Remote Programming Jobs: How to Find Them and Why You Should

I’m going to take a break from my aggressive war on status quo wage programming jobs today.  Instead, I’ll offer something a little more how-to-y and a little more upbeat.  And I won’t once try to talk you out of salaried employment.  Instead, I’ll try to talk you into it.  Or, at least into a kind of it.  Let’s talk remote programming jobs.

Some, But Not Too Many, Words of Caution

I am, personally, an introvert.  So I always find the cautionary tales around remote work to be pretty overblown.  They go something like this.

Remote work seems like it’d be great.  And, for the first few weeks, it is!  But then you start to get lonely and stir crazy.  Before you know it, you’re heading down to Starbucks for a human connection just content to have some teenagers giggle at you.  And the weight gain?  You’re working right by your fridge!  And not to mention… [blah, blah, blah]

And it devolves from there.  I always read these posts and think of the song, Space Oddity.  You’d think these people were loading themselves into a tiny capsule and blasting off for the Kuiper Belt alone, never to see another human.

Look, if you’re really a group-oriented person, an extrovert, or someone who strongly prefers collaborative work, you may struggle working from home.  But then, if you’re that sort of person, you’re probably not reading this post.

If, on the other hand, you like working alone, don’t let these obligatory cautionary tales scare you.  I’ve been working mostly remotely for years and totally remotely, non-stop for 8 months, mostly in a very small town.  And I’ve never yet felt the need to hug a random barista to slake a bone-deep loneliness.

You still have friends, right?  Family?  A phone?  You’ll be fine.

Things to Guard Against

Okay, so we’ve established that you probably won’t morph into a much needier person than you’ve ever been.  But there some things around which you need to take care.

Bear in mind that these are not deal breakers, nor are they insurmountable.  They’re just things that you need to manage, especially at first, until you settle into a rhythm.

• If you’re not used to imposing structure and discipline on yourself in terms of time management, you might need to learn this.  Maintain a schedule, set a todo list, and that sort of thing.
• On the flip side, some people in remote situations go too far the other way and start to work all the time.  Set boundaries.
• Depending on your work situation, you might need to get used to showcasing your contributions.  This holds doubly true if you’re in the minority as a remote worker.  Find a way to keep your boss posted on what you’re doing and your teammates engaged.
• Remote doesn’t necessarily (or even ideally) mean that you never have facetime.  Expect to travel for meatspace interactions from time to time.

After a few weeks, you’ll settle in and find what makes sense for you, perhaps tweaking from time to time.  Just make sure to keep an eye out over the duration of your tenure as a remote worker for things that you can do to improve your productivity and interactions.

Why Remote Programming Jobs?

Alright, now that we’ve gotten the cautionary stuff out of the way, let’s move on to why you would want this.  I’ll cite my own experience, in list format, talking about the benefits.

• Not commuting gives you back up to 2 hours per day.
• You can work remotely from anywhere.  This year, I’ve worked from a lake in the woods, big cities, and now that it’s gotten cold up north, a house right next to the Gulf of Mexico.  You can vagabond or visit family.
• Assuming you’re not a big time group collaborator, you’ll get work done much more productively without regular interruptions and distractions.
• Wearing whatever is comfortable is a nice lifestyle perk.
• Programming and similar knowledge work pursuits are deep work, which means some isolation lets you immerse yourself more in them.
• You have a much more flexible schedule to accommodate family life or various schedule restrictions you might have.

I’ve talked about cautions, but I can’t overstate how great a lifestyle this is, provided you’re comfortable with limited professional face time.  Your life takes on a sort of freedom and autonomy that’s hard to replicate when you spend your days in an office.

But I won’t sell any further.  Let’s look at how to get yourself into a remote situation.

Convert Your Current Job into a Part Time Remote One

I bet you thought I’d start with something else.  Maybe just plunge you right into the job search with some boutique remote work consulting agency?  Nah.

In a lot of ways, the easiest path to remote work is through your current, non-remote job.  That might sound a little far-fetched, particularly in relatively bureaucratic or rule-heavy environments.  But it’s really not.

Of course, you don’t go for the remote working kill shot all in one swoop.  You ease into this.  Start by asking your manager to work from home on irregular occasions.  Your child is sick today.  Someone’s comping to repair the water heater.  You get the idea.  This does a couple of things:

1. It gets you the infrastructure to work remotely (e.g. VPN software on your laptop, remote-enabled access, etc.)
2. It sets a precedent for this work taking place more often than never.

And that precedent matters.  Because after you work from home from time to time and it goes well, you’re going to use that to lobby for a day per week or every other week.  And the way you’re going to do that is by making sure your one-off days have always gone smoothly and by bringing forth an epiphany.

You know, boss, the few times I’ve worked at home lately have really let me clear the decks on feature implementation without distractions.  I think if I could do that once every other week or once a week, I could really improve my productivity.  Shall we run an experiment for a month or two?

Citing precedent and making the arrangement breezily non-permanent will make a yes decently likely.  You can use these strategies to gradually lobby for more time later, if this goes well.

Convert Your Part Time Remote Gig into a Mostly or Full Time Remote

This next strategy you can take advantage of whether or not you’ve done the part time remote thing I just described.  But you’re more likely to have success if you’ve gotten a day or two remote per week.

You could always try gradually nudging your way from full time onsite to full time remote, but at some point your boss is going to detect your game.  It might be when you ask for that second day each week, the third, or the fourth.  But sooner or later that will trigger a reckoning.

