Lessons From A Year Of Remote Work, Part 1: There Are Upsides To The Downsides

 There are upsides to the downside of working remotely

Word on the internet is that there are companies who rigorously monitor their remote workforce, watching them via webcam as they work, taking screenshots of their monitors, even dictating when and how often they take bathroom breaks. From my—admittedly very small—corner of the universe, that seems like a wasteful strategic error. When you try to imbue remote work with the same trappings and structures of onsite work, you miss out on the opportunity to cultivate a workforce dripping with personal responsibility. And isn’t that the hallmark lament of corporate leaders everywhere? We want self-starters! We want initiative! I mean, do you? Initiative, by definition, requires independent, creative thought and the willingness to take risks. If everything about your workplace says, “We’re watching you, and your compliance is our primary concern,” how likely are you to attract independent, creative thinkers who want growth more than they want to avoid risk?

Self-starters, this article is for you… don’t work for those companies unless you have no other choice. Get a real remote job instead, complete with all the downsides those big-brothery companies are trying their darndest to control.

Remote Work Cons Are Pros In Waiting

After a year of working remotely, it seems to me that most of what we call the downsides of remote are also opportunities for substantial growth. Leveraging them is a matter of recognizing your limitations and unmet needs and becoming willing to do something about them. (If that’s not self-starting, I don't know what is.)


Con: Enmeshment | Pro: Autonomy


The struggle to detach was the first pain point I noticed when I joined a distributed team. Because there’s no physical threshold between the office and home, it’s easy for remote workers to get stuck in work mode. There you’ll be, trying to enjoy pizza and Netflix with the family while wrestling with the interruptive sense that you’re technically at your workplace and therefore ought to be knee deep in spreadsheets, not lazing on the couch and gorging yourself on deep dish supreme. It’s uncomfortable. It’s also remediable.

  • Commute (sort of): I took a walk each morning before sitting down to work for my first 10 weeks on the job. Moving my body through space and time before work—as one does in a traditional commute—helped me teach myself that I was going to work, not living there permanently.

  • Use Startup and Shutdown rituals: Cal Newport’s book, Deep Work, inspired this one. I execute a series of activities each morning during Startup and a separate series of activities each evening during Shutdown. (Newport even says the words, “Shutdown complete,” when he finishes his end-of-workday ritual.) I still do both rituals every day. They make moving into and out of work mode easier than it’s ever been.

Ultimately the point (for me, anyway) isn’t to double down on the boundaries between work and home, which are traditionally external; it’s to bring more and more of your awareness to what being “off the clock” feels like to you and then creating your own personal path to that feeling rather than relying on something else—a manager, a timesheet, the mass migration of 9 to 5-ers at the end of the day—to tell you when you’re done. If you can successfully learn to detach from work whenever you like as a remote worker, you will have developed a level of personal autonomy that I’d bet few onsite workers achieve.

Benefit to the company: Autonomous workers are happier. Those that can detach at will are more resilient.


Con: Lack of Routine | Pro: Customization


Most of us are happier with a degree of structure in our day-to-day. And there’s no arguing with the fact that working remotely involves significantly less built-in routine. Here’s the beauty in that: To have the stabilizing sense of structure that’s a given in onsite jobs, remote workers must create it for themselves; in doing so, we get structure that’s tailor made for us. Bespoke routine, if you will. Like Andie in John Hughes’ Pretty in Pink, remote workers don’t have access to off-the-rack; but with creativity and determination, you can have something arguably better: a routine that’s alterable and uniquely your own.

Benefit to the company: When your staff has the freedom and initiative to create a routine that meets their needs, you’re more likely to get their best work. One software engineer puts it like this:

I am a night owl. You can tell me I have to have my butt in a chair within your line of sight at 8 or 9am, but that is very wasteful. [...] I will start being very effective around 11am and I really get going in the afternoon/evening. If you force your preferred hours onto me, both employer and employee lose. You get less output out of me!


Con: Isolation | Pro: Advocacy Skills


Switching to remote is the most energy-saving change I’ve ever made because I no longer tap out my internal resources just sharing space with people for forty hours a week. But if I go for too long without meaningful connection with my coworkers, I start to feel invisible. I struggle to pep talk myself into believing my contributions have any merit at all. It’s a real downer.* And I’ve yet to have the remote-vs-onsite talk with anyone who’s both worked remotely and not grappled with some version of this issue. The diamond in the rough here is that managing the isolation problem requires… well, management. I can’t just go about my day hoping that eventually someone will ask for my input, thereby relieving me of my existential burden. If I want to feel better, I have to communicate on my own behalf:

  • With management: If you’re like me, this is hard because you don’t want to give your boss reason to doubt your fitness for the job. But assuming your supervisor works remotely too, he/she might have practical suggestions for ameliorating isolation.

  • With coworkers: Also hard. Asking for a call when a text exchange would suffice sometimes makes me feel like a pest. But I know from experience that voice-to-voice contact has the power to render me visible again in a way that email or Slack messages simply can’t. So I do it anyway and trust that if my colleagues aren’t up to it, they’ll say so.

  • With self: When feeling invisible, my default is to communicate as if I am, as if my work is meaningless and has no impact. The frustration and powerlessness bleeds into my voice, and I come away from meetings feeling worse than ever. I’m learning to instead detach a little by pretending one of my coworkers is doing my job and then asking myself what their progress report might sound like. Then I give that progress report to the team. It helps.

*Managers of remote teams, pro-tip: You can help here. Your remote workers need some extra interaction. Schedule it. Don’t let out-of-sight-out-of-mind creep in. If you do, you’ll risk ignoring and starving your most productive people.

Benefit to the company: When your staff practices identifying limitations and asking for help, they build trust and get collectively more collaborative.

Again, the running theme in all of this is personal responsibility. Remote is kind of a DIY way of working. I have an employer, a boss, and coworkers, yes, but my level of job satisfaction is heavily dependent on my willingness to purposefully shape my day-to-day.

Remote: Ideal For Self-Starters

If you treat a remote job as if it’s onsite work, showing up in good faith and doing your thing to the best of your ability, you might struggle to find fulfillment. Why? Because remote isn’t onsite, where personalities mingle inside a dedicated location, and where group habits and workflow are shaped by that mingling, that location, and the influential physical presence of the bosses. With onsite work, we go to the company’s “house,” so to speak. With remote, the company comes to ours. As I see it, the key to getting the most out of working remotely is in never forgetting that it’s my house. As such, it’s up to me to keep it in order.

But then there’s culture... the rogue element that can undermine all of your efforts to turn remote cons into pros and the topic of part two.


Photo by Thomas Quaritsch