



Earlier this year I moved across the country, and I took my job with me. My family and I relocated from New York City, where Datadog is headquartered, to a small town in northern California, where I now work remotely. (That’s my new office view above.)

The move has been great for me and my family. It has brought my daughter much closer to her grandparents and extended family, and the slower pace of life here has been a welcome change after 12 years in NYC. But the transition to the remote work frontier has not been without its challenges.

In preparation for my move, I consulted with a few friends at Datadog who are veterans of the remote life. As a perpetually cramped city dweller, I had long idealized their lifestyles (no commute! a back yard! doing standups from the hammock!). So I was surprised by the evenhandedness of their responses. On balance, remote work had been great for their particular circumstances, they told me, but they really missed some aspects of office life. They found it hard to stay connected to a rapidly growing team. At times they found it isolating.

Their advice helped me identify a few steps I could take to ease the transition to remote work. Other things I’ve had to work out on my own. In truth, I’m still figuring it out. But I’m much more comfortable in my work than I was when I first got here. Below are nine tips for healthy, sane, and productive remote work, gleaned from my own experience and from stories swapped on the #remote Slack channel at Datadog.

Literal walls, if possible. A separate workspace makes it much easier to focus on work and tune out the sink full of dishes that might otherwise occupy your attention. Your workspace could be a room in your house, a desk in a co-working space (see item #9 below), or an office outside the home.

Having a door you can close is ideal, especially if you work from a home with young children or pets. Otherwise you might be interrupted at an inopportune time, as one of my co-workers can attest. He was doing a phone screen with an engineering candidate when “all of a sudden the cat came out from under the futon in my office, proceeded to screech, vomit, rotate 60 degrees, repeat, until he completely enclosed himself.”

The benefits of a dedicated workspace also go the other way—having a place that you can leave helps you switch off at the end of the day and return to your focus to family, friends, hobbies, etc. Otherwise it’s all too easy to “pop in” to work at odd hours, especially if you work on a team distributed across time zones. In short, if you don’t have a place for work, then you’ll always be at work.

It’s tempting to roll out of bed five minutes before work, open up your laptop, and get started. There are a couple problems with this:

Once you start work, you’re not likely to stop. So by the time you close your laptop, it’s dinner time and you still haven’t showered. You’re probably wearing sweats or pajama pants. The sun is setting, and you’re not even ready to face the day. Routine is important. Getting dressed for work helps you mentally switch gears into work mode. If you want to feel like a first-class citizen on your team, you need to be as present and available as everyone else. That doesn’t just mean responding to DMs—it means being reachable by phone or by video chat, too. Videoconferencing is a good way to stay connected to your colleagues, but you’ll shy away from it if you look unkempt. Adhere to the same dress code as your colleagues at HQ.

This was the main thing impressed on me by veteran remote workers. If your company allows it, plan frequent visits to HQ (or to a central gathering place, if your company is fully distributed). At a rapidly scaling company, you may need to appear in person as often as every month or two if you want to meet everyone on your team face-to-face.

The first time I came back to Datadog after going remote was a bit jarring. The office was jam-packed with new faces. It was like returning to your old high school after graduation. I had felt like I was part of the fabric of the place, and all of a sudden I was a visitor. One recent hire stuck out a friendly hand and said, “First day?”

If possible, don’t just visit for a day or two at a time. Short visits are great for re-connecting with your team and meeting new hires with whom you’ll be working closely, but you won’t get to meet new people in other departments.

Just about every article about successful remote work includes some variation on this old chestnut, but I’ll include it here just because it bears repeating.

People in office settings take breaks all the time. They break for coffee or lunch or just for a chat in the hallway. You should take breaks, too. Go get a sandwich from the deli, take the dog for a walk, or just stroll around the block. Step away from your laptop. Leave your phone behind, if you can. At the very least, disable email and chat notifications that aren’t urgent. (Slack’s “Do Not Disturb” feature is good for this.) However you do it, get out of the house! Fresh air is your friend.

