Why Do So Many Bosses Suck? How History Shaped Today's Worst Bosses
By Madison Utendahl
It's inevitable. At some point in your life, you're going to have a really bad boss. One so terrible they'll forever be imprinted in your brain. You might find yourself lying awake at night, wondering what the hell happened to them. Do they have friends? When was the last time they got laid? All these questions swirl around as you try to make sense of why your work life feels like hell.
Bad bosses lead to profound burnout. From imposing bizarre rules that seem more about their insecurities than actual work needs, to sending you into fight-or-flight responses unnecessarily, a bad boss can be a personal nightmare. Many of us have been there... You find yourself frantically checking your phone, laughing at their jokes that aren't funny, or feeling your stomach drop when they walk by your desk. Their incessant demands can push you to the brink. You exist in a state of inherent distrust and confusion. You question: Does this person want me to succeed? Are they enjoying my misery, or is this their version of hazing? Do they do this to everyone? Fun fact: I once had a boss who proudly had the company’s interns scrub toilets, claiming it was a rite of passage since they did it too 20 years prior…
Fucked up. No other way to say it.
I've endured my share of nightmarish bosses—I can even list their first, middle, and last names, peculiar habits, and questionable fashion choices. It took me years to get “over,” like an awful breakup. And yes, I’ve gone to therapy about it. Despite sessions on the psych’s couch and reaching a place of forgiveness, the thought of crossing paths with them again is a hard pass for me. Goodbye forever, thanks!
WE CAN ALL RELATE
Many of you reading this will deeply connect to what I’m saying. Every week, people reach out to me, sharing that their boss is a prime contributor to their burnout. There seems to be a modern plague where work/life balance is more unicorn than policy and it's often driven by one miserable person... one really bad boss.
Thankfully, my encounters with a truly bad boss are a thing of the past. It's also worth noting, I've been fortunate enough to work under some genuinely inspiring leaders since then. Yet, despite the time that has passed, the bad boss archetype is ALIVE AND WELL! Thriving and tormenting as ever. Every time one of you writes to me, exasperated by your own workplace tyrant, it makes me wonder, why is this still happening?
Well…unless we've sat down on a therapist's couch or had an intimate dinner where our bad boss candidly spills their past traumas (which, let's be honest, will NEVER happen), we're left to piece together clues behind their horrid behavior. We can only conclude that bad bosses are a product of two truths: American History (yikes!) and the perpetuation of terrible learned behavior.
BAD BOSSES: A HISTORICAL TIMELINE
Ahhh like everything in the U.S…It's systemic. The management styles and corporate structures that foster these tyrants often go unchecked and unchallenged. These bosses are often cogs themselves, shaped by a history of workplace dynamics that value control and output over genuine human engagement and empathy. They continue cycles of behavior that they themselves likely endured.
Understanding this doesn't excuse their actions but it does shine a light on the need for systemic change. In fact, we can trace the lineage of a bad boss in the American workplace through various historical milestones:
Early 1900s: The Dawn of the Cog
Frederick Taylor's Scientific Management
Taylor introduces scientific management, effectively turning humans into cogs in an industrial machine. Efficiency is king, and humanity is... doesn’t matter
1920s-1930s: Trying to Humanize the Machine
The Human Relations Movement & Hawthorne Studies by Elton Mayo
Mayo attempts to put a soul back into the workplace, highlighting the importance of social connections and morale. However, old authoritarian habits are tough to shake, and many managers decide they prefer their employees seen and not heard.
Post-WWII: Military Precision Meets Corporate America
Rigid, Militaristic Command Structures
After the war, corporate America loves the idea of running companies like bootcamps. Creativity and personal growth are ignored, while obedience and discipline rise through the ranks.
1960s-1970s: The Great Theoretical Divide
Douglas McGregor's Theory X and Theory Y
McGregor rolls out Theory X and Theory Y, showcasing two types of management. Theory X clings to the notion that all employees are potential slackers, while Theory Y sees them as self-motivated. Despite this, many leaders say, "Stick to the devil you know," and keep micromanaging like pros.
1980s-1990s: The Era of Management Fads
Total Quality Management & Other Trends
This era is the “trendy” management era where “Total Quality Management", " OKRS” and other buzzworthy initiatives make their ways into our lives. Sadly, they often promise high but deliver low, thanks to half-hearted implementation.
Modern Day: Digital Age Dilemma
Technology, Remote Work, and Flexible Cultures
Despite the digital revolution offering a chance to reboot management styles, some bosses prefer their trusty old playbook. They ignore calls for innovation and inclusion, sticking to traditional methods that continue to stifle creativity and morale.
Okay, I'm sure you reached the end of that timeline feeling a bit discouraged. You might be thinking, "Well, we're fucked. What's the point of all this?" The point is that despite a long history of bad bosses, the cycle isn't unbreakable. Let’s be real: history loves a good repeat performance, especially when we haven’t quite learned our lesson yet. The tale of bad bosses feels like a broken record, playing over and over because we’re too scared, too complacent, or maybe just too tired to switch it off.
With burnout rates climbing and bad bosses often at the helm of such crises, the urgency to act is now. The old saying, "If you always do what you've always done, you'll always get what you've always got," rings especially true here. If we continue to tolerate, excuse, or ignore toxic leadership, we perpetuate a cycle of dysfunction that not only diminishes individual well-being but also corporate health. Addressing this doesn't just involve swapping out bad bosses with good ones or introducing more employee-friendly policies—though these are important steps. It requires a fundamental shift in how we view and enact leadership. It involves cultivating environments where transparency, respect, and empathy are embedded in the corporate DNA. This shift can reduce burnout and increase employee satisfaction and productivity, fostering workplaces that thrive on genuine respect and mutual success.
To the bad bosses reading this: you know who you are. Treating your employees poorly is not cool…its an example of a lack of self-worth, something, with courage, you can change. Read, learn, and grow—not just for your sake but for the sake of those you lead.
To every employee stuck with a bad boss: speak up and stand your ground. Real change starts with you. If nothing changes, then consider moving on. If you wouldn't stay in a personal relationship with someone who treats you as poorly as a bad boss does, why stay in a professional relationship that's just as toxic?
Together, let's break the cycle. Let's bring about a workplace “revolution” where being a good boss isn't the exception—it's the expectation. Where every manager is a catalyst for empowerment, not an agent of control. Because ultimately, how we work together shapes not just our professional lives but our personal wellbeing too. Let’s not settle for what’s been done; let’s work towards what could be. Here’s to changing the narrative, one boss, one employee, one interaction at a time.
x
Madison