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Comment on Ask HN: Tell me your biggest pain and I will try to solve it

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I'm a junior/mid-level developer. I wanna know how will I know that I'm ready to be a contractor, also the dos/donts about being one.

Find your market. Suss out the places online and IRL where people with your skill set congregate, and where buyers for your skills are looking for talent. Start a portfolio web site right away, and optionally a blog. Put yourself on the market right now.

If you get a good offer (on-contract, upfront deposit) consider taking the plunge. Have 3-6 months of cash for a fallback - in case you fail and decide to re-enter the traditional job market. Or more likely, when you encounter an extended dry spell as you learn to build and maintain cash flow.

Prepare yourself mentally for a greater level of uncertainty. Your next paycheck is not guaranteed. Not only do you have to do the work to get a paycheck, you also have the additional work of getting to the next paycheck: keeping a full pipeline of good-paying gigs. Always be marketing and selling yourself.

Not all customers/clients are created equally. Know what you're selling, set your price and stick to it. You're probably not in a position to work for equity. (Since most startups fail "working for equity" is the same as "working for free"). Be prepared to say "no". Be willing to gracefully exit a relationship with a troublesome client.

Stay away from odesk, elance, freelancer.com, etc. These are highly regulated, tightly controlled markets with enormous pressure to push timelines and costs down to the lowest common denominator. Unless you're in a country where bidding for $500 fixed price jobs and $20/hr contracts can make you a good living.

I'm not a developer but I can help from a business standpoint.

Contracts and deposits. Don't take on work from people who won't sign contracts and always try to get paid up front. Don't work out of their repo unless you get paid in advance.

Licensing. Try writing software that you can re-use for multiple clients. Just be sure you license the software to them in your contract. Most clients on small projects don't understand licensing or intellectual property ownership. It's easier to close small projects by recycling code. It's legal so long as you retain ownership of the source code but provide the client with a license.

Jacques Mattheij has written a lot of useful stuff on this topic:

http://jacquesmattheij.com/blog/categories/consulting

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