New Regret Unlocked—A Vacation Not Given

Recently, I got to take my family on a high school graduation trip with a first stop in Rome. Unsurprisingly, it was astonishing. Yet, at one of the most iconic sites, what I felt was a profound regret.

Cats in the Cradle Meets Die With Zero

I’ve been on the move since I can remember. The Air Force was a great fit for me because I’m always ready for something a little more challenging, and it’s even better if I get to try out a new locale. When I left for college, that was it. My whole family–parents, brother, and two sisters stayed or settled in my hometown.

I came home for visits, but they were never long because, of course, I had a job and my own young family to sprint back to.  My entire existence, from high school graduation to Air Force retirement, was organized around upward mobility.  It didn’t leave a lot of time for reflecting on what I might regret missing out on, because I was experiencing a lot that I also didn’t want to miss out on.

My father was devout to four things in his life: his wife, his family, the Catholic Church, and baseball. He had a goal to see a game in every Major League Baseball stadium before he died, but his real target was “before he lost mobility.” He accomplished it, but I never broke away to join him for a game because there was always something more pressing in my own little orbit. I was happy that he got to see all the games and stadiums he wanted, but, yeah, it’s hard to say I shouldn’t have found a way to join him. Alas, I’ve already squared up with that regret.

My mother shared three of my father’s devotions, but baseball wasn’t her cup of tea. But both devoted their lives to their church. Neither ever made it to see the Vatican and all of the holy sites in Rome, a pilgrimage that would have absolutely filled their cup. Affording a trip to the Holy City was never within their means but they spoke of it with sense of somewhat resigned longing.

They were happy to share what they had to try to create modest abundance for their family where possible, but their reality was much closer to scarcity for most of their lives.

So, as I gaped at the grandeur of the Sistine Chapel and Saint Peter’s Basilica, it occurred to me: this is amazing, but my parents would have appreciated it so much more than I ever could.

Since my Air Force retirement, I’ve tried to live with a Die With Zero mindset. If the math and statistics indicate that I either have enough to fund my life, or am on that trajectory, then any excess is best used to maximize fulfillment when I have the nexus of time, health, wealth, and access to those I love.  That’s why my family is spending nearly a month traveling overseas this summer.  The time is coming when I won’t have enough influence over my daughters’ schedules to share such experiences.  I will save less this year, but I am maximizing fulfillment with my family while I can.

The regret came from a different place. If I’m honest, I’ve known my family’s finances were “above glidepath” for quite a few years.  Some of those years, my parents were alive, healthy, mobile, and still awestruck by the majesty of Catholic culture, heritage, art, and history.  Thus, one of my many uses for a time machine would be to fund a trip to the Vatican for my parents, while they could have enjoyed it.

As we age, money can become unusable trapped gas, but not everyone has that problem. My parents did not. It might have cost me a few thousand less in savings, perhaps even for a year or two, but I’m confident that my finances would still be on or above glidepath and even more certain my parents would have loved the chance to walk some of the most amazing holy ground on earth.

Cleared to Rejoin

I’ll do what I can to jink out of such future regrets and remain thankful that my parents put me on the path they did, but yeah, if I could go back, I’d buy them a vacation to the Vatican. I will not miss those dollars, and the fulfillment it could have brought them would have been priceless.

Fight’s On!

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