Why founders end up unemployable
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.
Arvid, this is a great write up! I agree with everything you’re saying. I learned the unemployable lesson myself in 2018.
I was stuck at $5k MRR for years, and wanted a change. I really really wanted to try out working for big tech. I thought for sure my skills as an IndieHacker would make it easy to get a job at one of the main tech companies.
But no one cared!!! I didn’t get a single call back from any of the places I applied at. It was so bad I hired a professional resume writer, but that didn’t make any difference either.
I then tried to apply at local companies here in Dallas. Even at this stage I had trouble getting my foot in the door. I finally landed an interview and got laughed out because I wasn’t able to complete their stupid white board challenge.
I eventually stumbled upon contracting/freelancing and found much better success. I think the freelance world is much more kind to Indie Hackers than the employee world is.
People looking for freelancers aren’t looking for the perfect employee, they’re just looking for someone to solve their problem. Which is exactly what we are good at!
I still someday hope to work for big tech. (Just for a year) But for now I’m really enjoying the Indie Hacking.
I know the feeling lmao
I didn’t get a single call back from any of the places I applied at... can you try cvscan.uk to see you can get any call back? contact me via the site, I'll give you a 100% discount. I just got an interview at Amazon :)
It sounds interesting, any other success stories?
Glad you found a way that works for you. I definitely admire the things you have accomplished.
hey, AWS is always looking. i work there and was employed after my company crashed and i wanted to try working for big tech. they like founders.
wow that was intense
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Covid gave us a little boost. And now we’re a real company with about 7 employees.
But had that not happen we
would’ve kept the MRR until everyone canceled. Of course it’s going to require some maintenance, and man hours. But $5k is meaningful revenue, and you can save that you to make your next venture easier.
I’d just keep it. Focus all of your efforts into automating away as many hours as you can.
This is among the most underappreciated insights in the world of entrepreneurship. To recycle an observation I left in a recent comment, the author Matthew Crawford perfectly captures how we should think about autonomy:
Counterintuitively to some: humans love rules. Humans need rules. They give us energy, purpose, structure, direction.
The reason why this is counterintuitive to some people is that they've largely only experienced heteronomous rule — listening to parents, teachers, bosses, police, etc. And thus they come to believe that rules per se are the problem, rather than the context in which the rules are delivered.
So some form of "anarchy" is the immediate impulse for so many people who find themselves freed from the yoke of outside rule. And this is almost always destructive. I know this is only anecdotal, but I've seen it so many times as the co-founder of a community of entrepreneurs:
I am glad I escaped the doom loop by starting to write. Externalizing accountability by starting a newsletter and a podcast did a lot for my lacking discipline. I’m now building a media business autonomously.
Thanks for making this so clear. This is an important concept.
This and your previous comment on the topic brought real clarity. It completely explains why I find myself working harder than ever these days, despite not really having to work any more. Self imposed rules and structure bring productivity and meaning to life. Thanks so much for the insight.
One addition to this is that you will definitely be (or at least should be) under the rule of your users. So, absolute autonomy is non-existent - you are building something for the people, and you need to comply with the people.
Just embrace that, and move on.
I’ve heard Jonathan Stark compare this to being an outdoor cat. Happy to come around, chase mice, and engage with the family, but don’t try and keep them penned up.
A friend of mine once said he felt like being an employee became difficult when he couldn’t find a direct impact tied to the activities he was participating in.
Having that blunt and ruthless desire to work on intentional tasks, and only those, matters the most.
Strong second might be fatigue of cleaning up co-workers’ messes, which feels a lot worse than cleaning up your own 😂
This is a really interesting perspective. As a founder, I don't think I would have any problem ascribing to a more traditional & structured job, but that might change greatly when I'm in that environment. All I know is I'm incredibly grateful to have the opportunity to be my own boss and work on my terms!
It really is the environment more than the actual job, right? I would LOVE to be able to focus on coding 40 hours a week and be paid for JUST that. But I certainly don't want to go to meetings that other people schedule :D
Exactly I would be even willing to work 1 extra h a day but without meetings and the other passive agressive BS. I went the entrepeneur way and busted very hard, now my funds are dwindling and I really really concerned about getting and keeping a normal job. I thin freelancing could be the salvation
Yeah, the environment is a big draw for sure!
