Looking at my shoes

The really strange thing, he told me, is that he always daydreams about huge windfalls. His current financial straits aren’t all that dire — he’s not going to lose his house or anything — but he’s unable to fantasize realistically about somehow getting just the figure that would put him right: a modest tax refund or an unexpected royalty check, something realistic and quite possible. Instead, it’s always piles of cash and oversize checks.

“Is that normal?” he asked.

Everyone daydreams about the lottery, I told him, unhelpfully adding that the other stuff he fantasizes about is weird. Daydreaming about being hit by a car because of the resulting insurance settlement is, I told him, something he needed to bring up with a licensed mental healthcare practitioner.

The truth is, I was the wrong friend to be offering advice. I don’t like to talk about money, especially with close friends. I follow the inflexible Episcopalian rule about never discussing personal financial matters with anyone but a certified public accountant, and even then, it’s best to couch things in vague and nonspecific terms.

Perhaps you’ve heard this old joke:

Q: How do you get an Episcopalian to look at his shoes?

A: Mention Jesus, or money.

The problem is, it’s impossible to talk about money without talking about how some people spend it, and it’s impossible to talk about that without getting into difficult and awkward subjects such as prudence, foresight, good planning, smart values, all of the things that close friends should never, ever discuss. My friend is a successful person with a flourishing career, but he spends too much money (in my opinion) on frivolous (to me) nonsense (again, per me) and ends up stressed out and frantic because he doesn’t have the discipline (in my judgment) to curb his foolish (as I see it) spending.

None of which I could say to him because a conversation about money is a minefield where friendships go to explode.

And also: I work in Hollywood. I am in no position to lecture anyone about financial prudence.

When I got my first job as a television writer, I was 24, and I drove a 15-year-old Subaru Outback. It was electric blue in the places where it wasn’t spotted by rust, and it emitted an alarming noise every time I made a left turn.

On the other hand, it was cheap.

But driving onto the prosperous, sun-baked Paramount Studios backlot, I was acutely aware that my rusted heap of screeching metal was ill-suited to the dazzling array of luxury cars around it. People, in fact, gave me nasty looks. My co-workers complained if I parked my car too close to theirs, as if an unfashionable car brand might infect their Bentley with some form of automobile COVID-19.

Eventually, I bought a fancy car. I blamed it on peer pressure, but we all know what was up: I was making real money in a status-obsessed business in a prestige-conscious town, and I wanted to cruise around in a sleek machine that, I presumed, befitted my station.

Once you make that mental adjustment, though — that expensive things project power and importance — you need to keep buying expensive things: cars, houses, seats on an airplane. And then, suddenly, you can’t button your shirt cuff because the watch you’re wearing is the size of a grapefruit.

The rule is, the more money you make, the more you spend. And as everyone knows, the more you spend, the more you have to make. Until you discover that you’re working simply to maintain a certain level of spending and that you’re unable to stop, which is when you start having daydreams about a Saudi diplomat clipping you in an intersection and paying you for your trouble with a suitcase full of cash, which is a lot harder to orchestrate than simply wearing a cheaper watch.

I didn’t say any of this, obviously. I was too busy looking at my shoes.

Rob Long is a television writer and producer and the co-founder of Ricochet.com.