Two concepts of liberty: what Isaiah Berlin teaches us about self-management

What are Isaiah Berlin's two concepts of liberty?

The short answer: Berlin split liberty into two kinds. Negative liberty is freedom from interference. Positive liberty is freedom to govern yourself.

Ask someone what liberty means and you'll usually get one answer. Berlin's point is that the word hides two different answers to two different questions. He wasn't the first to see it. Erich Fromm made the same split in 1941, more than a decade before Berlin gave his lecture.

Negative liberty: freedom from

Negative liberty asks: how much room do I have? What am I free to do or be without anyone getting in my way? At work, the question becomes simple. How much does my boss, or the wider company, interfere with me?

Positive liberty: freedom to

Positive liberty asks a different question: who is in charge of me? Who decides what I should be or do?

At work: do I govern myself, or does someone else (read: my boss) govern me? Both are deep human desires. But Berlin is clear that they are not the same desire.

Why Berlin thought the difference mattered so much

Berlin wasn't splitting hairs for fun. He argued that the tension between the two concepts of liberty fuelled the great ideological clash of his time: the Cold War between Western liberal democracies and the communist world.

He saw totalitarian regimes as twisted versions of positive freedom. They sold oppression as a higher form of liberty.

That sounds a long way from your Monday morning team meeting. It's closer than you think. The same two concepts play out in every organization that tries to remove its bosses.

Negative freedom at work: remove the bosses and you may get a jungle

Most transformations towards pro-autonomy organization start with negative freedom. Manager positions are removed. People are suddenly free from daily interference.

But that only creates freedom from the boss. And on its own, that rarely makes an organization work any better. When there is only negative freedom, I often see one of two things happening.

Chaos

This usually happens when removing the bosses creates a vacuum that nobody wants to fill. The result? Nobody coordinates. Decisions stall, or they collide.

Even organizations that handle freedom well feel this pull. At Everoze, a company that deliberately avoids heavy rulebooks, questions like "Who decides here?" come up regularly. They lean toward judgment and conversation over written rules, and accept that this can feel uncomfortable.

Informal hierarchy and the tyranny of structurelessness

The second pattern is sneakier. Here the vacuum does get filled, by the loudest colleagues, the best connected, the former bosses or the founder's friends. They quietly take charge.

Activist Jo Freeman described this in her early-1970s essay The Tyranny of Structurelessness. Writing about the women's movement, she argued that a structureless group doesn't exist. Once the formal structure is removed, an informal elite of friends takes over. Their power is real, but nobody can see it or hold it to account.

We've written about this before: organizations with no hierarchy don't exist. Power relations show up whether you formalize them or not.

Escape from freedom

Fromm described the same pattern back in 1941 in his book Escape from Freedom. He argued that people who get freedom without the inner capacity to use it often try to escape from it. They avoid responsibility. They conform to the group. Or they submit to a strong leader, formal or informal.

Freedom you can't use doesn't feel like freedom. It feels like a threat.

Two ways out of the jungle

No wonder leadership often starts to panic at this point. They conclude that the pro-autonomy ethos doesn't work in their workplace. Then they rebuild the hierarchy they just set out to remove, often in an even stricter form.

That's an understandable reaction. But it's not the only one. When freedom from has turned a self-managing workplace into a jungle, there are two ways out.

Restrict freedom again

This is the route many disappointed leaders take. They bring back the old boundaries, rules and managers. Sure, that works. But you lose what you set out to build, and people lose their freedom again. It's throwing out the baby with the bathwater.

Build positive freedom

The other route: invest in personal development so people can actually govern themselves. Think self-awareness, emotional intelligence, personal leadership, judgment, honest communication and the courage to take a stand.

When the Brazilian company EPPO moved to self-management, not everyone adapted, and some teams struggled to work through tensions without a traditional hierarchy. Their answer was to invest in group dynamics training and give teams resources to build the skills for self-led collaboration.

This second path is, of course, much harder. But it's the only one that leads where most of us want to go: a highly successful pro-autonomy organization.

So far, nothing new under the sun. I've written about this before, mostly based on Fromm's insights.

What Berlin adds is that the second path hides a danger of its own.

The trap of positive liberty: who decides who you should become?

Berlin argues that positive freedom often starts innocently: be the master of your own life. But that idea splits you in two. There is a "higher" self that is wise, and a "lower" self that is lazy or confused.

Next, that higher self gets identified with something bigger than you. A mission. A purpose. A "higher level of consciousness."

That bigger whole claims to know what you would want if you were wiser. And once it claims that, forcing you stops counting as oppression and starts counting as setting you free.

Berlin admits why this sounds reasonable. Sometimes we do push people towards goals they would choose if they knew better, such as public health. That is exactly what makes the argument so easy to abuse.

In organizations, this trap comes in two versions.

Top-down: leadership decides who you should become

"Personal development" quietly turns into conformity. The development program has one destination, and leadership picked it. Whoever doesn't want to change gets labelled "not conscious enough" or "not ready for freedom."

The old boss is gone while the old control is back, wearing nicer clothes.

Peer-driven: the iron cage of self-managing teams

The second version is harder to spot. Here the group decides who you should be, and restricts your freedom more than your previous boss ever did.

A famous example is a 1993 study by James Barker. He followed a factory that replaced its supervisors with self-managing teams.

What happened? The teams' own norms became stricter than any supervisor's rules. The workers had built themselves a new iron cage, with bars they could barely see.

Moral communities: keeping freedom alive

Luckily, anthropologist Christopher Boehm points to a way out. In the egalitarian hunter-gatherer bands he studied, norms were not held by a chief. They were held by the whole group. Boehm called this a moral community.

And the first people that community policed were the would-be bosses (and the free riders).

Braggarts and bullies were cut down through gossip and ridicule. If needed, they were expelled from the group altogether. Nobody got to define your "better self" from above, because anyone who tried became the problem.

But as Barker's iron cage shows, a group can tighten as well as protect. That's why I believe a moral community only keeps people free when (at least) two conditions are in place.

Permission to dissent

You can always openly disagree with the group without being punished for it. That includes disagreeing about who you should become.

Permission to leave

You can always walk away from a team, a role or the company without losing everything. Boehm's bands had this one built in. Anyone unhappy with their band could simply move to another. The same should hold for our workplaces.

Two concepts of liberty in short

Negative freedom is where most pro-autonomy workplaces start.
Positive freedom is where they need to go.

And a moral community, one that protects both dissent and exit, keeps that freedom alive. It stops the workplace from turning into a new cage.

I write about the long version in our new book, The Four Ways to Run a Deeply Human Company, which comes out on March 2, 2027. If you want early access and unpublished content, join the waiting list.

Until then, try a small test in your own team.

Picture yourself disagreeing with the group tomorrow, openly, on something that matters. What would happen next?

Want to know everything we learned after 10+ years of studying progressive organisations? Check out the Masterclass.

Learn directly from pioneering companies Buurtzorg, Haier, and Viisi's own leaders. Walk away certified, with a lifetime network of 1,200+ pioneers in 38+ countries.