Hit the Road

I had a fairly unusual job arrangement when I lived in New York City.  I was hired to work for a woman who held a very prominent position in the city, which she was in the process of leaving. During her transition out of that role, while her plans were still secret, I went to work for her husband, who was a founding partner of a very successful venture capital firm.  In this capacity, I did a lot of unusual tasks: booking George Will for the annual meeting, preparing reports and internal communications, translating financial documents into Spanish (using a dictionary, since these were pre-internet days and I don’t speak Spanish), working with a numismatist to value a stash of rare coins. My friends called him “Mister Pitts,” after Elaine’s boss on Seinfeld, and while I didn’t buy his socks, I did spend a couple of days crawling around inside his closet.

mr pitt
French cuffs, suspenders, and white tube socks…always a hit!

I loved my boss, who was a tremendous benefactor of the arts, served on a zillion boards, was an insightful and extraordinarily successful businessman, and — best of all — was unbelievably kind.  To me, he and his wife were the quintessential New York couple, engaged in work they were passionate about, and out every night at the theater or ballet or symphony.  He was funny, personable, and a fantastic athlete; when I knew him he’d run the New York City Marathon every year since its inception in 1970, and a brief internet search tells me he hasn’t stopped.  My tenure with him, and then with his wife, was very short, as I moved overseas within six months, but the impression he made on me has endured.

Our office was at 45th Street and 5th Avenue, so I took the subway to Grand Central every morning. There is a subterranean passage you can take from the subway platform out to the street, bypassing the main terminal, and that’s what I used to do, shaving a few minutes off my commute. But when my boss found out I was taking the tunnel, he told me that I had to stop, because I was denying myself one of the best sights in New York, and that if you stopped appreciating the beauty in the world around you — and sacrificed the things that couldn’t be quantified, like art and love and pleasure, to the things that could, like minutes on a clock — life would become very dark, indeed.


He had a point.

One of his pet peeves was having his business activities referred to as leveraged buyouts, not only because it in fact was not what he was doing, but also because of the predatory connotation that came with the LBO designation, which flew in the face of his actual business model, not to mention his intentions.  I remember sitting next to him one afternoon while a reporter from the New York Times was interviewing him over the phone; the reporter referred repeatedly to my boss’s restructuring investments as LBOs.  After about five minutes, my boss was completely exasperated; the reporter’s questions were becoming less and less relevant as he pig-headedly pursued his pre-determined line of questioning. In response to yet another leveraged buyout question, my boss said, “Do you have any questions that actually pertain to my company?” and the reporter said, very testily, “Well then, you tell me. What should I be asking?

My boss paused briefly, and then said, “I’d start with two fundamental questions: Is there a God? And am I living my life the right way?” and then hung up, dropping the handset onto the receiver with a thunk.

Less satisfying than slamming down a rotary, but much better than tapping END.

In terms of mic drops, this was a good one, and a model for young me on dealing with the press, which – after working at a national political party – was something I viewed with the same sort of dread as trying on a bathing suit: a necessary, but rarely pleasant, evil. Later in my life, when I was doing the interviewing, I always remembered the takeaway from that day: Don’t write the story before you begin.

I’ve thought about my former boss many times in the years since, not just the two questions he posed to the reporter, which are the foundation of hundreds of years of theological study, but also his advice to take the time to appreciate the world around us.

I think this is why I love to walk (but never run) and to cruise around (but not zoom) on a boat….and I LOVE a good old-fashioned road trip, as long as it doesn’t involve highways.

Possibly the most soul-crushing way to get anywhere.

While I admire the intention of the Eisenhower Interstate Initiative, or whatever it was called, I hate driving on the highway, for the simple reason that it is incredibly monotonous.  I recognize that there are people who enjoy it, for reasons of expediency, but I would rather take the back road and get there hours later, having seen a little segment of life along the way, than take the highway and show up on time.

The glory of the backroads is in the view — the glimpse into how other people live — and the experience: the little country store that sells an array of wigs, the lunch counter that serves shockingly good sandwiches, the gas station where you can buy crickets and corncob pipes and RC cola, but not gas.  And then there are the people…

One time, on a backroad trip from TN, my brother and I and our kids stopped, at about 7 am, at a diner in a tiny town in the mountains of NC.  My brother looked up at the waitress who was tossing cutlery onto our table, and, in his usual charmingly chirpy way, said, “Good Morning! Have you got any coffee?”  The waitress looked at him, rolled her eyes, and said, “What kind of stupid goddamned question is that?” and right then, we knew we were in for an excellent adventure.

The original sassy waitress.

Someday, I am going to do the whole Thelma and Louise thing through the Southwest — as soon as I can find someone to be my Louise. (That person should know that he or she will be called “Weezer” for the duration of the trip, and I will be called “Tee-Dog.”)  We will make numerous stops, for anything and everything that looks even remotely interesting, and we will not eat at any franchise food outlet.  And, the driver controls the playlist.

If these terms are acceptable to anyone out there, let me know! I’ve got some stuff to finish up, and then I’ll be ready to go.




2 thoughts on “Hit the Road

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