Embracing Bad Bosses and Bullshit Jobs

Welcome back to The Workaround. I’m Bob 👋

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We don’t have flying cars. And we still have bad bosses.

In last week’s post, I went on a rant about bad bosses and the rising gap between the commitment they demand and the commitment they are willing to make.

It felt good to get it out…for about a day. Then something bothered me about what I wrote. So I started scratching at that itch…

I pulled out an approach I use from time to time to examine beliefs—especially my own. I consider how this belief might be completely wrong.

In this case: What if it’s all…right? What if bad bosses and bullshit jobs have a purpose in the world? What if the pain they create is the “right” path forward?

I increasingly see the value of holding two opposing ideas as both true. The rising financial and environmental cost of oil also incentivizes solar power innovation. A person can be responsible for their crimes, yet also a victim of their poor upbringing. An axis of evil country can be a threat to our nation, yet also mainly comprised of people with whom you would enjoy a lovely meal.

Can awful bosses and bullshit jobs be soul-killing, yet also just what we need right now?

In a world driven by fears that rarely become reality, entertaining the idea that everything “is as it should be” might be closer to the truth than we know. At minimum, it’s a concept that can bring insights, help you fall asleep at night…or maybe, finally, wake the fuck up.

Let’s explore…

The only thing that stuck with me from my Economics degree thirty-one years ago is that the economy mostly moves through the power of decisions by individual consumers and small business owners.

Sure, there are plenty of big government decisions and big corporate oligopolies. Still, even these are driven by humans on the ground, selfishly thinking about how to keep their families safe and what might make them happier tomorrow.

The result is a massively complex adaptive system in which our trillions of daily decisions are the butterfly flaps that create something bigger and more dynamic than the sum of its parts—or any one person’s decision-making. The swirl of these forces drives the ebb and flow of consumer tastes and trends, company job openings, and the stock market.

Despite decades of research and finely-tuned algorithms searching for an edge, we can’t predict any of this stuff. All we know is someone came up with the idea of putting tape over their mouth before going to bed. Somehow, this became a consumer product category. It’s a version of infinite monkeys typing on their laptops until Hamlet pops out.

Speaking of monkeys…this pattern of individual changes moving a complex system is the power behind the evolution of life, too.

As science delves deeper into historical records, we find that evolution doesn’t occur through slow, gradual tweaks at a steady pace. Evolutionary change mainly happens due to big shocks in the system—like supervolcanoes, meteor strikes, and continent collisions. Or climate change that forced a tribe of apes out of trees and onto the savannah.

In the blink of an eye, they are writing Hamlet — and Substack posts.

“It is not the strongest of the species that survives, nor the most intelligent, but the one most responsive to change.”– Charles Darwin.

Still, we want to blame someone for the awful results of these systems we swim in. And each election, we vote for someone to fix all our problems. But complex adaptive systems are too complicated for individuals to choose the best direction for the rest of us. We re-learn this lesson whenever leaders announce 5-year plans, ban natural things, say AGI is here, or get involved in a land war in Asia.

So, we are stuck with capitalism, democracy, Wikipedia, and now ChatGPT. All are based on a complex system of individual actions, and all are the worst solutions—except for all the others.

Significant cultural shifts happen this way, too. Each generation has a kind of life of its own, and they, too, are made up of individual choices that add up into a movement. The next generation changes culture only when the current system no longer makes sense for them.

In a recent chat for our Leading Edge group, Peter Merry points out that when an environment gets more complex than the current model can handle, we have to tear it down and start over with something new that fits what’s happening now. To work, this new model must be more complex than what came before.

Life has spawned increasingly complex ecosystems and produced the most complex physical item we know of: The human brain. Our human brains have made more complex societies—moving from hunting & gathering, to agricultural empires, to the industrial revolution, to a global market driven by knowledge work. Each new step transcends and includes the previous step to add complexity and a higher quality of life overall.

Every movement in human history stems from individuals reaching a personal crisis point, watching their models for the world dissolve, and rebuilding something more complex that fits better.

“Individuals, like nations, come back through a process of rupture and repair.”—David Brooks

Peter Merry is just a more recent truth-teller. This pattern of human advancement through struggle has been described in sources including Buddhism, Stoicism, Greek Tragedy, Christianity, alchemy, tarot cards, and Jungian psychology. They all tell the story of the individual’s struggle on a Hero’s Journey—which, if successful, brings back a treasure of truth to help society move to its next needed stage.

