What's remote like after 4.5 years?


This blog post is not a HOWTO or an FAQ, I just wanted to brain dump about my experience over the past few years, so if that type of ramble appeals to you, enjoy! If you have specific questions on working remote, hit me up on twitter.

In June 2014 I started working as a Software Engineer at Yelp in San Francisco. A year later I wanted to move back to Canada to be closer to family and I have been working as a remote software engineer ever since. I’ve talked about this journey a lot with people, and I get a ton of questions about it, so I figure it’s time sit down and write about it.

How I tricked Yelp into letting me work remotely!

In January of 2015 I let me my manager know my intentions of moving back home to Canada. At the time I was working in Yelps San Francisco headquarters and even though I had only been there for half a year, I knew it was not going to last. So I pitched this idea to go remote. I could try it for 3~ weeks by visiting Canada and working remote, and if it worked out cool, and if not we could discuss me parting ways with Yelp.

I was told no very firmly. Yelp was not a remote company so they will not do remote. I was very disappointed, but I understood and appreciated that they didn’t string me along. I kept doing my job, and as we approached the summer I started looking for other places to work in Canada. Especially after I learned that a much more senior engineer went remote around the same time as my request, and after a month he quit. It didn’t paint my request to go remote with very much positivity and I figured there was no chance.

By April things suddenly changed. In a 1:1 with my manager, he told me “Okay. Go to Canada for 2-3 weeks, and we’ll try out the remote thing. Find somewhere you can have an office and we’ll see how it goes”. I did the 3 weeks remote, which was a smashing success, and the rest is history. We worked out some of the details and when the lease on my apartment expired, I flew back home and for the next 3 years I worked at Yelp, I did it remotely.

What was working remote like?

It was eye opening. I had done remote days, and I would extend visits in Canada by doing some days remote. But to move back home, living in my own house, doing remote work? It was bliss.

Firstly, Yelp was set up for remote, whether they wanted to admit it or not. They had been around for 10~ years at the time, and so the engineering org was pretty mature, compared to the industry as a whole. Overcommunicating was the norm, not the exception. Almost all communication was async, so if there was chatter it was on IRC, and I could read it the next day without skipping a beat. Meeting rooms already had high resolution cameras with wired internet. They already had a satellite engineering office in Germany, who laid a lot of the groundwork. I want to say remote was hard and a lot of work, but it wasn’t. It was easy, and Yelp was situated perfectly to make it easy.

Secondly, I am a natural homebody and introvert. This seems to surprise people, since I can have a lot of charisma, but my natural state is being alone or 1 on 1. Being in an office is very exhausting for me; I energize with alone time. This makes a remote position (or closed office) very appealing. When I worked in SF people would invite me to after hours hangouts, and most of the time I would avoid them. I needed time to relax. Eat some dinner, Skype with Sarah, watch some Starcraft, read some books, whatever. Not hanging out with people. Now that I’m full time remote, it’s a lot easier for me to have a social life, because work has not burned up all my social energy. I actually seek out after work hangouts; insanity! ;)

Thirdly, working remote is free of distractions. A lot of people who talk to me about their remote experience comment on getting distracted when they do a day from home. It’s important to recognize that doing a 1 off day is much different than doing it full time. As a remote engineer I am dedicated to crafting a productive work space. No cats are allowed near my office. I don’t have a TV or game systems in here. If something was distracting to me, I would remove it during office hours so I can focus on my work. In San Francisco when someone wanted my attention, it was not uncommon for them to just come to my desk and physically poke me. It removes me from what I’m working on, and I lose my flow. When I’m remote, you have to ask for permission to bother me. “Hey, do you have a minute?” as an IRC ping, I can finish what I’m doing, get it in a good place, before responding. My productivity really shot up when I went remote, and personally I found the distractions LESS.

I don’t think this was a detriment to the team, as the people who wanted my help still got it, and I wasn’t rushing to get back to what I was doing. I would try very good to give good and fast feedback on PRs.

Deep work also became a lot easier, and I felt like I could reach my potential much more easily. I could spend 2-3 days on something without any real distraction except a few 5-10 minute standups. Working remote helped me become a much stronger engineer because I could work on much more challenging things.

