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Pants Optional: Working Remotely

Andrew Powell
Javascript / Node engineer and enthusiast. I'm probably somewhere on a boat. 🌴
・6 min read

I've been working remotely for nearly 7 years now, and I couldn't imagine ever going into an office on a daily basis again. It's a magical setup that affords incredible freedom, and far more responsibility. I love working remotely, and I'm going to share with you my strategy for working in my own, pants-optional office.

I could never work from home, I'd never get anything done.

That's the response I typically get from anyone I've ever told about my setup.I've come to acquire several key lessons and skills that make working remotely a joy, so much so that I doubt I'll ever again take employment where reporting to an office is a requirement, if I can at all help it.

Never Say Never

The "I could never do it" response from folks isn't surprising. The last thing most of us want to do at home is think about work. In fact, many smart types will tell you that it's an unhealthy thing to do. And for those who work the typical 9 to 5 routine, I'd probably agree. But I live the software developer life, and I've come to find a method that makes it very easy to be successful remotely.

When Work Isn't Work

If work is work, you shouldn't be doing it from home. I'm lucky enough to do something that I'm fairly decent at, and that which I really enjoy. That's really key. Enjoying the work lets you turn on and off at will without contaminating your home with "the office". You'll be able to let ideas flow throughout the day and night. The official hours of your physical office will become more guidelines, whereby you need to stay available, but that which you're not constrained by.

Pants Are Actually Optional

Just don't forget them if you're planning on taking video conference meetings. You don't want to be that person that has to get up to shut the window and inadvertently shows off those new adventurous undies.

But in all seriousness, get comfortable. Choose a workspace that works best for you. Remember that you're not in an office! I personally choose to work from my dining table with lots of light and fresh Florida air. Some of my peers prefer a cordoned off basement office. Your workspace should be what keeps you the most comfortable throughout the day.

Part of a great workspace is surrounding yourself with things you love. My kitchen is about 20 feet from my laptop - my inner fat kid loves that. That also means that I have water and other beverages readily accessible. I've also got a solid TV on the wall and typically have Netflix going all day long. For me, some kind of white noise and the occasional mental break in close proximity keeps me sane throughout the day.

Creature Feature

Get a pet! They're an incredible stress reliever and amazing outlet for problem solving. Don't be afraid to be that crazy person who talks to their animals. Leelu frequently helps me out in a mental bind.

Communicate, Silly

Communication. Communication. Communication. You must go out of your way to communicate with your peers, your supervisors, even the person working at the reception desk in the office. There are reasons, of course:

Communication Builds Trust

Trust in you from your peers is key, and while it would be grand if we were all judged by our merits, many people can't trust until there's a base of communication that's usual and comfortable.

Communication Builds Rapport

Until you're in the office and have the chance at in-person face time with everyone you work with, you're the faceless (or single faced avatar) internet person who apparently gets paid by the same company bi-weekly. You may be fortunate and work for a company that has access to video conferencing, but even then you're still a floating head in a window. Great communication builds a familiarity with your peers that will ultimately aid in collaboration.

Frequent Communication Creates Value

Frequent communication is paramount. Vanishing for extended stretches of time has a negative effect. Remember that you're not in the office and people can't see what you're up to. For all they know you're out at the pool floating on a giant inflatable swan. When you reach out throughout the day, you're reminding people that you're there. When you share what you're working on frequently, you're reminding people of the work you're doing.


Working remotely can sometimes feel like a scene out of 28 Days Later. The feeling of isolation is something every remote worker needs to combat on a daily basis. Sometimes it's a slow day in the office, and others it's that the physical office is too busy. It's easy in that frequent situation to get discouraged, frustrated, or just plain bummed out. That's a good opportunity to step away and right your ship.

Since us remotes are also neglected socializing throughout the day, make up for that deficit when work is done for the day. I'm a social guy and staying in or isolated for too long gets me stir crazy. I make a concerted effort to socialize after-hours. Befriend some bartenders or others that work outside the 9-to-5 cycle. If you've a family, visit with some neighbors or take the kiddies out for something fun around other people.

Halt, and Catch Fire

Take breaks. Take lunches. Take naps. Decline meetings. Run errands. Play with the dog. Go for a walk. Go for a run. Get a hobby and indulge it. Watch an episode of The Walking Dead. Have an adult beverage if you feel the urge. I personally never like to work for more than two hours straight. Halting keeps me fresh and keeps me sane.

Stopping and taking a breath is one of my keys to the gig. Those incredible freedoms I mentioned earlier come into play here. Of course this depends on the company you work for and the folks above or around you in the hierarchy, but take advantage of the ability to do throughout the day what those in an office aren't able to. Just bear in mind that your responsibility to the work doesn't end. If you're going to play a little hookey, remember to make time later to cover your deliverables.

Expand Your Organizational Skills

When no one's available to chat, you don't always have the luxury of stopping work and waiting. You'll have to develop solid organizational skills that will allow you to revisit things that need discussing, or to resume tasks that you're blocked on down the line. A great degree of self-management is necessary regardless of the kind of management structure you're working in. A cautious level of independence will go a long way. You won't always have the time or the opportunity to discuss choices, problems, or solutions with your peers. Which brings us to...

