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Under No Circumstances Start A Company Because You Hate Your Job (thefailingpoint.com)
49 points by BrandonWatson on Aug 6, 2009 | hide | past | favorite | 25 comments



Interesting article, with some useful insight, but I don't agree.

I had talked about creating a startup for a while, but it was hating my job that pushed me over the edge.

Yes, starting a company is hard. Yes, it can be boring and frustrating and the only thing preventing you from going out of business is your own will power.

I'm not profitable yet, but even dealing with everything the author mentions, I'm still happier than working for untalented managers at a bureaucratic corporation.


Yes, but it sounds like your desire to start a startup preceded your acute dislike of your job. That's a different scenario than the one the author is targeting.

I had the same thing happen; I had various business ideas and was increasingly getting the itch to go out and do my own thing, and carried that itch through three more jobs. It is absolutely certain that the dislike of the jobs and the entrepreneurial yearning fed back on each other; although I'm quite certain I would have disliked my jobs for the same fundamental reasons anyway, feeling less invested in them because really, inside I wanted to go out on my own no doubt made me even more miserable than I otherwise would have been if I had no such compulsion whatsoever. Conversely, innate dislike of the jobs helped bring me closer to the jump-off point.

Even then, I didn't have the balls to walk away from a secure, steady paycheck. Instead, I just started performing worse and worse; I was up till 5 AM working on my own stuff, and, well, very obviously not showing up at 9 AM or what have you the next morning, and seemed kind of preoccupied and distracted at work too. Eventually, I ran into my last employer who was very (understandably) demanding and had no tolerance for that kind of crap, and was summarily fired.

That's what gave me the kick in the ass I needed, because at that point I had a choice before me: Do I look for my 7th job in 3 1/2 years, or do I grab this thing by the horns and find my own way to pay the (large) bills next month? I went for the latter, and that's how it's been ever since. But the thing is, before I got fired, I don't think there's a way I could've done that.

Sure, I dreamt about getting fired or laid off on innumerable occasions and halfway wished it would happen, but there's a long psychological gulf between that and just walking into your boss's office and saying you don't want the comparatively large, steady paycheck anymore. Obviously, the gulf narrows if you have substantial savings and/or a cash reserve and/or low living expenses, but I had none of these, so, there's no telling whether I would have left eventually--I just sort of sabotaged myself into being kicked out onto the street.


This is an awesome personal account. Thanks so much for sharing it here.


A great personal story.

It seems like you had both a push and a pull. Circumstances finally got you to leap off a cliff, so to speak.


Yeah, I think so.

I'm one of those people that really doesn't make a very good employee. Although I was considered talented and was prized for my technical abilities and interdisciplinary knowledge (and I say that not out of immodesty, but simply because I was told so in no uncertain terms numerous times), and was cut some slack in situations where a less able person might've been sent packing because they just can't get their shit together, I had - and have - the problem of it being damn near impossible to get me to do something I'm not interested in. Just impossible. I'll do it, somehow, but in a time frame and workflow that emits kicking and screaming in all the nonauditory ways.

It's not really a conscious protestation. I'm just mentally spoiled because I grew up developing whimsically, and for fun. Put me in situations where getting it done and accomplishing the objective is a thousand times more important than what it actually is and how it works, and I just don't thrive. I'll do well enough to not be fired, but nothing stellar. I have enormous productivity potential when I apply myself in enormous marathon spurts toward something I am motivated to do for one reason or another, but whereas some people have a consistent base line of performance even in things they don't care about, mine is pretty disappointingly low.

I want to emphasise how unconscious this sabotage of the task is; it's not because I'm whining inside my head. I'll just unconsciously structure my priorities in such a way that something I don't care much for will be extremely starved for timeslices, and that's that.

I think a lot of "creative" folks are that way.

Anyway, point is, I think there's a corollary to this tendency that expresses itself in the more general fact of unconscious sabotage. As I progressed through the employment world, it came to be more and more the case that if I just didn't want to be somewhere, I'd mentally sabotage it so as to get closer and closer to being fired or, at the very least, given a very stern talking-to. The last two jobs before the ultimate one weren't very pretty, either, it's just that the employers were a lot more progressive and tolerant of my work habits and lack of punctuality in exchange for getting what they considered to be a very high caliber of output. If they were as demanding as my last employer, I would've been fired even sooner.


It's an interesting point you raise about being happier than if you were at a large corporation. I can totally understand that, and in fact my point was don't have the fact that you hate your job be the reason. For you, it was one of the reasons, and in fact appears to be the tipping point.

My experience with some entrepreneurs is that they didn't really understand some of the pain and suffering that comes with running their own gig. Because of this, they get disenfranchised.


I think you're right to warn people, but I don't think you're right to equate the two very different kinds of pain.

When you are "forced" to do something for someone else you feel not only the pain of the task, but bitterness and indignation as well. When you're doing it for yourself all you feel is the pain of the actual task, which is not nearly as bad.

The difference between wiping your own ass and being forced to wipe your boss's ass.


