What I Learned From Working Remotely, and Why I Decided to Stop

A year and a half ago, I was presented with the enviable opportunity to leave my job and start working for a company remotely. At the time, I was sick of commuting through Los Angeles traffic, and relished the opportunity to work from my apartment without anyone looking over my shoulder.

I figured I’d get double the work done in half the time. No more inefficient, pointless meetings! No more commute! I thought I’d be living the dream. Maybe I’d even have time to pick up a new hobby. My last attempt at learning guitar got me halfway through a single Neil Young song, and I was excited to try to remedy that disaster.

My fantasies quickly gave way to the harsh reality of what working from home is actually like. Being a remote employee presents many challenges I hadn’t fully appreciated, and I recently decided that the benefits of going into an office outweighed the value I was getting out of working from home. I packed up and headed for the East Coast, and I’m composing this from an office in downtown New York City.

Every person is going to face unique circumstances and obstacles when deciding whether working from home is right for them — and I should note, I don’t have children, so the desire to spend more time with my kids or cut down on pricey childcare wasn’t a factor for me. But I hope that my thought process can help people make more informed decisions if they’re weighing the option of working from home.

I’ll share what I enjoyed about working from home (or WFH, as my cool tech friends used to call it) — as well as how these benefits come with a downside.

WFH Benefit: Freedom

You know those days when you feel like taking a walk at 10 a.m., just because? When you work from home, you can. As long as I had my phone on me and I could reach my computer in a reasonable amount of time, I was free to do what I wanted, when I wanted.

Even in the most lax office environment, there is unspoken pressure to be in the office from at least 9 a.m. to 5 p.m., unless you’re on your lunch break. When your office is your living room and your desk is a cardboard box on top of a counter, you can come and go whenever you want.

WFH Downside: Inability to Detach

In my experience, traditional office jobs haven’t required much after-hours work. I was able to switch my brain out of “work mode” when I left for the day. When I worked from home, meanwhile, I found myself constantly staring at my phone, wondering if something would pop up. There was never a clear start or end to my workday.

Further complicating things, the home office was based in New York, while I was living in California. That means they were operating on East Coast time, and if I woke up at 7 a.m., there was already a pile of emails waiting to be dealt with. I always felt a just a little bit behind, which is a stressful way to live.

WFH Benefit: No Dress Code

I’ve had one go-to outfit for pretty much my entire life: mesh shorts and a t-shirt. When I worked from home, I got to wear my favorite outfit every day. It was a dream come true. Most of the time.

WFH Downside: Being Caught Off Guard

My job requires a lot of calling, and quite a few interactions over Skype. A couple of months into my work-from-home stint, I accepted a Skype video call from a coworker. Then, I heard the laughter. I quickly glanced down and realized I’d only completed half my outfit that morning. I was now on a Skype call with coworkers… topless.

I quickly tried to duck down and display only my head, but the damage was done. The laughter echoed through the office and out of my tinny computer speakers. My boss was very nice and said he thought it was hilarious, but I was very embarrassed. I can’t imagine that a question like, “Remember the time Drew took a call topless? Does he do that with clients?” wouldn’t come up in an internal review.

WFH Benefit: No Commute

There are few things in life worse than a bad commute. They are stressful, boring, expensive, and, if you take a car, dangerous. When you work from home, you can roll out of bed, pop open your laptop, and you’re at work. If you’ve ever had a bad commute, it’s hard to overstate how glorious that can be.

WFH Downside: Lack of Routine and Movement

When working from home, there were days when I had no time to myself in the morning. I would sleep as late as I possibly could, wake up, and get right to work. Since the East Coast office was already humming, there was always stuff to do first thing in the morning. Next thing I knew, I’d look up and it would be lunch time  – and I hadn’t yet walked, stretched, worked out, showered, or meditated. I usually like to do some combination of those things each morning, and it kind of throws me out of whack when I don’t.

Since moving east, I’ve been walking an hour to work each day, and I like it. It was rare for me to take even an hour-long walk each day when I worked from home. Now, out of necessity, I walk two hours a day. I get to clear my head, experience fresh (by New York City standards) air, and call people I want to catch up with. Sure, I could have the discipline to do this every day if I worked from home — see the point about freedom — but it’s a lot easier to accomplish when it’s a requirement.

WFH Benefit: Reduced Office Politics

This one almost goes without saying. No one likes gossip, a scourge afflicting offices everywhere. No one likes being forced into a conversation in the kitchen when you were hoping to quickly grab your lunch and get back to work. No one likes being forced to talk about which team you’re rooting for (okay, I kind of like that one when it comes to basketball, but it’s a different story when your coworkers like the Bachelor).

Interoffice drama is draining and counterproductive, and there’s much less of it when you don’t work in an office.

WFH Downside: Reduced Relationships and Hampered Work Flow

While on one hand I can bicker about office politics and mundane water cooler talk, with the other I can point out that some of my best friends are people I met while working in an office. I even met my fiancee at work! Having a built-in social network is great, and working from home can be quite isolating in that regard.

Also, when it comes to getting work done that requires collaboration, it can be frustrating to rely on instant messaging. There is no substitute for being able to turn to your left and ask a question knowing you will get an immediate answer. Skype messages can be missed, and communication via typing can be slow and clunky, or even unclear. I’ve found that projects that could take a half hour when I worked remotely can be handled in just a few minutes when I’m in the office.

Those are just a few of the big pros and cons of working from home vs. working in an office. Here are some other factors that went into my decision:

Other Things I Liked About Working From Home:

  • Ability to take naps (rare).
  • Avoiding potentially harmful, low quality, recirculated office air.
  • Never having to pack a lunch.

Other Things I Didn’t Like About Working From Home:

  • I tend to procrastinate more when there’s less oversight.
  • No facetime with boss made job feel less secure.
  • No amenities, such as my fancy standing desk, big computer screen, and free coffee.

Ultimately, the draw of being able to do better, more efficient work felt like the best decision at this moment in my life. Financial security is my number one priority, and I felt like I would have more of it if I came into the main office every day. At this point in my life, that’s worth more to me than being able to work in a t-shirt and shorts.

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Drew Housman
Drew Housman

Drew is a former professional basketball player and a Harvard graduate. He is passionate about writing content that empowers people to improve their careers, save more money, and achieve financial independence. His writing has been featured on MarketWatch, Business Insider, and ESPN.

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