The Craptastic Age of Bosses Without Bosses

Everyone's got to answer to someone. Except for these clowns.

“I thought I told you to SHUT UP!” The battle cry of the bad boss.

We had a corner booth. Which was my habit. And beyond that I sat center booth so I could survey the room. Never thinking I’d get shot a la Crazy Joey Gallo but more…I just wanted to see the room.

Conversation with my date was light and convivial. Coming around the corner though I spied my boss. Recently separated he was with some contingent of his family, kids mostly. I waved and hollered a happy hello. My record with bosses is not even mixed. With my Asperger’s attention to detail, lack of interest in sleeping long hours and a real love for words, with minor exceptions, my bosses have been the best. Especially the ones that understood the calculus as laid out for me by one of my better bosses.

“You have one job and one job only.” Chris Gulker, a hotshot at Apple for a period of time and who was the only reason why I was at Apple other than Steve Jobs, who had just returned after his exile, was usually a very smiley guy. Only today he wasn’t smiling.

“What’s that?” I asked.

“Making me look good. You do that? And I’ll sign off on anything you want.” He pushed away from his desk and fixed me with a stare that let me know in no uncertain terms that he was not joking.

And he really wasn’t.

The most important point of which was and remains: never work for a boss who doesn’t have a boss.

The cat coming around the corner in the eatery with his family though had appreciated that I had also done so for him and so we were jake and he walked up to say hello. We also really liked each other. Or at the very least I liked him.

You see the thing about journalism is that it’s a trade, a craft, a calling but it’s pretty class diverse and the blue collar roots of the guy who was now my boss I dug. And he dug that I dug that. I was no J-school silver spooner and so…mutual admiration society.

Jonathan reached out to shake my hand and I can’t really say now from this remove of a few decades what was happening when I did this, but for some reason instead of offering a standard handshake I went Godfather on him. Which is to say I reached out with my left hand, which was the side he was closest to, and folded my fingers over his hand so that my palm was pressed to the back of his hand while my fingers curled over the top and into his palm.

He looked down at our hands. A dark shade passed over his face. I let go of his hand, he said goodbye to my date and wandered back to join his family. I started telling my date how cool of a boss he was while I watched him negotiate his family space. He was dawdling though and eventually turned back to face me.

Making his way back to our table he said a few more things. Things of not especially great significance. Then by way of saying goodbye, again, he reached out his hand, again, but this time he Godfather shook me. It had all been a pretense and amused as all get out I asked my date if she noticed. That she had not didn’t surprise me. That she thought I was imagining it did.

“It was probably just an accident.”

There was nothing about this that was accidental and failure to understand this was a failure to understand how being a boss works. Or at the very least an incomplete understanding of how men worked. No, he had to do this, and this I understood. But so began the beginning of my understanding of bosses and bossing.

The absence of accountability to anything but his or her own instinct or whim makes for an inherently unstable relationship. And shades of Martin Amis — “total control over another individual inevitably leads to torture” — and Captain Queeg.

The most important point of which was and remains: never work for a boss who doesn’t have a boss.

The absence of accountability to anything but his or her own instinct or whim makes for an inherently unstable relationship. And shades of Martin Amis — “total control over another individual inevitably leads to torture” — and Captain Queeg. Indeed, though my worst boss ever, the now-arrested Carlos Watson, did have a board of directors to answer to, as well as investors, as CEO he was often the last word on matters of real import. Which, very possibly, could account for the depth and the breadth of the charges against him.

Moreover, it seems to me, we now live in the age of Bosses Without Bosses. Rupert Murdoch? Yup. Elon Musk? Indubitably. Donald Trump? The very essence of.

All of which harken back to the bullshit American isolationist ideal of the sole and lone wolf who manages to do it all himself or to quote Tony Montana “Who put this thing together? Me, that’s who! Who do I trust? Me!”

Though 100 babies left out in a field for 100 days without any sort of help will always yield 100 dead babies, this is still a temptingly romantic way of looking at work, our contributions to it, and our place in the professional firmament. “I DID IT.”

While some of that is true the real limitations of that way of thinking long term play out as this is written: Murdoch’s Fox just lost a $787.5 million judgement. Musk’s lost millions trundle into billions at this point. And Donald Trump has been arrested in New York much like Carlos Watson.

It’s a weird myopia that fuels their understanding of themselves though and it’s leached into all of our daily doings of everything from our refusal to ask for help for just about anything, as well as our inability to believe that any one else really could. Being able to see this and process it though, made me resolved to, when next I was a boss, to not be that kind of boss.

Did I succeed in not being that which I so ardently hated? Well, you’d have to ask the people that worked for me, but I like to imagine I had. Which is part of the problem: every bad boss imagines that they are not. “No man chooses evil because it is evil,” said Frankenstein creator Mary Shelley. “He only mistakes it for happiness, the good he seeks.”

Additionally, the new zeitgeist lets bad bosses hide more easily than ever. You can now preach the gospel of the embrace of the total worker, use alternate pronouns, mimic some version of allyship and still be a small, credit stealing, backstabbing schemer.

Which is why it pays to be certain of the devil. To wit: the Bad Boss Brief, now on Youtube and soon to be here on Substack as well, is a great way to break down why you feel crappy if you have a crappy job with a crappy boss.

So, yeah. This has been a long commercial for the Bad Boss Brief (so subscribe). But if you still have a job, are looking for a job, looking to change a job, interviewing for a job, you need to give some serious and deep thought to the drug-addled, sex abusing, thieving, gaslighting tacticians that somehow weasel their way (see: business as usual) into controlling your livelihoods.

You can thank me later. With a nice hale and hearty handshake. Palm to palm. If possible/necessary.