A couple of years ago, a friend recommended the book Die with Zero by Bill Perkins. This post isn’t intended to be a book review, but I want to highlight one of the key principles from the book: identify what brings you personal fulfillment and optimize your life to “maximize the return driven by fulfillment.”

Historically, as a personal finance enthusiast, my focus has always been to maximize the return on our investments. But once you’ve taken care of the fundamentals—investing in passively-managed, low-cost index funds, automating contributions, maximizing tax-advantaged accounts like a 401(k), IRA, and HSA, and consistently investing in a brokerage account—you’re pretty much set. So then the question becomes: what do you optimize next?

For us, this book was a revelation. It helped us reflect deeply on who we are, what fulfillment means to us, and the actions we can take to maximize it. It didn’t take long to pinpoint what brings us joy: travel—and more specifically, intentional travel that creates lasting memories. The book also talks about “memory dividends,” and that idea really stuck with us. The only thing we’ve changed since is that we now approach travel with more purpose and planning.

Investing in Travel With Intention

Over the past four years, we’ve been very intentional—and structured—about how we invest in travel. That structure is mainly driven by our kids’ school calendar and the PTO policy at my job. But even within those boundaries, our experiences have been amazing.

Spring break has become a cherished tradition for our family. We’ve gone to Cancún three times, San Diego, and this year, Punta Cana. In the summer of 2024, we took our first month-long trip to Spain, visiting Madrid, Toledo, Barcelona, and Mallorca. This year, we’re headed to Italy for a month—a dream come true.

As I’ve shared in past posts, travel can get expensive. But with intentional planning, it’s possible to leverage creative travel hacking strategies to reduce fixed costs like flights and lodging. Let me walk you through how we planned our Punta Cana trip, including some of the hacks we used to save money—without sacrificing the experience.

Planning Ahead: Travel Agent Strategy

The first thing we did was check the school district’s spring break calendar—as soon as it was released, about eight months out. Then we tackled lodging, followed by flights.

Through previous trips to Cancún, we connected with a travel agent employed by the resort. This turned out to be a game changer. Travel agents can often offer discounted preferred rates, complimentary airport transfers, flexible cancellation policies, and even price adjustments if the rate drops before your trip. All of these perks came at no extra cost.

In our case, we booked our trip in August 2024. The rate was adjusted in November thanks to a Black Friday deal, and again in January 2025 with a 10% discount for my birthday. They also added roundtrip private transportation, which wasn’t included initially. It was all seamless.

Flight Savings with Costco & Travel Hacks

Flights from Denver to Punta Cana are notoriously expensive—especially during spring break. I used Google Flights to track prices but couldn’t find any great deals early on. We held off until November 2024.

One of my favorite resources is All the Hacks by Chris Hutchins—a fantastic podcast and newsletter that shares actionable ways to upgrade and optimize your life without spending more. One Saturday, Chris mentioned a deal at Costco offering 25% off Southwest Airlines e-gift cards. That was our move.

I had previously used Costco gift cards for movies, but never for travel. This time, we saved 25% on airfare—a huge win. Costco’s travel gift card section is now part of my regular routine.

A Trip to Remember

We arrived in Punta Cana on a Saturday. To our surprise, our travel agent had arranged private transportation—no van sharing. At check-in, the resort staff asked for our reservation type. I couldn’t remember all the details after six months, but it turned out we had booked “The Level” experience at the Meliá Caribe Beach Resort.

This upgrade included a better room, a private concierge, exclusive dining options, and a VIP check-in lounge. Our concierge helped with dinner reservations, spa appointments, and more. I’ll admit, we’re not used to that level of service. It felt like a lot at first—but looking back, it made the trip feel effortless. We just showed up and enjoyed.

That evening, we walked to the beach. It was too late to swim, but the turquoise water, soft sand, and warm breeze made us stop and breathe it all in. When our kids said, “Best day ever,” it brought a deep sense of joy and overall gratitude.

The Rhythm of Vacation

Our days were simple: breakfast, beach or water park, light lunch, nap or downtime, dinner, and then shows or dancing. One day, we considered a trip to Isla Saona, but decided to stay and soak in every bit of the all-inclusive experience. Next time, we’ll split the trip with time at a hotel to do more local tours.

At night, the resort came alive: a Cirque du Soleil-style show, a phenomenal Michael Jackson impersonator, and a DJ spinning Latin music—merengue, salsa, bachata. My wife and I danced to our favorite songs that have been part of our story for years.

But the highlight was the White Party on the beach. Music, dancers, lights—it was magical. Our boys, usually shy, joined us on the dance floor. That moment, seeing them dance and laugh under the stars, filled me with joy and deep gratitude. I turned to my wife and said, “Esto se siente como un sueño” (“This feels like a dream“). I gave myself permission to pause and be fully present. Sometimes we live on autopilot. But we owe it to ourselves to slow down, reflect, and soak in these moments.

We owe it to ourselves to slow down, reflect, and soak in these moments.

Intentional Travel, Grateful Living

As someone who loves optimizing life, I believe travel is one of the best “investments” you can make. It brings us together, helps us disconnect from daily routines, and creates memories that pay dividends for years.

We’ll continue to use travel hacking to stretch our dollars, but we’re not afraid to spend—or better yet, invest—intentionally in experiences that nurture our souls and bring our family closer.

None of this would be possible without a fulfilling job that I truly enjoy, one that pays well and offers generous PTO. That’s not lost on me. It’s one of the main reasons I remain with my current employer—and I’m grateful for it every day.

As I finish writing this, we’re on our way back from San Diego. We surprised our boys with a weekend trip to see the San Diego Padres—our favorite baseball team—for the first time. Their words? “This is a dream come true.”

We used some perks to save on flights and hotel, and I’ll share those in the next post. But for now, I just want to say thank you for reading and maybe getting inspired to plan your next memory-filled adventure.