What It's Like To Work Remote

April 16, 2019

Home Office

If you work in the tech industry, you have no doubt wondered about working remotely. I can't even count the number of tweets and blog posts I've come across that talk about how working remote is not only a perk, but the inevitable future for engineers. After two and a half years, though, I realized it wasn't for me and I took a job back in Boston to work in a physical office again. Within the first two weeks, I've had countless questions about working remote and what I liked and disliked, so I thought I'd take the time to articulate them in a blog post.

The Perks

When people would find out I worked from home 100% of the time, the most common thing they would say was:

I bet you were in your pajamas everyday, huh?

— Everyone, ever.

Let me defuse this (and stress that it can be a bit condescending). It never really crossed my mind to wear pajamas or gym shorts or sweatpants during the work day, but maybe that's just me. Also, I usually went to a cafe to grab coffee in the morning or run an errand and it's not like I would change back in to my pajamas if I left.... that would be weird. Not to mention that we had a lot of video calls and I was overly self-conscious of what I was wearing (...and whether I had bed-head).

So, no. Most remote workers don't wear pajamas all day (I've asked).


The job I had before was in an office, but I would usually do one day a week from home; if you're an engineer, you've no doubt had a few days from home here and there. I found those remote days were typically my most productive. So, it stood to reason that I would have nothing but productive days, right?

On days when I knew what to do and I wasn't blocked, I was definitely productive. That's what I realized about my previous jobs -- I often held off on bigger tasks for the days when I knew I would be working from home. Being in an office comes with some distractions and getting that "heads down time" can be nearly impossible. Saving those big tasks for remote days made sense but it may have given me the illusion that all remote days are productive.


I had a lot of healthy habits when I worked from home. Working for tech companies (especially ones with a "startup" culture), can be a recipe for unhealthy eating. I did so much more snacking when I was working in an office -- my previous two positions stocked a kitchen with cookies, crackers, fruit snacks, chips and more. Not to mention I drank much more coffee since it was readily available or there was always someone walking to Starbucks at any given hour. I'm not much of a coffee connoisseur and I drown mine in cream and sugar (doubly unhealthy).

But as soon as I had to pay for my own food, I was suddenly very conscious of what I was putting in my body. I made better lunches every day, I bought healthier snacks and drank much more water. ...Ok, I still do the sugary coffee because Starbucks was right around the corner and I love me an iced mocha.

On top of that, I was working out regularly when I worked from home. Typically, I would go for a short run or a quick trip to the gym during my lunch break, then just eat lunch at my desk as I worked. When you don't have to worry about finding a place to change or shower, it's hard to find an excuse not to exercise.


Scheduling appointments is so much easier when you work from home. Taking the car in to get fixed, taking a cat to the vet, doctor's appointments and so on, were immensely easier. When I was in an office, I procrastinated so much on things like going to the dentist or fixing my car because it was such a hassle to plan around work and commuting.

The Commute

Not commuting is the biggest perk, by far. I've done long and short commutes, both by train and driving. Any commute is stressful, even if all you do is sit on a train for an hour and a half. It's lost time that you don't get back and it can be so depressing when you realize your 8 hour work day is really 11 hours when you take the commute into account. I enjoyed the dedicated reading time when I was taking the train (I read all of the A Song of Ice and Fire books), but I'd rather just have the free time. Being able to wake up, make breakfast and walk ten feet to your office is an amazing perk.

Why go back to an office?

Upstatement Office

One of the common things I would hear from people who had never worked from home was:

I would find it so hard to be motivated.

— Most people.

I understand the sentiment -- being at home comes with its own distraction. However, I don't think the threats to motivation were any larger at home, versus in an office. Yes, it can be hard to resist your Xbox or watching something on Netflix, but the same can be said about walks to grab coffee or idle conversations with coworkers. My reasons for not wanting to be remote anymore really had nothing to do with motivation or productivity.

Learning is harder

One thing that you don't quite realize until you start working from home, is that you do not pick up new skills as quickly. You learn so much just from the people around you -- whether it's from overhearing conversations about new technologies or being able to ask someone an offhand question. Seeking out a solution or discovering someone else has run into the same problem you have, is much more difficult over slack. You have to actively tune into those conversations when working remotely and when you're busy or heads down on an issue, there's almost no way you'll see a conversation that doesn't directly involve you.

