The Perils of Remote Work

A good friend of mine asked me to write this post. Actually... to be more accurate, he asked me to write something about the hesitance of corporations to support remote work - and why they're being so shortsighted when they throw up roadblocks to the remote workforce. I fear that I'm not gonna write quite the article he was hoping for.

To be clear, I've worked remotely during several periods of my life. Right now, I'm a fulltime, fully-remote employee. And I absolutely love it. I hope to never be working in an office again. I scoff at many of the artificial barriers that keep coders chained to physical desks.

So why was I tepid about writing this article?? Well... as much as I love remote work, and as much as I truly believe that far more jobs should offer remote options, I don't quite see it as the panacea that some of my colleagues claim it to be.

Working remotely is friggin awesome! But it's awesome for me. And it's awesome for my current employer. But I'd be the first to tell you that it's definitely not "friggin awesome" for every employee - nor for every employer. Let me explain...

The Mirage

Whether you've worked remotely or not, almost all devs have thought, at one point or another:

I'm staring at this screen all day. I could be doing this just as well while sitting in my employer's cubicle, or while sitting in my house in my boxer shorts, or while sitting on a beach in the Cayman Islands.

And I'd be the first to tell you that you're not wrong. But you're not entirely right, either. To be clearer, you're not accurately representing all of the variables in the equation. Where you're physically sitting, while you code, is usually a very small factor in your productivity. Far more important is:

1. Where are your coworkers located?
2. How are you communicating with your coworkers?
3. What type of communicator are you?
4. How is your employer accustomed to managing remote workers?
5. Be honest with yourself - be really friggin honest: Just how well do you work by yourself??

These questions are not trivial. They can make-or-break your remote gig. None of these questions are meant to derail your desire for remote work. But I want you to think - very carefully - about these things before you dive blindly into a remote gig.

I've been on the wrong end of these questions - and I've paid for it by having several remote gigs that were... awful.

Everyone Else's Location

Although I can't fault anyone who's angling for remote work, you need to think, very carefully, about whether you truly want to be remote - if everyone else in your company is onsite. There are times, usually based on someone's personal history, when someone can leverage an otherwise-onsite gig into a remote position. And that's... great?

But if everyone else in your company is onsite, you need to think very carefully about whether it's a good idea to go remote. As much as I now adore remote work, I've come to the conclusion that, if everyone else in the company is onsite, you need to be extremely cautious about whether you go remote.

Too often, we assume the only "obstacle" to remote work is our employer's permission. But even if your employer wholeheartedly approves your remote status, it can still lead to massive problems if the company, in general, is an "onsite" company, and if the rest of your team members are all onsite.

A classic warning sign, in this regard, is when you find that meetings are being held without you - meetings of which you were never aware. I've been in the room when a remote employee says (via speakerphone), "When was this discussed??" And the manager, without missing a beat, says, "Ohhh... We weren't sure how to reach you yesterday afternoon, but we had an impromptu conversation about it here in the office."

In fact, I've witnessed this so many times in my career, that I've now formulated one simple rule about remote work:

If professional/corporate advancement is your goal, you should never work a remote job when most/all of the rest of your team is onsite.

I don't really like typing that. It doesn't feel "fair" to me. But it's true. If you're working for a company where everyone else is onsite, you need to be extremely careful about whether you accept/pursue remote opportunities with them. And if you still want to fill a remote role - with a primarily onsite company - you need to be prepared for the real possibility that, at some point, you will essentially be left behind.

I've also found that remote work is a near-impossibility if I accept a position with a company in my home town. Even if I interviewed with the explicit stipulation that I'm to work remotely, that stipulation tends to fly out the window if the employer knows that I live right there, in town.

If you live in, say, Chicago, and you deeply desire to work remotely, then for cripe's sake, don't accept a so-called "remote" position with any company with offices in Chicago. I know there are exceptions to this. But those exceptions are... exceptional.

Too many times, I've found that someone talks all high-and-mighty about "remote work" while I'm interviewing. Then, when I'm hired, they assume that I can absolutely slide into the office on a darn-near-daily basis if they know that I live in town.

When you're physically remote, no one assumes that they can schedule an in-person meeting with you. But when everyone knows that you live right here, in the same town, well... they tend to assume that they can also schedule you for onsite meetings.

Digital Communication Is Communication

Does your employer have a Slack channel? (Or a similar chat application?) Does your company work "well" over email? Are your coworkers comfortable jumping on Zoom? (Or a similar video conferencing medium?)

These are not throwaway questions. Even in our modern age, I find that there are some companies that rely heavily on digital communication. And others that always seem to fall back on real-time, in-the-flesh, face-to-face.

What does this have to do with you??

