Bitter or Better? Choosing Reinvention After Divorce in Your 60s
Kerry Breckle sat in the quiet of her newly single life, scared and uncertain about the future. She'd just gotten divorced in her early 60s, and a simple question kept echoing in her mind: How am I going to manage all this?
Then it hit her.
She had a choice.
"I could stay bitter. I could blame everything on other people, but this is my life now. Absolutely my life," Kerry told me during our podcast conversation.
But the Kerry I know now—the one who jumped into a hot air balloon over ancient Mexican pyramids, who got her first tattoo at 62 in a foreign country—is worlds away from the woman she used to be.
Exploring Viñales, Cuba [Cuba, 2025]
The Before: A Bird in a Locked Cage
Pre-divorce Kerry was "just existing."
She was afraid of flying. She didn't like being away from home for very long. She spent her days reading books—not to fuel adventure, but to pass the time, to live vicariously through other people's stories instead of creating her own.
"It was a sad place to be," she admits.
When Kerry described this version of herself to our tattoo artist in Cuba, she told him she felt like a bird in a locked cage. That image became her first tattoo—a birdcage with a small bird being released.
But getting from the cage to that tattoo shop required something radical: making a choice.
Kerry’s tattoo progression [Mexico City 2025]
The Turning Point: Deciding to Be Better
After her divorce, Kerry went to therapy and set a goal that terrified her: take a group trip.
Then came a gift from her oldest son, who she'd been caring for through his medical issues. "He looked at me and said, 'It's okay for you to go. I'll be fine,'" Kerry recalls. "What a gift he gave me. Wouldn't it be a shame if I didn't make it into everything it could be?"
Her therapist found an ad for my Cuba trip. Kerry had always wanted to go—fascinated by the preserved city of Havana slowly crumbling.
She booked the trip.
And she was absolutely terrified.
The First Leap: Cuba and Sleepless Nights
"I was so scared before I went to Cuba. I had sleepless nights."
The Miami airport almost broke her. She had to rush through the terminal to catch her connecting flight—only 20 minutes before boarding when she discovered something was wrong with her visa.
"I looked at the airline attendant and said, 'I need to tell you, this is the first time I've ever traveled on my own. If I don't make this flight, I don't know what to do, and I'm really scared.'"
The woman helped her. Kerry was the last person on the plane, shaky but triumphant.
In Cuba, Kerry discovered she could do this. She could navigate a foreign country. She could connect with strangers who became friends. She could be brave—in fact, she already was.
Her favorite memory? Giving a little boy a five-pack of matchbox cars at lunch. The boy kissed the box and hugged it. And Kerry realized: "This is how it's supposed to be."
She was no longer just reading about life. She was living it.
Touring Cuba in classic cars [Cuba, 2025]
The Evolution: From Terrified to Thriving
By the time Kerry joined my Mexico City trip, something had shifted. The nervousness had been replaced by excitement.
Kerry didn't think twice about climbing into a hot air balloon at 4am. "You throw your dignity out the door, and you just go with it. I had no doubt of hopping into this hot air balloon, looking over the ruins. It was an incredible experience."
She FaceTimed her best friend from the balloon. "I'm in a hot air balloon in Mexico City looking at the ruins. How will you ever top this phone call?"
Kerry decided to add to her Cuba tattoo. This time: a bigger, stronger bird. Lines showing movement. An evolution.
"It's my come full circle moment. I'm getting better, I'm doing more. I'm meeting the most incredible people."
Viewing the Teotihuacan pyramids the best way—via hot air balloon [Mexico City, 2025]
The Message: You Have a Choice
Here's what Kerry wants you to know:
Age is just a number. Kerry references Grandma Moses, who didn't start painting until 78 and created approximately 1,500 paintings before she died at 101. "I met a woman the other day who got divorced at age 79. And I admire her because she's got that same attitude."
Your story isn't over. "I had this chance to start over at 62. Wouldn't it be ridiculous if I didn't grab that opportunity and start to run with it?"
The fear is normal—do it anyway. "I was scared, but I thought, the worst thing that can happen is I'm gonna die, which is gonna happen anyway."
How you wake up matters. "Pre-divorce, I would wake up and think it's another day. I'm just existing. Now when I wake up in the morning, I'm like, 'What do I get to do today?'"
No one's coming to save you. "Take the chance. You may think that you've peaked or there's nothing else out there for you. Go find it. No one is going to knock on your door and say, 'Hey, I got a new life plan for you.' So do it."
Kerry and some of the crew celebrating Day of the Dead [Mexico City, 2025]
What's Next for Kerry?
Greece is definitely on her list. But the trip that would take her most out of her comfort zone? Kenya. A safari.
And she's already planning to keep adding to her tattoo—this time with color. "Just the reawakening of me. The better, stronger version of me."
If Kerry could sit down with newly divorced Kerry, here's what she'd say:
"Keep your mind open. You don't know what's going to happen tomorrow or next week. And if you're open to the experiences, you just might find something that's incredible."
Ready to hear more of Kerry's story? Listen to the full Type 2 Travel podcast episode where Kerry shares the wild rickshaw ride through Mexico City traffic and what it really feels like to choose "better" over "bitter."
The pre-divorce Kerry would never believe she'd travel to foreign countries with strangers, get tattoos at 62, or ride in hot air balloons over ancient pyramids.
But that's exactly what happened when she made a choice.
Bitter or better?
Kerry chose better.
What will you choose?
Kerry has traveled to Cuba and Mexico City with Laura Ericson Group Trips. Want to create your own transformation story? Check out upcoming trips here. Because sometimes the best way to find yourself is to get completely lost somewhere new.