Past that, if you want to learn something, you need to actively take steps to do it. I really had to set aside more time to read through documentation, watch tutorials and more when working from home. Finding a mentor (or establishing any professional relationship, really) is much harder over messaging apps and email.

Asking for help is more difficult

When you are stuck on something and you know there is a person who can fix an issue for you, grant you permissions to an API or talk through how something is implemented, but they aren't available, it can be infuriating. That's true for remote and in-person offices. The difference (I found) is that in an office, I can glance over to someone's desk and see whether or not they are engaged with something before bothering them. Or, better, I can catch them while I'm grabbing a coffee or stretching my legs and that exchange of information can happen organically. Working remote, there is no "oh, can you shoot me an invite?" type conversations that can happen in passing. Asking someone for a favor or advice is very deliberate and asynchronous -- you may end up sitting on your hands for quite a while before you get a response.

We all have days when we feel unproductive, but I felt they were doubly so when working from home. After all, it's not like you could look to your right and ask your neighbor to talk through something.

Engineering is a human endeavor

So many people in the software development world believe that engineering can be very detached (in fact, that belief drew a lot of them here). But there is an inarguably human side to engineering. Whether you're pairing with coworkers, reviewing code or working with clients, at some point, you'll have to interact with other people. The issue isn't interacting or doing code reviews (all that is easy from home), the hard part is learning to understand personality types, nuances and quirks of those people. Understanding your coworkers makes it easier to work with them.

We went through a hiring rush (within a year we had hired almost 40 new people). I admittedly found some of these new coworkers standoffish at first or I felt like I couldn't possibly gel with them on a long project. It wasn't until we had a retreat or work trip and I got to meet everyone in person that I began to understand them as people. I had a lot of moments of "oh, he just has a really dry sense of humor" or "oh, she just likes getting her thoughts out first and isn't actually trying to dictate." I couldn't have picked up on these nuances through just slack alone and I started looking forward to those work trips for just that reason.

Yeah, it gets isolating

The second most common comment I got about working from home was usually:

It must be so isolating, being alone.

— People without boundaries.

Yeah, it really is. I spent a lot of mornings working out of cafes or libraries, but that doesn't really solve the problem. You're still working by yourself -- you're just doing it around other people. I'm willing to admit that maybe I'm just a more social person that I thought but I wouldn't consider myself the most outgoing person in the world. After all, I used to really enjoy the occasional day from home, so I truly thought I'd function just fine from a home office everyday. It wasn't like I didn't talk to people online (I was lucky enough to have some close friends at my company), but socializing through chat never quite fills that gap. In fact, I probably ended up overcompensating and wasting more time on messenger apps than I should have to make up for the lack of interaction (...maybe I wasn't as productive as I thought...).

I missed the occasional walks to get coffee. I missed the random lunches or drinks after work. I think most people need that socializing in some way and the times I noticed it the most, are the weekends when I didn't have plans. Working in an office, I looked forward to a weekend with downtime to catch up on reading or a tv show. But when I worked from home and didn't see people regularly, those weekends of "down time" were grueling.

But working from home is the future!

I had a lot of coworkers and friends who said they could never go back to working in an office. Our slack was often filled with blog posts or tweets from "thought leaders" talking about how it was the only way forward for a lot of companies. Granted, I think a lot of that was just self-assurance but it still made me feel like I was the outlier. I knew within a year that I wouldn't be able to do remote work forever but I kept telling myself to stick it out because of how much the community seemed to support it.

Maybe it makes more sense from the perspective of a company versus an individual. Maybe it's just the latest trend in an industry of ever-changing trends. I won't pretend to have the answers. I just wish someone had reassured me when I was feeling isolated in my home office:

It's ok to not like working from home.

— Me.

And even if you really enjoy it right now, it's ok if you change your mind later. It's hard to tell what type of effect it can have on people, as most workers haven't been doing it for more than a few years. So, be sure to check in on yourself from time to time and really ask yourself if something is missing.