50 Two Stories of Enterprise: Learning, Failure, and the Right to Try Again

To see what this feels like in real life, let me share two stories about entrepreneurship in practice.

Let me share a personal story.

Just before I began my master’s degree, I was in the middle of preparing for exams, gathering documents, and trying to work out how to take the next step in my education. But life does not wait for plans to settle, and neither do expenses. Rent still had to be paid. Food still had to be bought. So, like many others, I looked for a way to earn a living while moving forward.

I started a small business.

In a shopping mall near where I lived, there was an opportunity to rent one of those small carts placed in the open spaces between large brand-name stores. You have probably seen them before, selling sunglasses, phone cases, perfumes, or small accessories. Mine sold NBA and NFL caps.

It was not a grand business idea. There were no investors, no branding agency, no business plan polished for presentation. There was just a cart, some stock, and the willingness to try. Every decision was immediate and concrete. How many caps should I order this week? Which teams were selling better? Should I lower the price slightly to move stock faster, or keep it where it was and accept slower sales? When the mall was quiet, should I wait it out or rethink the product mix?

Financially, it did not make me rich. What I earned was roughly what I might have made working for someone else. But the experience was fundamentally different. I was not just earning a wage. I was learning what it means to operate within a market. Pricing was no longer a theory. Inventory was no longer an abstract cost. Customers were not demand curves, they were people who stopped, looked, hesitated, asked questions, walked away, or smiled and bought.

There were long stretches of boredom, standing there watching people pass by without stopping. And then there were brief moments of satisfaction when someone said, “I’ll take this one.” Those moments mattered more than the money. They were small signals that my choices had connected with someone else’s needs or preferences.

What mattered even more was responsibility. Every aspect of the operation rested with me. If stock ran out, that was my fault. If prices were too high, customers disappeared. If prices were too low, the margin vanished. There was no manager to blame, no system to hide behind. This is often described as freedom, but it is a demanding kind of freedom. It comes with exposure and accountability.

When my master’s programme finally began, I had to close the business. There simply was not enough time to keep it running alongside full-time study. But I did not leave empty-handed. I walked away with experience. With an understanding of how microeconomic decisions feel when they are real, not theoretical.

That cart taught me something essential about markets that no diagram ever could. Markets are not neutral spaces where everyone competes on equal footing. They are shaped by access. I could rent that cart because the system allowed entry at a small scale. I did not need political connections, special permissions, or informal payments. The rules were clear. I paid the fee, followed the regulations, and operated openly.

This matters more than it might seem. In many parts of the world, small-scale entrepreneurship is blocked not by lack of ideas, but by barriers to entry. Licences are arbitrary. Rules change without warning. Informal payments are expected. In such environments, the kind of experiment I ran would be impossible or too risky to attempt. The result is not fewer entrepreneurs because people lack creativity, but because systems do not allow safe experimentation.

My cart did not change the economy. But multiplied across thousands or millions of similar attempts, these small ventures form the backbone of dynamic societies. They allow people to test ideas, learn from mistakes, and build confidence. They also create dignity. Even when income is modest, being able to earn through one’s own effort within a fair system carries social value.

This is why micro-level opportunity is inseparable from democratic values. The freedom to try, to fail, and to exit without fear depends on predictable rules and equal treatment. Where these conditions exist, small economic experiments become learning processes. Where they do not, people retreat into informality or dependence.

So when we talk about entrepreneurship at the micro level, we are not celebrating risk for its own sake. We are examining whether societies create environments in which ordinary people can act, learn, and contribute. My cart was small. But it sat inside a system that allowed it to exist. And that system is what turns individual effort into collective progress.

When Systems Allow You to Try Again

At the same time that I was running my small cart, a close friend of mine was attempting something similar, but on a larger scale. Instead of one cart, he operated several, scattered across different shopping malls. On paper, this looked like progress. Expansion is often treated as success. More locations, more stock, more exposure. But the reality was far less stable.

He struggled. Repeatedly.

Margins were thin. Foot traffic was unpredictable. Rent was high and inflexible. Some malls were busy on weekends and empty during the week. Others suffered from poor location or changing consumer habits. Each new cart added complexity, not just opportunity. Inventory had to be managed across locations. Staff had to be supervised. Losses in one place could wipe out gains elsewhere.

Several times, he went bankrupt.

In many societies, bankruptcy is treated as a personal failure, a mark that follows you indefinitely. But where legal systems function properly, bankruptcy is something else. It is a mechanism. A way to reset, to re-enter, to try again without being permanently excluded from economic life. My friend’s story unfolded in an environment where failure did not mean social death. He could start again. That mattered.