I wouldn’t go that route, though.  Instead, when you want to make this leap, do so prepared to potentially walk away from the job.  Talk to your boss and explain that you’re thinking of moving out of state.  Or that you need to spend time at home.  Or something that has you out of the office permanently.  I’d suggest not putting a specific timetable on it and not saying that you have a new job lined up (or lining one up).  Just say that you’re going to need to make a decision.

In my experience as a salaried employee, a salaried manager/executive, and a consultant, this often works on a permanent or semi-permanent basis, if you’re a valued team member.  The company will work out a remote arrangement for you.

But it’s always possible they shrug and say they just can’t swing it.  That’s when you start looking externally for remote programming jobs.

Look Specifically for Remote Programming Jobs

Okay, let’s start with the obvious.  I won’t spend too much time on this because you’re a smart person and you can figure out how to Google around and look for remote jobs.  So I’ll just list a few places that I’m aware of, off the top of my head.

• Stack Overflow has a section specifically dedicated to remote jobs.
• There’s a site called “we work remotely” and you can probably guess what they offer.
• There’s another site called flexjobs, but I think it’s neither specific to programmers nor to full time jobs.
• I think that with more standard job searches, you can also filter telecommuting gigs.

You also get a lot more flexibility if you want to work as a free agent or in other non-salaried arrangements.  But the stars of today’s show are remote programming jobs so I won’t go into that.

So besides just kind of combing the internet for want ads, what else can you do?  Here are some more tips.

Flex Your Network Muscle, But Not in a Desperate Way

Put it out there that you’re looking for a remote gig.  Mention it in social media, during in person chats, and anywhere else you feel it’s appropriate.

But I wouldn’t approach this with the sort of typical half-begging announcements of “full stack blah-blah-blah, I’m making this sound impressive, but please, God, somebody have mercy and give me a job.”  You don’t want to approach it with the premise of you getting a job.  Instead, float a message that’s something like this.

I’m interested in potentially transitioning to remote programming work, and I’d be interested to hear from people who have this experience and what they think of that.

You know what people don’t like?  They don’t like you begging them for jobs.  You know what they do like?  Talking about their experiences and helping you when you don’t seem desperate.

Network this way and get a lot more leads.

Give Preference to Remote First Companies

A blogger named Zach Holman once talked about the difference between remote first and remote friendly.  I won’t rehash it here except to say that there’s a difference, and it matters.

Remote-friendly companies are ones that mainly collocate but will let the occasional satellite person work from home.  Remote first companies are ones that started as remote companies from the get-go and operate with the assumption that you can never count on presence.  They develop remote-specific collaboration mechanisms rather than try to simulate physical presence for remote workers.

Examples, that I’m familiar with, include Github, Particular Software, Basecamp, and our nascent content agency, Hit Subscribe.

Beware of Traditional Agile Companies and Companies Undergoing an Agile Transformation

There was a company that I might have mentioned in the last section.  At least, up until recently.  That company would have been IBM, long known as a pioneer of remote work.

But recently, I read this article in the Atlantic, examining situations where companies were moving away from remote work.  They profiled IBM in the article, and if you look for it in the article, you’ll see all the telltales of an agile transformation.  You’ve got a guy training others in agile, people coming to sit in open office plans and getting really excited about “using the space.”

In what I’ll call “traditional” agile environments (fairly rigid adherence to a core, personal-collaboration-heavy set of principles) everybody collocating is either strongly preferred or non-negotiable.  That applies if a company has this as part of its culture or if, like IBM, they are moving in that direction.

Once you understand the correlation, it’s kind of a no-brainer.  If you want to be a remote worker, then you steer clear of companies that frown upon remote work.  Just understand that this often includes a certain flavor of companies practicing agile methodologies.

Beware of Companies in Flux

I could give you a second reason to beware of IBM.  It’s the same reason you would have wanted to be wary of Yahoo before Marissa Mayer called all of its remote workers back to home base.  Those were both companies in flux (due to poor performance).

If you find a company with sagging numbers, a company about to be acquired, or a company that’s just in a transitional state, you probably want to steer clear.  At the risk of sounding callous, leadership, in those situations, often just starts mashing the proverbial control panel with its fist, hoping that something snaps it out of the tail spin.

Often that mashing means just doing the opposite of what had previously happened.  “Welp, we suck and we have all of these remote workers — let’s make ’em all come into the office!”

Moral of the story?  If you’re looking to a company for its remote-friendly policy, make sure it seems stable and is on a good trajectory.

Be Open to Travel

There’s another way to maximize your options, and it’s to be flexible on travel.  There are certainly some purely remote jobs out there (or ones that require travel to the mother ship only a few times per year).  But there are also some gigs that ask for a week or two onsite per month, with the rest remote.

If you can deal with that arrangement, it’s a nice way to get a foot in the door, so to speak.  And gigs like that tend to lend themselves to more future flexibility than others.  They also give you experience as a remote worker, which can make it easier to interview for other remote jobs in the future.

Stick to Your Guns And You’ll Find a Remote Gig Eventually

I’ll close by suggesting that you be persistent.  As I’ve described earlier, the remote life is pretty sweet for a lot of folks.  This makes competitions for remote work fairly stiff.

So view the search for a remote gig as more of a marathon than a sprint.  You might not find such a gig in your immediate search, and you may even wind up taking another meat space job after your current job.  But keep looking, interview when they come along, and stay optimistic.

Sooner or later you’ll get that remote programming job.  And don’t buy into the hand-wringing — you’ll like it when you do.