Being remote also alleviated all of my work life balance guilt. At Yelp, even though nobody ever commented or made this the case, I always felt bad when I wasn’t at my desk. If I went for a walk, played a game of pool, or was in the bathroom too long, I’d feel anxious. What if people think I’m not working hard? What if this affects my bonus? etc. It was all in my head, but working remote was very much about output. It had to be. Nobody knew when I was working or not, so all that mattered was my output. I set aggressive goals in planning meetings to motivate myself to work hard, and I could take all the long walks or longer poops and it didn’t matter. I could take a break and watch Day[9] videos in the middle of work day; who cares? I do good work, and that’s all that matters. I could work early in the morning, go run errands, and then work in the evening. I could be incredibly flexible with my hours, without causing any harm to others, and improving my productivity. Instead of taking a half day of PTO to go to the doctors, I could just work around it. Work life balance became way more efficient and effective.

Lastly, the best part of being remote was/is being able to take a shower in the middle of a workday. Usually if I am working hard on something and I get it into a good state, or I need something to run, I’ll go have a shower. It’s a great time to meditate on a problem and feel completely refreshed. 20 minutes and I’m back at my desk, pounding at my keyboard like a new person. No office can compete with this, and if you work remote I highly recommend it.

That’s great, should I go remote? What are the downsides?

Remote work is not for everyone. At least, a lot of people have convinced themselves they cannot do remote work. If you’re at all considering remote, do my 3 week experiment. Set up a space at home, and try it for 3 weeks. No matter what do no go to the office, even to pick up some mail or have lunch with a coworker. Nothing, all remote. Do you like it more or less? Are you productive, or slacking? Are the problems your experiencing (like loneliness) solvable? Things may impact you in ways they don’t impact me, and each company may be set up in a way that makes remote work easy or hard. There are some companies I would not work for remotely, and some which would be dreams. As I talked about earlier, remote was easy at Yelp, but it may be impossible elsewhere. It’s worth mentioning though, even if it’s hard, doesn’t mean it has to stay that way. The challenges I faced at Yelp were all solvable.

Loneliness is a problem for a lot people I talk to. I don’t experience such weakness, but if you suffer this then there are solutions. Being remote from your company does not prevent you from getting a coworking space, which allows human contact without actually having to live in the same city as your workplace. You can also poop as much as you want without any coworkers wondering where you went, a true gift.

The biggest downside when I first went remote was becoming a work-a-holic. This might work for some people, but I find output goes way down the more I work. When I first started remote, I worked fairly long hours compared to my time in SF. I was saving time on my commute (10 seconds vs 30-45 minutes each way), but I would keep my laptop with me. If someone pinged for a code review at 6pm, hours after I was done working, I’d pull out the laptop, do the review, then go back to what I was doing.

It felt like I was doing a good thing, but I was just burning myself out. My motivation and work output started dropping because I was working all the time, and when I was harsher about restricting my hours my work output went up, not down. People learned when it was a good time to ask me for things, so when I was at my peak I gave better code reviews, faster feedback (doing a code review was faster), etc. I was also better at saying no. “JimmyJoe would be a great person to review this, I’m done work in 5 minutes” which more evenly distributed the load and knowledge stopped pooling with me for certain areas.

Is having remote workers worth it for businesses?

I made major contributions to Yelp in my tenure there as a remote person, and had Yelp just said no (as so many companies still do), they would have lost out on all of that. They were hiring as many people as they could, so it was a clear win to support my remote request even if it had some perceived loss of inefficiency. There are plenty of people who are insanely skilled, but will not move to your companies cities. Even if they live in the city, they may not want to commute. Being open to remote gives a huge advantage to hiring and quality of life for your workers.

Would you do non-remote again?

I am heavily recruited by many companies and I ask every single one of them whether they support remote. No? You want me to move to Seattle? Palo Alto? New York? Vancouver? Toronto? just so I can have the privilege of working for you? No thank you, I am much happier and productive as a remote worker, and I don’t have to uproot my whole family and move. This does narrow my options for changing companies, but there are enough remote positions out there and the benefits high enough that it’s worth it to me.

I won’t automatically say no to a non-remote opportunity, but it would have to be pretty damn compelling. CHA-CHING.