My dad was a founder and he often told me this. He also said I had a similar personality and I wasn't going to be happy in any job. He was right, though I didn't want to admit it.
Same thing is true for my parent. He runs his own business and he has for the past decade. It's been wild watching him build it from the ground up, and the first several years were very taxing on him. I never saw him in my early years growing up.
But now that he's older, and the business is more stable, I can see what he was working for. He comes home for lunch whenever he wants, and can play the piano, and if he wants to take a vacation he can do so when he pleases.
Growing up, and watching his journey unfold, I'm mixed as far as if entrepreneurship full-time is really for me. Theres been times when he was really emotionally stressed and I didn't recognize him. He also wasn't able to be there with me growing up since he was building his business, and I don't want to put business ahead of my family, even if it in the longterm its the right thing to do.
It's amazing to see how you growing up with this gave you a balanced perspective for your own choices. I threw myself into entrepreneurship without having a (truly comparable) entrepreneur in the family. It was a "grass is greener" moment that led to several mental health issues down the road.
Your perspective is one that founders-to-be desperately need to hear more of.
This perspective is the cause behind the great resignation that we're witnessing lately. If you go founder there is no coming back. I enjoyed your post, you are a great writer. Keep it up.
Thank you most kindly! I appreciate it. And yes, I don’t think I could go back either.
Supply and Demand. In Israel, it is currently High demand. I heard people with no school degree got hired on sheer determination and believe they could close the gap by sending them back to school on company money. Obviously these are outliers but explains how desperate companies are here. The local market believe in entrepreneurship and there is no problem hiring someone who was a co founder or a bootstrapper. On the contrary. This is a matter of cultural believes.
The submission tests are a really funny thing.
I worked for a company that used to promote it's employees once a year using a really humiliating process:
The process took around 3 months to complete, and your first salary bumb would come (hopefully) after two more months. During the process you would have to prove that you completed some tasks/PDP stuff, judge your self on a few given items, indicate other fellow workers to judge you one the same, etc.
So instead of just giving you more money for delivering value, they wanted to test your submission to them (and maybe, yes, maybe promote you).
That sounds like every FAANG out there! And the worst part is, more often than not they will just say “sorry, the bar for promotion this year has been unexpectedly high, but we for sure will do it for you next time”. Yeah, right.
The fact that someone signed off on that process bothers me so much.
I think one of the core issues that causes this is that there's a ton of completely arbitrary rules in the traditional corporate world that you don't really become fully aware of until you find yourself free of them.
We all saw this happen with the pandemic, which showed lots of white-collar workers not only that decisions like making them come into an office for 8 hours on a fixed schedule every day were completely arbitrary, but also what their life could be like if they didn't have to play by those rules.
Another really important issue is that working for a traditional employer inevitably at least somewhat alienates you from the work you do. Even if you have company stock (and that's a big if, even in tech where ESOPs are relatively common), it probably only gives you and your coworkers a very limited ability to actually influence the direction of the company, if any. How do you motivate yourself to care about the work you do in an environment like this, if you've experienced the other extreme of this spectrum, where you have complete control over the product you're building, and directly benefit from the value you create?
Wow, heavy read.
I've never thought about it like this. I always figured it would bring companies great value to have an entrepreneur on the team.
I think the trick is to remember that...
What a lot of things you have said Arvid!
Sometimes I find it incredibly painful how we extinguish in ourselves the desire to live (I consider desire to live, the flame within us that makes us want to do.) for fear of uncertainty.
Neurosis from psychoanalysis means "fear of not knowing", "anxiety of nothingness", "anguish in uncertainty".
I completely agree that if there still exists within us the desire to live, we must go for it without fear; because there is one thing for sure, failure , and even failing, you are inside life!
I'm not saying that whoever is employed lacks the desire to live, what I'm saying is if you have the maker spirit don't extinguish it for fear of not knowing what will happen.
