There Be Monsters in Working Remotely

cdvillard profile image Charles D. Villard Updated on ・4 min read

I'm lucky enough to have hit the one-year mark in June working as a web developer, and I couldn't be happier with it. It's come with some very nice fringe benefits; namely, the ability to work with a great team from the comfort of my home in Miami. I get pretty sweet weather, and the chance to work on my tan should I want to (still haven't).

This past year also gave me the chance to trip on many of the pitfalls that come with working remotely. You might be thinking I'm crazy for saying this, but working remotely, for all of its benefits, comes with its own set of baggage.

Don't get me wrong -- I subscribed to 37 Signals' manifesto well before I got my current gig. Working remotely was always the dream, before and after I ventured into web development. That being said, in my first remote job, I've come to learn that there be monsters in these depths.

Loose hours

You can't beat the flexibility of working remotely, right? You get to work from anywhere with an internet connection, and you can basically set your own hours. Well, typically, remote workers need to overlap at least half of their time with that of the main office, but you generally get to make it your own. Got kids in class? You can pick them up from school knowing you won't get wrung out for leaving your desk! Need to step outside for a bit? Cool! Out for lunch? That's fine - so long as someone knows you're away from the keyboard, you're good.

But when you start to feel like you could be using that flexibility for an extra-long lunch break? Watch out, because that extra 15 minutes can turn into an extra 45 minutes fast, and for any number of reasons. Remote work gives you some freedom, but you have to manage yourself. Keeping to a schedule seems easy enough, but it's not hard to get tripped up by something innocuous like traffic or other people.


With all the additional freedom can come additional sources of distraction. Being able to work from wherever you like is the other half of that flexibility, but it opens doors to other distractions. Working out of a cafe can be awesome, but you never know when a busker might come in and start playing 'Sweet Home, Alabama' on a rusty guitar. Even at home, the distractions can be plentiful. Especially so when you have kids.

If you can work from home and not mind any additional distractions, then kudos to you. Otherwise, make sure you find a place where you can enter a sort of 'flow-state' with minimal distractions. Some situations don't allow for it as easily, but try and get the consoles, comics, fidget cubes, or whatever might distract you away for at least eight hours. If you live with other folks, be it family or roomies, make sure to have an agreement that you won't be bothered as much. Obviously not one set in stone, but at least let them know that if you're working, you're working.

Also, don't forget about the biggest distraction of all, the one staring you right in the face right now. Your computer and the Internet, with all of its wisdom, has to be the biggest distraction of all! There are tools to help with this sort of thing, but they are only that. It's up to you to use them.


When you begin to work remotely, you might or might not notice a fine line between what's work and what's home. It can vary from person to person, but it's still an important realization to make. If you don't notice it, it can have an effect on your relationships with family and with work itself. One of the easiest pitfalls is to feel like you should keep pushing and giving it your all. It's a commendable sentiment, but it also defeats the purpose of working remotely: better work-life balance. Managing yourself also means managing when you're done, and when you can do that, you can make time for your personal goals and relationships.

This is probably the biggest 'gotcha' for me. Being at home with my wife and kid all day, I can end up working well past my personal work schedule before I realize what little time I have left in the day for them. Yeah, we get to have lunch together, but what's one hour compared to a whole afternoon or evening?

Now, I welcome you to take all of this with a grain of salt. Your situation and results working remotely will likely vary a bit from mine, but these are definitely things that can sneak up on you if you get too comfortable. I would recommend working remotely to anyone, but in the end, you have to be able to manage yourself well.

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Charles D. Villard


Web developer with a passion for front-end development and keeping the web accessible and available to all. His downtime is likely spent cooking, raising his kids, or reading up on development trends.


markdown guide

Do you ever miss having co-workers around?

Rarely. I work with computers because I don't like people.

(only half kidding)

Seriously, though: I miss having co-workers around because it's good to have people around you can bounce ideas off. You can usually get around this with email, Slack, Skype or whatever; but you've got to be careful that your office-based colleagues make themselves accessible this way. Scott Hanselman writes more about this imbalance (and other things) on his blog.

I've never been one for the "social" aspects of people in the office. I don't talk to people in the kitchen; I don't hang around the water cooler. I've got work to be getting on with, and I don't care what your kids are up to. If you want to shoot the breeze, we can do that outside the office over lunch, or after hours in the pub.

I should point out that this is the second time I've worked remotely. The first time I really struggled, mostly because of the lack of direction/idea-bouncing. This time I'm 14 years older (which might be a sign of emotional maturity, or just that I'm more senior and need less direction...), and I'm really enjoying it.

