🧠 brain.dump() ↩︎

Working Remotely

Disclaimer: This article contains my own thoughts and feelings on the topic of working remotely. Everyone’s situation varies, so please take what you feel works, and leave what you feel doesn’t. As always, the opinions expressed in this article don’t necessarily represent the opinions of my employer, and shouldn’t be construed as such.

The desk in my office. 2017 5K iMac (4.0GHz, 32GB RAM, 1TB SSD), 34" LG 4K TB3 Monitor, and a couple MacBook Pros (one work issued, one personal). All on a Jarvis standing desk.

“We like to give people the freedom to work where they want, safe in the knowledge that they have the drive and expertise to perform excellently, whether they [are] at their desk or in their kitchen. Yours truly has never worked out of an office, and never will.” 

—  Richard Branson, Founder and Chairman of Virgin

Remote work is a hot topic right now, with many companies looking beyond co-located teams in order to expand the available talent pool, and offering their employees a potentially better work/life balance. I’ve had the opportunity to work for Bleacher Report remotely for the last three years1, and wanted to offer a glimpse into my experiences over that time.

Background

A little over three years ago, I was working in an office2 when I got a message from one of my good friends3 that the company he was working for was bringing more of their iOS development in-house, and was looking to hire a couple engineers. He also mentioned that “they were open to one of them being remote”, which really piqued my interest. At that point in my career, I had done some freelancing remotely, but I hadn’t worked remotely for a company full time. Since I am a big sports fan, I figured I had to interview for the position to see if it was a good fit.

The interview process at the time consisted of a few phone calls and a couple video chats with members of the team, never requiring me to fly out to San Francisco (where the engineering team is based).4 In fact, one of my video chats was with another remote engineer working out of the Kansas City area5. The fact that the company was comfortable enough to evaluate a candidate entirely remotely was an encouraging sign that I wouldn’t be considered an outsider or an afterthought.

After completing the interview process and negotiating an offer that was fair to both sides, I accepted my first remote position. I was extremely excited to start working remotely and to help build on the existing remote-friendly culture at B/R.

Getting Started

As you might imagine, getting started at a remote job is a little different than showing up to the office on your first day. Before my first day, there was a lot of work that went on behind the scenes to get my equipment procured and set up in order to ship it to me by my start date.6

On my side of things, I had already prepped my workspace (we’ll discuss that more in just a bit) and was ready to hit the ground running as soon as my equipment arrived. My first day of work ended up being a lot of browsing Twitter and YouTube while I waited for FedEx to ring my doorbell.

Finally my equipment arrived. I unboxed everything and started downloading and setting up all the applications I needed to do my job. I went through the typical HR on-boarding (remotely via video chats), had many Slack conversations with various members of the team who introduced me to the different parts of our workflows, and started diving into the codebase.

My Office

One thing I decided long before working remotely was that for me to be successful I needed to have a different physical space to work in.

We’re all creatures of habit, and I wanted to plan for that and “hack” it for my benefit. By having a space that’s reserved for my work, I automatically do things when I arrive that help me to get in my work mindset. In addition, I don’t have to worry about cleaning up a mess or prepping my workspace for the day. My desk is reserved for work, which allows me to keep it clean and ready for work whenever I need it.

Some of the books and vinyls in my office.
One of my handmade mechanical keyboards. This one is a MiniVan by TheVan Keyboards.
Some great Star Wars prints by Rogie King.

In addition to my desk being reserved for work, I have the luxury of only utilizing my office for what I consider “work-like” activities. I often read or listen to music in my office, but typically do so on the couch, not at my desk. I write journal entries and blog posts in my office, but also typically on the couch. At times I’ve had a TV in my office for watching day baseball games, but didn’t use that TV to watch TV shows or movies. I strive to keep my office focused on things that will not be a distraction to the work that I need to do in this space.

I don’t do all of my work in my office of course. One of the benefits of working remotely is you aren’t tied down to a specific location. One thing I like to do is head out of town to visit family a day or so before a big holiday weekend, and work remotely from there until the holiday7. I’m able to beat the traffic by a day, still get a full day of work in, and “arrive” instantly at the end of that final work day. Sometimes those days working away from my office are more difficult without the normal routines I follow at my own home. Sometimes they’re easier because I’m not anxious about a long drive through holiday traffic. In both cases, it helps me appreciate the space I’ve set aside to get the majority of my work done.

My Morning Routine

I’m not big on routines (or at least I tell myself that). I like to think of myself as a spontaneous person that goes out and does things. That being said, there are definitely things I do in the morning before I start working that contribute to me having a good day.

One thing I’ve read from many people who work remotely, and something I try to do myself before starting my work day is getting showered and dressed. Just because I can work in sweats doesn’t mean that I should. Getting dressed for the day helps me to think about the things I need to do, and serves as a good marker for me to start focusing on work.

