Overview

Over the past few years I’ve been having conversations with folks who have started working remotely out of necessity, rather than choice. Obviously there are a ton of factors that play into this, not the least of which has been COVID, however historically this tended to be something that folks would actively seek out as a niche rather than a wide-spread go-to.

While there has been no shortage of content written on this topic with tips & tricks around WFH/remote work, it generally feels like few of these are from folks who have been doing this long term.

To set some context, I have been working primarily remotely for nearly 12 years across three companies with very different cultures and sizes (30 -> 300,000 people), with my teams spread not only across the continent but across the world.

In this article I’ll talk about things that have made a significant difference for me over the years, how I’ve seen others solve similar problems, and sometimes a bit of “do as I say, not as I do”.

Workspace

You’ve heard it everywhere, and I’ll repeat it. If you can have a dedicated space just for work, do it.

I often think about combining my work and personal setups into one mess of cords and KVM switches, generally as a cost savings measure on not needing two nice office chairs, but I also know that it means a further breakdown for whatever barriers I have between “me time” and “work time”. While these are blurry already, which I’ll write about later, it’s an important distinction to have.

If I’m in my office, my focus is work. If I’m not in my office, my focus is (mostly) not work.

Now, the reality for many folks is that dedicated space for a work setup just isn’t a thing, especially if you live in the city. With that in mind, other separations (technical or not) can be helpful. If you are using a shared setup for personal and work stuff, try to avoid making it too easy to switch between the two. If you are focused on boundaries between work and personal life, try to actually “shut down” work stuff whenever you decide to call it quits so that there’s a bit more of a barrier to entry to picking it back up.

Another common thing I’ve seen with remote work in shared spaces (e.g. small apartment) is to use room dividers so that there’s still some level of physical separation between work and home.

Beyond that, don’t be afraid to invest - especially if you have a dual-purpose setup. I can’t stress how much of a quality of life improvement it is to have the right tools for the job, and ergonomic ones at that. Look at ergonomic keyboards and mice, look into an adjustable height desk, explore the world of (perhaps refurbished) ergonomic office furniture. Make your setup work for you, and if you can get that done on someone else’s dime… even better!

Distractions

Building off of the overall workplace setup, it’s good to understand how to avoid distractions if you’re working in a location with other humans (or low hanging fruit like video games and TV).

The best advice I can give here is to discuss boundaries with other humans in your space - if you’re “in the office”, you’re working. I’ve seen some rather ingenious setups for this that make use of “on air” lights triggered by a Raspberry Pi or Arduino when Zoom is launched, or just a manual toggle.

If I’m working and my SO is also home and nearby, I’ll close my door to make it clear that I’m busy.

It’s also tempting to get housework done since you’re at home. Case in point, while writing this I’ve just remembered that I need to put my laundry in the dryer. There’s nothing wrong with doing this, and honestly I’d encourage it as it’s a huge perk of working from home, but don’t let that spill over into an attitude of you being a housekeeper and work coming second - have clear priorities. I’d suggest against undertaking a deep clean of your baseboards in the middle of the work day, but emptying the dishwasher or doing laundry gets a big thumbs up.

Beyond that, I suggest getting to know the tools you have for collaboration (also to be discussed later) as this may give you some other opportunities to avoid work-related distractions. When working in an office the thing I hated the most was having colleagues just walk up to my desk and throw me off whatever I was doing. If you can take advantage of something like a calendar plug-in for your messenger (e.g. Slack and Google Calendar) to automatically set you as busy and mute notifications, it can be a massive help. This is amplified by our next section…

Time blocking

I’ll start out by saying that time blocking is a bit of a dark art. It’s very easy to poorly estimate how long things will take, or even worse overestimate and endlessly frustrate your colleagues who are trying to track you down and/or book meetings based on your availability. You may also hear these referred to as “focus blocks”.

For anyone unfamiliar with the term “time blocking”, I’m referring to making use of your calendar both to prioritize your work and mark your availability. For example, if you know you need to get some documentation written, block off the period of time that you think it will take and get that task done. Ideally this will limit interruptions, and it will likely help you plan out your days.

