On Working Remotely

November 4th, 2021 • filed under Productivity

This post on remote work sat as a vague outline in my drafts folder for literally five and a half years. I first plopped this outline into Ulysses in February 2016 and added some things to it in May of that same year. From then on, it sat. This is my attempt at finally tying it off.

Fast forward to the last quarter of 2021, and as I’m cleaning things up after my move to the 2021 14” M1 Pro MacBook Pro (a great name), this rather in-depth coverage of my transition to remote work and reflections therein comes back to the surface.

I had a few thoughts. Do I delete it? Finish it? Put any time into it whatsoever and maybe get around to tying it off one day? Pretend I never saw it and let it language for another five years in my iCloud drive?

All are valid.

You’re seeing this post, though, so only one of those outcomes came to fruition. Guess which one.


When I put together this outline in 2016, my position was a lot simpler. I just took my first remote job and started my transition to work-from-home life. Back then, working from home was reserved for a slice of the tech-worker population in well-to-do countries: those with the resources to afford a space of their own to use for hammering out the wares they made. Some, like myself, had to make adjustments to their home environment to make things work, but they did.

Now in 2021, working from home has shall we say, changed. I could never have imagined the entire world would have been faced with such an event as the COVID-19 pandemic (I’ll probably refer to the time before the pandemic as the before times) that forced many folks to work from home. Hundreds of millions of people, who had never worked anywhere but an office a day in their life, were suddenly faced with an existential crisis.

Never mind that when it all started, the idea was it would only last a couple of weeks. No one was prepared for the long haul. I was because, by that time, I had already spent four years honing my remote work craft. Folks like my wife had no familiarity with such a concept.

The transition to a work-from-home environment for her was sub-par as I look back on it. I, an expert in remote work, had set her up with extra equipment I had lying around because I, too, was under the impression it was only going to be temporary. I fashioned her with a 2014 Mac Mini that was underpowered even when it was new and a 28” Acer 4K monitor. It was okay, but not great. If I had known she’d be spending the next year and a half working from home full-time, I would have invested in better hardware for her.

After we bought a house in March 2021 and moved in, I spent the money on a small workstation system for her. Her work is done entirely via remote desktop because of her career, so it needed to be good enough to handle that and nothing more. It has turned out to be a significant bit of investment, too. A refurbished Dell Optiplex 7060 Micro with a Core i7-something, 8GB of ram, and flash storage. How much? I don’t recall, and it’s not essential–remember, she doesn’t use the computer’s resources for much of anything. Zoom is about the extent of the local computing activity.

Watching her and her team establish a way to work remotely–as I write this, she’s still working from home three days a week–has been enlightening. I always joked that she and her team could do their jobs remotely, and saving I told you so for my internal satisfaction from which now thrive, they made it work.

Some of what I witnessed as they adjusted found its way into this post, too. Looking back on my original goals of this post, plus what transpired over the last nearly two years, I decided to pivot a bit.

Initially, I wanted to document my experience and what I learned transitioning from working in the office to working remotely and come back to it as time passed–30 days, three months, a year, and so on. I think some of that is still valid for five years, a pandemic, and a nearly two-year forced participation later. Of all that, though, the essential parts, I think, are the psychological, emotional, and ritual components of work and the change in the work-life balance that comes with remote work.

Also, when I originally wrote this outline, I wanted to focus on things like company direction and other career-evaluative stuff. The pandemic allowed enough folks to figure out what’s essential in their careers that another random bland white guy like myself doesn’t need to discuss it any longer. I think we, collectively as humans, have spent enough time figuring that out on our own that it’s worth skipping.

With that primer out of the way, let’s dig into the meat of the content.

Needs and Wants

Why am I doing this?

When I started looking for a new position in late 2015 and early 2016, I had already seen and heard a fair bit about the lifestyle of remote work. Naturally, what bubbled to the top of most the glitz and glam of traveling the world starts Monday in a coffee shop in Romania and has a meeting while in Italy the following week. The sub-genre of remote working advertised by digital nomads sounded nice, but I needed something that grounded me a bit more.

I’ve never been one to roam or even feel the need to travel constantly aimlessly. Other cities, states, countries, or continents sound nice, but I already have to spend a substantial amount of mental energy to think about traveling. Constantly doing the traveling is too much.

That’s not to say remote work can’t be fulfilling while at home, and that style is where I landed in the discovery and planning stage of all this. I intentionally described to myself what I wanted to get out of this potential new arrangement. I defined the boundaries I wanted to set and why.

