Optimist vs pessimist vs realist: 3 types of colleagues you meet in every change effort
You probably know the joke already.
Three people walk into a bar and stare at a glass of beer.
The optimist says, "It's half full."
The pessimist says, "It's half empty."
The realist drinks it and says, "Whose round is it?"
It's a small joke, and it usually gets a small laugh. But I haven't been able to let it go this week. Because every time the conversation turns to a company that runs without traditional bosses, where teams decide together and profits are shared, people sort themselves into the same three camps.
The optimist vs pessimist vs realist split is what actually happens around a meeting table when you propose changing how work is done.
The optimist
The optimist falls in love with the idea.
They hear about self-managing teams, open books, shared profits, and something lights up. They become lyrical. "This is the future of work. Why isn't every company doing this already?"
They write the posts. They quote the case studies. They cheer from the stands. They become the fanboys and fangirls of a way of working they've often never actually lived.
Because here's the thing about the optimist in the glass half full corner: ask them gently, and you usually find out they've never worked inside a place like that for a single day. They've tasted the idea, not the reality.
I say this without a hint of superiority. For the first few years of Corporate Rebels, this was exactly who we were. Visiting pioneers, getting inspired, telling everyone what we had seen. Cheering. Not yet building.
The pessimist
The pessimist looks at the same company and sees a mirage.
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There are two kinds, and they're worth telling apart.
Pessimist #1: The born skeptic
Some pessimists got there fast. They never believed in any of it from the start. They were skeptics before the first visit, and they're skeptics still. At least their position is consistent.
Pessimist #2: The burned optimist
The second kind is more interesting. This person was an optimist first. They once burned with the idea, ran their own experiment, watched it fall apart, and the disappointment hardened into something permanent.
They loved the dream while it was young enough to thrill them. When the thrill faded, they went looking for the next intoxication or gave up altogether. Now they tend to land in one of two places. Some go quiet and apathetic, done with the whole subject. Others get loud, and spend their remaining energy proving that the thing they once adored could never have worked at all.
Notice what optimists and pessimists have in common. It's the same thing. Both of them are still standing around the glass, describing it, instead of building one or working inside one.
That's the quiet trap of the pessimist vs optimist debate. The shouting hides the fact that nobody at the table has actually tried the thing.
The realist
The realist does the one thing both other camps skip. They try it.
That's the story of how we changed. Years ago we first heard about NER Group in the Basque Country, one of the most radical examples of decentralized organizing I've ever come across. It sounded intriguing, and more than a little radical.
So instead of arguing about it from a safe distance, we got on a plane. Then we did it again. And again. Going back to the Basque Country to sit with the people inside these companies and watch how the model actually behaves on an ordinary Tuesday rather than on a conference slide.
Curiosity turned into conviction. At some point we stopped circling the glass and started to drink.
Together with a group of experienced NER transformation veterans, we launched Krisos, an impact fund that buys traditional, hierarchical companies and rebuilds them into progressive organizations using the NER methodology. Today three companies sit in the portfolio, each at a different stage of the journey, each teaching me something I didn't know the year before.
Some of it works beautifully. A good deal of it is messy. That mess is what learning by doing actually looks like. It's the part the optimist doesn't see from the stands and the part the pessimist points at to say "see, told you so."
The realist doesn't argue with the mess. The realist works through it.
Why realism beats both optimism and pessimism
Here's what I keep relearning. Real change almost never comes from critique and commentary.
It comes from experimentation. From stepping off the sideline and onto the field, trying things, getting some of them wrong, and learning faster than the people who only ever talked about it.
That's what realism actually looks like in organizational change. Not lukewarm centrism between the optimist and the pessimist. Not "balance." Something more practical: the willingness to test your own beliefs against an ordinary Tuesday in a real company.
It applies beyond NER. It's visible in every pioneering organization we still visit. The people moving the work forward are rarely the loudest voices on either side of the glass half full question. They're the ones who put the glass to their lips.
So the question isn't whether the glass is half full or half empty.
It's whether you're going to keep describing it, or finally take a drink.
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