Making Travel a Way Of Life

Exploring the world with our daughters

Travel is important to many -- as a way to unwind, create memories, and avoid burnout. After the pandemic, the desire and ability to travel is something that shouldn't be taken for granted. For Jill Dawson, and her husband, travel has always been a priority. With two daughters and a business, it’s looked different over the years, but it has always provided a way to spend quality time as a family while exploring, learning, and experiencing.

Jill shared they have always preferred to bring the girls along. "We were more relaxed because we weren’t constantly checking in at home," she said. "This meant we could unplug and spend quality time together, while also making life-long memories."

In their early days of travel, this meant bi-annual trips to Fort Myers, Fla. to visit Jill’s parents, for some extra sunshine and warmth, along with a visit to Disney World in Orlando. Now, as business owners, travel is a part of their lifestyle. "I believe when you take time to get away and disconnect, you come back ready to kick butt," said Jill.

As business owners, they run two American Family Insurance offices -- one in Waconia and the other in Bloomington -- with a focus on hiring the best people and building a culture that supports great work and balance. When traveling, the team handles everything, creating a seamless experience for clients and employees alike, because the right people are in the right roles. They are empowered to make decisions and take action. And because she wants her employees to prioritize travel and time off too, they offer a generous PTO plan to encourage their team to do the same.

Making Memories

Something Jill does with her daughters on every vacation possible is parasail. It's something they enjoy doing together and if there is an opportunity, they always fit it in. They also celebrate vacation birthdays. Each day on vacation, they pick one person and act as if it's their birthday. This can include any number of activities but especially a special dessert. They use travel in lieu of gifts and now have travel traditions that have allowed them to teach their kids about the world and different cultures, all while building strong family bonds. One of those traditions is a trip every year, leaving the day after Christmas and returning in time for New Year's. “No matter the trip, travel lets our girls unplug and spend quality time together, in a place where they are not worried about what their friends are doing or what they might be missing out on. My parents still reside in Fort Myers, and I have to say, Orlando with teens is so much more fun," Jill said.

The Rhythm of Travel

Now yearly travel is a mix of two to three family trips a year and quarterly getaways with her husband, ranging from a long weekend away to a favorite all-inclusive resort. When asked about their favorite family trip, Jill recalled a road trip (which stood out since they normally fly) to Banff and Lake Louise in Canada. Because they drove, they could take their time getting there and sightseeing along the way. They spent a week in both Banff and Lake Louise, and every member of the family has said they can't wait to go back to this scenic destination and explore even more.

Tips for Memorable & Relaxing Travel

Something her family does a bit differently is avoiding the jam-packed itinerary. "We always know where we will stay, but then we tend to play it by ear so we have plenty of time to unwind," shared Jill. "Once we arrive, we each select one or two must-do activities, but the rest of the time is fluid and flexible."

"I believe when you take time to get away and disconnect, you come back ready to kick butt," said Jill. 

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