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The above picture is of me working while sitting with my dog, Hamlet, back home in Winter Park, FL on week two of my three week stay over the holidays. The fact that I can even write that sentence is entirely due to the fact that I work remotely. With that said, remote work requires a ton of navigating as our current society is really not built for this kind of work. More than anything, the problems and the perks revolve around social norms. Most probably view remote work as answering late night emails and phone calls long after they’ve called it a day. I worked remotely in college but interacted with people all day in class, at practice, walking around campus, in the library, etc. Looking back, I had the best of both words: no office and lots of human interaction. Now that I’m in the “real world” truly working remotely, I thought it was time to write down some thoughts. Note that these are all my personal experiences and aren’t the same for anyone who might also work remotely.

Navigational challenges:

The panic of needing help.

When everyone is in the office, you can easily find a go-to person for help with things go wrong. It’s also easier to see if someone is available to help or not. At Automattic, we use slack which sometimes likes to play games like showing someone as offline when they’re really online. Combine that with sometimes being the only person online at one point. I’ve hit an issue which urgently needed to be fixed only to find that I was out of my depth. While this is very humbling, it can also be very panic inducing because you literally can’t help.

Lack of “bad day” awareness

Sometimes you have a bad day or you’re sick or you have a headache. Unless you’re really good at faking your emotions, most of the time the people you are working with will pick up on you having a bad day. If you have really awesome co-workers, this means they’ll even reach out to make sure you’re okay/try to cheer you up. When you’re working remotely, you have to be vulnerable and state you’re having a bad day because, well, there’s no way someone else would know. Once you’re comfortable doing that, it becomes easier but I definitely had some bad days that went by unnoticed. Granted that can happen anywhere but I have found it’s much easier when you’re working remotely to have it happen.

Note: keep in mind that you could be overlooking someone else’s bad day! Make a habit to ask people how they’re doing whether you work remotely or not.

Not talking to another person all day. 

Unless you go to a coworking space, working remotely can leave you not speaking to another person. Being young and on my own without a family, this means that there are days where I won’t speak to someone for 9 hours straight. This requires some purposeful navigation because even as an introvert I know that we’re social creatures.

Societal Norms around 9-5 work days.

Welcome to remote work! Work whenever and wherever! This all sounds great but you soon realize that you are very much in the minority of the workforce. Combine that with social norms around the 9-5 workday and you soon find yourself working around the same schedule without thinking much about it. The worst part about this is that while you have the option to sleep in until noon or stay up until 3am in a spurt of inspiration, you’re also at the whim of your loved ones more rigid schedule if you actually want to spend time with them. I started an experiment working half days on Friday and then a couple of hours each day on Saturday and Sunday. I found that because of social commitments this was very hard to do. An internal survey actually found that that was the main reason people didn’t work more on the weekends. Eventually, I’d love to work Sunday to Thursday but that doesn’t seem like a solid option for me yet when the rest of my friends want to sit in Dolores park Sunday afternoon.

Forgetting to truly connect with your coworkers.

In the same vein as being unable to know when you coworkers are having a bad day, sometimes you forget to just chat with coworkers. We have a watercooler channel in slack where the company can do this but I find it too overwhelming and have actually “muted” it (won’t get notifications about conversations that happen there). I’ll peak in every once and a while just to see what’s going on but even then I’ve found that remote work prevents me from getting lost in conversation with coworkers. Many of my friends talk about going out to lunch with coworkers and talking for an hour or so. This is a bit of a rare occurrence in Automattic I’ve found personally. This is partially because there’s so much to do but also because the lack of body language and generally knowing how someone is truly responding makes it hard to jump into deeper conversations.

Reading into people’s responses.

I’m very guilty of this. Many of the more senior people at Automattic write very concise messages. This can leave me feeling like I said/did something wrong or that they don’t like me when in reality they are just used to being a bit more concise and to the point. Emojis help mitigate this but it is a very real problem at times because you have to make some assumptions no matter what when you’re just seeing a text response. Thankfully, Automattic believes “communication is oxygen” and this was only an initial fear that has since subsided.

Harder to turn work off.

Until I recently disabled mail and slack on my phone, getting away from work was incredibly hard. Being able to work from anywhere at any time can cause you to work too much without even realizing it. You have to be mindful to unplug or else you’ll find that working remotely just means you’re always working.

Reasons for Championing

Easier to take care of your health.

I have found that by being able to cook my own meals, workout midday, and get more sleep if I need it that I feel so so so much better. It’s unbelievable the more I think about it how lucky I am to be able to do the things I do. My job makes it so easy for me to take care of my health in so many different ways.

Set your own schedule.

This is an obvious one. As long as I communicate appropriately to my team, no one cares when or where I work. Have an awesome event you want to go to? Let your team know and go. Want to take a three day weekend? Let your team know and do it. Want to work until 3am on something because you’re completely in the zone? Embrace it and go for it then sleep in until noon the next day. I can go to the grocery store and the gym during off peak times thanks to my schedule.

Work with people across the globe.

This is probably one of my favorite parts about this job. Just on my team, we have people in Romania, Australia, France, Boston, and Pittsburgh. It’s incredible the strength this gives us.

Embrace moments of passionate work & withdraw during blah moments.

Remember those bad days I mentioned? Ping a team member and take some of the day off. Feel like you could just work forever? Go for it.

Travel as much as you want. 

Since joining Automattic, I’ve traveled to Utah, Denver, Boulder and Winter Park. In the next 6 months, I’ll travel for sure to Big Sur, San Diego, Vancouver, Auckland, Raleigh, and Boston. Not to mention that Hawaii and DC are strong maybes at this point. We only have so much time on this world and being able to explore it all is absolutely incredible.

Spend more time with those you love. 

I was able to go home for three weeks for the holidays whereas some of my friends were lucky to get three days off to see family. Being able to work from wherever let me spend time with my grandmother, aging dog, and caring parents. Beyond that, I was able to see so many wonderful friends who are still in college but had off for the holidays. Combined with being able to travel, this also means I can go visit loved ones without requesting time off to do so. This is an incredible gift that I don’t think I will ever take for granted.

No commute. 

Enough said.