Why didn’t they teach us this meta-lesson in school? I guess that would make life too easy. So, we muddle forward, and some of us eventually see the pattern…

We run into walls as we navigate the path of life, and finally figure out a way through the maze. Then our head gets too big, and when changes happen, we apply the old treasure map to the new world. And…we get our head kicked in. We’re left broken and forced to rebuild an aspect of our lives that fits its newfound complexity.

Ask anyone a story of when they learned the most in life, and they will give massive credit to the problems they faced. It took me over forty years to learn to see and appreciate this. Today, I love the people and situations that caused me grief. They were my springboards to reinvention and improvement. I would be a worse person had they not made me feel worse.

My friend, Maya, just shared how a layoff sparked her remarkable renewal. It’s a brand of LinkedIn post I seem to see more of each day. Good people are being let go by failing leaders—and they are bouncing back into something much better for them. They are sharing their stories more frequently.

I think this is the sign of a shift.

Maybe we need even worse bosses for these kinds of stories to add up and drive change.

As people are treated poorly and have less trust and commitment from their bosses, employees will either reach a personal breaking point and quit, or be broken down through a layoff. Either way, this is an opportunity for renewal.

Let’s throw some shade praise on the bullshit jobs, too…

Poor leadership in companies is just as likely to include adding staff who don’t add value. This quote from an anonymous manager landed hard and true:

“I manage twelve people. Four do actual work. The other eight… I don’t know. But if I fire them, I lose headcount and budget. So we all pretend.”

This is standard stuff, even in startups with a few dozen employees. And it’s a bad deal for everyone.

Bullshit jobs working for shitty leaders might be viable for a period of time, but they are patently unstable.

My friend, Paul Fisher, wrote up his conversation with someone who was restructured into a job that didn’t fit, yet stuck it out. After a few years, she was laid off and left wondering what had happened. Her resulting epiphany:

“Careers can be like Vegas. You lose track of time and direction.”

Just like in Vegas, people get stuck in loops—pulling the equivalent of a slot machine handle and hoping for a reward. AI can’t wait to take on these mindless jobs and bounce us out onto the street. At least, then, we may see the light.

But a lack of meaning in work might be the bigger trigger of change.

I got chills this morning reading Zoe Scaman’s personal story of realizing the amount of bullshit there is in the world of strategic consulting. She was a senior strategist working at one of the sexiest agencies with stellar brand clients. And yet…

“I’ve always felt like this, that uncomfortable nagging voice in the back of my mind saying, ‘Is this just performance art?’ Because that’s how it feels – not just in pitch (though we call it pitch theatre for a reason), but in every context. The creative check-ins where we perform strategic rationale. The brand planning sessions where we perform cultural insight. The quarterly reviews where we perform progress. It’s all theatre, every moment of it.”

Scaman increasingly felt a sense of shame in her work. Shame comes from looking within and not being happy with the decisions we have made and the people we’ve become.

But shame is a feature—not a bug—of our human programming; it challenges us to see the truth of our bullshit and rise to more meaningful heights with our one, precious life.

Maybe we need more shame in our lives.

“The shame is not the problem. The shame is the beginning of the solution.”—Zoe Scaman

I created countless similar strategy decks for my clients at my digital agency years ago. At one point, I figured I had presented to over half of the top 100 brands in the world. After a year or so of thinking I was making an impact, I eventually realized it was all bullshit theater. We knew most of our ideas would never be bought, and that it was all pie-in-the-sky vision to keep a client feeling smart about using us to make their boring banner ads and websites.

Like many people in careers like this, it helped to find another pocket of meaning. For me, it was in building a company culture where we found mutual trust and camaraderie. I drank too much during this time, too.

You probably wouldn’t be shocked to learn that none of us five members of the executive team continued doing this kind of work a year after selling our company. We all had some version of a personal crisis, reforged ourselves, and moved on to work that was more meaningful to us.