It might feel like those accounts and tax returns are done not for yourself, but for some paper-pushing bureaucrat. Bitterness and indignation could easily bubble back to the top - running a business is not a way to run away from arbitary demands from others, only your particular boss at the time.

Getting away from a bad work situation could be done by working somewhere else, not necessarily in a bran new business.


That having been said, the pain of the actual task can be very acute if the task is not interesting.


My suggestions based upon years of running my own business and working closely with entrepreneurs:

Never launch out on your own if your primary motivation is to escape a dreary job or career path (it is OK if wanting to leave a bad job is an incidental motivation for doing something you would otherwise want to do). Always build from strength. Always count the cost (which is great) and the risks (which are great). Weigh this against the rewards, which are potentially great (greater financial return, independence, pride of achievement). If you see a good opportunity before you, and your eyes are open to the downside, then by all means venture forth if it makes sense to you.

I have elaborated on these points here: http://grellas.com/faq_business_startup_013.html ("Tips from a Business Lawyer on Becoming a Founder").


I think it's spot on. The reality of starting a business isn't glamorous, people should realize that before they get into it.


I think this is because marketing feels kind of sleazy to technical types (does to me, and to my friends).


re:glamour, I heard Megan Fox would date me when I started my own company. Sadly...not the case. =)


It is one thing to say start your business for the right reasons but this takes it a bit too far. Hope people don't get discouraged.


I don't know about taking to too far, even if it is a rather pessimistic (or even realistic) view of things. Entrepreneurship is not for everyone, and a lot of people don't realize that. They only know what they see in the movies: lots of money, fast cars, etc. I know I fall into that same mental trap sometimes.


@amr - why do you think that this is taking it too far? I would love to hear your feedback. My personal experience with setting off on my own was just as I describe here, so maybe I am the oddity. I was surprised, and quite honestly overloaded, but the minutia of stuff with which we had to deal, especially when we got into the fund raising process.


I may just be a little absurd pointing this out, but is it really necessary to use twitter speak to preface a reply when the formatting of the conversation implies your target?

I know I am being pedantic and this is not adding much to the conversation, but this has been slowly creeping throughout the internet, much more lately, of the use of twitter speak in seemingly unnecessary places. What influenced you to use it? Is this a good way to track the influence of certain social networks, by their adoption of common idioms in other disparate networks? Can we follow through this idea and scrape networks to find where idioms are being generated and pinpoint hot-spots of the internet?

Ah, this is just opening a can of worms for such a simple style guideline, but what are your thoughts on this anyway?


Yes, but the pain you describe is worth it and makes you a stronger person. The pain of being in cubeland however is not so worth it (for me).

It's a question of what you will achieve after going through the pain of starting a company vs. the pain of being an employee of a traditional software company.


I'm totally in the invoice situation right now, and making that first call to the first client to ask them kindly to pay up was hard. Chasing it up again and again (it's 14 days overdue) has become a lot easier though..!


I disagree with the "under no circumstances" part. There have to be jobs that are so bad that even a bad experience working for a young company will be preferable.

Also, I never thought about leaving so that I could make my own schedule. What I wanted was a meaningful schedule, not one that was simply based on manager's whim or a policy book.

But I enjoyed the article. For disclosure, I have never actually started a company.


The "Under No Circumstances" is part of the construct for the titles of the essays for the book. The book is meant to be a collection of situations that went wrong, and hopefully how to avoid them. I decided to release the essays in early for for all to read on the web site, and will have the final versions online for free as well. Communities like Hacker News are giving me great feedback about how to make modifications.


I think one aspect of this that deserves more discussion is the difference between simply being self-employed and having a business model. Discussion around just "starting a company" in a generalised sense doesn't really capture this critical nuance very well, though PG's chronic highlighting of the distinction between being consulting companies and product companies does so very well.

I had to learn this the hard way, and still am.

Being self-employed ("working for yourself") intrinsically is not too different from a glorified J.O.B. It's just a bit more flexible in terms of location, working environment and, depending on what you're doing, some degree of creative control and, if you can afford it, perhaps some level of freedom to reject uninteresting or otherwise non-compelling projects. Instead of having one boss and having to do everything demanded of you, you have 8 different bosses and have to do most of what they demand.

Yes, it's definitely not the same relationship, but, if you need money to survive, you don't really have nearly as much freedom to not do what they want - on their terms - as one might imagine in the abstract. And, to be honest, it doesn't much matter what the hourly rate is; supply and demand works against you. Insane multiples of your hourly equivalent wage on salary don't offset that.

I encounter a lot of people with the misconception that self-employment, contracting and/or business ownership is somehow inherently lucrative just because it's not being a "wage-slave"; it's really not. I don't make nearly as much as I did at my last job, and I'm quite a ways off from that. Even if revenue doubles, most of that is going to be sunk into reinvestments, paying other people more money, etc.

