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Ya !! you can say "out of work" people have these thoughts, but then, what can one do :-P . My question is somewhat deep thought.

How can someone evaluate himself as a developer and manager to understand whether or not, he is fit for starting a commercial venture on his own. Starting a development company doesn't need too much of an investment and neither it requires a big team. If one is capable developer, then he can definitely get the ball rolling on day one. And may be that's the reason why there are so many freelancers around the world.

Doubts are severe thing and once they creep-in, they make travel tough. So, can there be some things or self-assessment kinda test that one must evaluate and pass to boost his idea of development venture.

Pankaj Upadhyay
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Start an open source project. This will test a lot of your skills, such as judging and meeting the needs of a market, managing collaboration, marketing, self-discipline, keeping up with changing needs and maintenance, etc.

Yeah, it won't bring in money right away. If you need income this second, you're in a bit of a bind, though something like ODesk might help you there. What it will do is keep your skills fresh, help develop new ones, and build your reputation. It's a good resume enhancer too, if the project is even a little successful. And, if it's very successful, there's ways to pull some income from it (write the how-to book on it, charge for support, etc.) If it works, and you like doing it, you can start a proprietary company either building on that, or with something else.

kylben
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I think maybe being a great developer is like being a great chef: the fact that you can run a kitchen doesn't mean you can run a restaurant. So first maybe you should think about whether you enjoy business as much as you enjoy development, because they are very different things, and running a business will take a lot away from you being a developer, too. Also, with freelancing, all you have is yourself to worry about. When you become an actual business with an EIN, employees, etc. you have to consider legal matters and other things, which could potentially be very expensive and also emotionally draining.

I like kylben's idea about starting an open-source project first. Because to make money at it the key is reputation; unless have plenty of people to support you and plenty of momentum already, you shouldn't be considering a startup yet, I think.