you’d like to share with our readers who might just be starting out?
One of the best pieces of advice I can give is to invest in relationships with the people who invest in you. Some of the most impactful mentors in my career weren’t assigned through a formal program—they were people who saw potential in me, challenged me, and were willing to open doors.

I still stay in touch with mentors from my very first job out of college, and they’ve continued to be trusted advisors through every stage of my career. Looking back, I wish I had realized even earlier how valuable those relationships would become. Skills and experience will open opportunities, but the people who believe in you can truly change the trajectory of your career.

Contact Info:

Group of people posing on a grassy area in front of a building with a sign that reads 'JETSET' and 'SUPPORTING THE BEST IN THE BUSINESS'.

People practicing yoga outdoors near a building with a blue sky background.

Group of people at an outdoor event with a table and promotional materials, in front of a building with large windows.

Group of people practicing yoga outdoors on mats in a park with trees and grass.

Group of people at an event, some posing, some walking, with branding and stage in background.

Instructor leading a fitness class with participants lying on mats, raising arms, in a bright studio with logo on wall.

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