Six Uncommon Lessons From a Year of ‘Working From Home’

Whatever term you use to describe it—working remotely, telecommuting, freelancing, etc.—there are endless nuances to a life of working from home. And nearly all of the nuances are counterintuitive.

Here are a few things I wish people would have explained to me before I started
Here are a few things I wish people would have explained to me before I started

A little over a year ago, I decided to take a job working from home.

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I know what you’re thinking: Big deal. Everyone’s doing it these days. But I was in a different situation from many workers who choose this lifestyle: Unlike many recent (and not-so-recent) college graduates of the millennial generation, to which I belong as a 28-year-old, this was not an option of last resort. This was a strategic decision.

When I started working remotely full time, I had all kinds of ideas of what that would mean both personally and professionally. I imagined kicking back, feet in the sand, tropical drink in my hand, while all of my friends forced themselves into cramped cubicles in dreary office parks. It was a simplistic and naive vision, but it was also unavoidable. After all, I had read The 4-Hour Workweek like everyone else. I had witnessed co-workers seemingly jet off at the drop of the hat in the middle of the week to places I always wanted to go. I had seen all the adorable pet threads on Reddit posted by owners who worked from home and I assumed I would finally have time for a dog. I thought I would be living the dream—and in some ways, I am. But a year and a half later, I have a much clearer grasp on what it means to work remotely and how that lifestyle impacts my life. Here are a few things I wish people would have explained to me before I started:

1) It’s unexpectedly easy to stay motivated

When I tell people that my job does not require my presence in an office, the first thing they blurt out is almost always some version of, “I could never do that. I don’t have the self-discipline. I’d sleep all day.” It’s a natural reaction, especially for recent college graduates who have mastered the art of waking up just in time for brunch, but here’s the funny thing: it doesn’t take an uncommon amount of self-discipline or self-motivation to work from home. All it takes is the motivation to stay employed, and lots of people muster that much motivation every day without having to try too hard.

That seems like an obvious point, but it regularly gets glossed over: The fact is, going to an office and doing zero work is basically as easy as staying in bed and doing zero work. It’s the work itself that matters. And that’s actually the more interesting—and, depending on your view, somewhat troubling—subtext to the mindset of  the people who would  stay in bed all day long. It means, in a very real sense, they consider showing up to work a major contribution. They believe their presence alone is valuable. That may be the case if your job is an extra for crowd scenes in movies—but that’s only because your job, in that instance, is simply to be. Most jobs require a little more activity. Yet many people cannot conceive of a job that is wholly predicated upon producing results. One where you can’t simply show up and hope to stay employed, you have to produce work.

Physically being in a place usually isn’t that important. In my job, I rarely meet face to face with the other people in my company or with my clients. For all they know, I’m in Timbuktu—and that doesn’t matter at all as long as there’s wifi and I deliver prompt, solid work. What this forces me to do is to really focus on the work itself—why I’m doing it, what the quality is, and how to get it done fast. The fact that I don’t have to make water-cooler chit-chat, spend time in meetings, and all of the other assorted distractions of office life means that the work takes on a greater clarity and urgency.

But that’s why it’s easier, not harder, to stay motivated. Once you see the work and know what it is, that’s it. That’s all there is. There’s no posturing or explaining to be done. No office politicking. Just do the work and do it well, and you’re finished.   

2) You’ll travel a lot less than you think

One of the biggest motivators for detaching myself from a physical office was the freedom of being location independent. I wanted to be able to travel far and wide, especially for extended periods of time, especially because I’m young. Back when I had an office job, my mind  wandered (often at work) to the thought of living a completely nomadic existence. Never mind that not once did I really consider why I wanted that.

Here’s what I realized: a work-from-home life is less conducive to travel than you may imagine. For starters, the very nature of having to work while traveling really takes the wind out of one’s sails, so to speak. It makes traveling almost harder to rationalize. Why travel to Buenos Aires if you’re just going to have to stare at your laptop for long hours in some internet cafe or hotel room that that has almost everything you just left back at home? It makes you feel guilty for traveling there in the first place and spending the money and time. Plus, working remotely from a coffee shop in Miami is shockingly similar to working from a coffee shop in Memphis, which is strikingly similar to working from my favorite local coffee shop down the street. Work environments being equal, why bother with the hassle of schlepping there?

My friends imagine my life as one in which I can jet-set to Hawaii for the weekend and just be plugged in for work. Turns out, it’s not all that glamorous. For one thing, who wants to travel alone all the time? It’s tough to find people to travel with at the drop of a hat, and so more often than not, you’ll be flying solo. Which isn’t the worst thing in the world, but it is markedly more boring to travel by yourself, and this is coming from a mostly introverted person who spends a large chunk of any given day alone.

Don’t get me wrong, there are plenty of great reasons to travel, and having a job that allows you to work remotely can definitely help facilitate increased travel. It’s just probably not going to be the nonstop globetrotting journey you think it will be.

3) Your diet will improve—by default

For some reason, office culture in America has turned into donut culture. In offices with a community kitchen, every single day someone will bring in Dunkin’ Donuts, Einstein’s bagels, brownies, birthday cake, cringles, pies, cinnamon rolls, or cookies. The sugary carb train runs on time every single day.

