Saturday, May 09, 2026

A Retirement 'Journey'

  Mother’s Day tends to come packaged in the usual ways — cards, flowers, reservations, and a few familiar phrases about gratitude. There’s nothing wrong with any of that. But it also flattens something that, in real life, is anything but simple: the steady, unglamorous work that holds everything together long before anyone thinks to acknowledge it.

A recent driving trip out West brought that into sharper focus for me.

Now, my wife and I had been talking about making this particular trip for years. We had specific things we wanted to see, and a rough idea of their proximity to each other. And, thanks to a speaking engagement, we had a departure date, and a “jumping off” point. 

Now, on paper, a road trip sounds straightforward enough — pack the car, set the route, go.

In practice — and especially when you’re traveling with two dogs who are very much part of the family structure (and not very accustomed to travelling), it becomes something closer to project management. Timing, supplies, stops, accommodations, contingencies. It’s not complicated in any single step, but it is relentless in its accumulation.

And almost none of it is visible in the moment you actually leave the driveway. But heaven help you if you haven’t given it (all) consideration before you do.

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As it turned out, what struck me most on that road trip wasn’t the driving itself, or even the destination(s) — though there was plenty to consider on both fronts. Rather, it was everything that had to happen beforehand for the trip to feel effortless once it began. The coordination around our four-legged “children” — what they would need, where they would be allowed (national parks, btw, have gotten very particular about such things), how much of their special diets would need to be accommodated, how the days would (have to) be structured around them — wasn’t an “add-on” to the trip. It was the trip. It just wasn’t the part anyone sees. 

Well, except for my wife — and the pups — whose experience would have been significantly less enjoyable had it all been left to me.[i] And that’s the part that sticks with me. Every successful trip has someone accounting for the details no one else wants to think about. 

Retirement has been described by some as a journey — one that requires thoughtful preparation ahead of time — one that needs to consider contingencies, and one that sometimes takes longer than contemplated in those preparations. 

And yet, when it comes to retirement, a surprising number of people still pull out of the driveway without much more than a vague destination and a hopeful estimate of how far a tank will take them. Surveys consistently show that “retirement needs” are often little more than guesses — revised up or down depending on what the market did last quarter.

So, yes — at a high level my wife and I planned the trip together — we plotted our route, booked hotels, and packed our respective suitcases. But the details of the trip itself —  snacks for the car, medications that we’d perhaps need, coffee, and the various accouterments that our pups required — well, those details, and they were absolutely essential to a successful trip — fell to my better half. 

Now my wife has been doing these mental travel preparations for decades. So much so in fact that I have largely taken them for granted. But this was a longer trip than our usual undertakings — which complicated both the type and volume of packings. And while some of it surely is just “routine” at this point, the longer the trip went on, the more amazed I was at the preparations — and contingencies — she had already considered.

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Retirement planning isn’t just about having a destination — it’s about making sure someone is responsible for thinking about things that can go wrong along the way.

So, as you think about your retirement road trip — perhaps focused on the finances, market volatility and the like — who’s taking into account all those inevitable bumps in the road, the potential road closures, the unplanned interruptions that impact your anticipated arrival times?

And if the answer is “no one,” I’d suggest you rectify that before you get on the road. Because, much like the work, we tend to notice only once a year on Mother’s Day, the things that make the journey work are usually the things no one thinks to celebrate — until they’re missing.

  • Nevin E. Adams, JD

 


[i] Trust me, I thought travelling with three kids was…challenging.

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