When I was 18 years old, my sister Tarrin and I were visiting our grandmother when she suddenly said something very direct during dinner.

“When I die, I’d like to leave you both some money.”

Tarrin and I looked at each other, both unsure how to respond to that kind of statement. Gamma was in her 80’s and in good health, so it seemed kind of morbid to suddenly bring this up over crab cakes. In unison, we replied with a long, drawn-out, “Ohhhhkaaaayyy…”

“But before you answer, I have a question for you,” she continued.

“I can leave you the full amount… or, if you’re interested, we could take some of it and go traveling together.”

She quickly assured us that she wouldn’t be hurt by our answer and that she would support whatever choice we made.

Without hesitation—probably in less than ten seconds—my sister and I immediately said we’d rather travel with her.

I’ve always felt lucky to have a sibling who’s on the same page as me. We spent the rest of dinner reassuring our grandmother just how much we meant it. I think part of her felt nervous asking—maybe she assumed we’d pick money over time with her. But for us, the choice was obvious.

I’ve always been someone who chooses experience over things. Even in my marriage, people are surprised that David and I don’t exchange gifts—ever. For birthdays or anniversaries, we’re much more inclined to plan and invest in an experience together. Sure, maybe if we lived differently, we’d have a bigger house or a nicer car. But to me, nothing compares to the adventures we’ve had seeing the world together.

My grandmother had been taking cruises since her 30s. I remember flipping through her old photo albums while she shared stories about the fun she and my grandfather had, exploring the world by boat. I loved seeing the photos of her with my granddad, dressed so elegantly as they boarded the ship. Back then, passengers would leave their shoes outside their cabin to be shined by morning.

She used to laugh until she cried retelling the time—after perhaps a little too much champagne—that she and my grandfather swapped everyone’s shoes outside their cabin doors. The next morning, they listened to the commotion from the mix-up and giggled mischievously over their coffee.

After that dinner conversation, she planned our first family cruise through the Panama Canal.

One of the things I love about cruising is how perfect it is for multigenerational travel. On that trip, I was just 19, and my grandmother was well into her 80s.

I’ll never forget dining outdoors as we passed through the interchanging locks of the canal. We played card games, read books, and had great conversations as we watched the ocean go by. Those memories are forever rooted in my heart.

This experience with my grandmother taught me something I still carry today: the most meaningful investments we make are often not in things, but in moments. Love, laughter, and presence are the true currency of a life well lived. It’s a powerful spiritual practice to ask ourselves regularly—am I choosing what truly matters to me? Whether it’s a trip, a phone call, or simply showing up with intention, those choices shape the legacy we leave behind.

I’m sharing this story with you because I’m excited to be creating new memories this October, when Radleigh Valentine and I host our very first cruise together!

Radleigh and I have co-taught several retreats over the years and are so delighted by the beautiful circle of participants who come together. We keep brainstorming ways to make them even more memorable. That’s how The Lightworker’s Journey Cruise was born—our most in-depth and thoughtfully designed experience yet.