So you eat a bagel or a piece of cake (it was Shelly’s birthday!) for breakfast. A cookie or two with your second cup of coffee at 10 AM. Then you eat lunch. Hopefully something nutritious or, mercifully, a salad. But let’s face it. You’re busy and you’re grabbing something on the go. For an afternoon snack you look over the corpses of cut-in-half donuts (while cursing monsters who do this under your breath). You pick the least sad option and wash that down with a can of soda. Not to mention you’re literally sitting around all day at your desk doing very little physical activity.

No wonder we have an obesity crisis.

Now, company culture varies and office environments are all different, but make no mistake, when you work remotely, you’ll never again be able to justify cake for breakfast. If Dunkin’ Donuts or bagels find their way into your kitchen it’s going to be entirely on you. A sin, not just of commission, but of omission–you actually have more time to cook for yourself at home, so why aren’t you doing it?

4) Prepare to become your own IT department

Working remotely brings with it unique technology challenges. And in every case, you’re on your own.

If something breaks, it’s up to you to fix it. There’s no tech support department, IT guy down the hall, or even a tech savvy cubicle mate. Couple that with the fact that when your technology fails you can’t do your job—and you can quickly find yourself in hot water. That’s why it’s critically important to have a working understanding of the software you use. Having some basic knowledge of computer networks will also vastly improve your life as a remote worker. Beyond that, knowing a bit of the language of tech—literally what things are called and what they do—makes life significantly less frustrating. (Also, crucially, a little coding skill can go a long way.)

Being able to troubleshoot your own software and hardware issues is only half the battle, though. You will have to teach yourself how to use all kinds of new programs—many of which are designed to overcome the various communication hurdles that arise from not being able to discuss work items face-to-face. Not being able to quickly learn how to use new programs and services will cause your productivity to flatline, which puts you at a tremendous disadvantage and significantly lengthens the time you spend on any given task.

5) Everyone will assume you’re free all the time

A warning: when friends and family find out that you don’t have a morning commute and a traditional office job, they will begin to assume that you don’t work at all. Suddenly, crazy requests come flying in:

  • Grab breakfast at 10 AM.
  • Fill in for golf league. Tee time is 3:30 PM.
  • Meet the cable guy at their house. The appointment is sometime between 11 – 3 PM.
  • Go with them to an afternoon SoulCycle class.
  • Give them a ride to the airport in the middle of the day.
  • Hang out on their boat all day.

They vaguely understand that you do work, but in spite of that, they will ask to do these things during the week and usually at the last minute. To be sure, they are not asking their desk-bound friends these kinds of things.

In a way, it’s flattering. And I’m not complaining about being included, nor am I above doing the occasional favor for friends. But the friends and families of the work-from-home types would do well to remember it is no coincidence that the “work-” comes before “from-home.” It’s no different than the “work-life balance” that 9-to-5ers struggle with. Work comes first there too. And you suit-and-tie morning commuters don’t see us barging into your offices at 3:30pm shouting, “OKAY, IT’S TIME FOR LIFE!” Do you? So I’m sorry, but I cannot take you to the airport at noon and then fill in for you at golf league…assuming of course the cable guy sticks to his service window. I have work to do.

6) Your parents will have no clue what you do

Making a living by way of remote work usually means making a living, in some capacity, by way of the internet. It also implies an understanding of how the internet works and enough knowledge of the economics of the internet to be able to profit from it. But if you’re of a certain age, it also virtually guarantees that your parents can barely use the internet, let alone understand how it works or the various facets involved in profiting from it (What do you mean drug dealers make a living online, sweetheart?!?). Even if your job is ostensibly straightforward (salesman, say) there will always be a disconnect lurking just below the surface between you and your parents.

In my own life, I tell my parents (and everyone else) that I’m an editor. Which is mostly true, but not nearly sufficient to explain what my job entails. Editors have strong opinions about grammar, syntax, style guides and the Oxford comma. Or at least that’s what people assume. I don’t have any of those things, nor am I even that great at spelling, but I am an “editor” nonetheless. One who works remotely, full time. How? Sometimes it’s even difficult to explain to my peers, and I’ve long since given up trying to explain it to older generations.


Whatever term you use to describe it—working remotely, telecommuting, freelancing, etc.—there are endless nuances to a life of working from home. Some are great (sleeping in an extra 30 minutes on a Monday and not having to worry about being late to work). Some are less than ideal (when it dawns on you that all your neighbors think you’re unemployed). Some are what gamblers call a “push” (never having to deal with a morning commute so when, on the rare occasion you do get stuck in traffic, you become apoplectic). And nearly all of the nuances are counterintuitive.

For instance, most people think of working from home as some kind of radical change to their life and work. The reality is: Working from home is not all that different from working a  traditional office job. It’s more like moving offices within the same company, than leaving the company altogether. And you’ll have an easier time adjusting to it than you imagine.

But remember: if you don’t get your work done, and it’s not high quality, you’re just as likely to be fired, except it will be by email, sent by someone you may have never met.

Kevin Currie is an editorial manager at Brass Check. Find him on Instagram: @kevin_currie.

Six Uncommon Lessons From a Year of ‘Working From Home’