The other problem - this one being the more central preoccupation of PG's advisory writing - is that there's just a very hard limit to the amount of money you can make this way. You're not working 40 billable hours a week, and you can only do so much work as an individual, especially given that you also have to tend to all the auxiliary aspects of running a business and, of course, the selling, marketing and project management part that ensures that you have more work in the pipeline after the current project is over.

And if you're like me and don't have much money while having significant living expenses that you got yourself into while living the good life employed, you can't afford to float lengthy projects either; you pretty much need things that can turn around within a month from conception to final delivery and collection because of cash flow imperatives. Your bills are due monthly, but that timing resolution has no imaginable correlation to how your customers are going to schedule and implement anything. The small guys suffer from a shortage of time as much as a shortage of cash; you may get them the final product, but then they'll drag their feet for a month before doing any kind of acceptance testing and sign-off, which is required before you get paid.

Working out some sort of pay-as-you-go terms can solve this problem to some degree, as I've had to figure out, but there's only so far that's going to carry you because from a customer's point of view, an 80%-complete project is just a lump of useless code; there's a synergy that happens at the 100% point that gives it orders of magnitude more utility (specifically, the kind that's worth paying for) than when it's less than 100% complete. So, for the most part it's some kind of relatively small down-payment at the beginning, and a big lump sum at the end, whenever they feel like declaring it's done and paying you. And maybe another 10-45 days from there if they have a lengthy AP process. There's no reason the customer is going to want to pay you 7/8ths of the money by the time the project is 7/8ths done.

Besides, they all suffer from the same pervasive fear (or "fear," if it's just a matter of principle that they take this posture, which for many is the case) that you're going to screw them, by which it is meant take the money and run - without the necessary "follow-through" and post-sales support and tying up loose ends. So, customers often believe it necessary to "manage" you with carrots, and unless you're just drowning in work and positively don't need anyone who gives you the slightest bit of untoward attitude, you grin and bear it. Facing that kind of condescension and prejudice - if you choose to look at it that way - can be more than a little bit reminiscent of how you felt as an employee before "fashionably cynical" managers and/or businesspeople, with all their accounts of how lazy employees steal/embezzle/fuck them all the time and how they don't trust anyone too much and all that good stuff. It's a pretty crappy place to be in when you just need to be paid cash, like, tomorrow.

In a linear business model like that, it's like a barber shop; you want to make twice as much money, you have to cut twice as much hair. The only way to make any serious money this way is to have a nontrivial amount of other people working for you, and that is a whole new set of problems, especially if you're doing something highly specialised and yet can only afford to pay fairly entry-level salaries. There's just no way that the knowledge transfer can be made effective without talent transfer, which, as we all know, is not really possible in the balance of things.

That doesn't mean you can't be a worse ("Here! throws manual at employee YOU figure it out!") or better ("Let me sit down and explain and show you everything you need to know about this new system") manager, but if it's not their thing, it's not their thing.

Having a product puts you in a very different place, especially if it's a take-it-or-leave-it shrinkwrap product. That's something around which you can build reusable business processes that you can replicate and scale at _decreasing marginal cost_. That's very important from a hiring standpoint, if nothing else; if something is narrow enough, you can specify enough process that more people can do it to a higher - and even more importantly, a more consistent - standard. It also lowers the per-unit price and makes your product more attractive, and so on and so forth. The most important point about product is that the marginal cost on making another deployment/adding another user/whatever is almost negligible, at least in the software world. Doing another one-off consulting project very much lacks that indispensable quality, and thusly limits your profitability.

In short, being self-employed in the former sense can easily be twice the work for half the money, and there's absolutely nothing about it inherently that's going to liberate you from the essence of what you most hated about being employed, whether generally or in a particular place. It's something you have to approach very pragmatically and with the right goals.


This is a great analysis, and spot on. Having a business that can run without you, and thus sell 24 hours a day, is very different than taking on project work where you are paid by the hour or by the project. Repeatable == scalable when you are talking about a product. You want to be able to ramp production, and, better yet, enable others to sell for you.


You're very welcome!

I think repeatable doesn't inherently signify scalable; the key is that it's repeatable at a low marginal cost. Consulting projects are repeatable too, in the sense that you can - theoretically, if two clients wanted it - do the same thing over from scratch.

But if your first project let you build scripts and infrastructure and training and process so as to let the second one happen in 1/3rd of the time, that's the kind of repeatable that's scalable. Of course, if you only get to reuse the infrastructure once, that doesn't do much for scalability either, but if it allows you to lower the price it may work out better. It just depends on what it is.

Having a business that can run without you in a literal sense is a pipe dream, except perhaps in a rather large, mature company. Even I could afford to develop an actual product and hire people to sell, deploy and support it, I'd still have my grubby mitts all over the process, and it's got less to do with the fact that I'm a control freak and more with the fact that it's just a specialised area of endeavour, and I'm unlikely to be able to afford to hire someone with more perspective and experience in the exact same interdisciplinary nexus as I.

But I'm not too concerned about that; the goal isn't to avoid work, but simply to get higher returns on one's time by replicating at a lower cost.


Way to go, nutpuncher!




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