Planning international travel with my wife and kids is one of my greatest pleasures out of proportion.
When you plan something far out in the future (whether a trip or a purchase) and spend time anticipating the joy it will bring you over a long delay period, you enjoy it all the more when it comes to fruition. I can optimize the cost, drizzle small luxuries at key moments, and load the itinerary with destinations and activities that delight and surprise those I love the most.
When we started carving out time for three week trips together every summer, back in 2018, I was master of my domain. I made the plans, everyone else just packed a bag on the appointed day and showed up.
I planned early - bought international flights using credit card points and placed deposits on fully refundable airbnb's by January, booked in-country connecting flights, ferries and timed museum entries, and had a full itinerary set to go months in advance. It felt great to set it and forget it until departure day.
Since my family knew very little about the plans ahead of time, everything was an unexpected delight.
As we went on more trips, I offered each family member the chance to plan a day. My wife and son declined. My daughter accepted, and planned a tour of a market near the Royal Palace in Madrid followed by a Spanish hot chocolate from a cafe that's been making them sweet and dark for over 100 years. From that trip on, she's planned one day on every trip we've taken, as she seems to derive the same pleasure in making others happy with discovery that I feel.
After a few creative misses with housing, my wife asked for veto power and a say over the airbnb's we rented. I was reluctant - I dislike it when someone slows my roll or otherwise interferes with the curated experience I aim for on a trip - but where we stay turned out to be a ten for her and maybe a three for me, so it made sense.
More recently, I've fielded family requests on a number of levels. I've always told my kids not to mistake the benevolent dictatorship I run for a democracy, but they seem to want to cast votes in spite of my castigations. It's clear I need to learn to compromise more than I have in the past.
There's also the specter of memento mori - remembering that we are hurtling toward death, some of us faster than others. The arbitrary nature of health is something that was always front of mind as an emergency physician, but it felt at an (admittedly artificial) remove. Samuel Shem wrote about the contrived distinction in The House of God: "The patient is the one with the disease."
An increase in ill and dying friends, combined with a shrinking window during which our kids will remain under our roof, has resulted in a sense of urgency to do some milestone travel. I'd been postponing higher cost trips for a time when they'd be less impactful on our savings rate, but the loss of those we loved raised the fear that later could be too late.
There are financial costs to this decision. Even accounting for my skills at exploring the most economical options for prestige destinations, this summer's travel spend will be nearly double what we spent last summer. We will burn through our hoard of half a million Chase Ultimate Reward points in just one summer.
Yet the averted costs, in terms of foregone regrets, make it the right decision for this year.
I am a control freak in recovery. My need to control our family travel, using cost control as a pretext, is been a pathology with utility. Learning to let go of this need for control is an area I am working on, with mixed success to date, and a long way to go.