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Why founders end up unemployable


Original Article: Why founders end up unemployable

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In most entrepreneurs’ lives, there comes a point where they jokingly claim to be “unemployable.” It usually happens in the middle of a conversation about the benefits and drawbacks of having a boss. After setting out on their first self-directed business journey, many founders have a hard time imagining themselves back on the clock as an employee.

They feel like they can’t handle the restrictions of a regular job.

I feel very much the same way. Building my own businesses has liberated me from several ideas and conceptions that I believed to be true in the past. Most of it has to do with how we work, what we should work on, and how we organize ourselves.

And I am not alone in that: many indie hackers find that after building a business, they have a very different perspective on how they want to spend their working hours.

Why is that? Why does the reality of our lived entrepreneurial experience clash with our expectations?

It starts with our educational upbringing.

I vividly remember a day in my 9th grade English class. We were given the assignment to write a story, a page or two. In what I recall to be an extremely enjoyable flow state, I penned a 20-page narrative with multiple characters and a whole plot arc.

It probably won’t surprise you that instead of being praised for creating something that could be rightfully considered a piece of written art, I got reprimanded for not following the structural expectations of the task. The story that was a deep and honest expression of myself received a failing grade. Over-delivering was punished, and severely so.

School teaches us that compliance with someone else’s expectations is desirable. At the same time, we’re asked —and through grades, forced— to suppress our creative impulses. We are told that overstepping the formal boundaries of a task is failing the task itself. The fact that teachers have the power to dish out punitive grades at any point creates a power dynamic where we are expected to submit to external pressures and absorb them into self-imposed limitations: a good student is a student that has trained themselves to stay in their lane.

This compliance may have been helpful in a world of factories where the safety of everyone involved required workers that would blindly follow orders, but the knowledge economy needs a different mindset. Most Indie Hackers operate solidly on this digital side of the knowledge economy, and they struggle to break the bonds of self-imposed creativity suppression.

Now, let’s get one thing straight: teaching dozens of students simultaneously needs formal requirements to avoid chaos and a lack of measurable results. But what are we really measuring in school? What do grades convey, and who is looking at them?

This is where the compliance moves beyond the educational system. Because it’s not just parents and teachers who care about grades. For some reason that escapes me, employers to this day are interested in seeing the school grades that I received several decades ago.

In a way, it’s not surprising: systems change slowly. Even modern corporate businesses don’t operate in a vacuum: their internal processes result from many decades of managerial and operational experience. It’s not that strange to think that someone who has been working in HR for 30 years would apply some of ...

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