By the time I step into my office for the first time in the morning (Red Bull in hand), I usually have a pretty good idea of what I’m going to tackle first. All that’s left to do is put my headphones8 on (to block out any outside noise), hit play on some music9, and get going.

Respect the Commute

When I worked in an office, simply being in the office was a catalyst toward working a full day. I was already there, surrounded by the tools (and people) needed to do my job. Even when I worked in an office that was an eight minute drive from my apartment, I didn’t want to go home in the middle of the day only to need to head back to the office to get something done10.

Working from my home office, the other activities in (and out of) my house are seconds away. There isn’t as much of a mental barrier between work and starting up something else in the middle of my work day. Some days all I want to do in the afternoon is take a nap, play a video game, go golfing, or any number of other fun things. And some days, I do end up taking a break to recharge. Most days however, I try to live by a concept that I call “respecting the commute”.

Respecting the commute is named for my past physical commutes, but refers to the mental commute away from work that is much harder to quantify. Some days, a quick distraction can be no big deal, and other days I find it almost impossible to get back into the flow of what I was doing. By respecting the mental energy it takes to “commute” into a workspace, I’ve found a greater ability to stick it out until my day is done11.

Communication

Everyone I work with is out of earshot, their desks are more than a quick walk away, and most are in a different time zone. With those constraints, it’s easy to imagine that getting anything done that requires multiple people is next to impossible. However, that’s really not the case.

Communication with a remote team definitely has challenges, but when structured well there are more pros than cons. Most workplace communication can be asynchronous, so it doesn’t matter if someone is in the next cubicle or across the country. Eventually they’ll see my email or Slack message, read the attached Google doc, or review the proposed design. And most asynchronous communication is in written form (text messages, emails, docs, etc), which doubles as documentation of the decisions you make as a team.

For the times when it’s easier to discuss something in person, video chats are great substitutes for being in the same room, and enable more nuanced dialogue than text usually provides. Every meeting automatically gets a Google Meet (née Hangout) attached so everyone can attend12. Even when meeting in person, we try to ensure there’s an artifact of any decisions that are made so we don’t have to rehash things down the line when memories fade (and so that those who weren’t able to attend have an idea of what transpired during the meeting). This also allows team members that work in an office to work from home when needed, not feeling like they’re going to miss out on anything important.

There’s always room to improve communication, but during my time at B/R I’ve seen us grow immensely in this area, and I know we’re still not satisfied.

Miscellaneous

Those are the main topics that I wanted to cover in this post. As I remarked on Twitter the other day13, it’s been a wonderful three years, and I’m excited to continue learning and growing with this team. I’ll end with a few random thoughts that didn’t fit into the broader narrative of this post:

That’s it for now. I’m sure I’ll write more about remote work life in the future, but if there’s anything in particular you’d like to chat about, please let me know!


  1. Well… almost three years. I started at Bleacher Report in June of 2016.
  2. I was working for Bloom Built on the Day One journaling app at the time.
  3. 👋 Tory!
  4. We’ve since tweaked our interview process a bit, but it still isn’t required to fly out to the office for any of the stages of the interview, they can all be done remotely.
  5. 👋 Jonathan!
  6. Again, we’ve since changed how some of these things work since I started. We now recommend new hires schedule a trip out to the SF office for their first few days so they can receive their equipment in person, meet some of the people based out of the office, and (if schedules permit) meet their manager in person.
  7. For example, last year I went to visit my family in Idaho for Thanksgiving. I left my house on Tuesday night after work, and worked a half day on Wednesday from their house in Idaho (thanks B/R for giving us that extra half day off!). When I wrapped up work around 1pm, I didn’t have a five hour drive ahead of me, I only needed to put away my office equipment and join the festivities.
  8. I swear by the B&O H6 (rev. 2) cans. When I heard they were discontinuing them I bought another pair as a backup.
  9. I will write another post on music I work to. Most mornings lately it’s been The Glitch Mob, Chevelle, or Waveshaper.
  10. Arguably, this can also lead to wasting time sitting in a chair to keep up appearances. It’s definitely a double-edged sword, and should be handled carefully in or out of an office setting. In most cases, nobody is benefited by you spinning your wheels when you could be taking care of yourself by living your life outside of work.
  11. I should note that this doesn’t mean I try to stay in my office all day. Eating lunch away from my desk is something I try to do every day, even if it’s downstairs in the kitchen. I also try to take walks or Boosted rides to think through problems. Whenever I do these other activities, I’m not “checking out” for the day though.
  12. And every meeting room is equipped with the proper hardware and software setup to join the meeting.
  13. Yes, I’m back on Twitter after taking a break for a while.
  14. Da Bomb is no joke people!