Thankyou Arvish
Spot on comment. After two decades on this journey, I've come to realize that my greatest skill is my ability to wrestle with and tolerate uncertainty for long stretches of time.
Despite our best efforts, things won’t always go as planned. Expectations will go awry, unexpected events will blindside us, and we will experience disappointment and rejection.
If uncertainty is unacceptable to the bootstrapper, we will only amplify our fears and end up at war with ourselves, resisting and arguing with life rather than living it.
You can't be SURE that you will succeed, but if you think just a little bit you will know that it is NOT SURE that you will fail!
Uncertainty goes beyond fear of failure.
Good luck cowboy!
I like that - the inverse makes a lot of sense. All the best to you as well!
Excellent article. My two cents:
Sometimes, everything you want to do is to be yourself, an individual. On the other hand, your county, the government, wants you to be everything opposite: a uniformed citizen, working a steady job with predictable events in life. In order to organize millions, you need uniformity. And only your luck can help you that your teacher in school, or your parents, think differently and let you express yourself in the early stages of life.
Honestly, I don't see that changing in the near future.
Everything mentioned here is broken. Both recruiters and applicants are aware of that. And still, they both agree to convey that strange dance of reversing linked list, upon which recruiters conclude the applicant is a good fit since he performed a task he knew that he is going to perform. Hallelujah.
In order to hire a good engineer, you need to look for a good (in the most naïve sense of the word) man/woman, who is intelligent, and knows how to code.
The first point requires a deep understanding of human psychology. The second and third can be, to some extent, concluded during the programming interview. You need to find out does the person sitting in front of you knows how to code and can he get things done. Can you do that with a task that zigzags through a binary tree, on a whiteboard, while three recruiters sit in silence and watch your every move? Hardly.
As noted, given that he knows that your company has that kind of interview questions, all he needs to do is spend a couple of weeks learning those algorithms, and he will be good to go. Does that mean that he will accomplish the daily tasks that are going to be given to him? Who knows. Maybe he will, maybe he will not. You, as an interviewer, don't know that (but you hope he will).
A better approach is to try to extract a real-life task you are already giving to your engineers, and work with them on solving it. You are a backend service that provides data via APIs. Give the applicant a PC, let him share the screen, and let him write an API. Talk with him during the process. Preferably, in ten minutes, you will know if he can get solve a ticket you have in your backlog.
This process can be improved, but I think it will work better than solving already solved problems.
I agree with the sentiment introduced in the article, but I think this is just another problem that needs to be solved.
I was once a specialist. Now, as an indie hacker, I have to learn a lot of things a didn't know (marketing, sales, etc). That switch, from specialist to generalist, is painful but possible. If I am ever to go back to working for a company (which I hope will never happen), I'll need to switch from generalist to specialist. It was going to be painful, but again, possible.
After some time, you get used to your new role, whatever it is. And, as with other things in life, sometimes what you think is going to be the problem happens to be a breeze. And vice versa.
Definitely agree. I think when we obtain a certain level of autonomy, it's hard to undo it. Life happens, it may even humble us into climbing up the levels again we once reached.
Ironic, but when I read "Rich Dad, Poor Dad" for the first time in high school, I knew deep down inside that there's a completely different mindset that I wasn't raised with.
Working through that going into my 30s and having mild successes here and there has proven to me this is possible with enough dedication towards it. My problem is that I'm very employable, just that I don't want to be. That's why I do IHing.
What I find interesting is that at a certain level of professional work, you do regain your autonomy like you would a founder. The big question is what side do you prefer to be on?
Great insights. I totally agree. Especially what you cite about HR practices. HR people are a total joke today. Because I'm multi-skilled, I try to make it easier to show how the certain specific experiences fit the specific role, plus share how other experiences I bring can be transferable. You'd think they'd appreciate not only the self-awareness but the ability to make connections. I discover that HR folks (particularly in large corporate settings) are functioning as sales reps. They rarely read and have poor discernment. As with the example given about the teacher's inability to see your talent as a writer, they punished you for being exceptional and different. I find many, not all, do similar. They pass up potential great fits cause they don't check all the boxes of a job description their client is demanding. As clients are operating on antiquated hiring marketplace protocols and demanding their "recruiters" follow.
