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Suppose you are a programmer in your mid-20's who has had several years industrial experience working for both big tech and a few internet startups but now you'd like to try contracting in the hope you'll be able to choose more interesting and varied work and be able to have a few months off between jobs to focus on things like open source, travelling and developing your own startup ideas.

Now this is possibly one of those 'grass is greener' daydreams.. Even if in the workplace you manage to have the enthusiasm and skill to work equally alongside much more experienced co-workers, how realistic do you think it would be for someone with too few years of experience to appear 'specialist' or 'experienced' to compete for contracts and afford to live this lifestyle?

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up vote 8 down vote accepted

There are contract roles at all levels therefore for all levels and I've seen people contract with 12 months commercial experience (though that was in a good market). That said you'll see more (and better paid) opportunities the more experience you have. Ideally I'd suggest that you're either at or close to senior developer type experience (5 years +) but in most places it's really not impossible with less so long as the market is OK at the time.

In terms of the lifestyle though, some words of warning.

I know a lot of people who went into contracting with the intention of doing a bit of time on a bit of time off and it never worked out that way.

When things are going well the temptation is to keep working while the going is good because there might be a downturn on the way and you should make hay while the sun shines.

When things are going badly you're so nervous about being out of work that you're desperate to get back in a position. Even if you don't need the money in a bad market contracting is a bit "you're only as good as your last role" so gaps on the CV aren't great.

You can make it work but you're going to need to be disciplined and budget for plenty of time out of work to give you the assurance that you're not going to leave yourself in trouble when it comes time to go back and can't find something immediately.

That financial security is the thing that's going to make your goal possible so it's critical to understand what your average wage over time working and not working will be rather than get carried away with what you're earning when things are good.

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+1 Yep, you do need to be strict with your finances and plan, with the invoice periods of some companies it can get tight at the start. I've been contracting for the last two years (developing for over ten years) and you have to plan your contracts well, this gets easier over time, after a while the agencies come to you with offers when they know you have a contract ending. – G3D Nov 11 '10 at 11:50
and if you're in the USA, count on taxes taking almost half of your income – Steven A. Lowe Nov 11 '10 at 16:45
"I know a lot of people who went into contracting with the intention of doing a bit of time on a bit of time off and it never worked out that way." - I've seen this too. But I'm still looking at going into contracting with this intention next year. :) – Bobby Tables Nov 14 '10 at 22:20

You don't have to be specialist or experienced to get contracts as a freelance.

When I started my business as a freelance developer, I didn't have any professionnal experience in the field but small examples of websites I've built after work.

All you have to do is go for it.


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A few years of industrial experience should do. But you also need some non-technical skills, e.g. self-marketing, (business-)networking, negotiating, self-management, accounting.

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Not sure how long of breaks you plan on taking, but you better look real good on paper and in the interview to explain why a quality programmer has been out of work. It happens especially in these economic times. Working on an open source project may be you best answer.

Sometimes we worry about a contract not lasting long enough. In your case you may find they want to hire you longer than you wish. Putting your limits on the length of the contract may hinder your changes of getting hired. The offer may be for 6 months, but the client will prefer it to be open-ended in case they want you to continue working. This is the luxury of hiring contract labor.

I say start looking for contract jobs. Then you'll know if you're qualified. You don't have to accept an offer if you don't like it.

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All of the contracts I've seen on job sites have specified a fixed term rather than "when it's done". Do companies looking for more open-ended contractors somehow end up stipulating this is a requirement on the signed contract itself, or do they try and determine this about you during the interview process? – jond3k Nov 11 '10 at 13:33
I never pay much attention to pre-defined contract periods. More than once I've been hired on a six-month contract and ended up working on multiple projects, in one case six years. – tcrosley Nov 11 '10 at 14:07

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