The Awkward Boss Pep Talk

At a particular media job in the distant misty past, I had a weekly fight with the CEO about paying freelancers. This company had a notorious reputation for paying extremely late, or not at all, to the point where my editorial predecessors had typically given up and passed the buck—telling angry freelancers it wasn’t their fault, they weren’t in charge of payments, and so on.

That was all true—the CEO insisted on personally approving and signing all checks, and he was a huge fan of “slow paying” anyone and everyone. But I felt like I couldn’t just abdicate responsibility for payments, even if I didn’t have the actual power to pay. The least I could do was go in there each week, suffer through a predictably unpleasant managerial confrontation, and try to pry a few checks loose. Only my constant nuisance presence seemed to inspire the CEO to pay contractors and freelancers who otherwise had no advocate, and that only grudgingly.

However, one day, when I came in for our weekly fight over money, the boss had a new agenda. “I want to show you something,” he said mysteriously and importantly. He turned his laptop around with a video cued up. It was the scene from Saving Private Ryan where Private Mellish (Adam Goldberg) struggles with a German soldier, ultimately losing and getting slowly, excruciatingly stabbed in the chest, while his nearby fellow soldier Private Upham (Jeremy Davies) is too paralyzed with fear to help.

In a movie filled with graphic violence, this is probably the hardest scene to watch. I was horrified that the boss was showing this to me without explanation, and the long, painful scene was made even worse by the fact that the laptop’s connection kept resetting. We’d get about halfway through the stabbing, then the internet would go out, and we’d have to reconnect and start all over.

After the fourth restart, I finally couldn’t take it anymore and said, okay, yes, I’ve seen this movie, what is your point here exactly. The CEO—now flustered and angry that his big reveal had technical difficulties—blustered through a speech about how our business was in a constant struggle to survive, the media industry was in big trouble, cash was our most precious and scarce resource, and he wanted me to understand that we had to be prepared to do whatever it took to make it work. That’s why he wouldn’t pay people on time.

Much as I wanted to argue with this rationale, I couldn’t get past the magisterial missing of the point—this was the lesson he took from that scene? Was I supposed to identify with the American soldier who struggled valiantly but ultimately died in terror and pain? Or with the Nazi soldier who killed him while whispering tenderly about how his enemy should give up? Or was I supposed to simply admire the high stakes and brutal dichotomy of their struggle that only ended with one victorious over the other?

As a psychological defense mechanism, I instead entered a temporary fugue state where I simply decided that last few minutes didn’t happen. I nodded blandly and launched into my usual rundown of outstanding payments. The CEO seemed puzzled, but I suppose he adjusted his own psychic worldview to interpret this as acceptance and submission, because he actually approved a couple checks that day. I’m sure in his mind he was being magnanimous, but I’m still not sure if he thought of himself as stabber or stabbee.