Shane is me|

On Going Remote

November 16, 2019

Note - This was written before the ongoing pandemic. Much of this has very little to do with remote life during a pandemic, that is a quite different blog post...

Regularly what you do for a living comes up in conversation. “I write software” is either a conversation starter or killer, depending on the audience. The obvious follow-up is where? “I work remotely for a company in San Francisco...”. The reaction to this is some variation of “you lucky asshole”.

I am a lucky asshole, but there are some things you should know before taking, or changing to, a remote position.

When I say remote position, I mean real remote: off-site and on your own schedule.

It’s not for everyone

This might seem obvious, but it takes a certain person to work fully remote. If you think you won’t be able to keep yourself on task, or think you’re just going to INSERT PERSONAL LAZY VICE HERE, there are some tricks I do that are helpful for me.

Self-motivation is a core tenant of surviving remote life. If it’s difficult for you to follow through on self-made timeframes for getting things done, you might want to level that skill up a bit before you jump into the deep end. Or, if you find yourself needing more supervision and/or micromanagement to keep on task — maybe try a new career if that’s at all feasible? But definitely don’t take a remote position.

Loving what you do is a huge benefit. It’s quite simple to stay on task if you love your job. Being able to do your job when you want is a quick win. I tend to be more creative and clear-headed first thing in the morning... so if I didn’t have a preschool age child at home I would probably work then... Since I can’t realistically work whenever I wanted, loving my job makes it easy to jump in when I can.

Having a private space is a must. I don’t think I’d be nearly as effective in the daily grind if I couldn’t close my door and keep distractions away. When I worked in an open office before I transferred to remote, I had my headphones on nearly constantly listen to music to drown out the cacophony. I find that these days I rarely listen to music, except when I really feel the urge.

You will miss the good things about the office. Unless your company requires all decisions to be in writing somewhere, you will miss out on impromptu conversations that will likely lead to decisions that will likely affect your project in some likely big way. You will miss the general human connections that are made, and although you can get close with tools like Slack it’s just nowhere near the same.

It’s not for every business

Obviously there are some jobs that simply cannot be done remotely, but I’m not speaking about those jobs. A vast percentage of jobs can in fact be done remotely, but for one reason or another the business simply isn’t compatible with it.

If the place you work would “hire remote for the right person”, you should ask them why they hire the wrong people and cram them all into one building. Many businesses just aren’t built to handle remote employees. This is mostly, in my experience, due to a lack of trust.

Your employer needs to be willing to make space for remote employees. They need to make a lot of concessions that don’t make much sense if your workforce is all in the office. How much do we need top-tier audio-visual in conference rooms when everyone is in the same room? Why do I have to stop a conversation and go write it down to include those that aren’t here when it will take five times as long to come to the same conclusion?

There are thousands of reasons why a company doesn’t want remote employees that go beyond spending a bunch of money on cameras and microphones. You have to hire the best and brightest and trust them to do what you’re paying them to do — this is hard.

It’s much easier to allow remote employees from the beginning of the business rather than transitioning to it, however if you are fighting for that transition to occur ask for something small: one day a week, any day that’s convenient for the employee. If you pick a day that everyone works from home, it’s not the same feel.

Your company gets lots of wins out of allowing remote employees. The most obvious: the best people to work at your company do not live in the city of your office. Of course, not having to handle another body at the office lowers overhead on real estate.

Having face-to-face time some of the time when you have fully remote employees. It’s important to bring everyone in once or twice a year for some solid socializing. That’s a major expense that could be offset elsewhere, but that’s a difficult spend if it’s not built into the culture.

I’m never commuting again

... if I’m lucky.

I sometimes say that just the thought of having to commute again causes me to break out into a sweat. This is very true. If I can work remotely for the rest of my career I will.

There are definitely things I miss about working inside a bustling office, but it’s definitely not on getting to said office. The time and flexibility I have in my work day is frankly ridiculous.

Lack of humans surrounding me has pros and cons, but having regularly scheduled onsite visits can help decrease the feelings of solitude. I’m not sure I’d work at a place that wasn’t at least flexible about coming into the office a few times per year.

Working at a place that fully embraces remote employees is not just critical, but in my opinion necessary. You can’t be the only one, or one of a few, that is treated like a contractor. It has to be baked in for all employees, even if they live in the same city as the office. It starts from the top, if they’re not all in I’m not sure it will work.

What I do, a concrete list

Every morning, I get fully ready as if I was going into the office. I am privileged enough to work fully casual, so your mileage may vary.

I try to emulate the good parts of the commute. In the morning I sit at my desk and read the news or a book, possibly an episode of a favorite show. This is something that's a little harder for me as I feel the pull to go play with the family right away. However, when I force myself or feel like it, the disconnection from the day-to-day home life and back is really helpful for me.

I disconnect from work for all but emergencies when not at my desk. I put in a solid work day and I go away. I don't have work emails on my phone, or my work calendar, and slack puts me set to away after my work hours. If I had time to disconnect, it makes the transition of walking downstairs much more smooth - and really this is good advice even if you don't work remote!

I try to have social time as much as possible with my coworkers. I like to have informal 1:1's or group chats just to catch up, talk about weekend plans, the usual. I have to go out of my way to make this happen so when things get hectic this does tend to fall by the wayside. I sometimes have set times on the calendar for this, but it usually putters out after a couple months. Still trying to figure that out.

These things help me try to introduce some of the good aspects of being on-site vs. remote, while maintaining all the good things of being remote! I do still miss sharing a physical space, but, for me, the benefits far outweigh anything else.


2021/09/1 - added note at the top, removed the Basecamp recommendation :(, added the "What I do, a concrete list" section as it always bothered me I never actually talked about that.

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