Peer Dependencies

(That's a poor NPM pun, for the nerds reading this)

Your peers are going to mean success or failure in a remote gig. When interviewing, make sure you're asking questions as well. You'll want to interview the folks doing the interviewing to make sure they know how to work with remote developers. Some companies are freshly wading into hiring remotes, others are seasoned, and yet others have no idea what they're getting into. Management should be on board with and see value in remote employees. It also helps to jump into a gig with peers that have experience working with remotes. Talk to the folks that will be managing you and your projects to get a feel for how they expect to work with you. Never be afraid to share your ideas early on.

Time For a Whisky

I hope that the lessons I've learned can give others in or considering remote work something to think about and help out if needed.

If you've been thinking about remote work, there are a plethora of resources
that can help:

Awesome Remote Jobs
Remote-friendly companies
Remote OK
Working Nomads

And those are just a few. Good luck!


βˆ™Β Β βˆ™Β Β βˆ™

Originally published at on November 28, 2016.

Discussion (10)

shortjared profile image
Jared Short • Edited

Working remotely can also quickly lead to burnout. I've worked remotely for more than a decade at this point. Sure, I love my work. But I've found that if your work and hobbies intersect to the point the line is blurred, you need to be very deliberate in when and where you work, even within your own home.

The number one tip I can give people is have a clear and distinct hobby that isn't work. For me it's video games with friends, some of which are even my co-workers. This helps fulfill some social needs.

The second thing is I always stop working at regularly time to prepare dinner or even just play a game or two. This helps that shift in mindset from workmode to relaxation. I can still go back to workmode later if needed, but having regular practice at that switch is mentally helpful.

shellscape profile image
Andrew Powell Author

Absolutely agree with both tips!

wesgrimes profile image

Great article Andrew! I am coming from a traditional office environment for the last 16 years and I will most certainly be pointing back to this for reference as I start my first 100% remote position later in the month.

jackharner profile image
Jack Harner πŸš€

I'm definitely interested in working remotely. One of things I get a lot of mixed reactions about is the idea that you need to work in-office with a software team before even being considered for a job on a remote team.

I've got a decent amount of portfolio work, have worked for a company as their main "Web Dev" guy, but never on a team of people working on a product together.

  • Do you think this specific hole in my experience is preventing me from getting a Remote job?
  • Did you do the traditional office life before remote work?
arielcamus profile image
Ariel Camus

We train software engineers in 65 countries and prepare them for remote jobs, and 70% of the entry level developers we have trained are now working in remote positions as their first job. So no, experience working with a co-located team is not necessary, but it could definitely help since the mentorship is usually better (unless it's a remote first organization that knows how to build a strong remote culture).

shellscape profile image
Andrew Powell Author

Thanks for commenting Jack. To answer your questions:

I don't think that you have a "hole" in your experience. If you've been successful in on-site roles, then you're ready to be successful in remote roles. And that's regardless of whether or not you've been part of a large team. I've worked remote roles where I've been "on an island" and roles where I've been a part of large teams. If you're ready, you're ready. Good remote developers are adaptable.

I did personally start with an on-site roles; two of them to be exact. Once I moved to remote work I reflected on my time with both of the roles I had which were on-site and it blew my mind how much time was wasted on both. Commuting, lunch times, and meaningless meetings eat into one's day. Since my first remote role I've been far more productive.

It sounds like you've got about as much experience as I had before my first remote role, and I would encourage you to pursue one.

desi profile image

I love working remotely, and have been thinking back on how my journey has changed. When I first started, I LOVED the idea of working from bed, and did it often. I had a dedicated corner in the living room of my small one-bedroom apartment that served as my β€œoffice” at the time.

Now, I have a dedicated office setup (including a treadmill desk that I love!) as well as a β€œtraditional” seated desk. When the weather is nice, I make a point to ride my bike to somewhere and work - usually outside at the local Starbucks - and it’s great!

elliot profile image
Elliot • Edited

I was one of those people who said

I could never work from home, I'd never get anything done.

but I've just started dipping my toes into working remotely and I find it rewarding, albeit challenging some times.

Some days are fantastic and I get a ton of stuff done. Other days are full of frustration because I can lose focus. That being said, over time, the days have become more consistently productive, with less high highs and low lows. I've found staying organized and communicating help a lot with motivation and focus.

There's a whole other set of skills you need to work on (like self-discipline) when working from home. At the start it was actually hard to get anything done, then I had a very productive day here and there. I like to think I'm learning and getting better.

shellscape profile image
Andrew Powell Author

Thanks for sharing your experience πŸ‘ We've all been there. It gets easier (and more rewarding) as time goes on!

mshappe profile image
Michael Scott Shappe

I agree with a lot of this. I've also been blessed with a career that has allowed me to work remotely most of the last 7 years or so--and even before that, I often managed finagle random telecommuting days on a semi-regular basis. It's pretty awesome.

There's one and only one part I take issue with...but I also recognize this is entirely a "me" thing and not an "everyone" thing.

I always--always--wear pants if I'm actually working. It's a mindset thing. If I'm at home, and wearing pants, it's work-time. Any other time of day I'm at home, pants are bullshit. But work-time == pants and vice versa.

Similarly, I always start my day with a shower, and all the other routines of someone who is about to go out and deal with other human beings. A shower, almost more than my caffeine addiction, is just part of waking up in the morning--it's not really today if I haven't showered yet.

I eat both breakfast and dinner out a lot of the time--which is not cheap, I'll freely admit. But because I spend my whole day at home otherwise? Getting out of the house is actually a part of my sanity and self-care. Unless it's snowing. Then I stay the hell home :-).

And, as at least one other person in the thread as mentioned, I start and end my day at more or less regular times. Keeping boundaries around "work time" is important whether or not you work in an office!