The Realities of Remote Work in 2019

Have you ever seen the movie Up?

You know the dog that they find along the way that gets distracted by a squirrel every thirteen minutes?

I am that dog. And the squirrel? Well the squirrel is a metaphor for any and everything that makes the slightest bit of noise or catches the light at just the right angle. Right now, it’s the tarp being dragged across the roof of the coffee shop that I’m working in as it’s being repaired.

This is the simplest way to describe remote work from my perspective. Ask anyone who’s worked remotely for a while and they’d probably describe their daily life as something similar.

But if you’re new to the game, let’s start with the basics.

What is Remote Work?

Remote work (or “telecommuting” if you’re 80) is defined as “a situation in which an employee works mainly from home and communicates with the company by email and telephone.”

Simply put, it’s the ability to work anywhere where there’s an internet connection.

Technically though, working from home has been around much longer than email or telephone. In fact, pre-Industrial Revolution, pretty much every one worked out of their homes. Then someone fucked it up for everyone and built the first factory. Remote work as we know it, however, really kicked off in the 1990s, when the internet was introduced. Since then, it’s been steadily gaining momentum, with an estimated 43% of the US workforce having worked remotely at some point in their careers. And for the most part, workers have experienced nothing but positive effects from spending less time in-office:

  • Improved work-life balance

  • lower stress and boosted morale

  • Keeps older workers in the workforce longer

And their employers agree with them, reporting:

  • Decreased real estate costs and overhead

  • Increase worker productivity

So what’s the problem, Andy? Seems pretty great. You must just like to complain, you complainer. Well, dear reader, you can find thousands of articles online about how great remote work is, but very few will get down to the nitty-gritty, behind-the-scenes about the headaches that it can bring. That’s where I come in.


Reality #1: Squirrels galore

Remember those squirrels that I mentioned earlier? They’re in your phone, on your nightstand, in your fridge, under your bed, in your closet and even under your nails.

I’m talking about distractions — they’re everywhere. Sure, you can daydream at work, but eventually your boss is gonna come around and ask what the hell you’re up to. When you’re working at home, however, it’s easy to get into your head and...

Hey look, a squirrel!

Reality #2: Your time is yours

This is obviously not an inherently bad thing. It can, and should, be a fantastic thing. But I think it’s easy to underestimate the amount of discipline that it takes to wake up at a reasonable hour when you don’t have to be to work at a certain time. In theory, it’s totally doable to say, “I’m gonna watch two episodes of Arrested Development and then get straight to work.” In practice though, it’s a lot more difficult.

On the flip side of this, it’s also incredibly simple to overwork when there’s no one locking up the office at 5:30. There’s the risk of having too much free time on your hands, but there’s also the risk of working to the wee hours of the morning because you’ve finally gotten into your groove. Speaking of early mornings, don’t expect to sleep in every day because...

Reality #3: You’re always on-call

If you work a traditional 9-5, the odds are very slim that your boss would ever call you into work at 8pm on a Saturday. However, when you’re working from home, no time is off limits. Half of my team is located in India, so I’ve woken up to the panicky pop-pop-pop of Slack messages at 4am on several occasions. When you work remotely, you risk losing the luxury of free weekends.

For some, like myself, this may not be that big of a problem because you’ll often find that...

Reality #4: There’s no reason to leave the house

Think about it: if you didn’t have to go to work every day, how often would you really leave home? Once I went remote full-time, I quickly discovered that the answer (for me) was close to never.

The first few weeks were great, of course. Working without pants? Yes, please. UberEats for breakfast and lunch? You got it! My apartment at the time even had laundry in the complex, so I didn’t even need to go to the laundromat. Really, the only time I had to step out was when I ran out of toilet paper, and even that could’ve been avoided if I planned ahead of time (shoutout to Amazon Prime!). This was all so great...until it wasn’t.

You’ve heard of the calm before the storm? This felt like the storm after the calm. Once a refuge, my bed started to feel like a prison (I lived in a studio apartment at the time, so furniture was sparse). It’s a good thing that I didn’t need pants to work, because when I finally decided to put some on, most of them no longer fit. Since my only physical activity now consisted of me walking up and down the stairs to collect my UberEats twice a day, I managed to put on quite a bit of weight. Not only that, but my skin wasn’t too happy with my new eating habits either — the greasy selections that I’d been making had caused my face to break out quite a bit. My bank account wasn’t looking so great either.

To be blunt, I was disgusted with myself. And I fell back into depression fairly quickly.

Luckily, I was able to fight my way through it and develop better habits: cutting out takeout, walking to and from the grocery store a few times a week, making it a point to get dressed most days, even if I didn’t plan on going anywhere.

While I’m still not perfect, I’ve managed to keep most these habits in place. I now make it a point to work from a coffee shop at least 2 or 3 days a week so I don’t find myself in that same rut from 2 years ago.

Reality #5: What’s A social circle?

Oh man. I’ve probably got this one worse than most people because I’m already fairly anti-social. Whether you realize it or not, the people that you work with provide a lot of socialization in your day-to-day life. I may not have done much socializing outside of work, but in the office? I had friends. Y’know, work friends. We’d grab lunch, go to office parties together and throw friendly jabs at each other in staff meetings. Hell, we even had a group chat. Though it seemed very run of the mill — obligatory, even — at the time, I didn’t realize how much those little interactions with other people kept my spirits up during the day.

Now? Freddie Mercury is my best work friend. We spend the whooole day together. If I want any actual social interaction I have to go out and seek it intentionally.

I’m one of the lucky ones though — my partner also works from home, so I’m never really lonely. But this won’t be the case for most people.

Reality #6: I’ve got -$5 on it

I’m fortunate to have a full-time employer, so this one doesn’t apply directly to me, but I’ve heard it from a lot of freelancers: Money isn’t always consistent. There may be some months where you land $6,000 worth of gigs and other months where you’re lucky if you hit $900. Financial responsibility is important no matter what type of work you do, but it’s especially important when your next paycheck isn’t promised.


It goes without saying that, for the most part, the pros of remote work greatly outweigh the cons. I’ve worked remotely part-time since late 2016 and made the transition into full-time remote work in mid-2017. The number one pro that this transition has brought into my life is a complete 180 in the state of my mental health. It’s allowed me to see the world on my terms, which has always been priority #1 for me.

But, as with most things in life, it’s not all rainbows and lollipops. In short, working remotely requires a level of self-discipline that many traditional workers may not be used to. If you do decide to transition into working from home full-time, be prepared for the learning curve that is sure to come. In the words of Uncle Ben —

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Got any specific questions about working remotely? Let me know in the comments!