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Getting Ahead

Working Remotely? How to Defeat Tech Breakdowns, Office FOMO, and Other Common Challenges

person working from home
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It’s no secret that working away from the office is increasingly more popular. Six out of 10 companies offer their workers the chance to telecommute (that’s three times higher than it was in 1996!); and 43 percent of all employees work remotely at least some of the time, according to the latest workplace statistics from Gallup.

Remote work may be more common than it used to be, but it still comes with its challenges—especially if you’re one of the few WFH’ers at your company and the rest of the team is in the office. Here are a few common remote-work pitfalls and how to sidestep them.


Challenge #1: You Have Trouble Managing Your Time

Many remote employees work from home, which means ample distractions (the dishes, the laundry, the un-mowed lawn, maybe your children and spouse)—and it’s all too easy to get sidetracked. Plus, there’s no over-the-shoulder accountability to keep you off Instagram.

If you’re ambitious, consider using time tracking software (try TimeCamp or Toggl), which allows you to log time spent on various tasks or categories of tasks. Like a food diary when you’re dieting, just the act of time tracking can make you more aware of where your hours are going. If you really want to dig in, you can look at the data for patterns—do you tend to fall down a Facebook hole when you’ve got a major deadline looming? Do midday conference calls throw off your afternoon rhythm?—and adjust your schedule accordingly.

No matter how you manage your minutes, it’s a good idea to build a schedule for yourself that you can stick to—and is transparent to your boss, especially if your hours aren’t 9–5 or within the same time zone. “They [should] know when they can reach you,” says Nancy Halpern, an executive coach with leadership development firm KNH Associates in New York.


Challenge #2: You Just Can’t. Stop. Working

With no commute or way to leave the office, it can be hard to separate your work and personal life. “You can check work emails, chat with co-workers on Slack, or do work any time you’re on Wi-Fi,” says Rebecca Safier, founder of remote job board Remote Bliss, who works remotely from Thailand. “As a result, it’s easy to keep working into the night, well past the time you said you’d finish up.”

Plus, you might be worried that your boss thinks you’re not working since you’re off-site, so you overcompensate to appear busy.

“Unplugging at the end of the day is important,” Safier says. “If you don’t, you’ll feel like you’re on call 24/7. Sign out of your work email, get off Slack, and truly allow yourself to stop working for the day.”

Still have trouble detaching? Call in reinforcements! Ask your partner, friend, or co-worker to keep you accountable. Have them ping you at the time you should be off. “My friend Laura also works from home and she’ll text me at 6 p.m. to make sure I’m not working anymore,” says Chandra Turner, CEO of The Talent Fairy, a New York recruiting agency. “I actually feel guilty if I disobey her!”


Challenge #3: Team Communication Feels Fragmented

When you’re not in the flow of in-office traffic, you’re going to miss impromptu lunches, coffees, or spontaneous deskside brainstorms. So it can occasionally feel like you’re not getting the full picture or like you’re the last to find out about things.

“Sometimes I just need a quick yes or no, or a time frame of when something can get done, and our internal communication tool doesn’t cut it,” says Kim Koga, a solutions engineer at web content management firm Zesto.io. “I could wait hours for what could be a quick response in person.”

To address communication gaps, some teams adopt a messaging platform like Slack where everyone—remote and in-office—can chat in real time about issues as they pop up, or use cloud platforms for documents so everyone can collaborate. Video calls are also a good strategy—and leave your camera on, because managers like to see your face. “We’ve used Zoom and Skype just so we can see one another on occasion,” says Kenneth Johnson, a diversity recruiter and career coach at East Coast Executives. “It’s remote, but you do feel connected after those conversations.”


Challenge #4: Technology Trips You Up

Office technology is usually business-grade and quick. But your remote internet hookup (or cell signal) may not be as reliable, and that can be a problem.

Check that you have the right technology to support connectivity—an extra powerful router, for instance. “It may sound like a small issue, but many remote workers have suffered and failed trying to work from locations where phone coverage and internet speeds cannot meet the requirements of the job,” says Ron Humes, who works remotely for marketing firm Post Modern Marketing. “Make sure to check your service providers and even run necessary tests before settling on your remote location.”

Similarly, if your team collaborates on projects or documents, make sure you can tap into a file hosting service so the team can work together on things without version issues. You should have access to the same technology that your team does. And if your team has no collaboration tools? Lobby your boss for them! It’s the 21st century, after all.


Challenge #5: You’re Literally Not Visible

Sure, you get to work in whatever you fell asleep in, but you’re also not on your boss’ visual radar every day. That could mean getting passed over for plum projects or even promotions. “In a previous position, my supervisor was inexperienced with managing a remote team,” says Becca Borawski Jenkins, who works remotely for financial site FinanceBuzz from Cortez, Colorado. “His baseline assumption was that remote people weren’t doing any work. It was a challenge to constantly have to explain, prove, and justify what I was doing when I was, in fact, highly productive.”

To amp up face time, get out of the house. Try to attend conferences and work from the office occasionally, if commuting in is an option. Show up for team events even when you’re not required—like going away parties, monthly status meetings, or the occasional lunch with co-workers or your boss.

“You might also want to investigate some ways of letting your manager know, on a regular basis, what you’re up to, so your accomplishments are never hidden,” Halpern says. “You may want to do video one-on-ones with your manager every week or send them a quick recap at the end of each week to let them know what you’re working on.”


Challenge #6: You’re Feeling the FOMO

Being in an office with a group brings with it a certain camaraderie. There are inside jokes, spur-of-the-moment after-work drinks, and spontaneous events (“Girl Scout cookies in the kitchen, now!”). Working remotely can feel like you’re standing outside the circle.

“I do sometimes feel that I’m missing out on ‘water cooler talk,’” says Caleb Chen, who works remotely from Houston. “I personally found this surprising, because in my previous office jobs I’ve found water cooler talk distracting. Sometimes, when I’m catching up with my manager via audio, I’ll hear my peers interacting with each other in the background and they always sound so jovial.”

There’s no substitute for being in the office full-time, but popping in occasionally and communicating copiously can help you maintain connections and feel like part of the team.

“My company pays attention to the need for all employees to interact with each other,” says Lori Lite, a remote worker with Actualize Consulting. “They have annual retreats, team challenges, and cause-related events that give us a chance to connect. We share family vacation photos on Dropbox and include them in our monthly emails.”



No matter what the challenges, take heart: Research shows that remote workers are happier and more productive than their in-office counterparts. They report lower stress levels and their carbon footprint is smaller with no commute.

Plus, you can work without shoes on.