When I was working from the office, my manager and I had a 1-1 meeting scheduled every two weeks, and we often missed a meeting (or two in a row!) when one of us was unavailable. The fact is, we didn’t need to meet all that often, because we were in meetings together, we sat across from each other, we ate lunch together, and we could quickly hop into a conference room any time we needed to chat.

A few weeks into my remote work tenure, we realized we were falling out of sync. Our team doesn’t have daily standups, so he didn’t really know what I was working on, and I wasn’t 100 percent clear on how I should be prioritizing my tasks and projects. We were in touch via Slack, but that’s not a great way to have big-picture discussions. We agreed to start syncing up over video chat every week instead of every two. It’s worked amazingly well. Not only are we now on the same page as far as my work, but I’m also a lot more caught up on what’s happening in our team and across the company.

It’s easy to skimp on yourself, but setting up a comfortable workspace is a worthy investment. You’ll likely spend about 2,000 hours at your desk this year, and that’s a lot of time to be hunched over, squinting at a tiny screen. You probably don’t need a $1,500 standing desk, but it’s worth spending a bit of money on a good desktop, a chair that’s easy on your back, and a full-size monitor and/or keyboard. If you’re often in a shared workspace, invest in a good pair of noise-canceling headphones.

The Wirecutter has a lot of great recommendations for office gear, even if you’re on a budget. This is one area where employers can step up to support their remote workers by offering reimbursements for office basics.

You may be remote, but you don’t have to be on your own. At Datadog we have a #remote channel in Slack where the 20-odd remote workers can share advice and ask dumb questions. Since you probably won’t have officemates, a chat room for remote workers provides something of a virtual watercooler where you can share stories of battling the wasps that have invaded your office or post a photo of the doe that just wandered past your window. Remote work is just a bit different, and it’s nice to have people around who understand that.

A few HR and operations people also participate in the #remote channel, which is great when a teleconference link for an all-hands meeting isn’t working or when someone posts a question about travel or expense logistics. It also helps the remote workforce have a louder voice in the company. After a remote employee pointed out that videoconferences sometimes suffered from spotty connections, one of our operations people saw to it that all conference rooms were outfitted with wired Chromeboxes.

When you’re working alone, it takes more discipline to stay focused on your work. This is especially true if you’re working from home, where potential distractions abound (“I think I’ll just fix myself one more snack…"). There are countless books and time-management frameworks out there; the challenge is finding the strategies that work for you.

A couple of us like the Pomodoro technique, which is built around 25-minute “Pomodoros” of focused effort separated by 5-minute breaks. I don’t adhere religiously to the Pomodoro technique, but I find it valuable as a crutch when I’m having a hard time focusing on a particular task. I especially like how simple it is: all you need is a timer. Personally I like pomojs, a very simple command line timer.

Working alone can be isolating, no matter what you do to stay connected to your co-workers. Some people thrive in the solitude of remote work (and in fact prefer it), but many of us benefit from making contact with humanity IRL during the workday. If you’re a laser-focused cyborg who can tune out any distraction, working from a cafe every now and then may do the trick. If you require a bit more calm and quiet, see if there’s a co-working space nearby where you can be productive. Many of them have flexible pricing models for occasional use. Or look into splitting a private office with someone else—in my small town, I found a number of workable offices for as little as $325 per month, utilities and Internet included.

I opted for an office share, as it’s just too hard for me to focus at home with a toddler running amok. It took a few months and a few false starts to find the right place, but now I feel almost as comfortable here as I did at Datadog HQ. I do miss group lunches, stocked fridges, and the camaraderie of office life, but my desk faces a wooded path where I’ve seen black-tailed deer, wild turkeys, and countless squirrels. And my three officemates appreciate a good midday walk just as much as I do.

Thinking about going remote? Come join us at Datadog! We’re currently hiring for remote-friendly positions on our site reliability engineering team, our support team, and our evangelism team. Or you can browse all open positions here.