I think there might be more pockets of our lives where worse works out for the best…

Maybe our government needs to get even worse. No one is happy with what we have now, yet there’s no alignment on what we need and how to get there. Perhaps the growing chaos is key to finally getting us on the same page, counting on each other more than elected officials, and rebuilding a model that works better for who we are as citizens of a city, state, and country today.

Maybe our colleges need to get even worse. Let them keep raising tuition above inflation, hire more administrators than teachers, mock the idea of student-athlete, and ignore the widening gap between academic research and real-world teaching. As we continue to question the value and pursue alternatives, these schools may finally be forced to rebuild for what we need going forward.

Maybe our rising generations need to struggle even more. A few days ago, an old friend sent me a post written by his daughter’s head of school, Jay Rainey. He writes about parents’ fears of how AI will affect their children’s job prospects. But he fears today’s youth are missing an audacity that has driven previous generations to level up the world at critical periods.

That’s right—the leader of a top-flight, elite college-prep school in the suburbs is asking his students to break out of the boxes they’ve been trying to check off. Those boxes don’t matter anymore!

The generation that has been coddled more than any other is overdue to break out. The opportunity to lead us into a renewed world is just waiting for them to grab. But it might take even more mind-crushing work and depressive soul-searching before they finally wake up from the dreams of their parents and other power-holders.

As their struggles mount, one by one, they are going to wake up and take their birthright.

Now, you may think I’m happy with or encouraging this chaos. I’m not, but I do believe the old cliche “it’s darkest before the dawn” is repeated because it’s true.

This doesn’t mean we sit back and wait for the world to burn down, or wait for someone else to pick up the pieces. Remember, these changes work because individuals like you and I do something—anything—positive in our own little pockets of power.

Adam Mastroianni nailed this last week in talking about how too many people get caught up in big picture awfulness, thanks to news apps promoting misery as a business model. Too often, we are frozen by the feeling of the enormity of problems.

But as he was told in high school: “People see bad things in the world and ask why God doesn’t do something about it. But God did do something. He sent you.”

“Yes, things are bad. No, it’s not your fault. Unfortunately, the world was under no obligation to straighten itself out by the time you arrived. These are the problems we got. Would you like them to be better? Then here, grab a sponge and start washing.”

Whenever we become frustrated with what’s happening in the world, and when we worry about the future of our culture, we must remember that we, too, can help shape it.

The small, positive actions will add up, just as the law of compounding interest proves. But it’s even more potent because our actions are seen and heard by others. Positive actions become social signals. It’s as if looking at money in the bank made the interest rate increase further!

Every day, I see more examples of individuals figuring it out for themselves and sending a message to the rest of us:

A friend is launching a new, old-school business despite threats of AI. People need it, are willing to pay, and he’s confident he can use AI to his advantage if and when it moves through the hype cycle.

I’ve now heard of three friends who left their bullshit jobs to become professors at universities that are shifting to real-world instruction.

I learned about someone else who deleted their social media apps.

Another school in my city decided to ban cellphones.

I watched a guy in my neighborhood walking his dog and picking up litter as he went.

I’m still writing about how we might change our minds for the better, with business as a testing ground. And you’re still reading. Both are baby steps, but they move the whole project forward.

Thank you.

“The individual alone makes history…That infinitesimal unit on whom a world depends.”—Carl Jung

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A little something I found meaningful. You might agree…

Neither There Nor Back Again

To drive his point home at the end of the post I referenced above, Adam Mastroianni drops this wonderful allusion to The Lord of the Rings:

“In the classic formulation of the hero’s journey, step one is the call to adventure, and step two is the refusal of that call. I think we’re all stuck at step two. Gandalf’s at our door, but we literally just sat down to lunch, and have you seen the forces of Mordor? They’ve got trolls. Obviously, it would be great if someone did something about Sauron, but I don’t see why it should be me.”

Well, I’m proud to have beaten Adam to this point in imagining how Tolkien’s universe would look a lot different if a mere Hobbit denied his call to the Hero’s Journey. Last year, I wrote “Neither There Nor Back Again”—a very short remake of a tale that Peter Jackson stretched into three, 3-hour movies.

My story ends with Bilbo closing the door on a certain gray wizard. It was fun to write (and read, check out my voices by hitting the play button), but it left me a little sad thinking about how many people in our lives will leave this earthly journey without testing their limits.

Neither There Nor Back Again

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