Jessy Kyle on the Freedom to Dream Again

In this interview with Jessy Kyle, three-time cancer survivor, inventor, and Founder & CEO of Betterly Bra Company®, we explore how resilience, gratitude, and perspective have shaped the way she approaches life, business, and success. From overcoming extraordinary health challenges to redefining what it means to live a life you love, Jessy shares the habits, lessons, and mindset that continue to guide her journey.

When Every Day Becomes a Gift

What does a life that you love look like for you? And are you living it?

I’m a person of faith, and every day I thank God for another day. I’m truly just so grateful.

I was diagnosed with Hodgkin’s lymphoma when I was 16. Then it came back at age 27, and then it came back again at age 36. Now I play Powerball because my oncologist said that doesn’t really happen. Each diagnosis at 16, 27, and 36 was a completely different stage.

That first experience helped me put things into perspective. I didn’t realize I was learning that lesson until later in life.

I’ll give you an example. I grew up in South Jersey and was treated at CHOP. They found it early, and the doctors told me, “Next year is going to be awful. You’re going to have surgery. You’re going to have chemo. You’re going to have radiation. You’re going to lose your hair. You’re going to get sick. But in about a year, we think you’ll be okay.”

At 16, I knew cancer was bad, but I don’t think I really understood how sick I was. Hearing that from the doctor made me think, okay, I have a goal. There’s an end point. I understand it’s going to be tough. Just put your shoulder down and do it.

I think that was a true life lesson. I’m definitely a goal setter. I’m a doer. I think that came from that experience.

The second lesson I learned was perspective. People hear my story and say, “Oh my God, what I’m going through doesn’t compare to what you’re going through.” I’m always like, it’s not a contest. Everyone’s journey is their own, and it’s significant. But I also believe in putting things into perspective.

When I was going through chemo, a very good friend of mine had a friend who was in a terrible car accident. She was in traction with pins in the hospital for weeks. I’d always ask how she was doing. My friend’s husband finally said, “How are you doing? You have cancer.”

I said, “But I’m fine. Yes, I get my treatment. I get sick. But I can go back to school on Monday. She’s way worse off than me.”

I remember realizing that, yes, I had cancer, but in many ways I really was better off than she was. That has stayed with me. No matter how unfortunate or difficult my situation is, it could always be worse. So I try to accept the cards I’ve been dealt and then deal with them.

I feel like I’m living a life I love because I’m just so grateful for it. I’m happy for what I think are the reasons people should be happy. I’m healthy. There’s an asterisk there. We’ll talk about that in a minute. But I’m healthy. I have a wonderful husband. I have an incredible daughter that we were told we couldn’t have, but we do. We have a business. We have a really great life.

I’m not morbid, and I want to be here another 50 years. But if this were it, Jessy had a really good life.

Finding Strength in the People Who Show Up

How has community played a role in your work and through your health journey?

I’ve been very fortunate to have a great family and great friends.

When you say community, I feel like I’m just getting back into it. Over the last six years, I’ve had significant health issues because of the treatment I received many years ago. I wasn’t really part of the community. I wasn’t out and about.

Even the event where I met you was one of the first times I was really getting back out there. So I feel like I’m almost new to the community again, or maybe being reintroduced to it.

I’ve lived in Philly for a very long time, and I certainly know a lot of people in the city, but I feel like I’m just reconnecting. Even in the last year, I’ve met so many great people, yourself included. I’m just dipping my toes back into the community, and it’s been very welcoming.

Happiness Is the Greatest Measure of Success

What is your definition of success today?

I think being happy is being successful.

People measure success by saying, “I made this amount of money,” or “I made partner.” Those are great metrics if that’s your gauge.

It probably sounds simple, but to me, being healthy and happy is success. When you’re healthy and happy, you can go live your dream, whatever that dream is. You can pursue that goal, write that book, or do whatever it is you want to do.