I'm so glad the T-shaped skill set description is gaining popularity in the spaces that I desire to work (Fintech, product development, UX research and writing) because it appreciates a broad knowledge base and a depth. It makes it easier for me to communicate the range of my experiences and the valuable skills I've accumulated--since I'm in my 40s.
Previously, it appears I've been overlooked by recruiters as "all over the place or unstable" but the T-shape skill set framework changes the conversation. It enables me to concisely show what I bring to a team and talk about them with confidence.
Thank you for sharing this. Very encouraging to find a space with like-minds.
"In short: to be a founder, you need to unlearn all the limitations you were trained and ended up training yourself in."
I never learnt the limitations. They tried hard, but failed to train me to be their factory worker. I do play by their rules to make a living. A living, to keep the entrepreneur in me alive and kicking!
"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."
This line hit me hard! @arvidkahl ❤️ Excellent writeup. Thank you.
Great article. This resonated so much with me. I recently went the employment route again and while I joked about being unemployable, I didn't realise the truth in it at the time.
You took the words out of my mouth.
It is so hard to work for someone when you have that mindset. You start to think about things and want to try them so badly, but you are not in a position of decision-making. I feel locked inside a cage.
You gave words to a inkling I have been carrying along time, thanks for that!
Also: That part about the school assignment is very much like one of my own experiences. But honestly I WAS still a little shocked when I read yours.
It still hurts to think about. What was your experience?
So this was 4th(?) grade, I turned a 5m show and tell in 20 minute physics class about light. I brought a prism and my dads drill to spin a disk with colors I colored myself, creating the illusion of seeing white light (sort of).
I got criticized for not talking about my pets or hobby (explaining things was my hobby) and scolded for going over time (which is okay btw). Did pass the assignment.
My friend was worse btw: This is 5th/6th (i wanna say 5th) grade. He had a book report due, wrote his own book (about 10 pages including drawings), did a report on that, and got a failing grade. (His parents then removed him from that school)
Fantastic read, Arvid.
Thank you for this.
Thank you Simon.
Can't agree more. You told my story. Really enjoyed reading your post.
Glad you enjoyed it.
Thank you!
Thank YOU!
Really interesting take (and great podcast recommendation!). Appreciate your work across the web Arvid!
Thanks, Hugh! Most appreciated.
Good one
Just stumbled upon this article and read it until the end. Thank you for this thoughtful story. I can also recall my teacher in grade 6 ripping up my story book because I was working on it during his lesson. I remember feeling extremely sad because I wasn't falling in line like the other students. I guess some of us were born with a gifted mindset and deserve to do more. Your article definitely hit home.
Very insightful and I largely agree. However, I think there's a difference between willing and able: the former is about whether you would want to, and the latter is about whether any company would take you on. I'd say you become more attractive in a job market as more companies start realising the shift towards autonomy and new generations of people entering the job market have views not dissimilar to yours.
Willingness is a different thing. The amount of autonomy goes without saying, but it's the amount of learning and growth gained from these activities that attracted me to do it and continue to do so.
Keep building and you always have something next on the agenda :)
Amazing insights and details. Totally on point!
Yes, entrepreneurs are a different breed
Simple, but a powerful brain shift.
Insightful, accurate, and well-written 👍
Once you walked the indie route, you won´t return to the employment treadmill. We are unemployable because we are indies.
Interesting write up I just have to say
Im currently in this situation myself, sold my website recently, but looking into acquiring other websites now to continue financial growth. Get's me excited, but also nerve wrecking, because you dont want to go back to a point where you didnt have that financial freedom. Great topic!
I'm absolutely unemployable. LOL I shake whenever I receive unsolicited job offers on LinkedIn
Job offers or invitations to interviews?
Haha both!
This is such an inspiring read. Thank you Arvid. It's clear from this post that you have a talent for written prose, you had me hooked on every word, I couldn't agree more.
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. it is true and each line of this post is a gem! I will save this for motivation.
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