Ask HN: How will I know when I'm ready for contract work?

After I got my bachelors and moved in with my girlfriend I figured I would make a living freelancing. I had a few contacts from having done moonlighting and part time contracting work while in school. First thing I do is I call this guy I know out Arizona. We'd work together when he was doing some contract work before his current stable gig. Two days later he called me back with a great project that was kicking off "next week". That was May of 1995, it still hasn't kicked off so far as I know.

I took a regular job three weeks later. We'd talked, it was still "a week or two out." Eventually over the years, my Rolodex expanded to where I could take another stab at it when an economic down cycle made my job evaporate and I was kind of more or less able make it work.

You're ready to start when you have a signed contract and the retainer check has cleared. Software contracting is no different from any other type of contracting. 80% of it is sales. The other 80% is doing the work. Nobody who hasn't already asked you to do a project for them is likely to care on the day you open the doors and hang out a shingle. The three most important things are:

  1. Get the job.

  2. Get the job.

  3. Get the job.

Good luck.

The biggest secret to contracting is that your technical skills aren't nearly as important as your ability to sell. I'd rather be a great salesman and a mediocre developer than the other way around.

Hey everyone, thank you for these replies! All of them were helpful. I came up with these takeaways:

- Frame your services as creating solutions to business problems, rather than trying to sell developer skills. This explains the value in terms that a client understands, and more simply, it lets non-technical clients know what you do in a way that “AWS, Go, JavaScript, PostgreSQL” can’t.

- Focus on getting clients. This is a bigger barrier to entry than how good you are at creating software. Don’t expect to do well just because you are good at making things.

- You’re probably qualified to do this if you've been a developer for a few years.

With this information, I'm going to follow the plan I already had, but with more confidence and focus since I feel more like I'm on the right track. I'm going to launch a few nice side projects with moderate levels of complexity to solidify my skills and figure out how long things take (important for estimates), and then I'll try getting clients using those projects to showcase what I'm capable of doing.

Thanks again everyone!

The question is what you want to be doing in 5 years or so. You should start taking steps towards that goal. If you want to be freelancer, then you should start taking steps towards that goal. Your first goal might be to get a regular job to save enough money for 6 months of living expenses. Or maybe you don't need to save any money then start now.

As for technical skills, let me tell you a story of my friend. He was an average or below average programmer in university. We all got jobs in brand name companies; he could not get even an interview. Honestly, he was really bad programmer, I don't fault companies.

He expanded his job search from big companies, to smaller companies, to finally anyone posting a gig on Craig's List. He wanted to get hired by a guy who was setting up his band's blog. He had no idea what he was doing.

Eventually, he did a few fixed price contract work for setting up blogs. Then he got a contract to build Facebook for $500. He thought he could do that in a month. As deadline approached, he asked one of his unemployed friend to help him with it, who was also a bad programmer. They still thought they can deliver it within a few weeks. Of course, they never finished and not sure if they even got paid anything for it.

But they kept on bidding projects, taking on too much work to handle. They asked their friends including me if we wanted some side work. Of course, we said no when we saw type of work and money involved.

Eventually, they started a company to look professional. They hired part-time programmers. They even started an internship program with a local university.

Now 7 years later, they have 20 people working for them. They still like to code and they know they are bad programmers. They tell me that their programmers hate it when they get involved in a project. They are supposedly still working on Facebook clone website.

Now to be honest, they did had several advantages over many people in the US. They lived with their parents, so had no living expenses. Their education was paid for by their parents, so they graduated with no debts. So their success might not be easy to copy if you have bills to pay.

Also pretty sure all these perks came with daily nagging by their parents though.

I started contracting after about 3 years of perm work. And have been contracting since then. So you are probably ready.

Contracting is mostly about delivering business value. Solving business problems is what you get hired as a contractor for, tech is usually not that important as most companies that hire contractors don't have a good understanding of tech anyways. So they'll be happy to let you recommend the technical solution that solves their business problem.

You're ready right now. If you keep waiting for the right time to come or the perfect conditions to fall into place you'll quite likely never start but keep asking yourself that question.

So, start by talking to potential clients and try selling your services. At the very least this will provide you with invaluable information as to which skills you might need to improve or acquire.

I'd say when you've saved up, say, 6 months of living costs.

If you can fog a mirror, you're ready.

When you land a contract.