I started contracting when I was 19 and have never looked back. The only jobs I worked were from age 12 to 19.

I outlined how I did it a little in a post yesterday:

https://news.ycombinator.com/item?id=5805627

This is two brain dumps in two days, maybe I should be putting this on a blog, apologies if that's more appropriate. Apologies for typos or grammar, I'm writing this in one pass before heading out.

To dig into the comment about finding your first customers.....

My formula, which I recommend you consider trying some or all of (and has worked for friends making the jump):

- Keep your job. You are not here to learn developer skills, but business skills. You will build up your part time income to take over what you make full time. Too much work? It's probably a fair comparison to how much work getting and fulfilling contracts will be until you get the hang of it so dive in. Just be prepared to work more to have the flexibility to do what you want. There are some incredibly insightful tips in this thread overall, especially the few at the top.

- Business skills are something you will be learning forever, like coding.

- The first business skill you need to learn is value. Then, creating it, in a reasonably sustainable way that you can then start to rely on.

- The second business skill you must do is come to some sort of working peace with money if you have any issues with making it or issues with what your professional value is. I regularly bully/coach friends into business for themselves and can be available to give you a few words of advice. For me, it's becoming like credits in a video game to do other thing I want on top of interesting and meaningful work. I do some tougher work that pays better, so I can spend time with a startup or idea I like at a discounted rate, or put in more time than normal where you like.

- My currency is respect and customers who know it get way more from me without me being able to help myself. The ones who don't seem to filter themselves out. This may or may not be for you but whatever it is for you, the sooner you can get a sense of what it is, and develop it forever, the easier you'll have a compass to know if something is right or not.

- You're welcome to dive in to beat the statistics, but you will stand a better chance if you start freelancing and slowly building it up by finding long term customers.

- SMB's want one guy to shoot. They don't care that it's the server's fault, the isp's fault, a bug in the code, or a bug in the platform or framework. They want the one interface who is like a department or interface to them to get that wing of their business sorted out. They'll be ok if you find someone and manage them for cost + 10% if they don't want it.

- The more they think of you when they have problems that need solving, the more you'll end up having long term customers for 4-10 years like I have. I don't say yes to all the work, sometimes I help them hire, sometimes I help them find a vendor, sometimes I hire the vendor for them and train them, sometimes I sub them out under myself, it totally depends on the situation, my availability and interest, but bottom line is I'm paid well for my time to figure it out for them and monthly retainers become that much more valuable to them

- Many small to medium businesses may not have a full time position, but have enough to afford $500-$1500 a month. Either this work needs to be right up you alley, or trivial for you to do and deliver effectively and consistently. It might be a technical retainer, or a certain amount of bug fixes, or features, etc.

- Don't have an ego. I started doing networking, IT support, fixing printers, and then once I did the six month "network stabilization" the customer naturally turned to software support. I wasn't above doing anything. If the computer needed to be cleaned out from dust, I did it. That attention to detail is what one day had me doing the replenishment orders for a billion dollar retail company on a weekly basis by analyzing what they sold in the past week and what they should try the next week as an experiment.

- I'm a full stack guy though and it helped me a lot get in the door to fix something trivial or figure out something finicky and after I did that, the relationship was great. Being that person that came in and took care of a small thing that was important is a great way to get in, most of my referrals came this way too because business owners like showing off their people to other business owner buddies. I recommend you be as full stack as your honest interest allows. Along the way you will find the things that you love more than others, and I lump them into necessary evil (complex hosting hosting the projects I build) vs what I love (building the software that never goes down)

- It is far more preferable to find 10 customers who will pay you $1000 a month (that's 100 hours billable at $100/hr) than to look for all of it in one place. If one dies, changes, or disappears, you won't sink. Chances are you might find 4-5 customers that pay $2000.

- Deliver monthly summary reports of the value you provided. Number of requests, what you solved, what you looked into on your own initiative, savings you helped create or increase, money you helped them make, etc. Attach it to the invoice every time. It's the only permanent record you'll have when you look back in 4-7 years.

- One thing that didn't exist as much 10 years ago was remote development and remote access. PCAnywhere was the king and it helped me learn how lay down a remote developer life with visits in person as needed. What I did was to offer not to bill customers for travel time, or a minimum on-site bill and instead charge them by the quarter or half hour if they'd let me work with them via screenshare (if it was necessary). It's a fair trade with the right customer. Be open to learning how well screensharing as needed can work for you.

- As you're starting out, reach out to small and medium size businesses like yourself. They like the one on one, "I'm dealing with someone like me" approach. They should not balk at expecting to pay $500 to $1500 a month for something they need, or to have you on call.

If you want help crafting such a pitch, I can help you. I have helped friends learn to win small contracts on CL, etc, and work their way up. I believe that there's some level of business skills you learn here that here that are hard to learn anywhere else. Once you know you can make a relationship and deliver value, possibilities can open up.

Hope some of this was useful or at least interesting, if anyone has any questions, feel free to get in touch.