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John O’Leary shares the real magic within vacation; the reminder that the little things, aren’t.

Because of a speaking engagement with my friends at Marriott Vacations Worldwide, last week I had the opportunity to travel to Hawaii.

After cashing in a bunch of airline miles, I was fortunate to bring my family along to create special memories in Maui. We reveled in its unmatched natural beauty and lived the spirit of Aloha. It was simply awesome.

While thinking through all the things we did together during our trip, though, a comment from one of my children reminded me that sometimes it’s not the big things that matter most.

Sometimes, maybe even most of the time, it’s actually the little things that matter most. Let me explain.

On our flight back home, one of my boys and I made a list of all the cool things we did together. I asked which was his favorite memory.

Was it snorkeling and seeing sea turtles?
Watching the sunset from a sailboat?
A Luau on the beach?
Building sandcastles?
A car trip to a volcano?


The real magic within vacation isn’t the money spent, hours trekked our meals eaten, but rather it is this.

The highlight didn’t involve an extravagant day trip. It wasn’t a delicious meal on the beach. And it wasn’t even the epic, gorgeous, and utterly perilous drive his dad took them on. (One we were just grateful to survive! Search Kahekili Highway… you’ll understand why surviving a childhood gasoline explosion now ranks as the second hardest thing I’ve ever gotten through!)

So what was his highlight?

“Dad,” he said. “I think the best part of the trip was playing  cards with you.”

So, we just used all of our airline miles, flew 12 hours, had a once in a lifetime adventure to Hawaii for a week… And his highlight was playing cards?!

His point, wasn’t that the trip wasn’t awesome. The deep suntan and constant smile as we chatted on the flight home made that clear. It’s just that he found the very best was in the simplest of things.

My friends, as vacation season begins it might be worth considering what a truly perfect one looks like. We worry about getting to the perfect place, hoping for perfect weather, having a perfect time. But before you load the minivan, board a plane or enjoy a staycation, consider what truly matters most.

While the places we go and the people we meet certainly matter, what matters even more is often less noteworthy and perhaps more important. The most remarkable of vacations are the ones where you are fully present with the ones you love most.

So let’s take a lesson from my son. In slowing down, being present, giving and getting individualized attention, and sharing an experience with someone we love. That is the magic of vacation.

He just happened to be playing cards in Hawaii when it happened.

And looking back on everything else we did as a family, that was my favorite part of the vacation, too.

This is your day. Live Inspired.

16 replies on “The Real Magic within Vacation”

This is so true! As my mom slips deeper into dementia and withdraws more from us, we spend a lot of time talking about better days with Nana. But for all the wonderful trips and places she took my children on, their favorite memories are at her home spending the night and sharing a bowl of her cream of wheat she would ‘dress up’ to taste like warm vanilla ice cream. It just made you feel special when she made it for you and you could sit with her alone and just talk. I have the same memory on mornings when I would be home sick, everyone else would shuffle out the door and then she’d let me come down and out came the cream of wheat pot and little special time with mom.

Thanking you sharing your beautiful story. As a blessed Nana, I sometimes feel that I need to keep my grandsons entertained by visiting museums or farms, etc.. the real truth is, they love just hanging out at home with me to talk and laugh and have down time! These times will make the greatest memories❤️

Thank you so much for this reminder. I am on an extended work from “home” vacation. After being by myself.a lot for the past year and a half I have had to make a conscious effort to stop writing and engage with everyone even if we are just waiting for dinner to be ready. Some of the simple times do hold some of the most special moments!

Really loved this JO! I would say this is one of the greatest gifts I received from the last year and a half. Those little moments mean everything . As always, thank you for shining your light on everyone around you.

John-thank you for sharing your inspiration. Sometimes we go throughout our day and forget those little things that brought us so much joy. We are often reminded by those little ones who see it so clearly. Here is a sweet story from our friends’ 6 year old twin girls who took their first trip to Disneyland. After one of their days spent at the park, meeting Disney Characters, enjoying the rides, and purchasing souvenirs, their parents stated with excitement from one of Disney‘s mottos, “Isn’t this the greatest place on Earth!” One of the twins turned to their parents and paused for a moment and said, “No! Home is the greatest place on Earth!”
I agree with you John…although I’m sure those little girls will have memories cherished for a lifetime, it’s within every moment we have a chance to make each one the best. Here’s to you for starting our weeks and reminding us we are in one of our best moments!

I love this! We have a similar story early in our marriage, we wanted to take our daughter to Disney World. At the time, we had no business financially to even contemplate going. We saved and scrounged up enough money to go. We have been blessed to go on many trips around the country – including Maui over the years. The summer before my daughter headed out of state for college, I asked her – what has been your favorite memory so far in life? It was not Disney World or Maui but the times we laid under a big oak tree in our backyard with a quilt reading books to each other. This hit me hard and made me also reflect, it’s not the things, it’s the moments spent together being truly present.

So heartfelt! Time together with loved ones! As I reflect on my life, the quiet moments in my husband’s embrace watching sunsets were precious. Whether on ocean, front porch overlooking the CO Rocky mountains or hand in hand walking at sunset, the serenity and love filled my heart of moments together.

When all is said and done….it will be the moments we spend with one another that remain. Accumulating stuff will not be the measure…instead, it will be the meaningful moments we share that remain. May we be purposeful in loving one another today.

Thanks for sharing- stay tuned . Our experience has been the older your children get the more they reveal about their great memories of the family vacation. Always rewarding and a good time to laugh about being together.

Thank you John OLeary for always reminding us of the simpler things of life. Spending quality time together is key and that is with any age. I spend a lot of time with elderly from our church and what they need most is an uninterrupted chunk of time with someone listening attentively! So keep reminding us to slow down and focus on what really matters!’
God’s blessings to you and your precious family! 🙏🙏🙏🙏

I love this. You and your wife are doing something right for your son to value that one-on-one time. My husband and I say the same thing. Our favorite time is always just hanging out in the hotel together, laughing and talking, with no pressure to get anywhere or do anything.

Like you, your son is blessed with a gift for appreciating the things that matter most. Thank you for sharing this beautiful story.

What an awesome reminder of what’s important in life; hanging out with loved ones, regardless of where that is. Thanks John! Glad you had a wonderful vacation in beautiful Hawaii.

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