While he was struggling, the wider environment was changing. Traditional shopping malls were losing their appeal. Online shopping was growing rapidly. New generations were changing how and where they consumed. Malls that once felt vibrant began to feel tired. Stores closed one by one. Empty windows appeared, covered with posters saying “coming soon,” which often meant “nothing is coming.”

For mall owners, empty shops are more than lost rent. They signal decline. Fewer visitors come. Remaining stores suffer. The atmosphere shifts. The mall becomes a place people pass through rather than linger in. This is how systems deteriorate, not through a single shock, but through cumulative withdrawal.

Most people saw this decline and walked away. My friend saw something else.

He realised that empty shops were a problem not just for him, but for the mall owners themselves. He approached the management of one mall with a proposal. He said, “You have empty stores that bring in no rent and make the place look half-alive. Let me use one of them temporarily. Not permanently. Just until you find a long-term tenant.”

He added a crucial condition. There would be no long contract. If a major brand appeared and wanted the space, he would leave with one day’s notice. No legal battles. No delays.

In return, he asked to pay only a symbolic rent. Something minimal. Enough to cover basic costs, but not the high rents charged to large brands. His argument was simple. The shop would be open. Lights on. Customers browsing. From the outside, it would look like business was happening. That appearance mattered.

The mall management agreed.

This agreement only worked because the institutional environment allowed flexibility and trust. Rules could be interpreted pragmatically. Contracts could be negotiated. Neither side feared arbitrary punishment. This is often invisible, but it is central to how real markets function.

He started selling low-cost clothing. Everyday items. Nothing luxurious. Nothing branded. Products people might buy on impulse. He priced them just above cost. Low margins, high volume. Because his rent was minimal, the model worked.

Customers came. The shop felt busy. The mall looked alive again. Management was pleased. They offered him another space. Then another. Soon, he repeated the same model in a second mall, then a third. What began as a temporary survival strategy turned into a scalable business model.

Eventually, he was running pop-up style stores across multiple regions. He became a millionaire.

This outcome is often misread. It is tempting to say he succeeded because he was clever or resilient. He was both. But that is not the full story. He succeeded because the system allowed repeated failure without permanent exclusion. Because entry and re-entry were possible. Because negotiation was legal, transparent, and respected.

In many countries, this story would be impossible. After the first bankruptcy, doors would close. Credit would disappear. Trust would vanish. Failure would be punished rather than treated as information. The result would not be fewer mistakes, but fewer attempts.

This is where microeconomics and democratic values meet. The right to try again is not just a legal detail. It shapes behaviour. When people know that failure will not destroy them, they take calculated risks. When they know it will, they retreat into caution or informality.

My friend did not exploit the system. He used it as it was meant to be used. He identified a failing structure, offered value to all sides, and adapted. Customers benefited. Landlords benefited. He benefited. This is what markets look like when individual initiative and institutional design reinforce one another.

And yet, when I congratulated him, I also challenged him. I suggested that what he had built was not just a profitable business model, but a foundation. A platform that could be used to create something more ambitious, something that integrates responsibility, sustainability, and long-term social value into the core of the business rather than treating them as optional extras.

He smiled and said, “I think it’s too late for me to dream that big. I’m past that phase.”

He was in his early forties.

At first glance, this sounds like a personal limitation. But it wasn’t. It reflected something deeper. His response was shaped by culture, by social expectations, and by the unwritten rules about what ambition is supposed to look like at different stages of life. In some societies, dreaming big is encouraged well into adulthood. In others, ambition is quietly narrowed over time, redirected toward stability, respectability, and staying within what feels appropriate.

This is not about lack of ability or imagination. It is about the boundaries that societies place around aspiration. Cultural norms signal when it is acceptable to take risks, when it is time to “settle,” and what kinds of goals are considered realistic or respectable. Over time, these signals become internalised. People stop not because they cannot imagine more, but because imagining more begins to feel out of place.

This is where micro decisions meet collective culture. The difference between societies is not only in the businesses they create, but in how long they allow people to think expansively about their role in the world. Some environments normalise the idea that small ventures can grow into institutions with social purpose. Others encourage success, but only up to a certain point, beyond which ambition is seen as unnecessary, disruptive, or even inappropriate.

What moves a society forward is not just economic growth. It is the cultural and institutional space to imagine better systems, and the freedom to believe that one person, one business, or one second chance can still evolve into something that serves the wider public good.

Further reading for 49.2

• Joseph A. Schumpeter, Capitalism, Socialism and Democracy

• Karl Polanyi, The Great Transformation

• Mariana Mazzucato, The Entrepreneurial State