I can end up working well past my personal work schedule...

I find the flexibility in hours to be a double-edged sword: overall it balances out, but some days I feel like I've not done enough, and some days I'll do 12-13 hours or more.

The fact that I don't have to commute any more means I have time to spend with the kids -- I walk them to school in the morning, for example, while my wife is on her commute.

It's important to have a place you can call "work", so that your family or housemates know not to disturb, and that you can set up properly. Sitting hunched over the kitchen table on your laptop is a recipe for a bad back. Get a decent-sized desk and an ergonomic chair, just as you would if you were working in an office.

You're going to be even more sedentary than a regular office worker, so be sure to get regular exercise. Walk at lunchtime, join the gym, take up swimming. Whatever works for you.


I like running after stand-up. I get my running shoes on when I wake up, practice the piano, have coffee. Tell my partner I'm going to get to work, see what branch I'm on and what my notepad says, and just sort of start working. I have a big desk in the middle of our house with a nice monitor and lots of light. After stand-up, I run to the river and meditate on the Mississippi. I run back, and do errands, I come back to work after an hour or so and sometimes take my laptop somewhere else and work until my battery dies, then I take a break, plan dinner, and go back to my desk. This next few hours I'm way more productive, mostly because I've had exercise, meditated and made sure most of my personal things are done.

I sometimes need to bounce ideas off of someone, I usually just ask someone on slack if I can just type them a bunch of messages and that I don't expect them to respond. Sometimes I start a call with someone. Usually gets me past the block. If not, I save it for our after-standup meeting.

I haven't gained any weight since starting working remotely, though I've tried to lose some and only marginally succeeded .


I've been actively trying to make it out to the gym after I gained 15 pounds in nine months.


Do you employ any mid-day exercise when you're working from home?

No, not really. I've only recently started hitting the gym near me, and I try to sweat it all out there in the morning. That said, my daughter gives me plenty to chase during the day.


+1 "I've got work to be getting on with, and I don't care what your kids are up to." lol


The distinction between playtime and worktime is the biggest challenge for me. I don't have a place of my own yet, so my bedroom is my office for now. I try to change the scenery every now and then. Just pick up the laptop and move to a different room. But, it's challenging to have a clear separation between work and play when the environment is very similar all day long.


I have the same feeling. It's really hard to separate playtime and worktime if they happen in the same space. This idea just popped in my head as I'm writing: maybe there could be some furniture that is specific for work/play, or some item -- a headset or maybe a mug -- that means, "Okay, I'm in work mode" or "Okay, it's playtime."

Also, you mentioning this reminds me of this article or something that I read a long while back about how a famous programmer had the same issue, and finally decided that if he was going to work from home, he would work in his closet. In that closet, the only thing he would do is code. Apparently, that worked out really well for him. Wish I could find that article (or maybe it was a podcast?)... 🤔


There's a chapter in REMOTE that touches on that sort of idea. The author approached it with footwear and attire. Some pants or shoes during work hours, and slippers and sweats during downtime.

Ahh, I'm glad I'm not the only one thinking of it. I think it's a good start. I've had many times where I got sick of my jeans though and switched back into sweats. (oops)

Definitely will keep thinking about ways of differentiating my space at home for work purposes though.

Has the book helped you a lot with working remote?

It's been a while since I've read through the book, and admittedly all of these comments are encouraging me to give it its second read. It definitely helped me to pick up a few tips from an office of veteran remote workers. The advice in the book isn't just for employees though. It offers a lot of advice for employers interested in offering remote options.

Also, don't forget about casual Friday. :P

Ahaha yes. I think if I were full remote I would definitely have casual Fridays. Gotta give legs a break from the pants.

Jokes aside, I would take it seriously. It's a bit counterintuitive, but having a day where I wear whatever I want at home, while working, would really make me want to work.

Also definitely going to check out the book. As a team we're trying to work on how to properly have a remote-friendly workplace; so far I'd say we're doing pretty well, but it never hurts to try to be better.


I'm experiencing the same exact situation. Can't wait to get my own place to setup a home office. It can be mentally exhausting to work and relax in the same room every day.


I think the biggest hurdle I have had when working remote is getting focused right from the start. Commuting to work has sort of been a ritual for me, one where I gather my thoughts and get focused on what I need to do. However, when working remote, having no gap in time really before I get to work physically has been something I've been learning to overcome.

So far, a strategy that seems to be working is to get up earlier than I would have if I were going in the office so I can follow some routine or ritual and prepare myself mentally to work at home.

