I’m a man of many lists. In some cases, that qualifies as a personality disorder. In my case, it’s the only way I can keep my priorities straight in a complicated work and personal world. I maintain separate reporter-style notebooks for day, week, long-term and groceries. I relish the simple pleasure of striking through missions accomplished.

My most important organizational tool, though, is my weekend notebook. Like most people who work at high velocity, weekends are my time for recharge, for spiritual and recreational renewal. I typically start my weekend list on Monday. Depending on the season and the weather, I’m thinking about the “ings”—hunting, fishing, cycling, hiking, skiing or, of course, boating.

Some people adhere to the hackneyed maxim carpe diem. I’m one of them for sure, but I’m really more aligned with carpe volutpat vestibulum, which translates as “seize the weekend.” And as list-intensive as my life is, sometimes the random, unexpected event or opportunity can deliver great rewards.

I was tentative about an invitation to go sailing in late August with my old friend Dan five hours up the road in Chicago. True, sailing was on my summer list, but I was resisting a bit because of a heavy work docket and other listy things closer to home. We had agreed to watch the weather and make the call midweek. As the proposed date approached, the forecast appeared nearly perfect: sunny skies, a civilized 10 to 15 knots of breeze and manageable seas. I loaded up and hit the road.

Dan and I have been close since our freshman year at Michigan State in the mid-’70s. Geography separated us for some of the interim, but we stayed in touch and converged whenever we could. In the early 2000s, we found ourselves on the same longitude and started getting together more often. My sons learned to sail and paddle on a great string of vacations with his family at their cottage on Lake Michigan. We share passions for a number of active outdoor sports, in spite of being a bit less nimble these days. Sailing is one. A few years ago, he bought a small cruising sailboat and installed it in a city marina on the big lake, just south of downtown Chicago. The boat is great, and the backdrop is dramatic.

As sometimes happens, our enticing forecast didn’t play as expected. The first of our three days featured a bit of breeze, but also lumpy seas from an overnight blow from the north. We ended up motoring up to the Loop, where we encountered an unexpected treat. Upon our arrival, the U.S. Air Force Thunderbirds began a rehearsal for a weekend air show. The F16s flew low and fast as we meandered through a large fleet of boats anchored behind the breakwater off Navy Pier. It felt like we’d stumbled upon a free Bruce Springsteen show in the park.

The second day dawned gray and breezy with gusts and seas out of the south. Again, unexpected, but it proved to be a fun, albeit adventurous sail. We may have had more fun than Dan’s wife and daughter, who would have preferred a little less rock ’n’ roll, but a good time was had by all.

Our final day was a Hail Mary for sailing, but it paid off in other ways: just Dan and me motoring out for a couple of hours in dead calm on a sunny, late-summer morning. Again, not ideal sailing conditions, but we had an opportunity to catch up on nearly everything on our lists.

The experience provided a wealth of great moments. Living off the list generally works for me, but I’ll concede: Sometimes, improvisation has its merits. Carpe volutpat vestibulum. 

This article was originally published in the Winter 2023 issue.