Please don’t think this is what remote work is like

chris at home

I’m in my 7th year here at iwantmyname and 9th year doing full-time remote work, and I have a PSA for people testing the remote waters for the first time… this isn’t what it’s like.

If this is your first foray into working from home, you’re probably wondering how anyone gets anything done. Even with all the time saved from not having a commute and not having to get yourself dressed in the morning, everything feels like a slog. All your meetings that usually take 30 minutes end up taking an hour. Instead of just asking your cube-mate questions on demand, you have to ask questions on Slack, or in a Zoom meeting. The loneliness probably feels oppressive.

If this is the future, you’re asking, you’d probably just rather opt out. The truth is that this mandated isolation is hell. Even remote veterans think it’s hell, because the reason we found ourselves remote jobs was so we could be free. Not free of wearing pants—free to get lunch wherever we want, whenever we want, with other human beings. Free to meet for coffee without asking a supervisor. Free to work around other friends who are also doing remote work.

For a remote worker, not being able to leave the house is so much harder than for a desk worker. None of this is a novelty. It’s amplifying the worst parts of remote work and canceling out all the good.

My fear here—aside from catching the plague—is that this experience will dissuade people around the world from diving into remote work down the line. So I want to set things straight. To explain, as clearly as I can, how nice remote work can be, what it’s is all about, and how to make it work for your company.

Thing 1: You can wear whatever you damn well please

Long ago, right after the dot com bubble popped, my dad quit his Big Corp investment job to go his own way (y’know, as a subsidiary of a slightly smaller Big Corp), eventually moving from a rented office space to his spare bedroom. He started out in formal clothes, presumably to feel more business time. Then he moved to polos, because polos are the casual Friday uniform—still business appropriate, but not really. Now he just wears his tennis clothes so he can go from work to life with maximum efficiency. That’s what remote work is all about. You’re not saving all those commuting hours to be able to put more work hours in; you’re saving them to get your life back. So stop dressing for the job you want. Dress for the life you want.

My uniform? Gym shorts and a hoodie. If it’s cold, I wear a robe.

Thing 2: You can work wherever you feel most comfortable

It’s different for everyone, but I short circuit a little when I see people spending thousands and thousands of dollars on home office setups when they first go remote. You don’t need it.

I’ve worked for seven years floating between a bar stool, my breakfast table, and a patio table outside. None of my chairs are ergonomic. Heck, none of them even have padding. But there’s a ton of natural light, my speaker system always has good tunes, and I do most of my thinking on a skateboard in my hallway.

Not everyone would be comfortable with my setup, but that’s kind of the point. Don’t let anyone tell you there’s a right or wrong way to set up a workplace. If you feel like you need a work throne with multiple monitors and a perfectly organized desk to get things done, then go for it. If you don’t, you don’t.

(Also, don’t force yourself to fit into a coworking space. They work really well for some people, but I just don’t work well in big office settings. I’m the guy who would book meeting rooms for my small team to get out of the open-concept bullpen, and would do just about anything to sneak out and work from a quiet coffee shop. Some people really like the frantic energy of an office; I tend to like calm spaces.)

Thing 3: You get to plan your entire day

Sitting in an office all day can feel oppressive. Schedules are made for you, you’re supposed to be consistently available, and there always seems to be someone looking over your shoulder (I previously worked in an open concept, so maybe cube farms are a little different).

As a remote worker, your schedule is yours, and you can do with it as you please. It’s incredibly freeing—but if we’re being completely honest, it can also be a little toxic. When you’re sitting by yourself at home, you’ll find a million things you need to do that aren’t related to work. You’ll find yourself doing laundry, cleaning the house, excessively walking the dog, cooking elaborate meals, running errands that don’t need to be run. It’s a thing that’ll happen… I promise.

The way to beat it is to embrace inefficiency. If you get down on yourself every time you feel like you’re being inefficient, you’ll spiral out of control. Instead, try to plan out blocks of focused work, then let the rest happen as it may. Use your focus time to turn off comms, tune out the world, and do the actual work that needs to be done.

I try to separate my day into three blocks:

  1. The first two hours I do comms and simple tasks. I drink my coffee. I plan my day. Sometimes I head off to places to work.
  2. Then I take on a four-hour block (cut by lunch) where I try to get real work done with no distractions.
  3. In my last two hours I try to fit everything I’m doing into the broader picture. I upload files, talk to people, finish tasks, plan the next day, etc.