Working remotely (from home) was going to solve a few specific things for me (You might notice similarities in these things):

  1. Commutes. At the time, I lived in Santa Clara, CA. The Bay Area is alright, but it sucks to commute in or through. The cost, all three of financial, chronological, and mental, were a lot. I was also working through personal events that had a strong suggestion toward moving out of the Bay at some point soon.
  2. Location. Knowing what I knew about the potential for my existence in the Bay not to be long, the last thing I wanted to do was look for a job that puts a lot of weight on considering staying. My interest in the area was quickly lapsing–save for the weather, I’ll always miss the weather–and I knew if I stayed because of a job, I’d either resent myself for doing so or resent the job for keeping me there. The position I take should allow me to move away when I need to and keep myself in the best state of mind.
  3. Work-Life Flexibility. The traditional grind of waking up, commuting, working, commuting, spending a few hours doing stuff, and sleeping didn’t feel like the best use of my brain space. I often found myself unmotivated to do much of anything during the week, and by the weekend, I felt I needed an entire day of doing nothing to recover from the week prior. By day seven (Sunday), I didn’t feel like I had enough time left to get everything finished. Before I knew it, Monday was rolling around again. Skipping commuting and adding a bit of daily flexibility to my life and schedule meant pressing matters could be addressed when they need addressing–provided the employer allowed that level of accommodation.

In essence, I needed a position that was tailored for this type of work-life balance. A company built around butts in seats and fields of desks in an office but is trying to do its first remote thing was not going to cut it. The remote-ness of the work must be deliberate.

A side note on offices: when I wrote the original version of this outline almost six years ago, I was on the downward swing of appreciation for office space. I more or less hated the idea, and the few times I spent in an office over the coming years never felt right. I could have very well biased myself with my strong motivation to avoid an office.

Today, I’m a lot less hostile toward them, but I still stand by my position that a distributed team can be successful if the distribution is intentional. The tooling needs to be there, and the processes need to define how everything works. To paraphrase the great Ron Swanson, the team must whole-ass being successful while remote, or it’s doomed to fail.

I saw this play out in my wife’s transition from working in an office to working from home. The team started relying heavily on Microsoft Teams for conversation and Zoom for regular check-ins and discussion. It wasn’t the same as meeting in person, sure, but they made it work.

Imagine how powerful the transition could be if they intentionally switched to being a remote, distributed workforce rather than doing so out of necessity.

On Distractions and The Ritual of Remote Work

Time for focus, time for fun.

A substantial hurdle for those with families, pets, kids, roommates, small spaces, studio apartments, etc., is that the level of potential distraction is significant. When I eventually moved away from California back to my home state of Washington, I looked for a place to live that had a dedicated workspace. In my case, I was looking for an apartment with a second bedroom or den. It didn’t need to be fancy, but I needed to replicate the ritual of starting and stopping my work.

Part of what commuting did, in all its sadness, helped me get into the mindset of work. It was a slow, soul-sucking version of it, but the idea was still something I needed to replicate. Having a dedicated workspace meant I could have my morning routine and see or hear nothing that had anything to do with my day job. Likewise, when the day was over, and I logged off, I could both physically and mentally leave everything behind, even if everything was just in the other room. I rarely entered this space on the weekends.

When my wife entered the work-from-home force, we didn’t yet have a dedicated workspace for her. She sat at the dining room table. Remember the equipment I cobbled together for her? Yep. The dining table became a desk, full stop. It was fine most of the time, but it lacked a couple of critical things: separation through ritual and privacy. If I wanted to make lunch and she was in a meeting, I needed to be extra quiet. When I was in a meeting, it wasn’t a concern for her because I had my own space. This level of unfairness always sat in the back of my mind. Even though she wasn’t going to work from home forever, I told myself I wasn’t going to let her settle and break one of my cardinal rules about remote work.

(I even offered to let her have my office, and I’d work either in the dining room or on the couch. She declined. Then again, she refused when we still thought that this would be a short-term arrangement.)

After upgrading to a larger home, I wanted to ensure that myself–and thanks to the pandemic, my wife–were afforded that same ability to switch on and switch off by having dedicated working spaces. While temporary, we’re consuming two entire bedrooms to make that happen, and we’re glad we have the resources to do that, but it’s what was needed. Her needs will eventually change, and we’ll adjust our space usage accordingly.

Another component in the pool of distractions are temptations. In the before times, I could pretty reliably expect a quip on working remotely from those who had never done it that involved something to the effect of:

I don’t know how you do it. If I worked from home every day, I’d probably sit and watch Netflix and never get anything done.

(If only they knew…)

The joke is less relevant now, especially after a much-forced shift to remote work, but it still has validity. The temptation to do anything but work is accurate. I don’t have a background in psychology, nor do I fully understand where a lot of this might come from, but I do know how I would think about it. The biggest driver for me has always been whether I’m engaged and interested in the work I’m doing. In other words: do I enjoy my job?