Well, if your company still relies on that back-slapping, in-yer-face kinda camaraderie, then you need to think very carefully about whether you really wanna be the "remote person" on the team.

Set your judgments and emotions aside for a moment. I'm not asking whether they should be so dependent on in-the-flesh communications. I'm asking you whether they are dependent upon them. Because, if they are, then it won't matter where you think they should be. All that will matter (for your career), is where they are, right now, as a company. And if they're stuck in that "old boy" mentality, you could be shooting yourself in the foot by going remote.

You may be thinking, "Oh, mannn... I hate Slack." And I'd agree with you!!! And you may be thinking, "Oh, mannn... I hate Zoom." And I'd agree with you!!! But if you're working remotely, there needs to be some kinda way to "connect" with your coworkers. And if you're working remotely, and your company isn't comfortable with any kinda chat/video solution, there's a great chance that you'll find yourself becoming increasingly marginalized as time goes on.

Remote Work Is NOT For Introverts

I'm gonna say this again. Cuz I fear that some of you may have blown a mental gasket with that last headline:

Remote work is NOT for introverts!!!

On the surface, remote work probably sounds like the ultimate solution for the ultimate introvert. Right?? But I'm here to tell you - that is not the case. In fact, I believe strongly that introverts have possibly the hardest time dealing with remote work.

Remote work is a lotta things - but "introverted" isn't one of them. When employees are remote, they need to behave in distinctly extroverted ways to foster the proper function for themselves and all around them.

Think about this: If you're alone, on a mountainside, with absolutely no physical interaction with the "outside world", how do you ensure a meaningful, ongoing collaboration with your team members??

The answer is: through copious communication. Probably a lot more communication than you'd need if you were in the same physical space as your colleagues.

Let me put this another way: How do you maintain a healthy, loving, long-distance relationship? Is it by clamming up and limiting your communication? Or is it by going out of your way to communicate even more than you would if you were in the same physical space??

I'm raising my hand here. When I'm "nose-down" on code, I'd really appreciate it if I didn't have to talk with anyone. Just leave me the-eff alone. But that leads to massive, near-immediate problems when you're working remotely.

Remote work doesn't cater to the introvert. IMHO, effective remote work punishes the introvert. I truly believe that many introverts thrive in an onsite environment, where they can be physically present (and thus, available for the occasional "drive by"), but they can hole away in their cubicles.

When introverts work remotely, they tend to avoid status updates. They tend to shun chat and conference calls. And this leads their managers to wonder... just what in the heck they're doing?? And if you really wanna set introverts off, give them a long interrogation about what they've been up to.

Culture Counts

Whether you're considering a brand new company, or whether you're angling for a new role with your 20-year employer, I want you to think - deeply - about the particular culture that you're in.

Specifically, there are just some companies with an outright hostile viewpoint toward remote workers. They assume that remote workers are lazy, or trying to "get one over" on the company. There are some - nay... many - companies that simply will not view remote workers in a fair light.

Of course, there are some companies that understand remote workers. Some even embrace them. But as much as I adore remote work, I'd be the first to tell you that remote work only makes sense if you're with a company that has a nurturing culture.

This is particularly difficult for some people to accept. They get this "dream" in their head that they want to work remotely. And then, after sufficiently bullying their management chain, they get "approval" to work remotely. But after weeks or months, they're shocked to find that the arrangement has not turned out to their favor...

You see, even though I routinely advocate for remote work, I'd be the first to tell you that you can't force an onsite-centric employer to suddenly embrace remote work. It really is a culture thing. As recently as a few months ago, I've met CEOs of companies who openly professed to hating remote work. And you know what??? I'm inclined to believe them! If your employer isn't on that "remote train", it might be a waste of time to try to drag them onto it.

Know Thyself

This is the biggest part of remote work. I can't possibly emphasize it enough. Remote work is incredible... but only if you can be honest with your employer (and yourself).

There can be this overriding peer pressure to declare yourself in favor of remote work. And remote work is awesome - for those who are suited for it. But not everyone is suited for it. And that's... OK.

Some people have natural distractions at home: kids, spouse, poor work-from-home environment, etc. And there's nothing wrong with that - as long as you can be honest about it.

Some people really need that structure that comes with a "formal" office environment. And there's nothing wrong with that - as long as you can be honest about it.

Some people just have too many distractions in their home environment. And there's nothing wrong with that - as long as you can be honest about it.

You see, despite what some people might espouse, the simple fact is that I don't promote "remote work for everyone". Because... I know that remote work is not for everyone.

If remote work is for you, and your employer just doesn't understand, then I sincerely recommend that you put yourself in the market for a new employer. But it's silly to assume that remote work would be better for every one all the time. If you care about your career, you should think - very carefully - about the pros and cons.