What’s the real reason you hate your boss?

If I had to guess at the most-said phrase at happy hours around the world — but especially in the United States — I’d wager these are the top three:   

  • “Another one? Sure, why not?”
  • “I hate my boss.”
  • “Have you been to that new hipster cheese shop that’s also a distillery?”

I’m probably wrong on No. 3, but I’m not wrong on No. 1 and No. 2.  I’ve been to maybe 19,000 happy hours in my life, and “I hate my boss” comes up a lot. This isn’t a surprising fact. The employee-manager relationship is somewhat doomed from the start in many cases, and it doesn’t help when stats like these exist:

All these are problems. You can’t sugar-coat it. So if you’ve ever uttered “I hate my boss,” I’m with you. I myself have hated many a boss, and been blessed (#blessed) with a few good ones along the way too. Remember: management isn’t intuitive to most people.

But have you ever stopped and thought about why you say “I hate my boss?”. It’s actually very rooted in anthropology and sociology and psychology and the like.

I hate my boss: Let’s establish Paul Graham’s reputation first 

Paul Graham is a co-founder of Y Combinator, which is a very powerful Silicon Valley accelerator. The current head guy there is Sam Altman, who The New Yorker just profiled. That’s an amazing article. Read the whole thing if you want to understand the current American economy and where everything is headed, including AI. That’s just a plug for a magazine, I guess, but it’s a great article. It’s also about 20,000 words, so be careful.

In that article, you have this quote:

The venture capitalist Chris Dixon told me, “They created the greatest business model of all time. For basically no money”— YC gives each company just a hundred and twenty thousand dollars, to cover expenses—“they get seven per cent of a lot of the best startups in Silicon Valley!” Collectively, YC companies are worth eighty billion dollars, a valuation that has grown seventeenfold in the past five years. 

Alright. So by now, hopefully you realize that this Paul Graham guy is fairly smart. He also makes money, which is more important than “being smart” to most people in business.

Some of the smartest people in Silicon Valley realize we weren’t meant to have a boss. 

We just “vetted” Paul Graham. Now let’s move to some of his theories.

I hate my boss: The anthropological side

Paul Graham wrote this blog post in 2008, right around/during the recession. We all probably touched on the ideas of hunter-gatherers and human evolution in school somewhere, but here’s a point worth noting:

Humans also seem designed to work in groups, and what I’ve read about hunter-gatherers accords with research on organizations and my own experience to suggest roughly what the ideal size is: groups of 8 work well; by 20 they’re getting hard to manage; and a group of 50 is really unwieldy. 

Whatever the upper limit is, we are clearly not meant to work in groups of several hundred. And yet—for reasons having more to do with technology than human nature—a great many people work for companies with hundreds or thousands of employees. 

Alright. I’ve always wondered this. It makes literally no sense at any psychological or anthropological level to have a 75,000-person company. It’s moronic. And yet, many exist. The best rationale I can see is “more people = we make more money” and/or “more people = solve more problems.” Neither really makes that much sense.

So here’s the first reason one utters “I hate my boss.” You don’t even hate your boss, really. You’re just working in a structure and system that makes almost no sense.

I hate my boss: The tree analogy side

We’re going back to Graham here. Here’s one quick quote he has on how many organizations are arranged:

In the group one level up from yours, your boss represents your entire group. 

Think about it. You work on a team of 12 people. That team has a boss. When that boss goes into meetings with his/her colleagues, he/she is seen as the representative of all 12 of you. In this way, you basically don’t exist as an individual two levels above wherever you reside.

This poses problems. Hierarchy is not going anywhere. You want to yelp at me about self-management? Go ahead. It cannot be taken to scale. The real reason hierarchy isn’t going anywhere? It essentially forces conditions of respect on people that probably don’t deserve it inherently. You typically must respect a VP, but not because they achieve a ton. You respect them because they’re a VP. That’s how it works.

But in our confusion about work — it’s not logical, it’s emotional — we forget about this tree structure. Your boss represents all 12 of you at some meeting. But your boss has 10 colleagues, so there’s 11 middle managers in that meeting. Now the head of that meeting goes to another meeting, and he represents those 11 people — and their direct reports. It’s a giant tree.

In that tree, you lose basically all semblance of individuality or connection back to the purpose of the org. “I hate my boss,” you mutter. But again, no. You really just dislike the system.

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I hate my boss: Yes, bosses do crappy things

Brief interlude here. There are reasons to objectively say “I hate my boss.” Your boss might be a “sense of urgency” as*hole. He might be a target-chaser. Here’s one we’ve all seen: the micro-manager. These are all true, real reasons to say “I hate my boss.” Oh, I forgot one. The idea-swatter. Oops, I just remembered one more. The hair-trigger jackoff. I could probably do this for days. I won’t bore you.

If you’re reading this post and think you can relate to some of the ways I think about work and marketing and management and productivity, subscribe to this newsletter I do every Thursday. It’s fun. I promise. 

So bosses can be awful, yes, but in reality, the problem ’tis …

I hate my boss: No one really cares/thinks about people issues at work

To most men (predominantly men) who rise up at companies, these things matter:

  • Making money / getting a fat bonus
  • Processes and protocols
  • Products and services

You could flip No. 2 and No. 3 and still be right, but those are the top three. See what’s missing? People. You want the easiest way to tell that no one cares about people at work?

HR owns it.

HR is a joke. They’ve been chasing the “seat at the table” for 50 years, and the revenue hounds who run companies still won’t give it up. Why? HR is for cover-your-a*s moves and compliance. It’s not where the financial dragons are slain. Never has been, and won’t be for another 20 years or more.

The guys that run companies pay lip-service to these topics. “The war for talent!” That’s a farce. No one cares. You know how many CEOs would automate your a*s to a robot in less than five seconds if it meant more scratch for them? Probably 60 percent or more. “We need A-Players!” LOL. Most CEOs can barely name all their lieutenants, much less some product marketing manager they’ll never be pitched by. It’s all a big joke and we nod and smile and let it happen.

We just hope, despite all the happy hours where we say “I hate my boss,” that we’ll never be sent down to HR.

I hate my boss: Sum it up

I got fired at my last gig. Some Type-A target-whiffer who read this far just said “Oh, he’s bitter about that. That’s the issue!” No. This blog post is actually about different reasons why people might claim “I hate my boss.”

In reality, at that gig I mostly liked my boss. She was cool!  But it soured towards the end, which I’d say was 75 percent me and 25 percent her. (Maybe 60-40. Depends on what day you ask me.) I hate my boss? Nope.

But you know how it goes when it goes south. It’s all about the “performance improvement plan” and “process for the sake of process” and then one Friday, you’re out on your ear and drinking beers across the street. Life happens, you know? You grow from it.

It’s so easy to say “I hate my boss” or “He/she doesn’t understand me” or even “He/she sucks.” But there’s real human psychology and emotion behind this stuff, and that was the point of this post. (Oh, and organizational foibles too.)

What else have you got on the “I hate my boss” culture and concept?

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