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Things I’ve learned from 12 years of WFH

I’ve read a lot of articles in the past week about folks kind of discovering working from home and telecommuting for the first time as a serious thing. I’m finding myself eye-rolling at some troubles folks are having – but then I remember I’ve been doing this for over 12 years. I’ve all but forgotten the troubles I had, way back when.

So, I’m trying to remember. I’m not sure if anyone needs to hear this stuff from me specifically. To be clear, I am not a perfect paragon and often make mistakes. But, I’ve thought about this stuff a lot over the years and I have some standards & notions that I try to apply to myself:

Telecommuting isn’t trivial. If you expect to just jump into it and have everything go great right away, you will be disappointed and waste a lot of time – both your own and others’. That said, telecommuting isn’t impossible and I’ve found it so incredibly rewarding that I never plan to consistently work in an office ever again, if I can help it.

Telecommuting requires some of its own specific skills & habits. So does working in an office. But, since working in an office is more mainstream, those skills & habits are way more common & well-known. I think a lot of frustration & disappointment is that folks are surprised when a mishmash of habits from work & home fall flat.

Telecommuting is a lot about ritual and projection. That is, the rituals by which you govern yourself and the persona you project to others. Putting this all in a semi-magical frame has helped me make sense of things, so I hope you can forgive me straining some metaphors here.

You need a ritual space. An office provides that. At home, you’ll need to mark off the circle for yourself. Clearly delineate where work happens. Reserve a room if you can. Have at least a corner with a special table & chair. Don’t work where you relax & have fun. Try not to work where you eat. You need set & setting specifically allocated for work – this both trains your mind into a certain configuration and helps signal to other housemates that you’re in work-mode.

You need ritual garb. More set & setting. In the beginning, I put on a polo & jeans & shoes in order to signal to myself that it’s Serious Work Times and not time to go play Rock Band on my Xbox because no one’s watching. These days, after years of practice at conjuring up a proper frame of mind, I’m productive & comfy in a hoodie and pajamas. Sometimes I wear a silly hat because I like my hat and it’s warm. However, I did, at one point, literally have separate silly home & work hats. A good chunk of magical practice is putting on little dramas for audiences in your own head.

You need ritual time. In an office, the natural flow of people can act as a clock. Time to chat; time to work; time to meet; time for lunch; time for snack; time to leave. Early on, you might need artificial support to establish these rituals in your new space. Maybe make appointments with yourself to lay down a new rhythm. There’s nothing worse than getting caught up in work (or putting off work) to realize you’re two hours late to eating, which might sound trivial but can make you feel like garbage and wreck the rest of the day.

You need to practice projecting yourself as intended. Doing this in person is far more natural, at least to people who go out into the world to work on a daily basis. Doing this while mediated through technology is less natural for most folks.

In either case, whether you realize it or not, you are performing a version of yourself through the medium at hand. So much of telecommuting consists of projecting a persona through audio, video, and text. You will need to apply mindful intent to these things.

At the risk of putting too fine a point on being performers and portrayers – here, have a musical interlude:

When I first started, I tried some mock calls. I recorded myself with my setup and reviewed the results. Yes, it’s cringe. Do it anyway: take notes, make adjustments, get better.

It’s easy to miss social feedback signals when mediated by wires rather than air. You don’t get the same echoes back that we’ve evolved to react to as social primates, you have to lean more heavily on awkward analytical judgement. I can’t say I’m anywhere near perfect, but I have internalized this as a thing of which I need to keep aware.

For example: Are you quiet when you enter a physical conference room with a meeting in progress? Is your microphone muted when you enter a video conference room? This is a thing you have control over – not controlling also sends a signal. How’s your volume; can everyone hear you typing; are your clothes scraping on your microphone; are your dogs barking; are you coughing and sighing? Is that what you intend to project?

You may need to project simulated signals of availability. You will find that you receive unusual demands on your time – quite often as part of unexpected assumptions around your presence. For example, in many chat systems, you may look open for messages when you’re not. You might be busy, you might be done for the day, who knows?

I’ve found a few ways to deal with this: I tend to keep regular hours. I try to explicitly announce when I’m around or not. I block off openings in my calendar.

Sometimes, I intentionally ignore messages or defer a response for later. This might sound passive aggressive. It might even make you feel guilty. But think about it: What happens when you’re not at your desk? At least then, you’re projecting a signal with your absence. You may have to intentionally & artificially simulate the same thing via technology.

You will need to work on your writing. You’re going to have to do a lot more of it. Are you projecting what you intend with your words? There is a balance between clarity & formality vs being casual & comfortable. That balance changes if or when your writing becomes more of a primary channel – versus being able to pop over to someone in person to elaborate.

Additionally, written comms tend to more easily become part of a persistent record. This is a benefit, if we’re considering maintaining knowledge for a team or working between disparate time zones. But, recorded misunderstandings can come back to haunt. Again, I’m not perfect, but this is constantly on my mind.

I’ve gotten more sanguine about this over the years. But, if you want to read me rant on this subject – check out my old post “Too long? Read anyway.


You need better tools. Your phone’s out-of-box earbuds are bad. Get a better, comfy headset. That, or a good speaker phone. It matters. Make sure you appear as intended on camera. Again, practice & review despite the cringe.

Try not to use WiFi – instead get a wired connection to your work machine. Get better internet to your house – if you can, maybe even look into a business-class connection with a better service-level agreement. You might be out of luck, but this can make a difference too.

Get a nice chair. Get a nice desk. Get a nice monitor, mouse, and keyboard. Pay attention to how you feel and get precious about the placement of things, because you’re going to be in this place & posture for hours. Believe me, wear & tear on your wrists & spine happen so gradually and are almost impossible to fix.

Enjoy and assert your flexibility. Go out, take a walk when you can. Take your laptop somewhere different to work for a change. Maybe out in the sun at a table under an umbrella, if the season allows. Run some errands during the day. Catch up on a few hours of work later at night.

Admittedly, this is kind of an advanced stage: Your management needs to trust you and not micro-manage. You need to trust yourself that you will get things done, for that matter. You need to have a good grasp on balancing day hours versus night hours.

I’m still working on this. I go in cycles. Sometimes I’ll take myself out to matinees in empty theaters on days when I have no meetings. Some days I feel guilty stopping to grab lunch. It’s a process. But, it is one of the huge benefits to this way of working and it’s a shame to waste it.

You need to be part of an organization that supports all of this. As opposed to everything else I’ve written about so far, this can be mostly out of your control. Maybe management isn’t comfortable with the necessary level of trust – and so your assertion of availability & flexibility is strained. Maybe the company won’t provide or pay for better equipment. Maybe you’ve been tossed abruptly into the whole work-from-home situation and haven’t had time to assess or improve anything.

Focus on controlling what you can, when you can. This starts mainly with your rituals & projections. Improve tools when possible. Beyond that, if you’ve got the energy, maybe you can push your organization to do better. Part of why I’ve been where I’ve been for so long is that my organization has already figured a lot of this stuff out, so I’m lucky. There are a lot of folks here who fiercely defend our remote work culture.

Anyway… I don’t have a great closing statement for all of this. And, of course, many of these things don’t apply solely to telecommuting. Improve your your rituals & projections with mindful intent. Hope your organization supports all of this. Help your organization support it, if you can.

Ideally, you can find the good parts in all of this. Maybe a balance between work and life that grants you more interesting flexibility than the standard nine-to-five. Just don’t expect it to feel immediately natural – expect to do some work to adapt. I know I’m still working at it myself.