Inefficiency will happen, and every day will be different than the one before. That’s life. Sometimes you’ll feel like you need to work out, and sometimes reading a book can get your mind straight.

Thing 4: You don’t have to work a complete 8-hour day

The majority of an office workday is spent on nonsense. Nonsense meetings. Nonsense checkins at your desk. Nonsense team building efforts. Nonsense reporting. People treat work hours like they’re a checkbox that needs to be checked, but in reality, work is about scope. My role has X scope, and I really only need to work until the work gets done. A good manager knows this, and doesn’t care if you work 5 hours or 12. The results are the key—burning the candle at both ends should only happen if someone’s:

  • a slacker who tends to do things last minute
  • scared they’re going to get fired
  • so energized by their work that they’d rather be working than sleeping

If you’re managing a team, the difference should be obvious. And if you have people joyously working long hours, congrats—you’ve successfully ignited a spark. Now tell them to log off and live a little.

Thing 5: Be sure to set work/life boundaries

One of the harder things you’ll encounter is explaining to your significant other that just because you’re home, you’re not handling home responsibilities. It’s challenging. Yes, you can technically do a grocery run, or take the dog to the vet, or vacuum the house, or do the laundry, but it can’t be the expectation. When you’re at the office, you spend your downtime socializing, getting coffee, or blankly staring into space. Treat your home exactly the same. You’re fine to take on domestic tasks if that’s what helps you clear your head, but if you don’t make work your priority, it… won’t be your priority.

Thing 6: Everyone will quickly realize that meetings are an inefficiency

There are three and only three reasons you should ever have a scheduled meeting:

  1. To start a project
  2. To talk through a major obstacle
  3. To infrequently appear somewhere so you remember what your coworkers look like

To be clear, I spend a decent amount of time each week on Zoom chats, but they’re usually reserved for talking about movies, philosophy, and how dumb things sometimes are (everyone needs to vent). They’re chats. I mentally try to keep them to a minimum, but if you have a good conversation going, you can always chalk it up as team building.

Meetings, on the other hand, are almost always a waste of time, and everyone knows it. Aside from infrequent checking to clear hurdles, most meetings are designed for managers to feel like they have a grasp on what’s going on. But it’s a trap. I’ve been a manager—if your team isn’t getting anything done, it’s almost always because the project is significantly flawed, or the work you’re asking for is dreadful. As one of our devs likes to say, “yes, I’ll shovel shit… but it’s not going to be pretty.”

So if you’re just getting into remote work, stop scheduling daily meetings. Just stop it. Send an email. Learn to express your thoughts and communicate effectively over text. Scope projects to where everything is visible, all the moving parts are accounted for, and no one is tasked with doing “the awful thing” alone (there’s always an awful thing that needs to be done… never assign the whole pile to one person).

Thing 7: Asynchronous communication is freeing

When you’re in an office, you can just ask someone a question and get an immediate answer. I imagine the lack of instant communication is killing people newly working from home right now.

A good remote workplace takes this need away. You’ll quickly learn that if you scope projects correctly, document your thoughts effectively, and put trust in your team to make the right decisions, your need for immediate responses fades away. Not completely—there will still be a need for a quick Slack every once in a while—but it’s minimal.

The key to making this work is to find the right tools. If you want to reduce friction, every project should be mapped out on a platform designed by people who care about UX, built for people who aren’t necessarily devs… or managers. You don’t want to build out a project for a copywriter on GitHub Issues. GitHub is not a delight to use, and will absolutely drive a non-dev to madness. Find a platform that’s a joy to use, and set loose expectations on how to operate it.

This, again, is where written communication is critical. If you want to rely less on face-to-face communication, you have to get good at writing your thoughts and properly explaining situations. It’ll feel weird at first, but over time you’ll see that asynchronous written conversations can be much more thoughtful and reasoned than quick chats could ever be.

Thing 8: Just be sure to minimize the tools

Back in the old days of iwantmyname, we ran through countless platforms to find the right balance. At one point we were using different platforms for every tool, at another we were trying to force everything into platforms that didn’t quite fit. We did project management through GitHub, email, Trello, Monday, until finally landing on Basecamp, with GitHub on the side for devs. We’ve used productivity trackers, countless text, audio, and video chat tools, every file storage system imaginable. On and on.

Unfortunately, there’s no perfect solution for a remote team. Even our situation—it feels pretty functional now, but it’s impossible to know how it’d scale. The key from top down is to be empathetic, be consistent, and to realize that the more complexity you introduce, the harder it will be to get everyday tasks accomplished.