By Kerry Frank
When I started down this entrepreneurial path, I quickly realized something that bothered me deeply: it was hard to find examples of women at the top, CEOs, founders, leaders, who hadn’t lost something precious along the way. Marriage. Family. Connection. Many had sacrificed relationships in order to build companies. And while I understand that sometimes leaving a partner is necessary for your wellbeing, I was intentional from the beginning that I wanted to build differently.
I didn’t want success to come at the cost of my family. I wanted my kids to be part of the story, not footnotes in a chapter I would write later. So I started intertwining my business life and my family life wherever I could. Over the coming months, I’ll be sharing more of those stories here on the blog, but today, well, today I’m taking a break from mass cooking for our annual family camping trip to Hayward, Wisconsin.
This trip is sacred to us. We’ve been doing it since my oldest was two years old, and we haven’t missed a year since. It started out of practicality. My grandparents had a cabin in Hayward for years, and when they decided it was too much work to maintain, they started camping there every summer. At the same time, it was the only vacation we could afford for a long time. But year after year, it became something so much more than that.
We’ve made a lifetime of memories there, kids catching their first fish, learning to water ski, and the infamous time a bear wandered into our camp and stood just two feet from my son (don’t worry, everyone was fine, and we’ve retold the story a hundred times around the fire since). It wasn’t glamorous, but it was ours.
For a while, I felt guilty when other kids came back from Disney trips with glittering stories and shiny souvenirs. I’d wonder if my kids were missing out.
Then came our first annual Comply365 conference in Orlando. We had 17 airline executives attend, and I was so proud. Since our kids were involved in the business, I invited them to the welcome cocktail hour. My son Aaron, maybe 10 or 11 at the time, showed up in dress pants, a shirt, and a tie. I hadn’t picked out his outfit. I just told him to look nice.
Not long into the event, someone walked up to me laughing. “Do you know how your son is introducing himself?” they asked.
I had no idea.
“He’s walking up to each guest, shaking their hand, and saying, ‘Hi, I’m Aaron Frank. Are you a client or a potential client?’ If they say they’re a client, he says, ‘Thank you! Our family is so grateful for your support.’ If they say potential client, he says, ‘Well, let me tell you, my mom is the best, she’s honest, and she’ll take great care of you. You really should become a client.’”
I looked across the room and saw him working it like a pro, one handshake at a time. That moment will stay with me forever.
After the conference, we finally took the kids to Disney. I had been scraping every spare penny for months to make that trip happen. We’d only been there for about four hours when one of them looked at me and said, “Can we go?”
“Go where?” I asked, confused.
“Back to the hotel,” they said. “This is really cool and everything, but it’s not our favorite. I’m not sure why kids get so excited about this. Our other vacations are way better.”
I was stunned. But in that moment, I learned something profound: Kids don’t need magic kingdoms. They need you.
They want your time, your attention, your willingness to unplug and just be together. The trips they still talk about as adults are the ones when we were broke, inventing adventures together in the woods.
So here’s my reminder to you, don’t measure the quality of your vacation by how much it costs or how impressive it looks online. Go where your family wants to go. Make memories that don’t need receipts. Cherish the small things: the marshmallows, the campfire stories, the unexpected moments of laughter and connection.
Because those are the memories that last a lifetime.
Posted: June 5, 2025