Jake McCrary

Tips for working from home

See all of my remote/working-from-home articles here.

I’ve been working remotely since October 2013. I can barely believe that nearly three years have passed and I’ve probably spent about two weeks in a traditional office.

It took me a bit of time to adjust to working remotely. I’m better at it now than I was three years ago. The rest of this post describes some of my learnings.

But first, some background. My remote experience comes from working at Outpace and Lumanu. Both are remote first companies, almost everyone works remotely with a few people occasionally working in a San Francisco office. The work is remote but it is not asynchronous. Both companies value pair programming and real time collaboration and, as a result, employees tend to work a core set of hours. My observations are probably most applicable in a similar environment.

Setup a home workspace

Before working remotely I did not have a great home computing setup. I worked using a 13-inch MacBook Air either sitting on my couch or at my dinner table. This worked fine for the occasional work-from-home day and for evening and weekend programming. It didn’t work fine when I was spending extended hours at a computer every day.

I’ve written about my setup before. Below is a list of the improvements I made to my home working environment.

  1. Outpace provided a beefy MacBook Pro and two 27-inch Apple Cinema displays.
  2. I upgraded my chair to to a Herman Miller Setu.
  3. I bought a mStand Laptop Stand to raise my laptop to a better viewing height.
  4. I upgraded my desk to a sit-stand desk.
  5. I built my own ErgoDox keyboard.
  6. I switched to an adjustable monitor arm so I could adjust my monitor height.

With each change my working experience improved. Each improvement left me feeling better at the end of my day. Many, if not all, of these improvements are things I’d expect to have in a traditional office. Don’t skimp on your setup because it is in your home. Part of your home is your office now.

Introduce a habit that delineates work from after-work

One of the great things about working from home is that you no longer have a commute. You don’t have to dodge cars on your bicycle, squeeze into a train, or sit in traffic while driving. This is a huge benefit.

A downside of not having a commute is that you lose a forced intermission between work and non-work. My commute was either a 30-minute bicycle ride or a 30-minute public transit ride. That time acted as a forced decompression period where I focused on something that wasn’t computing.

It took me months to realize that not having this intermission was stressing me out. The intermission helped me shift between working and non-working mindsets.

I reintroduced a decompression activity between work and non-work and became less stressed and generally happier. I’ve replaced my commute intermission with reading, cooking, or riding my bicycle. I’ve found doing a non-computer activity benefits me the most.

Stop working

When I first started working from home I was very guilty of overworking. It was so easy to just keep working. I would get invested in a problem and all sudden realize it was time to go to bed. Or I’d actually stop working, only to find myself checking our application’s monitoring or pulling up the codebase when I originally sat down to do some personal task.

In an office you have signals; your coworkers leaving, the cleaning crew vacuuming, air conditioning turning off, etc., that provide a hint that you should think about stopping. You don’t have these signals when you are working remotely. There also isn’t that spatial boundary between your office and your home.

You can search online and find many articles about how overwork is detrimental. You and your employer benefit if you are not overworked.

Get out of your house

I live in Chicago. During the winter the weather is very cold. Chicago is also a big city, so all sorts of food delivery options (both cooked and uncooked) exist. The cold weather combined with food delivery makes it easy to stay inside. During the winter, I’ve realized many times that I haven’t left my apartment for days. My girlfriend can tell when I haven’t gotten outside because I’m grumpier.

If I get out of the apartment for a while I almost always come back feeling better. It barely matters what I do when I leave, after an extended period of time inside of my home just getting outside and doing anything helps. A change of scenery is good for you.

Don’t just talk about business with your remote coworkers

When you work in an office you are pretty much forced to have non-work related chats with coworkers. You should do the same with your remote team.

Having non-work related conversations helps you make better connections with your coworkers. These better connections can lead to better communication, both with voice and text, and humanize the person on the other side of the screen.

Its even better if you can do this in a video conference. Then you get to learn the facial expressions and tone of voice of your coworker. This can make it easier to interpret text communication in the way they actually mean it.

Meet in person occasionally

It is great that technology and Internet speeds have progressed enough that working remotely works well. If you want, you can make it feel like your pair is sitting right next to you. This is great.

There are still benefits to meeting in person though. The main one is that it helps you make connections with coworkers. You can eat a meal together or play board games (though, you can do this online as well but it is a different experience). It can also be easier to have certain types of group discussions (video conferences do have limitations).

When you meet in person, I’d recommend doing something different than your normal day-to-day work. Don’t just exchange remote pairing for local pairing. Try to identify that are difficult to do remotely and do them in person.

I don’t have a concrete recommendation for how often your remote company should meet but I think it should be infrequent enough where you don’t feel pressure to do normal work.


Working from home has its challenges but with those challenges come many benefits. It is a different experience than working in an office and that experience isn’t for everyone. The above recommendations are things that have helped me adjust to working remotely. Some of these tips are actionable at an individual level and some require buy in from the company. Hopefully this list can help give guidance towards improving your remote work situation.

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