Five years ago, I made a decision that changed my family forever. I followed my gut, quit my safe marketing job at Microsoft and started a startup. Everyone thought I was crazy, including my own parents, but I forged ahead. A startup is like having a new baby: you are sleep-deprived, obstacles and frustrations are everywhere … yet, as with kids, you love it harder than you ever could have imagined.

Having two other “babies” in my life has meant a lot of juggling and tradeoffs these past few years. My kids are now 10 and 12, and the teen years are approaching fast. It always feels like there is never enough time with my boys, and one-on-one time is particularly rare. I wanted to slow down and create special memories together to deepen our bond – which, hopefully, would also help us ride out the teen years ahead. 

Enter the “10th Birthday Trip.”

I had first heard of this idea from a travel blogger friend, Kim-Marie Evans. She gave me three reasons why 10 is a great age for a “mommy and me” birthday trip:

  1. They are young enough to take out of school without ruining their pre-college GPA.

  2. They still think you know everything.

  3. They are old enough to remember it forever.


Two years ago, I tested it out. I took my oldest son, Harrison, to Palm Springs for his 10th birthday, and it was awesome.

We swam, played volleyball and visited the local zoo. Every night, he would crush me in a heated game of UNO after we cooked dinner together. There was no sibling rivalry, homework, or domestic day-to-day distractions. Just the two of us, having fun, creating memories with each other and a lot of “inside jokes” along the way. We were two peas in a pod, chilling in the desert together. It was bliss.

  Flytographer Ashley in Palm Springs

Flytographer Ashley in Palm Springs

This February, my youngest, Jack, turned 10. He had been anticipating this moment for a while (his very own 10th birthday trip!), and chose Maui. We had fun doing research on where to stay and what to do; I think the planning together was half the fun!

We stayed at the Grand Wailea, and if you are a ten-year-old boy, it’s pretty much pool paradise, a waterslide jackpot. There are four jungle pools, four intertwining slides, a whitewater rapids slide, a Tarzan pool with rope swing, a sand beach, six waterfalls, caves, three Jacuzzis, an infant pool, the world’s first water elevator, and a swim-up bar (my favourite part). We slept late, went for long walks, took photos, played in the ocean and swam like fish. We saw humpback whales, ate shaved ice, and took day trips to Lahaina and Paia.

We created our own little rituals in Maui, such as the “Crazy Elevator Dance.” Every time the elevator doors closed and we were alone, we danced like crazy until they reopened, and then stood solemnly side-by-side, sneaking smirks at each other as people came in.

Our little secret.

At night, he whispered stories, asked questions, and shared fears, curiosities and interesting observations from the innocent lens of a 10-year-old. His guard was down, and we bonded in a way we simply couldn’t have with all of life’s daily distractions. It made me appreciate his unique little personality in new ways. The memories are priceless.

Back home, months later, the magic of these memories still lives with us. Last week, at our local juice shop, the cashier turned his back and Jack smirked at me. I smirked back knowingly, and we broke out into a crazy dance for 10 hilarious seconds. When the cashier turned around, we froze and stifled laughs.  As we walked back to the car, Jack said, “Mom, you’re pretty fun to hang out with.”  I smiled back and said, “You too, buddy.”


I glowed with joy the rest of the night. I think he did too.

  Flytographer Wendy in Maui

Flytographer Wendy in Maui

This story was originally featured in Twist Travel Magazine’s Summer Edition. To see this story, and other great summer family travel tips, check out the full magazine below!