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 the standards they know were working back in the day.
This delayed awareness of a paradigm shift in recruiting employees leads to stunning perversions of an otherwise useful process: the illustrious whiteboard leetcode interview. Regularly, software engineers are asked to solve previously solved problems without a computer, in front of interviewers, on a whiteboard. The fact that this is common practice blows my mind. The reality of most software jobs is that when you need a particular algorithm, you look it up. You find a peer-reviewed (often open-source) implementation, and you integrate it into your work. Why on earth would you have to come up with such an algorithm —without a computer or the hivemind that we tap into when we code— in an interview setting?
Well, this is about compliance as well. “If you really want this job, how far will you go? Will you learn all these easily looked-up problems and their reference implementations? You won’t need them for the job, but you will need them to show your submission to our process.”
Most employees are fine with this. After all, they gain a safe and long-term job after jumping through these hoops. And often, these problems are interesting for a technically-minded person: removing duplicates from datasets or calculating the number of permutations of a string can be fascinating research projects for a coder.
But they have very little to do with problem-solving capacity.
And that’s what an entrepreneur needs: unbounded, explosive problem-solving capacity. Thinking out of the box, intersectional application of knowledge in unexpected and novel ways. We won’t be able to run a business on leetcode-interview-compatible techniques. We need to learn how to listen to our prospects, understand their pains and challenges, build a solution to their most critical problems, and implement it in a way that is both quickly prototyped AND usable by non-technical folks.
In short: to be a founder, you need to unlearn all the limitations you were trained and ended up training yourself in.
Being unemployable starts exactly here. It’s not just that you expand your capacity or skills: you start understanding that you can do much more than anyone ever asked of you.
That’s because no one is asking anything of you anymore. You become autonomous: you don’t have a boss. You ARE your own boss. If there is anything your boss needs to be done, it’s up to you to define and execute it. There are no more formal requirements for you to hold onto. If you can imagine it, you will work on making it happen.
A quick word about autonomy: just because you don’t have an external boss doesn’t mean you don’t need to make hard decisions anymore. This isn’t anarchy. You’ll still be under the rule of someone, even if it is yourself. But the choices are now yours, and you are the one to set the goals as well.
That’s the unemployability seed: you start understanding that as a founder, there is nothing you wouldn’t explore if it promised an improvement for your business. No one would hold you back or remind you of a hierarchy you signed up for.
There are downsides to this, of course. If you are lazy —or motivationally challenged, as I prefer to call it— you will have a lazy and unreliable boss. You’re left with the task of motivating yourself to be motivated. That’s a very bootstrappy thing: it’s logically impossible. But you’ll find methods to keep motivated and accountable. I personally find external expectations to be helpful. Every week, I have to write an article, as my readers, listeners, and viewers expect it to appear on their feeds. That keeps me going.
Most founders do precisely that: they keep going. To their surprise, they also keep growing. Sometimes slowly, and occasionally quite fast, they learn, improve, and build something that matters. There comes a time in every entrepreneur’s life where they look back on their journey and get to see that it was their own work, their grit and tenacity, that got them to where they are today. This observation leaves us founders with an indestructible level of self-respect. We did this. Ourselves.
And that’s why it is so incredibly hard ever to consider taking up employment again. We know our potential. We know how adaptable we can be. As wielder-of-all-the-roles, we have trouble considering limiting ourselves to one role again.
We have learned that we are so much more than just a cog in the machine. We have become linchpins in our own businesses: without us, things fall apart. We’re indispensable. This severely limits the lure of a stable job in a position where we can be easily replaced.
This also affects the way we negotiate for ourselves. When we do consider taking up a job —no matter if it’s post-exit or because our project failed— we remember the freedom that our autonomy gave us. We know that we’re more than our job title. The life we had a glimpse into was one of balancing many things: the business, the family, and our life as a whole.
When we negotiate about vacation time, we don’t do this out of disrespect for our potential employer; we do it out of respect for ourselves. This respect is an often painful consequence of going at it alone. It’s a consequence of the unlearning we had to do to become proficient at more than self-imposed compliance.
Now, I have the utmost respect for anyone who chooses to be an employee. There are no silver bullets — we all have aspirations and situations that lead us down one path or another. I have lived all these lives: as an employee, a freelancer, an employer, and an unemployed worker. You can find purpose and fulfillment in all of these. But you’ll have trouble changing back from being a founder.
At the same time, prospective employers may have difficulty understanding why you are so different from their other candidates. Your willingness to negotiate for yourself in a system that expects submission will stand out — and it will signal something to your employer that you might not even intend. From their point of view, you are unreasonably selfish, while for you, it’s just maintaining your status quo.
For me, it’s always been problematic even to imagine returning to the office power dynamics. I know that’s quite a privileged thing to say. After all, as a founder, I hold all the power, and giving some of it up for a paycheque seems to be a fair trade. But there is more to that. My self-perception is linked to my capacity to live autonomously. To make my own choices about anything related to what I am working on. I am living the Indie Hacker lifestyle.
Of course, this all changes once we start building a team where role diversification kicks in. Then, we focus on our strengths and hand over the work we don’t enjoy to people who do.
But that’s not the Indie Hacking I am talking about. The unemployability problem mainly affects solopreneurs. Indie Hackers that are forced into learning all the skills needed to run a business become jack-of-all-trades: with an increasing scope of skills, the specialists turn into generalists.
And generalists are not sought after by employers, particularly not in the lower rungs of the corporate ladder. Solopreneurs end up being overqualified in the most confusing sense: they have too much interdisciplinary knowledge to fit into well-defined roles.
It feels strange to think that in the eyes of an employer, one would have to apologize for having opened up your mind and learned all these incredibly powerful and valuable entrepreneurial skills.
There is a podcast called The Solopreneur Hour by Michael O’Neal, and I really enjoy this show. It runs with the tagline “Unabashedly, Unapologetically, PROUDLY UNEMPLOYABLE.”
Most solopreneurs end up feeling this way about themselves.
And I think that’s perfectly fine.
