How can I make a living as a freelance software developer/musician?

You'll want one freelance contract because otherwise you won't have the time to manage the business. It will need to pay something like $100 per hour to be equivalent to your current job, maybe a little less, and you'll need to bill nearly all of those 20 hours. And then there's the non-remote chance you'll become a really successful self-employer and be but by the entrepreneur bug like everyone else. You might wake up 20 years later and realize you've mostly abandoned your music, the opposite of what you wanted. Again, it's a vote for a contract that's as job-like as possible. As a freelancer who used to be able to play the organ in church and no longer has enough time to practice, I warn you to be careful about what you're signing yourself up for.

Can you talk to your company about going part time as a developer? If you could live on that, it seems to me that it would be more secure, and possibly actually take up less time than freelancing. The people I know who freelance in their professions end up spending more time on marketing and networking and so on, and less time actually doing the job they like to do, so I'm not sure that freelancing would solve your time problem the way you think it would.

Can you take this thought: "I would like to leave the office behind and become a freelance developer so I can spend more time on music." And reduce it to this thought? "I would like to spend less time doing non-musical work so I can spend more time on music." If you can, a freelance life is not necessarily what you want. Freelancing in any field is very time-consuming, especially at first, and will always involve a fair amount of overhead beyond the actual billable hours. So if freelancing itself isn't extremely attractive to you, the stable, overhead-free, W2-paid, health-insured work hours you have would be quite valuable to hold on to if you can. I'd ask your job about any possibility for flexible arrangements (working half-time, working fulltime but taking frequent unpaid sabbaticals, etc.). Make it clear you would love to keep being part of the company and contributing there, but you simply don't want to work fulltime anymore. If they can't be flexible, there are definitely part-time telecommuting W2 jobs in dev and QA fields out there.

A former coworker has written some thoughtful posts about his work as a freelance software developer, covering his challenges and how he's made the job work for him: http://mrooney.github.com/blog/2012/07/01/freelancing-a-6-month-retrospective/, http://mikerooney.rowk.com/2013/01/28/a-year-of-freelancing/, and http://mikerooney.rowk.com/2013/03/26/freelance-income-sources-and-the-8020-rule/. (http://mikerooney.rowk.com/2013/02/01/the-startup-double-standard/ for quitting his old full-time job: "When I asked if I could do work on the side for another company, it was rejected. I then asked if I could work part-time so that I could diversify my time between work and personal growth in other ways. The response was that that would be tantamount to quitting, so I had to choose.") To help with your estimates: when I was looking for individual health insurance, I used the automated estimated quote feature of various insurance provider websites, such as https://www.anthem.com/ca/health-insurance/plans-and-benefits/pb-overview. And "The http://en.wikipedia.org/wiki/Self-employment#Self-employment_in_the_United_States in the United States is typically set at 15.30%".

I'm going to add a few more things: * Contract work through an agency that hires out developers will probably pay more per hour than what you make now, but less than you would as a freelancer with your own business. The flip side of that is, if you start your own software business, chances are, you'll be spending around 60-80 hours a week on both your work and drumming up new business. (And you will get stiffed a lot your first few years due to inexperience.) There's truth in this freelancer joke: "I felt like I deserved to work just a half-day today. Yup, only 12 hours! (I'll make up for it over the weekend.)" * Musicians usually earn crap. $100 for up to a 3-hour service is a good rate here in Florida. In my personal experience, gigs fueled my discretionary income. My web work is what actually paid the bills. * This is a combo of careers in which you will be working. All. The. Time. (I'm counting practicing as work.) This is ideal for me because I hate being bored. If puttering around with nothing to do sounds like a fun thing for you, do NOT freelance 100% in both of these careers.

More advice from another thoughtful acquaintance who writes from experience (he's an interaction designer instead of a software developer but the business parts are similar): http://beingagrownup.org/post/46781659642/i-know-a-lot-of-the-contributors-to-this-blog-do (notes on networking, setting boundaries, billing, coworking, etc). He's written in more detail about his work on his blog: http://blog.nickd.org/2013/02/20/sell.html, http://blog.nickd.org/2013/02/10/billing.html, http://blog.nickd.org/2012/11/05/legal.html. Hopefully all these links help you get a sense of the practicalities of freelancing.

Hmm... Great points guys. I am not so sure that my company would go for that, but it's worth a shot I suppose. Do half-time software development jobs exist?

I did this! I quit my job last year so I could take a break from work and focus more on music, but I had the luxury of my job asking if I could still contract for them. So now I steadily do contract work for them and with an updated LinkedIn profile and some contacts within the industry I get requests for freelance work all the time. There are weeks in which I don't work, and then there are weeks I do somewhat of a 9-5, but it's flexible. If you build up a little nest egg, it's totally worth to try to invest in a freelancing lifestyle even if for a little bit. It is REALLY nice to have days off in which I can practice, take day gigs, or even show up to gigs early for set up and sound check which I used to previously not able to because of work. So, step #1 in my opinion is to ask if your current job allows you to contract for them. If not, I would try to look for contracting gigs. Search around job sites, tech meetups, mailing lists, etc just to see if there's anything suitable. About health insurance -- shop around for individual plans. It's easy if you are in perfect health, just apply. I would say high deductible plans for a single person can range from $150~300 a month, and don't forget potential out of pocket costs for any checkups, prescriptions if not covered by a plan. Also you may be on the hook for your own dental/vision costs. Taxes - every time I get a check from a company I try to sock away 25% in a different bank account to account for tax. Also I would look into hiring an accountant for tax filing to get the best deductions. You can deduct a lot more from music stuff too! Also I believe you may have to file more than once a year, you should ask an accountant about those rules about freelancing taxes. You probably have to spend some time to work on the business logistics of being freelancer at first, but the eventual benefits really pay off if you want more time for music. Oh also, half-time software development jobs do exist. Obviously not as common as full time jobs and you really have to work to find them. One of my freelancer friends got into a nice situation in which she only works 20 hours at most for a startup doing web development. A few places in which I've worked at had half timers doing development. It's not that common, but it's not impossible either.

If you're good and find the right clients this can work, but it may be tricky. It's harder to be a part-time freelancer because, most of the time, people want things done as quickly as possible. Often that's why they're bringing in a freelancer, to cope with excess work or when they suddenly realise something is beyond the abilities of in-house staff. So ideally you'd need a retainer-type situation, where a couple of clients need ongoing updates/maintenance and buy regular chunks of your time. Also, freelancing needs to suit your personality. People who are comfortable in a rigid corporate environment, or are just money-motivated, often tend to be miserable/stressed as freelancers (and vice versa, of course). I make less self-employed than I could in a job, but do it because I prefer the lifestyle, variety and freedom. Currently I have nothing confirmed beyond next week and am absolutely fine with that uncertainty. And leaping into freelancing when your motivation is something other than the freelance work.. well, that won't make things any easier when it's 2am and you've still got a tricky bit of code to finish by the morning. As your day job pays well, the safest option would be to cut down your living expenses, save more for a year or two, then try to reduce your hours or use the savings as a buffer to pursue any promising freelancing opportunities (e.g. you hear of a client with a maintenance contract up for grabs).