Tips from 16 years of working from home

I just read Mike Davidson’s great post on remote work advice after a year of it at Invision. I realized I’ve been remote for four and a half years at Slack and before that I ran my own company from my home office and before that I worked remotely as well. Since I moved to Oregon in 2003, I haven’t worked in a traditional office and I wanted to share the things I’ve learned.

A dedicated space is vital

The most important thing that made this a stable, reliable, and workable option in my life was getting a dedicated room in my house set aside for work. Having a home office with a door that cut me off (mostly) from whatever else was going on in the house was key to making it all work.

I freelanced for years in San Francisco from a desk in the center of a tiny apartment and my work was inconsistent. It was always a challenge to concentrate and get into a flow with distractions everywhere. Later in Oregon, I had a larger apartment with my own loft space dedicated to my desk, but it was still open to the rest of the apartment’s various noises and continued to derail me.

When I moved into a new house in 2005 that had a dedicated home office with a door (just like any other bedroom, but with no closet), everything changed. Now I had a place to work, even if my commute was just down some stairs. I could shut the door and have a quiet space, even when I had a toddler in the house early on. The door is mostly glass, but my family knows if it’s closed completely that I’m in a meeting. Having a glass door was a good middle-ground between total isolation and still knowing what’s going on in the house, so if something urgent was happening I could see it and help out.

Simply put, having a dedicated space lets you do more concentrated work, take video meetings in peace and quiet, and also helps separate your work from your home life when you have a room as a work-only space.

Coworking spaces are ok, but far from perfect

I want to mention coworking desks because it’s not a bad solution for remote employees. You get a work space that isn’t in your home that you can commute to, you can interact with others, and you still get your work done. After trying out a few different options, I found that even though coworking spaces were slightly cheaper than trying to get your own small office, it wasn’t drastically cheaper. Where I live, a very small office might run $400-500/mo while a coworking desk is closer to $250-300/mo.

Coworking’s biggest problem for me is how you have video meetings in peace and quiet. At a busy coworking space, often people put on headphones in the middle of a large table full of people and just participate in their meetings. I find that behavior obnoxious and of the three coworking spaces I’ve experienced, all had different options for “a quiet room” that ranged from hard-to-get free phone booths to requiring you to book a private space for a meeting (some charging up to $50 per half hour).

Being remote means you’re going to have a lot of video meetings, and this is where a very small private office somewhere for slightly more money can make more sense.

Pro Tip: Your local library is like a coworking space, but free

Most local libraries (ideal ones are college libraries open to the public) have decent wifi, desks, and places to work alone for no cost. Doing video meetings is still an issue, but it’s a great place to work without bothering anyone or being bothered. I tend to listen to white noise (from Noisli) on headphones and I can get more focused work done in a small cubicle study desk than even my own home office. The college library I often work out of even has dedicated quiet rooms I can borrow for occasional meetings when students aren’t using them.

Remember to get out and interact with people

Six months after I started working from home, I was at a cocktail party when someone asked what I do and how things were going and I suddenly clammed up. I stammered out something and later I realized I had become terrible at making small talk by being out of practice on my own.

Ever since, I’d made a point of getting out of the house every day even if it’s wall-to-wall meetings and I built into my budget going out to eat lunch in town most weekdays, just to regularly interact with strangers.

It may sound silly to extroverts, but I warn everyone who starts working remotely for the first time to remember to keep deliberately practicing small talk by interacting with strangers because it’s way too easy to fall into a hermit lifestyle in your own space.

Video is important and worth taking seriously

Video conferencing has been awful for 25 years but in the last few years Zoom has really transformed video for meetings by just being reliable and smooth and is a killer tool I use many times a week. Zoom is now my lifeline to colleagues and for something that important, take it more seriously than using the default camera that came with your laptop.

Have a clean, clear room as people may obsess about what’s behind you

Place your desk in your home office so your background has very little clutter. Be careful of windows since it can throw off your camera’s exposure and make you look weird when backlit.

Find a webcam with the widest possible angle camera lens

In modern offices you’ll often be shown in a room on a 65″ TV monitor and it wasn’t until I was visiting an office and I was in a meeting with someone else working remotely when I realized just how HUGE the remote person’s head was when they’re the only one on video.

