Advice for Newcomers to Remote Work: Lessons Learned

“What did you do today?” asked my aunt. “Take a nap? Watch TV?”

“You know, I work a real job, Auntie? They pay me and everything.”

Making some of my family and friends understand what I actually do from home is tough. If it is a family member I don’t really like, I sometimes respond, “I work — probably harder than you.” In all seriousness, over time, you learn to roll with it. In 2020, more people are accustomed to the concept of remote work than ever before, so the conversations have become easier, even with family and friends.

With the latest coronavirus strain (COVID-19) becoming widespread, many companies and people are looking at remote work options. I am not sure if the world is ready, but it is a part of our new reality. Those of us within the WordPress community can lead the charge by sharing our experiences and advice.

I am in my twelfth year of working from home. It is hard to believe that there was ever a time when I went into an office or commuted to a watermelon field in the middle of an Alabama summer. I was the first person in my family to work from home. Now I have siblings who do much of their work remotely, a nephew who is using the internet to jump-start his career before leaving high school, and a cousin who is “exploring some options” (he really just doesn’t like wearing shoes). Still, the overwhelming majority of the people I know are required to work in a physical location. For many, working from home is not an option. However, others are now facing a wild swing in how they will work for the next few weeks, months, and perhaps beyond.

What follows is my advice for newcomers to remote work. I have spent nearly my entire professional career behind a laptop at home and have had to learn some important lessons the hard way.

Before diving in, my top tip is to get a comfortable chair and work from the front porch if possible. Enjoy nature. Watch the birds. Breathe fresh air. Don’t trade one stuffy office for another.

Organization and Structure

I have worked remotely ever since I returned home from a teaching stint in South Korea. I had spent a over a year teaching English as a second language, mostly to kids who would have rather been out playing. Teaching is tough work. You enjoy imparting knowledge upon young minds. However, you must be part caregiver; part administrator; and part judge, jury, and detention-giver for the kid cussing you out in a foreign language (tip: always learn the bad words when teaching in another country). At the end of the day, you are exhausted, but you get up the next morning because you’re passionate about what you are doing.

For me, one of the best parts of going to the office was the structure. To that point, I had spent my entire life within rigidly-defined systems. From age 5 to 23, I was in school. Nearly everything I did or anywhere I went was decided by someone else, whether that was my parents, teachers, coaches, or boss at a part-time job. Moving into a job that was likewise structured seemed natural.

My days felt like they had a purpose because of this structure.

In the month before I moved back home to the States, I launched my business around WordPress. I was excited to work from home. I was unsure what that actually meant, but I was going to do it. I would no longer be constrained by administrators or bosses. I could set my own schedule.

The idea sounded great…in theory.

While I had successfully launched a business that I would continue for over a decade, there was an essential missing piece of the puzzle. I had no structure. In some ways, this was exciting. I never knew what a new day would bring. I could choose my own adventure each morning.

However, that disarray eventually took its toll. It took a toll on my health as my waistline continued to expand. It took a toll on me mentally as I slept and worked at random hours. I knew I could not continue along the same path.

Before setting out on my own, all structure in my life was determined by others. I had not learned the basic skills necessary for organizing my daily routine. I thrive when I know exactly what I am going to do. A little spontaneity is not bad, and my schedule does not need to broken down by the hour or minute. However, a little planning and outlining goes a long way toward kick-starting my day.

When talking with people who are setting out on their first journey into working from home, I always stress the need for structure. This becomes even more important for people who are married or have children. Not everyone needs to be rigid with their organization and map out each hour of the day. However, it is good practice when first starting out to have some basic outline in place, at least until you get a feel for what works for you.

For me, this means having daily goals. In my current work setting, this is about having the next day’s story lined up plus a couple of backup stories in case the first falls through. It means knowing who I need to contact for an interview and touching base with sources. In the past, as a developer, I would set up daily feature development or bug fix goals. This system leaves me wiggle room while still setting me up for success. I also play with the formula a bit when I feel like I need more or less structure.

Everyone will be a little different, but jumping into remote work is a massive work and lifestyle change. Having some level of organization and structure can set you up for easy wins early on.

Social Health and Relationships

The worst thing about working from home can be the loss of social structure. More often than not, co-workers become part of our inner groups. You find someone to be your gym spotter from your department. You start a weekly poker game with folks from the office breakroom. Often, where we work defines a part or all of our social circle.

It is also easy to get too caught up in your work when no longer commuting to the office. It becomes easier to skip a night out to the theater when you have been working on your latest project for 16 hours. It is easy to forgo family dinner because you want to wrap up a few emails. Your spouse suddenly becomes the only one reading the kids their bedtime story as you do a final check-in for the night.

The biggest regret I have about working from home over the years is missing opportunities to spend with family and friends. Far too often, I was working on my next “big” project. I had to build out that feature that was going to revolutionize whatever I was working on.

There is rarely something so important that it cannot wait until the morning. While we all have to put food on the table, our social well-being is just as important as financial stability.

Even those of us who prefer to be alone most of the time still need other people in our lives. This connection with others is part of what makes us human. It is not something we can afford to sacrifice. You do not need to say yes to every social invite, but make sure you do not miss out on all human-to-human interaction.

If nothing else, at least get a few furry, feathery, or scaly companions. My cats, chickens, and ducks certainly keep life entertaining when I am not out in the world.


For those of you who work from home, what are your tips? Share your experiences, lessons, and advice.

6 responses to “Advice for Newcomers to Remote Work: Lessons Learned”

  1. I can relate thanks for this, not everyone is brave enough to open up about this stuff… One of my main issues is pulling too many all-nighters. Organization and Structure are probably the most important.

    • Fortunately, I no longer pull all-nighters. I’ve done more than I can count. I don’t think I could handle it today. Definitely focus on getting rest. The truth is that we can tackle projects better on a good night’s sleep and approaching problems with a fresh mind.

  2. Far too often, I was working on my next “big” project. I had to build out that feature that was going to revolutionize whatever I was working on.

    I fully sympathize with this statement. It’s my never-ending experience too. However, I don’t think this happens because of working from home (which I do), but from being an independent developer, creating my own product, hoping time and again that the world will like it, and being unable to take that constant voice out of my head: “How to fix that bug? How to implement that feature? How would it work better?” Even when I’m not working and trying to enjoy my time, I can’t fully concentrate on the here and now, because of that nagging voice.

    Sometimes the issue is working from home, but some other times it is being your own boss, so we need to pay attention which is which when setting-up the plan to enjoy our lives.

    • It’s not an issue that’s necessarily caused by working from home. It may be more of a personality trait or the simple act of enjoying your work. However, the issue can be exacerbated by a home-work environment. Instead of having to get up from the office and take the train home, a forced break, you just keep going. For me at least, a structured setting would have helped me know when to stop early on. I am good at finding that stopping point today, but it took many years of self training.

      I can definitely relate to that nagging voice even when not working. I’m not sure if that ever goes away for some of us. :)

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