Oh, and thanks for the article! You made a lot of good points that my mind hadn't put into words.


What kind of routine have you been trying to employ? I've been trying out meditation with Headspace and exercise.


Since I'm an early bird, I wake up, write in my 5 Minute Journal, and walk the dog. After that I sit down for 5 - 15 minutes and focus on what I want to accomplish. It's a similar routine of what happens on my commute, but I have a lot more time to think on the train (if it's not too crowded).

I'm definitely thinking of incorporating exercise, too. In the past, I've had a lot of good experience with exercising as part of a routine. Been out of shape though and just avoiding it with excuses...


Do you ever miss having co-workers around? I've heard people complaining that it's too lonely WFH 100% of the time.


There are definitely times when you wish you were closer to co-workers. Lunch with other people is nice. That's the part of the trade-off though. Flexibility lets me be around family, but there's a distinct lack of that physical team awareness that comes from an office.


This will be a hurdle for me as I look to do a bit more remote work. As much as I really like remote work, I've always been parts of teams I see almost every day, dating back to clubs etc. in school.

At the moment I have no plans on doing the fully remote thing, but if I add one more day, I'll see if I go stir crazy.

I'm currently working from home and damn this is nice.


I've been working full-time-remote for most of the last 5 years, and occasionally-remote for most of my career (27 years).

The item you call out that I think is by far the hardest is distraction, but that's true in any environment. Let's be really honest here: being in the office doesn't keep people off of the "social" parts of the Internet. Firewalls may keep us of Facebook if they're really stupid but we always find ways to be distracted.

Also, co-workers can be just as distracting as cats and family members and realizing your laundry is almost at the point of an emergency. Water cooler conversations can be very valuable, but sometimes they're really just about what was on the tube last night.

So basically, what I'm getting at is: if you're a distractible person (I am!), you're going to be distractible at home, or at the cafe, or at the office, or standing on your head in a tank of live goldfish. Learning how to be productive despite being distractible is what matters.

Extra hours? I used to do that in the office all the damned time, too. Sometimes the work actually requires it, especially if you're distractible! Again, it's up to you, the worker, to decide how much, and where to draw the lines, and this is true at home or at work.

I will say this: I always get dressed for work. Granted, my idea of work attire is pretty casual, but despite laughing right along with everyone else who says, "Must be nice to be able to work in your skivvies", I never do. I also never work in bed. If I'm actually working from home, it's in my office, at my desk, wearing clothing. If it's from someone else's home (I sometimes work at my dad's place) I pick a space to set up as if it were my "office" for the time I'm there.


Working and living the dream, creating stuff on my own for projects from the ground up, in agreement with with the client. I'm the one-man-army guy with 20+ years of expertise.

Working remotely was always what I wanted. You'll need discipline, but nothing can beat the fact that you're the only one who watches over you. Also, no office politics, no distracting or annoying people to agree with. Whenever I need some company, I reach out to and organize something with friends.

Surely, this is not for anyone. Said discipline is no joke. If you can't apply it to your life, you'll be better off in an office with a 9-5 day job.


Well I was working from home about one year and half, after that I decided to quit for some reason that you wrote above.

I understand you when you say Do you ever miss having co-workers around? because I think it's the part that I miss a lot, when I was struggling in any problem I didn't have a co-worker near, many times I sent a message in chat and I get a response 1 hour later (that not help me). Also is pretty good when you invite other a coffee or tea, because here you can share a lot of thing even resolve code issues.

Other thing that made me change was, that I don't have a private room where I can work and when someone was arriving at home distract me, and many time made me lose the focus on my code.

Another point is that many of the bosses that I had, were thinking that I was 24h/7days in front on my pc, Although I was trying to think that it's like a normal no remote work, It wasn't. That made on me a lot of stress and I colapsed near 2016 new year eve.

So These were my thoughts about working from home, I honestly think that if I had had a private room the story would be different.


Thanks for sharing all this information. ☺️


May I add Communication? Direct against any kind of remote communication. So much easier and better.


Direct communication means you have to catch the person you want to talk to, make sure that this person has some time to talk to you. And even you are very polite, you still make an interruption. If that person is "in the flow", that's never good. Moreover, there're no traces left of what's been said.

It is so much easier to write an email :)


I didn't include communication on its own because it's a basic building block of a team. Without it, you're just not working, and this is both true in any sort of environment. I've worked on "teams" with absolutely no communication, even while their desks were next to each other. I can understand where you're coming from, though. Sometimes it'd be nice to shout a question at someone.