Zoom’s office video cameras are extremely wide-angle so you can fit a whole room in, and you’ll want to shoot for your head taking up less than 50% of the frame, and a wide-angle lens is key in your home office as well. An old GoPro can make a great super wide-angle webcam, but it’s kinda tricky to setup. My favorite nearly-as-wide 4K webcam with an easy setup is the Logitech Brio. It’s plug and play on a Mac and it’s less than $200. You’ll get better color and lighting in video than a default laptop camera, and going wide-angle also means your head won’t be 4 feet tall on a monitor in the main office, since there will be more of your surroundings in the shot.

Light yourself

Another pro tip: put a Seasonal Affective Disorder light on your desk, next to your monitor but aimed at you will brighten your face up considerably. Trust me, you’ll look much better with some light on you (and maybe by accident in the winter you’ll feel better—who knows).

Apple AirPods, 1000% percent

Apple AirPods are the best simple headphone/mic combo that works great with Macs and Zoom. Your ears won’t sweat or overheat like over-the-ear headphones and the newest ones can run for 2-3 hours between charges. They’re so small they barely show up on video and without wires to trip you up, you can move around as needed during a meeting. They’re pretty much perfect for video conferencing, even if you think they look silly (and yeah, they’re a tad expensive).

Remote is better for some roles, unfortunately

Mike mentioned this in his post, but I would agree with him that today, remote jobs tend to favor more senior, specialized positions where it’s easy for someone with lots of experience to take on a self-directed role. My current one is ideal for remote work, where as a senior writer with 20+ years of experience I can go off to write by myself for hours, and it doesn’t really matter where I am doing the work. Other writers on my team tend to do the same, working frequently from home or in the office library—wherever they do their best work—and it’s rarely at their office desk.

For now, it’s likely harder for junior employees in new roles to have a great experience while working remote at most companies, but I hope it’s changing as remotes roles become more accepted and companies implement it in a thoughtful manner. In 5-10 years this should be much more accessible to junior positions but it may be a bit more of a challenge finding jobs that support you remotely for now.

It sucks being the odd one out

I work for a big company with offices around the globe so whenever we have cross-functional meetings, having 3-4 people in various locations over video conference is the norm, and those are the easiest meetings to feel equal with your colleagues. On smaller projects and in smaller teams, I’m often the only person not in the main office and those are tougher. I don’t know why but it gets WAY easier if there’s at least one more person on video with a larger team in the main office. Just something to keep in mind—when you’re the only remote person on a team, you’ll have to do extra work to feel like you’re on equal footing with your office coworkers.

A good Slack team makes it all possible (but only if it’s good)

I’m biased of course (I work at Slack), but a Slack-first company where everyone communicates in Slack and tracks projects in Slack and does standup meetings in Slack makes being remote as close as humanly possible to being in the office. The first time I visited Slack’s early SF office, I couldn’t believe how quiet it was, since everyone was “talking” in Slack instead of over their desks. It made it easy to work from home, since I knew I wasn’t missing much aside from hallway rumors, as everything else took place in Slack.

It does require discipline in how your company uses Slack. It’s good to have a bit of water-cooler chat in #random, but also have a team channel with your immediate colleagues where you check in with each other every morning. For distributed teams, doing work in project-focused channels is a great way to coordinate everyone’s efforts. It also helps to have a culture where asynchronous communication is OK. Not every Slack conversation I have with others has the expectation they’ll answer me immediately. In fact, in my own team of writers, we tend to chatter away in Slack the first hour of our work day, then it slows to a trickle until the end of the day with people checking in and updating everyone on their work before they head home. There are times where I get 3-4 hours in the middle of the day without a single ping from Slack, and it’s only because everyone is conscientious of how and when they choose to alert others. It takes a lot of discipline and practice and people that are thoughtful about how they work together.

