Why Do We Tolerate Workplace Dictatorships in the Land of the Free?
I’ve been wrestling with a question that won’t leave me alone.
How is it that in the land of the free, most of us spend our working lives in environments that operate more like dictatorships than democracies?
I live in the U.S., a country that claims to value freedom above all else. Regardless of political affiliation, we get extremely upset when our freedom is threatened.
Yet, we spend half our lives in environments where freedom is almost entirely absent. If you live to 80, you’ll likely spend 40 years (22–65) working. That’s half your life under a system where one person, the CEO, makes all the decisions.
Consider what this actually looks like in practice. Companies monitor when you arrive and leave, down to the minute. Adults must ask for approval to take vacation days they’ve supposedly “earned.” They’re told exactly what words they can and cannot say to customers or clients. Internet usage is monitored. Personal social media accounts are scrutinized. You must wear specific clothes, arrive at exact times, and sit in assigned locations for eight hours straight.
If we described this to someone from another planet, they’d assume we were talking about a prison.
Even our language gives it away:
Wage Slavery
Corporate Prison
Golden Handcuffs
Human Resources
Cog in the Machine
The contrast between our societal values and workplace reality is stark:
In society: Freedom of speech. At work: Say only what’s permitted.
In society: Right to privacy. At work: Monitored communication.
In society: Due process. At work: At-will termination.
So, in a country that values freedom above everything else, most people spend the majority of their lives with very little of it. It’s no surprise, then, that when people leave the corporate world, the number one reason isn’t money; it’s freedom.
The Trade We Forgot We Made
This freedom paradox is historically recent. For most of human history, people worked as farmers, artisans, or small business owners. A blacksmith decided when to open shop, which orders to take, and how to price his work. A farmer chose what to plant and when to harvest. They had autonomy over daily decisions.
They also lived one bad season or decision away from starvation.
The Industrial Revolution offered a different deal. Give up your autonomy, and you’ll never have to worry about finding customers, managing cash flow, or the uncertainty that destroyed your ancestors. Someone else will make the hard decisions. You just show up and follow instructions.
We took that deal. Decades later, we’ve forgotten it was a choice. We traded our birthright of autonomy for the promise of security. But what happens when the security we traded for is no longer guaranteed?
The Moment It Hit Me
When my daughter was in first grade, a severe snowstorm started early in the day. The school called to announce early dismissal. All children had to be picked up by noon.
On the way to school, I stopped by my boss’s office to let her know I was going to pick up my daughter. I wasn’t asking for permission. I was just being considerate in case she was looking for me.
Her response: “During the day, we expect all our employees to be at their desks.”
That moment made me realize that the freedom I thought I had was an illusion. I was living the paradox I’d never questioned. It was the beginning of the end of my corporate career.
I’m not alone in this. Dickie Bush recently shared a similar story about the moment he decided to leave BlackRock.
A couple of years later, when an unexpected opportunity presented itself to join another company full-time, I approached the negotiation process differently. By then, my kids were 8 and 4. It was non-negotiable for me to be the one dropping them off and picking them up from school and daycare. The job was in New York City with a 1.5-hour commute each way. It was impossible to do both.
When I received the offer, I said the only way I’d accept was if I could work from home three days a week and come to the office two days. On office days, I would have to leave at 4 pm sharp. The initial response was predictable: “We don’t let our employees work from home.”
This was years before COVID and the rise of hybrid work. I repeated my terms: three days at home, two in the office, and I leave at 4 pm. They agreed.
What made the difference was that I had a unique skill set they needed. I wasn’t easily replaceable. That gave me leverage to dictate terms.
Most people don't have that leverage.
What We Don't Want to Admit
There’s another layer to this paradox. We tell ourselves we want freedom, but many of us are secretly relieved when someone else makes the decisions. Psychologists have long known that too much choice can be paralyzing. Barry Schwartz’s “Paradox of Choice” revealed that unlimited options often make us less happy, not more.
Some people genuinely prefer being told what to do. They find comfort in clear hierarchies, defined roles, and predictable routines. For them, corporate structure isn’t a prison. It's a relief from the burden of constant decision-making. They can go home at 5 pm and truly disconnect, knowing that strategic decisions are someone else’s responsibility.
This explains why so many people complain about their lack of workplace freedom but never pursue more autonomous paths.
Why Organizations Need Control
Corporate hierarchies don’t exist because managers are power-hungry dictators. They exist because large organizations require coordination to function. When McDonald’s serves identical burgers across 40,000 locations, predictable systems generate predictable profits.
The bigger the company, the more standardization becomes essential. Individual autonomy threatens collective efficiency. If everyone at Amazon decided their own delivery schedule, packages would never arrive on time. If every Google engineer used different coding standards, the software would be unmaintainable.
The most successful companies often have the most restrictive work environments. Success requires eliminating variables, which means eliminating individual choice.
This creates a fascinating contradiction. The economic system that has generated unprecedented prosperity and innovation depends on constraining individual freedom during the most productive hours of our lives.
What I Can't Figure Out
When people ask me about the future of work, they focus on surface trends: “Will we have four-day weeks?” “What major should my child choose in college?” These questions miss the deeper dynamic.
The questions that fascinate me are different:
How do we reconcile our love of freedom with our apparent preference for constraint?
Even when people have the leverage to choose independence, why do so many still opt for traditional employment?
What does it say about human nature that we voluntarily spend half our lives in environments we describe using prison metaphors?
What Do You Think?
Perhaps the real question isn't why we tolerate workplace dictatorships, but what kind of freedom we truly seek and what we're willing to risk to attain it.
I don’t have the answers, but I do know this. The collapse of career guarantees is forcing us all to confront choices we had forgotten we made. We traded autonomy for security, but now that the security is disappearing, we're left wondering why we continue to accept these constraints. If you’ve ever felt this paradox or found your own way through it, I’d genuinely love to hear your story.