With the pandemic, I think it forced a lot of folks to think about that, themselves. In the days of commuting, doom-scrolling Twitter or YouTube videos on eclectic crafts may not have had as much influence. There’s no one to see you decide that it’s PJ and Judge Judy day at home. Your manager may not know how you woke up at 10 am, how you took a three-hour lunch, or instead of doing whatever random thing you’re supposed to be doing, you’re re-watching season 5 of The Office.

There isn’t a magical solution to this part of the problem, though I stand by my vague hypothesis related to interest and engagement. We’ve already–hopefully–considered this aspect and have built routines and implemented different life processes to prevent at least some of this for those who intentionally are working remotely.

On Being a Nomad

The world is your ~oyster~ office.

Earlier in this post, I classified being a digital nomad as a sub-genre of remote working. Taking up the lifestyle of doing the opposite of “planting roots” or “settling down” is a substantial shift and requires a specific mindset. Remember how I said that remote work has to be intentional? Being a digital nomad doing remote work is intentional++. If it sounds easy to get distracted by watching Netflix instead of working, imagine the level of potential distraction of sitting on a beach or skiing instead of meeting with a client or finishing a feature for your company’s app.

To be clear: if this is something you can handle, definitely consider it. It’s a fantastic idea. I wasn’t ever a massive fan of it, but I also want to ensure I’m not discounting the idea.

There’s remote work, and there’s Remote Work™.

You’ve made it this far. You’re ready and fully committed to the adjustments necessary for the remote work life. Fantastic.

I considered removing this section of the post because my original intention was based on an incredibly different view on remote work that I thought society had. Back then, we saw a lot more cases where remote work was frowned upon by corporations. Finding a remote-friendly job was substantially more complex and required knowing where to find the uber-niche job sites.

Today, companies like Apple are embracing the idea, at least for some of its roles. There are names on that list that I would have never imagined would appear there. Some of those names also feel like no-brainers, given the space in which they exist.

LinkedIn added a “ Remote “ filter for jobs. LinkedIn added a “ Remote “ filter for jobs, the real turning point that sealed the idea of remote work being a mainstay rather than a fad and temporary requirement was when LinkedIn added a “Remote” filter for jobs. At this point, I don’t have a lot to say. Companies that are willing to fill a position using remote workers outright say so in their job listings. There are over 200,000 jobs on LinkedIn tagged as “Remote” as I write this.

What I still want to make sure I discuss in this section is selling yourself to the hiring manager and recruiter on your ability to transition to a remote role if it’s your first. If you’ve never worked remotely before (that’s way less likely in the current and post-pandemic eras), you’ll need to be able to explain how you’re able to adjust. With most office folks having gone remote for at least a while, that may not be such a hard thing to do. I put everything I did above this section to help aid in that.

Everything I Left Out

Some other semi-relevant musings.

I had entire sections on building out your workspace, establishing a routine, and a handful of lifestyle changes that felt incredibly relevant in 2016. In late 2021, I’m not sure they matter so much. The vast majority of office workers spent time working remotely. Each of them was thrown into the deep end and forced to adjust their work-life balances and home life routines. Many of us bought Pelotons, figured out that pants are now optional, commuting is for suckers, and made substantial shifts in the way we live life.

As offices re-opened, a lot of folks embraced going back to them. Sheltered life was never really for them. Perhaps they were more excited about just returning to the way things were than anything else, trying to forget the last year and a half. Compartmentalization is strong. A lot of folks, though, didn’t do that. The lightbulb appeared over millions of folks’ heads, and pushes for remote work came from all directions. With companies embracing it, folks figured out permanent solutions and built new lives and routines.

The first months after the lockdown started and solidified, think pieces were aplenty on adjusting to this new lifestyle. If I had the forethought back then, re-surfacing this content and speaking as what would amount to an expert at remote work would have made a lot of sense. That ship sailed, though, and so did the relevant content.

This might be my selfishness talking, and I wish it was on better terms and wasn’t stimulated by a global pandemic, but seeing folks take working from home seriously and finally understanding how we remote workers managed to make collecting paychecks work in our spare bedrooms feels terrific. Even my mother, in her sixties, who has worked office jobs the better part of 40 years, has embraced it. She goes to the office a couple of days a week, but she enjoys the days where she doesn’t. Her daily routine has changed significantly, but she found what works for her. I probably shared some essential advice about habits and deliberateness, but the rest just fell into place in a way that made sense.

Neither my mother nor my wife read mile-long blog posts from tech dudes like myself on making this work. When asked, I opined, and especially in my wife’s case, was able to offer resources to make the transition as painless as possible given the circumstances, but we never had lengthy conversations.

Now, there’s nothing left to talk about. It’s all figured out. It’s for the better, too. Will some new entrants have no idea what to do? Today, though, resources abound.

Maybe waiting six years to write this so thought leaders could do their thing was subconsciously always part of the plan.