5 Tips for Working Remotely

Before joining Automattic in 2019, I worked as a freelancer (remotely) for about 12 years. During those years, I learned a great deal about managing my time, creating systems, and staying motivated while working from my home office and all of the distractions being at home brings. Of course, I’m still learning new ways to be effective and organized (never stop learning!), but I thought I’d share some of my tried and true strategies.

1. Know Thyself

Socrates was really onto something when he said, “To know thyself is the beginning of wisdom.” I would venture to say that it’s nearly impossible to change your life if you aren’t at least somewhat aware of what makes you tick. I’ve always been a fan of the study of personality types and have found that particular knowledge is incredibly useful when it comes to both understanding myself and understanding others. My favorite source for determining one’s personality style is 16personalities.com. I’m an ISFJ-A, meaning I am an Introvert, yet I am deeply social, I’m organized and detail-oriented, and I have a tendency to overcommit. 🙂 Of course, there are other traits to my personality type, but these are the ones that I’ve seen really come into play while working remotely (or anywhere, really!). Another good tool is the Enneagram (here’s a free test!). Knowing your Enneagram type is especially useful in determining what you tend to do when under stress.

Knowing why you do what you do and react how you react is a great tool to have in your wheelhouse, whether at work or in your personal life.

2. Have Realistic Expectations

I am not a morning person. This is a fact that you will learn quickly if you encounter me before 9am. I get up earlier than that most of the time; however, I do not want to talk to anyone. At least not until I’ve had my coffee (or two or three coffees). I really hit my stride around 11am or so. I know this about myself, so I know how I should structure my day for me to be the most effective…and tolerable to be around. 😉

What does that look like on a practical level? A few of my rules of thumb:

  • Don’t schedule early morning chat support sessions (when I was a Happiness Engineer) – it’s not pretty, and I struggle to troubleshoot effectively.
  • Avoid early morning meetings. I mean, I can attend these meetings; I’m just more engaged if my brain is warmed up first!

In short, I know and accept what my limitations are. I am probably never going to be a chipper early-bird. And I’m a-okay with that!

3. Have a Dedicated Workspace

I realize it’s not always practical to have an entire room for your office. If you’re unable to dedicate an entire room to your office, at least have some sort of visual barrier like a curtain or screen. This is helpful when you have children at home to remind them that you are working. This also works for chatty partners at home.😉 A visual reminder that this is your workspace will also help you put work down when the day is over. Who likes to stare at a pile of work when they are off the clock? While working from home, it is especially important to your mental health to have a clear division between when you are working and when you are not working.

4. Don’t work in your PJs

Okay, so I will be honest that many of the people I work with work in their PJs. And that works great for them. I, too, like to be comfortable while working. I mean, that’s a serious perk of working remotely! That said, I find I’m more productive when I make some sort of effort with my morning routine. This includes getting dressed, brushing my hair, and brushing my teeth. 🙂 (Pro Tip: Sweatpants and leggings are pants, so it counts as getting dressed!)

5. Take Breaks!

When I first started working remotely, I essentially kept myself chained to my desk. That made for some really long days and nasty headaches. I’ve learned over the years that I need to take occasional breaks and step away from my workspace. I’ll walk my dog, help my son with schoolwork, do a few chores, or sit on the couch and simply take a breather. Sometimes I’ll even take a 30-minute power nap. Taking breaks throughout the day is not only helpful for your mental health, it’s also good for your physical health! Be sure to give yourself plenty of time to stretch your legs, stretch your neck, and get away from the screen for a bit.


Interested in becoming a Happiness Engineer at Automattic? Visit the Work with Us page to learn more about how you can apply!

2 thoughts on “5 Tips for Working Remotely

  1. Hi Missy,

    You shared really incredible insights there. I’m not a morning person either, and what I experienced while working from home is that looking presentable made me feel more in control of the day ahead, productive and confident in case an unscheduled meeting drops in my inbox. So, you Pro Tip is on point 👍🏾😊.

    My biggest challenge was taking frequent breaks, not because I was a workaholic per sè but more concerned about the workload on my plate, meeting deadlines and an urge not to disappoint the team and clients. Unfortunately that didn’t work in my favour when burnout started catching up with me, while expectations remained the same.

    In the big scheme of things, it was always rewarding to receive a note of gratitude from both internal and external clients.

    Over the years I came to the realization that 3pm my brain goes south, and I try as much as I can not to attend to anything that require strategizing or intense focus.

    Thanks for sharing your experience with us.

    Liked by 1 person

    1. Thank you! Yes, burnout is a really thing! I’m still not great at it, but learning to say “no” has made a big difference for me!

      Thank you for sharing your experience!

      Liked by 1 person

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