by James Quinlan

My name is James, and I’m a Software Engineer at a company called Yesware, based in Boston. Yesware is the fourth job I’ve had in which I’m paid to write code, but it’s the third time now that I’ve transitioned from being an in-office employee to a remote one.

Since I’ve handled this transition a few times now, in varying degrees of complexity/difficulty, I figured I probably have at least a few words for anyone else looking to begin working remotely.

But first, a warning: survivorship bias guarantees that your mileage may vary with regard to anything I say here. Switching to a remote position has worked for me in the past, but that in no way means it will work for anyone else in the same ways.

You don’t often see articles entitled “How I Completely Failed to Work Remotely and Botched my Dream Gig”, but I’m sure there are many cases of folks doing exactly that. That would actually probably be a more helpful article, so consider this an open invitation for someone to write it as a response.

Also, I talk about my place of work in this article a fair bit, but I’d like to state clearly that I wasn’t asked to, or otherwise encouraged to at all. Any reference I make to my employer is included only because I see it as relevant or helpful to others, so as to get an idea of how a company might support its employees.

Why Remote?

This is a question I won’t dwell on too much because there are endless blogs, listicles, and books written on the subject (Remote: Office Not Required is a decent intro to the benefits of remote work, but it won’t tell you how to do it. It’s also roughly half pictures).

Remote work is fantastic for some personality types as it affords much more freedom. Some folks just enjoy being able to move, to be able to go where their friends/family/bucket-lists take them. Being able to take your job where you want to go is, in my opinion, less stressful than having to factor in finding another one if you decide to leave. Simply put, it resolves any dichotomies between having a job you enjoy, and anything else you want to do.

You can have your cake and eat it too.

The phrase above should always be accompanied with a resounding “within reason”. I suspect your employer wouldn’t be too keen on the idea of using remote work as a means of somehow having another separate full-time job somewhere else.

Why Not?

Remote work can be much harder depending on a myriad of details related to one’s personality, the nature of their work, their company’s culture, etc.

Are you the type of person who can self-regulate and ensure you’re allowing for extended periods of focus, wherever you are? Is the work you’re doing something that can be done without any coworkers immediately available? Is the company you work for willing to put in the extra effort to ensure you feel connected and valued? Do you have some misconception that remote work means doing any less work? Do you have a spouse or other close family member who this will affect? Is the Wi-Fi going to be any good where you’ll be based?

I’ll leave you to ruminate on those questions, but there are many reasons that being remote wouldn’t be a good fit. They each warrant an honest discussion with yourself, those close to you, and your employer.

How To Tell Your Company

Eventually, you’ll need to broach the subject with your boss, and while there are various ways to do this, there is only one I recommend.

The worst way I ever went about it featured me telling my boss that I was moving in two weeks, no ifs-ands-or-buts about it. I was essentially abruptly quitting, without really offering to discuss the matter. I knew I had to go, and I was ready to leave my job to make that happen, but I feel as though I had cornered my boss.

After my spiel (“I grew up here, I’m ready to leave, I need to do this”, etc.), he told me to just work from Boston, and that there was no reason I couldn’t stay on the team while working elsewhere. This was incredibly surprising to me, and something I hadn’t considered. I ended up taking the offer. A few weeks later I was in Boston working the same job as before, and paying significantly more in rent.

This method felt wrong for a few reasons. Namely, I didn’t bring the idea up as a conversation, and I went in defensively, expecting the worst. Also, I didn’t value my role in the job enough! I didn’t expect that I was valued enough by my company to warrant letting me move and stay on the team, and that was unfair to myself.

By the next time I had to have the same conversation, I was already 9 months into my tenure at Yesware. I had an opportunity to move to Spain with a friend, but I valued my job an enormous amount.

I was simply learning and growing too much to justify leaving.

While this honestly wasn’t factored into the decision to stay at Yesware, I was also going to need an American job for my residence visa in Spain anyway. Without them, I almost certainly wouldn’t have been able to go.

Since I felt more comfortable at Yesware than any previous company I’ve worked at, I figured I’d just talk to my boss about the opportunity openly. I wrote him an email one morning stating plainly that I had an opportunity to move to Spain in the upcoming Fall, and I wanted to talk about if that would be possible while still working for Yesware. I dug up the original email, and the sentence that best captures its spirit was “I just want to open this dialogue to see what is and isn’t possible, without any expectations.”

My boss and I immediately had a short 1-on-1 meeting to talk about the idea further, and we agreed that, while it was unlikely to happen, we could at least see what it would take to work. If there were no legal reasons we couldn’t do it, and the company felt confident that my work wouldn’t suffer, we felt as though it should be fine.

Over the next few months, we discussed what it would take to demonstrate that I can handle remote work, and that our team can. We organized a month long experiment where our engineering team of ~6 people would be remote every day, and I used this as an opportunity to show that I can be perfectly productive (often times much more so) while at home. Eventually, once we had clarified everything with the Yesware legal team, I was made aware that I could work from Europe if I so chose.

“brown concrete buildings” by Alasdair Elmes on Unsplash

The most important thing I learned from this is that discussing big changes like this requires one to be honest, upfront, and realistic. By making sure Yesware knew I wouldn’t leave the company if they said no, I helped make the process easier for them to consider. We also put in the extra work to make sure it would go over smoothly by making sure the team would be comfortable with me being remote, and by proving that our productivity wasn’t jeopardized.

What Does It Actually Take To Work Remotely

I’d like to take a moment to reiterate my warning message at the beginning of this article, in which I claim that just because this works for me, it doesn’t mean it will work for anyone else. You’ve been warned.

The biggest struggles I expect one to encounter when starting to work remotely are, in no particular order, managing to keep a normal schedule, creating a space conducive to focusing, and feeling connected to your team. They are also 3 sides to the same geometrically-impossible coin. For me, managing to succeed in one of those areas makes succeeding in the others easier.

