The floor to ceiling windows created an L-shaped vista on our Hawaiian Paradise. Below, broke the reliable waves of Waikiki. To the east, we were what felt like eye-level with Diamond Head. I was 15 years old and my mother had flown myself, my two sisters, brother and Aunt out for a weeklong Christmas vacation on Oahu. It was 1980 and my mom was an absolute BALLER.

My mom, Betty, greeting friends at her 25th Wedding anniversary

In addition to the mega suite we shared high up in the tropical ether, we packed countless adventures into every day we were out there. There was the essential visit to Pearl Harbor with the solemnity of the USS Arizona. Mom drove us out to Makaha Beach and we bodysurfed for what felt like hours. The waves were ridiculous and there are some days I still get a twinge from the knee that came down a little too hard after I’d got lost in a savage barrel. Mom piloted us up to the North Shore and we took in the absurdity of the Banzai Pipeline. There was a Luau and I did so much Boogie boarding off Waikiki, my nipples bled for days.

At night, we’d sit up in our big suite and order room service Mai Tais and hoover baskets of Macadamia nuts. There was nothing that we wanted that my Mom didn’t provide.

To this day, I still think of this vacation as the standard bearer for what time off should look like. There wasn’t a moment of tension in the entire group (incredible for our Irish Catholic family) and joy seemed to fill every second. Which is exactly what my Mom had hoped for. Because it was the first Christmas we celebrated after my father had died.

As one can imagine, a parent’s death changes the family dynamic in extraordinary ways. My Dad was a powerful, no bullshit, authoritarian. We did things his way: luckily, he had enough charm and wisdom that this was mostly a palatable endeavor. And my Dad provided a significant income: I never felt rich but I never wanted for anything either. Travel and education were huge for Mom and Dad and they spent on it with ferocity. But my Dad made some mistakes/omissions with his legacy plan. There were a few documents that were not executable upon his death and our family income plummeted by about 90%.

When my mom took us to Hawaii, she blew a large chunk of available cash on one crazy, good time. She could have saved it, made it last longer, done a more “responsible” kind of spending but she chose not to.

During the pandemic, like most people, I had a lot of free time on my hands and I watched many of my colleagues get laid off. This combination of truths led me to finally take a look at my finances, establish a budget and start thinking and planning for the day when I would have no work. My future retirement monthly nut doesn’t look that great, our lifestyle is going to feel very different to how we live now. That’s okay, I know what I’m heading into.

Recently, my immediate family was talking about one Last Hurrah for Fiona’s graduation. Provence was mentioned, maybe Portugal. Fiona has always wanted to go to Hawaii. After an initial enthusiasm for the idea, the responsible part of me (such as it is) started pulling back the reins.

It’s an important question to answer, “what’s too expensive?” Is the cost ultimately measured in dollars or the memories that still return decades later and fill us with happiness.

Can’t take it with you.