Touching base with the mothership helps a lot

I know a lot of remote-first companies do giant company trips where everyone meets face-to-face and they plan their work ahead together in person, and some companies do that once a year and some do it twice a year. Over the past few years, I’ve found an ideal cadence for me is going down to San Francisco every 1-2 months for a couple days of meetings. It’s only an hour-long flight for me, but I find if I haven’t been down to SF in 3 or 4 months, I start to feel a bit out of touch with my team. I tend to pack my days in the office with meetings with people from all over the company and we typically plan the next few months of work. I find the best type of work in person is brainstorm sessions where the ideas come fast and loose. You can still do those meetings as a video chat, but they just work better when everyone is in the same room riffing off each other.

Work/home balance is an obvious problem

One of the thorniest issues working from home is learning to separate your work hours from your home hours. At an office, the change of location and scenery makes it obvious. At home, I feel weird taking a whole hour to get lunch. I tend to check in on things at night, and sometimes I start my workdays early. Studies show remote workers tend to work 10-20% more from home because it’s so easy to lose track of your time.

It took years of working way too much from home and having trouble shutting down from work mode to realize I do my best work when I give myself boundaries. Maybe it’s don’t start work until 9am or walk out of your home office every day at 6pm and don’t return until the next morning. It might be no laptops or phones after dinner. Whatever system you devise, figure out your guardrails to protect your off-hours. When I ran my own company I didn’t have an unplugged weekend for over a decade and it was awful for me and all the relationships around me. These days, I relish my time off and the more I wall off personal time from my work hours, the more diligently I can work during the day.

Don’t forget to move around

Another obvious one is you need to build exercise into any remote work arrangement. When you’re not commuting and you’re in your own place you’re going to walk much less. About a decade ago I started going to a gym with a trainer waiting for me twice a week in early mornings. We mostly do core and flexibility work, and it keeps me from getting injured whenever I go out and do physical things like cycling, running, or kayaking. Without a trainer, I couldn’t motivate myself to do this regularly, so that part is key to make it stick for me.

Outside of gym days, I also try to do before or after work exercise, and this year it’s been early morning runs and weekend cycling, and during summer months I try to ride my bike around town as much as possible.


The benefits of remote work can’t be ignored. You get to live where you want and support your family without having to spend a lot of time away from them commuting to an office. On the flip side, the company gets the best possible person for the job and it’s probably cheaper for them in the long run, but every company is different in how they support remote employees. Depending on the role and the company, it can be a challenge to feel connected and part of the greater team and takes constant upkeep. It’s been a great experience for me personally, and I hope it becomes the norm for a lot more people and companies in the future.

3 thoughts on “Tips from 16 years of working from home

  1. If you’ve got the space a wide angle lens is great. If you use a backdrop, a pop up or a hanging green screen for your Zoom virtual backgrounds a wider angle betrays the edges of your backdrop. Or in smaller areas hints at compromises in your home office set up if you’re in a city with limited real estate and smaller rooms.

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    1. I have a big room but a weird window and a messy clutterpile to one side, but in a similar methodology I got an aftermarket camera (okay but not great, on purpose) and put it up higher and farther away from me than monitor distance, so it’s nearly two arms’ lengths away. That still reduces Big F’n Head Synrome some.

      I’ve also been fully or partially remote for 20 years, and I don’t think I’ve seen anything change culture as fast as Zoom has. It just works, in ways that gotomeeting never did and skype never even dreamed of, and the recording function is so easy and usable that we now record everything for cya purposes, but also I can record a user getting an error and send that over to the devs, or I’ll record myself alone and send to a customer instead of finding a meeting time to train them on some quick thing, or if I’m the first person on my team to have to dive into a new feature/add-on, I’ll record that and give it to them. My team is all remote, and we have a monthly happy hour on video.

      I still hate video meetings because it means I can’t just roll up to my desk with my bedhead in full force every day, but we’re still conservative in our application probably in part because of camera limitations. It’s coming, though, I can tell from the way our very online/younger hipper clients are accustomed to video-on default.

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  2. Great article. I started working remotely early 2018 (my physical activity reduced) and within six months I gained about 10kg. I felt good but my energy and productivity level dropped significantly. So you are absolutely correct about incorporating “regular exercises” to daily routines as a remote worker. Thanks for the library tip. Will definitely try it…

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