Here are some ways I do that, and some ways that my team supports me:

Stick to a routine: Pick a chunk (or chunks) of time every day to focus on work. While a remote schedule often means some degree of freedom when choosing when to work, we can get a lot out of maintaining some sort of normal hours. I tend to stick roughly to working hours EST (which is 3pm to 11pm for me in Spain), but I also know I’m most focused first thing in the morning, so I always do an hour or two in the morning, then trim a little off my evening hours when my team doesn’t tend to schedule meetings.

Schedule time for casual conversation: By being remote, you’re going to miss out on casual chats at lunch with your team, and you’re going to be deprived of spontaneous conversations with other departments at the proverbial water cooler. These can be vital interactions, however, and they warrant being protected. Find time to engage coworkers in non-work discussions so you can continue to develop natural friendships with those you spend so much of your day with.

For example, my team often uses our bi-weekly retro meetings to talk about whatever we want for an hour. We do end up being able to talk about things that have gone well or poorly since the previous iteration of the meeting, but we don’t worry about being completely distracted for an hour with a coworker’s photos from a trip abroad, or the grizzly details of an ongoing murder investigation (this is just run-of-the-mill morbid curiosity, nothing to be alarmed by, I promise).

Our daily standups can also get a little carried away sometimes, but as long as they stay within the allotted 15 minute window, everyone is happy to chat a little bit about whatever. It helps to bring the team a little closer in a small but ultimately meaningful way.

Set up your ideal workspace: This is a big one for me personally. There is a profound difference in my productivity when I am working with all the tools I need versus when I am not.

For example, I’ve realized that the correct keyboard for me is a dealbreaker, and I tend to work faster with another monitor hooked up to my machine. Also, my back gets achy after sitting for too long, so I usually use a standing desk, or an ergonomic chair.

Invest in your workspace, and the boost you’ll experience in being able to focus will ensure the money is made back. Yesware has a generous employee expensing policy, so I’m encouraged to buy what I feel I need to be healthy and productive on the company’s dollar. If your employer can’t make the same offer, it’s still important to spend what you can on having a proper battle station.

Get out of the house: Now that your consummate work station is complete with an ergonomic keyboard and mouse, powered standing desk, miniature koi pond, 4K monitor, and Newton’s cradle, leave it all and go somewhere else. Work a part of your day at home, and maybe finish the evening at a coffee shop, or library, or a friends house. Do everything you can to not get stuck inside, because when you work where you live it’s a serious risk.

When I was in the US and working remotely, I would always either skateboard or go for a walk immediately after finishing work (now I just do it before). I also purposefully avoid buying any sort of coffeemaker so I need to physically leave the house to get coffee, and my regrettable caffeine addiction mandates that I leave at least once to satisfy the craving. Some folks go so far as to pay for a membership at a coworking space just so they can actually go to work. While I haven’t made this jump quite yet, I can understand the appeal.

We need to carefully illustrate the differences between working and not working. It isn’t as easy when the place where I work is also the place where I unwind.

Hop on a video call: This is one of the more team-oriented pieces of advice for making a remote job work. When it comes to getting answers or clarification on something, or needing to discuss an issue that’s even partially technical, it can be much easier to just hop on a video call instead of having to type everything out in Slack, or whichever medium you use for such communication.

Our goal is to make our being in another location as simple and straightforward as possible for our team, and that often means acknowledging that talking can be better than typing. Since going remote, I’m now more likely to just hop on a call with a team member to discuss something, rather than spending 15 minutes discussing in Slack. Plus the face-to-face time is just nice anyway.

Iterate: If this is the first time you’ll be working remotely, or your company is making the transition to support remote workers for the first time, it’s going to take some trial and error to make everything work fluidly. Check in with your team or manager to see how things have been (this would be a perfect topic for retro), and experiment with different practices if there are issues.

For example, because Yesware recently started to open up our engineering teams to remote applicants we’ve had to experiment with different video conference solutions to see what works best for our space. It’s an ongoing endeavor, but we are closing in on what feels like the right product, which will ensure remote workers (hopefully) never have a problem calling into meetings and planning sessions. Besides, any large transition is going to demand time before feeling comfortable, so give it a couple weeks being remote before panicking that you can’t handle it.

Meet up every once in a while: Being a remote employee doesn’t mean never seeing the rest of your team or company. Schedule a trip every year to go to headquarters for a week, or go once a quarter just for some of that coveted face-to-face time. Or work remotely from the same city, and head into the office when you feel like it. Being remote doesn’t necessitate being hundreds of miles away, and we can still gain a lot by regularly working from home even if the company’s office is nearby.

“person using laptop” by Kaitlyn Baker on Unsplash

While those are practical tips for being comfortable while working remotely, the actual switch can be fairly daunting. To make that transition smoother, try easing into it one day at a time.

When I was ramping up to move abroad and work remotely, I started by working from home every Wednesday, since it was uncommon for my team to have anything special on that day. After a month of that, I worked from home 2 or 3 times a week, and purposefully chose days that had important planning meetings, so I could get a feel for how to navigate critical meetings without being in the room.

By the time my entire team began the remote experiment, I was already fairly comfortable, and after 3 weeks of being completely remote, I felt even more productive than I was in the office. If you can afford to, begin the switch to remote work slowly.

I’m sure you totally expected something like this at the end of the article, but Yesware is hiring engineers of all levels. Again, I haven’t been coerced into saying any of this, I just genuinely love where I work and I’m excited for our future. I’d be a fool not to encourage kind, driven, and smart folks to join us. Check out our company page for a list of positions, and to get a feel for us. And yes, we’re accepting remote applications.