Designated Drivers, Fearless Leaders, and One Alleged Accountant

I recently returned from my 21st annual baseball trip with my high school buddies. This year, accompanied by our wives, we spent three toasty days in Tampa—sunning, swimming, dining, and watching the White Sox play the Rays in their temporary, makeshift ballpark. The White Sox won, the threatened rainstorms never materialized, and we all had a blast.

But now the hard part begins.

During our trips, we have a Fearless Leader to set things in motion, an Admiral to keep us on course, and the rest of the gang are our designated drivers, humorists, and philosophers. But once we get home, I take center stage as the Alleged Accountant.

How I was entrusted with this position is unclear. Perhaps it’s because, in addition to my medical degree, I have an MBA. It’s from a graduate school maybe one or two notches above Trump University in reputation, but hey, it’s an MBA just the same. Once we’re home, I dust it off and swing into action.

While on the trip, one person pays for each meal—no restaurant wants to handle six credit cards at breakfast. Same with the vans we rent. One person picks up the tab. Game tickets? One order, twelve seats. All these go into a theoretical “book.” By the end of the weekend, one person may have spent hundreds, while another has forked over just twenty-five bucks. My job is to make that “book” less theoretical. I collect receipts and do the balancing act. Who owes what—and to whom?

An Excel spreadsheet helps me through the first round of calculations. My rule is simple: charges for all meals and transportation are split evenly. That keeps things straightforward—until someone misses Monday’s dinner or skips Tuesday’s lunch. I don’t want to charge them for meals they didn’t eat!

It takes a few passes through the spreadsheet, but eventually I reach a reckoning and send out my preliminary analysis to the crew. Inevitably, someone points out a detail I got wrong—maybe I split a bill six ways instead of five. Eventually, the whole megillah gets reconciled to everyone’s satisfaction.

Then it’s time for those who underpaid to Zelle or Venmo (or even send a check) to those who overpaid.

And then, finally, I get to retire my accountant’s green eyeshade—at least until next year.