Part memoir, part unsolicited advice. Read at your own risk…

I’ve worked from home more often than not for 25 years. As a writer (mostly of software) who craves and sometimes requires a minimum of interruptions, I have often preferred the home office to the work office.

Even so, working from home is often difficult, and in a time when many of us are exploring the home office for the first time under arduous circumstances, I thought I’d write a post to confirm that yes, working form home can be very tough, share some solutions that have worked for me, and try to make the case that working from home can require developing a complex set of new skills that can take months and years to master.

Firstly, my heart goes out to everyone who is having to work from home in a sustained way for the first time in these trying weeks. Last week was about as scattered as I’ve ever been. The news is distracting. My 16, 14, and 11 year olds were home from school and I was continuously at a loss for what my role should be as a parent (of course they need much less from me than they did when they were little, when a single child at home could be enough to utterly derail everything). Working from home is my happy place, and last week was all sorts of challenging, even with everyone healthy and in good spirits. So if this is new to you, know that you’re trying to play a new game on the hardest setting.


Creating boundaries around work has always been hard for me. I like to get lost in my work in the best of times. When I’m not at my best, I try even harder to lose myself there. This has meant years of work figuring out how to manage boundaries. I was inspired 25 years ago by the story of a home worker who would put on a suit in the morning, walk out the front door with their attaché case, and walk around to the kitchen door in the house to “go to work.” At the end of the day, they’d do the reverse commute. For many of us it is really important to find a way to “leave” home and “go” to work. I don’t watch TV when I go to work. I don’t work when I’m at home.

Some of you are naturally good at boundaries. Hooray for those times in life when a hard thing is easy! The rest of us wrestle with them to some degree, and many of us do so in very different ways. I often want to jump into work first thing, perhaps at 4am. We all get that this is never a good idea, right? In my case, it’s generally not a good idea for me to start before 7am, unless I’m working with people in different time zones, in which case it sometimes makes sense to be flexible. But if I start work at 5am, I need to make sure that I don’t try to work a full afternoon because I’ll get loopy, or worse.

Those of us who need boundaries all need different boundaries, and where a good office often provides useful norms about work and non-work times, what constitutes work and what doesn’t, etc., when we’re at work we’ll have to figure this stuff out on our own. If you’re like me, it may be a slow process with lots of trial and error. Be kind to yourself if you’re at all self-conscious or impatient about learning new skills. Be kind with your colleagues!


Teams change all the time. Someone joins or leaves a team, you will often learn that you’re on an entirely new team. Someone moves away and becomes remote, you may have a new team; working next to someone isn’t the same as working with someone who is three time zones away. Assuming they’re diligent, they’ll probably get more of some types of work done. Assuming you’re both human, communication and collaboration will evolve, and will likely be harder. The work that remote people do is different in nature, tone, feeling, and innovation. Sometimes better, sometimes worse. Usually different.

If your team transitions from the meatspace to cyberspace, you may now be on a different team. Your role may evolve in ways you don’t anticipate, and perhaps in ways that you don’t much care for. The people you work with are likely to interact with you differently, and to perceive the way you interact with them differently. Parts of this will be amazing, for example when you find out that a colleague has a skill that you didn’t know about. Parts of this may be hard, like when activities that once came naturally to you are suddenly challenging.

Maybe it’s because there’s a pandemic. Maybe because there are kids in the background. Perhaps it’s due to reasons that will never be entirely clear. Even if your team was already virtual, when the economy goes into free fall and everyone is worried about the health of loved ones you may find that you’re all of a sudden on different team. We never step in the same river twice.

My assumptions are often wrong

This has very little to do with being remote. I make silly assumptions in the office. I do it at home. I jump to unfair conclusions too often. If this is ever something you struggle with, it will probably happen when you work from home too. But if you start making different sorts of assumptions, you might find yourself discovering new ways to be wrong.

Dozens of new skills

I like to tell people that learning to work remotely takes about a year. I’m still learning how to do it 25 years later, so it’s not the kind of journey that has a destination, but it’s helpful to remember that it takes many months.

In additions to boundaries and getting familiar with your new team:

  • Object permanence is hard for humans. People will forget about you if they don’t see you across the table from them. You may forget about them. If someone forgets about you, try to reintroduce yourself. Sometimes you may need help from others if they’re really missing a chance to notice information that you’re trying to share. Conversely, be more curious than you would otherwise be. You’re likely to miss things that you’d have noticed in the office. So it goes.
  • Learn to use new collaboration tools. For example, I spend a fair amount of time watching other people’s screen when they code, and sharing my screen when I code. If we don’t write together, we’re not working as a team. Learning to collaborate virtually means using tools I’m sometimes uncomfortable with. Seriously, learning new tools and collaboration habits is challenging, and hardly any of us get good it without being bad at it first! Tens of thousands of teachers who have spent years honing their classroom management skills are about to step into virtual classrooms, often for the first time. What an incredibly brave thing to do! Learning new skills is courageous.
  • Take lots of breaks! Sometimes, working on something for a very few minutes is enough. It’s rare for it to be productive to work for more than an hour without a break. Synchronizing breaks with remote teams is hard. Do it anyway. People need to get up, stare out a window, go the bathroom, etc.

If you’re creating a new process with new tools and a new team, you’re doing 20 new things. It may be slow at first. Practice. Try again. This is hard.

Thanks for coming to my Ted talk!

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