You really can’t do any of that unless you’re happy. Once you’re happy, I think that makes you successful. Everything else is just icing on the cake.

Small Daily Choices That Change Everything

What are some of the habits that you have currently that have allowed you to get to your level of success and your definition of that?

Over the last six months, I’ve made a few small changes that have really helped.

One is no TV on Sunday nights, unless it’s the Eagles, at least during the school year. That’ll probably change in the summer.

I’ve also been trying to read more. Not every single day, but more often, and without the TV on. I don’t have the TV on at all during the day anymore. That’s been a really big deal because the news is just mindless. It’s not helping me.

I love TV and movies, but they’ve become a distraction. Instead, I’ll put on some music in the background so I can sit down and get work done.

During the school year, I drive my daughter to school. So getting up and working out before I take her has made a huge difference. This feels like such a first-world problem, but taking her to school can be an hour-plus, door to door. If I came home and worked out afterward, it was already 10 o’clock before I even started working.

Now I get up at five, and by 6:15 my workout is done. I feel like I’ve already conquered the day.

Those little things have really helped me stay focused.

Your Instincts Know Before You Do

What is a hard lesson that you’ve had to learn?

A hard lesson I’ve had to learn is to always trust your gut.

The first thing that comes to mind goes back to when I was in that girls’ group. We signed with a manager, and I remember signing the contract because he was really pushing us. I wasn’t strong enough or confident enough, I think I was 19 or 20, to say, “Wait, let me really review this.”

I remember signing it and thinking, well, if this doesn’t work out, we’ll see you in court.

That’s exactly what happened. We got a small record deal, he took our money, and when he was supposed to file our group name with all of us included, he didn’t. We lost our name.

I didn’t follow my gut. That’s the first thing that sticks with me when you ask that question.

The Comfort of Certainty Can Hold You Back

What do you think keeps women from taking risks and doing the hard thing?

It makes me think of my mom.

She was a teacher, and years ago she had a business idea. I don’t remember exactly what it was, but her grandmother was willing to finance it. This was probably 60 years ago.

My mom said she just felt more comfortable knowing exactly how much money she was going to make. It’s the bird-in-the-hand scenario. She knew what was coming in, knew she could pay her bills, and even though she could possibly make much more, that certainty mattered more.

I think that’s really a personality issue. Maybe it’s a gender issue too, but I feel like it’s mostly personality. Some people just need to know they’re going to make a certain amount every week so they can pay their bills and take care of their kids.

That’s probably why people are risk-averse.

Never Stop Dreaming Big

If you were to think of yourself as 10-year-old Jessy, what advice would you give her?

I don’t know if I really have advice for my 10-year-old self because I was lucky to have a wonderful childhood.

Ten-year-old Jessy was happy.

A lot of who I am comes from my parents. My dad has passed away now, but both of my parents gave me the space to dream. It was never, “Oh, that’s never going to happen.”

In fact, when I said I wasn’t going to college, they said, “Okay, but you have to go get a job.” This was back when everyone wanted a record deal. They said, “Nobody’s going to knock on your door and hand you one. You have to go out and get it.”

Within about two years, I had a small record deal.

So I guess if I had to say anything to 10-year-old Jessy, it would really be what my parents gave me, which was the freedom to dream.

Meet Jessy Kyle

Jessy Kyle is a three-time cancer survivor, inventor, entrepreneur, motivational speaker, and Founder & CEO of the Betterly Bra Company®️, dedicated to helping women feel confident, comfortable, and beautiful. Betterly’s patented design gives women a custom fit bra without the custom fit price. Betterly wearers get their best fit every time!

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Meet Jessi Sheridan

Jessi Sheridan is the founder, coach, and story-gatherer behind Habituelle—a community for women ready to lead boldly and live meaningfully. 

With nearly two decades of experience guiding mission-driven leaders, Jessi brings a rare blend of heart and clarity to every conversation. Her approach pairs intentional coaching with real-world leadership know-how—meeting you with both empathy and action.