From cubicle to rustic cabin, the slow and steady way.

April 20, 2015 2:26 PM

I'm a junior Java/Oracle programmer. Five years from now, I'd like to be skilled and savvy enough to be able to move to a rural town and work mostly remotely as an independent contractor. What should I be learning and doing now to begin work toward this?

I hate it when people say "Oh, what a great field you work in - you can just become a contractor and work from home!" As if it were the easiest thing in the world and I was tuned in enough to automatically know what's in demand, magically learn it and know how to market myself for it. My current job is far from the cutting edge - it's a boring corporate gig and we build reliable business applications. Thus, I have no idea where to start. But I have schooling. I have (a small amount of) experience. And I have time.

Can you help me come up with a long-term plan? What should I learn? What contracting services would I offer? For which (type of) organization? As it stands right now, I can do database programming, java web apps and I have a tiny bit of experience with android and iOS apps. Thanks.

posted by kitcat to Work & Money (5 answers total)

The Hacker News forum has a monthly "Who's Hiring?" thread where the posting guidelines say to include whether they accept remote work. You can try applying to some of them now (why wait 5 years?)!

Here's this month's. Here's the submission history of that account, to see past ones, as well as related "freelancer" posts.
posted by losvedir at 4:14 PM on April 20, 2015

I don't have anything specific as far as what to learn, but java/oracle isn't the worst choice - there is plenty of work to be had there. These are none academic suggestions though:

1. Network, network, network. If you work in a corporate gig, there are likely contractors there, somewhere. Get to know them. Ask which recruiters/companies they go through.

2. If #1 isn't feasible due to the culture at your job, consider a different job.. and consider a different job anyway, just to meet and network with even more people.

3. Remember that not all work-from-home programming jobs are contract jobs. I work for a large bank and, though I live about a 15min drive away from the office, they have no problems with me working from home. I only go into the office about twice a year.

4. Do your research. Some companies are all about work-life balance and allowing things like flex time and work-from-home arrangements. Some are not. Some that aren't will nevertheless try to pretend they are. If you are diligent about networking, you can ask your these resources which companies are and aren't truthful about these things.

Good luck.
posted by mbatch at 4:15 PM on April 20, 2015 [2 favorites]

We Work Remotely is my go-to for remote work jobs, though as mbatch mentioned, many aren't contracts. I'm not sure if you're set on contracting, or if it's just the "work from anywhere" aspect you want. There are lots of companies that hire full time permanent employees to work remotely, if that's something you're open to.

Maybe it's just my limited perspective, but it seems to me that the companies that are more progressive with allowing remote work (whether it be contractors or employees) also tend to be using newer technologies. Think Node and Angular more than Java and Oracle. We Work Remotely is skewed toward Rails I'm sure at least partially because it was created by 37 Signals. But Java is ubiquitous in the larger marketplace, so it should be fine.
posted by primethyme at 5:28 PM on April 20, 2015 [2 favorites]

On the other side of your question, you will need to find a rural area that has high-speed internet available, which can be harder than you think.

Also I have some friends who do this in Illinois, and it helps to live on the Amtrak lines, because every now and then the company wants you in Chicago to meet physical people. It's not too far to drive or anything, it's just easier if you can hop a train.
posted by Eyebrows McGee at 6:11 PM on April 20, 2015 [1 favorite]

Don't wait 5 years. Just start hassling recruiters, HR people at companies you have connections at, your entire network, and bosses at your current company for permission to work as a contractor from home. 99% of the time it won't work out and you'll get shot down. But you'll learn more from the failures than you would from asking strangers.....
posted by miyabo at 9:48 PM on April 20, 2015