I tend to (loosely) plan out my weeks prior to wrapping up on a Friday, or sometimes on a Sunday prior to the start of the week if things have been hectic, and it gives me a pretty good idea of what my priorities are going to be, and whether or not there are things I can defer/delegate/drop compared to other tasks that need attention.

As a word of warning, I strongly recommend against blocking off full days on a regular basis unless you have a very clear need to do so. This is a great way to alienate colleagues and cause scheduling nightmares for anything that needs you involved in a real-time capacity. There’s nothing wrong with blocking off hours at a time, but be mindful that other people will likely try to book time with you if you work in any sort of a synchronous workplace.

Work/life boundaries

This is going to be a “do as I say, not as I do”, but trust yourself on this one either way.

For a very long time my attitude was “it’s 5PM, I’m done for the day”. There’s nothing wrong with this attitude, however I’ve found that it can have some interesting complications when working remotely. Specifically, if you’re like me and you take advantage of breaks in work to get personal stuff done, or appreciate the flexibility to work split/off hours, having a very firm schedule can be counterproductive to getting things done.

On the flip side, if you are very strict about your work hours and availability, you may find that you have a much easier time separating work and life, and (though it varies person to person) may have less stress as a result of it.

I’d generally recommend going into remote work with an open mind about this, but with a plan for firm boundaries. If you find that you want to flex from there, do so! With that noted, be mindful that it’s very easy for work to become a 24/7 thing if you get into the habit of “after hours” checkins.

A colleague of mine made a great video touching on this and while I have a very different view of it, it goes to show that there are multiple ways to approach it rather than a one-size-fits all.

My overall takeaway is to try to keep a sane total number of hours. It may not matter when you work, but you want to avoid going overboard with the time commitment on a regular basis.

Building connections

Here’s the real hard part of remote work. Human connections. There’s no way to sugarcoat this - it takes effort.

If you come from a background of lurking in IRC chat rooms and shitposting on forums then that level of effort will be second nature to you already. Do that, just do it professionally, and the connections will flow.

If you have no idea what I’m talking about in the paragraph above this, my recommendation is to look for opportunities to help with projects - chime in on problematic scenarios, share any insight you have from past experience where it’s relevant, and strike up conversations about interests that others may/do share.

I’ve seen many people join companies and only ever speak when they specifically need to, and never go beyond their assigned work. Just like eating at your desk and never seeking advancement in an office setting will lead nowhere, the same is true working remotely.

I will take a moment and note that some workplaces make this much harder than it needs to be. At the risk of offending some, I’ll say that Teams is the direct antithesis to making connections due to it’s design of avoiding free-flow conversation and lack of custom emoji support. If you find yourself in this scenario, just be aware that it’s probably going to take additional effort to seek out a sense of belonging.

Lastly, and one that certainly cannot be taken for granted - if you have an opportunity to meet your colleagues in meatspace (aka IRL) take full advantage of it. Working remotely doesn’t mean that other humans don’t exist and that you shouldn’t see them. You can make some excellent connections in only a few minutes of banter that otherwise wouldn’t happen over a Zoom meeting or Slack.

Collaborating asynchronously

While this will of course vary depending on how your company operates, it’s important to remember a few key tenants of working with a globally distributed team (or one that doesn’t all share common hours):

• If it isn’t in writing, and you can’t link to it, it never happened.
• Be as detailed as possible in written communications, and try to anticipate, and answer, the questions the reader may have.
• Clearly detail the requests that you have, and the expectations that come along with those.
• Be respectful of time differences. If something doesn’t need to be done live, don’t try to force it. No one wants a 6AM or 11PM meeting. No one.

I wrote a lengthy article detailing written communication techniques that I’d encourage you to read, as a lot of these concepts carry over directly.

That’s it. A quick brain dump. If you’ve got questions, feedback, etc feel free to reach out to me on Mastodon to chat!