I’m about to start working remotely, and it’s sort of freaking me out

In about two weeks, I’m moving from Seattle, WA to Nashville, TN. This is awesome for a number of reasons. Nashville has less depressing winters, some great friends and family live there, there’s an NHL team, and I’m really excited to reacquaint myself with the city I grew up in. (That said, I am going to really miss Seattle. This place is amazing). There’s just one part that makes me a little nervous: Working remotely. It freaks me out. It shouldn’t, but it does. Kind of a lot. Several people at RescueTime work remotely, and they make it work just fine, but I’m still uneasy.

You see, I’ve worked remotely once before, and I was terrible at it. I mean, I still got my work done and all, but I fell into just about every conceivable work-from-home trap in the process. It was several years ago, and I was living in Boston, working for a small web design company in Anchorage, AK. The four hour time difference meant my work day didn’t start until noon (which is awesome), but it meant I was working until about nine (opposite of awesome). I didn’t have to keep those hours, but between everyone else being on Alaska time and me not being a morning person at all, it was an easy pattern to fall into. Finishing work so late each day sort of wrecked my motivation to go out and do anything afterwords, so often times I would just keep working. That’s a really bad habit to fall into, and led to some pretty bad workaholic tendencies (also not so great for my social life :\). I was working out of my house, so the isolation started to get to me. For days at a time, I found myself with literally zero reasons to put on pants. In a way, that sounds luxurious, but it stops being fun real quick. After a while, I figured out ways to get a little bit more balanced, but it never really got to a spot where I could say I actually enjoyed it all that much.

So you can see why getting back into a remote work situation would be unsettling. But I’ve got some reasons to be optimistic this time around.

I’m not the only one in my company working remotely

The last time I worked remotely, I was the only one in the company not in the main office, and that caused a huge disconnect. I felt guilty being the odd man out, like I was burdening everyone with my weird schedule and the fact that I couldn’t be there for meetings. At RescueTime, more than half the team works remotely, so I don’t feel that same pressure. It’s already a part of our culture. And the folks I work with have been doing this for years, so I don’t have to figure it out all on my own.

Technology is way, way better now

Before, the main options I had for interacting with my coworkers were phone calls, email, and FTP. Now I have all sorts of options to stay connected. We sync files through Dropbox, share code with Git, and share all sorts of random knowledge tidbits with Evernote and Google Drive. On a more social level, Google Hangouts makes it so we can see each others faces (and screens) whenever we need to. And we use HipChat for group chat, which has been surprisingly effective at making everyone feel a little less spread out across the country. On the time management front, RescueTime helps me steer clear of some of the really bad habits I’m prone to by keeping me aware of how my days are shaping up.

There are other options for not working strictly from home

I know that working from home drives me crazy after a short while, so I have to get out and find somewhere else to work. This time around, I have two things working in my favor. Coffee shops are a great option now that I’ve developed a fancy coffee addiction (thanks a lot, Seattle!), and Nashville has an abundance of coworking spaces that I can go to give myself some structure (as well as some physical distance from home, so I can draw the line when I’m done for the day). I’ve spent a few days at CoLab Nashville, which has been great, and there are several others that look really good. I have a lot of options.

Nashville-to-Seattle is way different than Boston-to-Anchorage

It’s not as hard to go back. Flying to Alaska was always a huge, expensive undertaking, no way around it. (To be fair, a huge, expensive undertaking that also involved moose, bears, Northern Lights, and a bunch of other completely magical stuff.) Seattle is still far away, but I’m only crossing two time zones, not four. (No direct flights though, so that’s sort of a bummer.) I’m not really sure how necessary going back will end up being. Going back to the first point, the other people working remotely give me some new options for face to face time. There are two RescueTimers in Atlanta, and that’s only a few hours’ drive.

Remote work is actually a thing people think about now

In the time since I last worked remotely, the conversation has gotten a lot more interesting and sophisticated. In addition to all the tools I listed above, there’s just a better understanding of what the tradeoffs and pitfalls are. A lot of people have put effort into figuring this stuff out, so there’s a better roadmap. It also helps that I have a pretty clear idea of some things that simply don’t work for me (living and working in the same space, all the time, for example). This time around it feels like there is a lot less that I’ll have to sort out by pure trial and error. I’m about halfway through reading Remote, by 37signals, and it’s a really nice rollup of the dos, don’ts, and current thinking about remote work.

So I think it’s all going to work out ok. Still, got any tips?

While I’m optimistic, I still know myself and know the traps I’m apt to fall into. Does anyone have any good tips or strategies for remote work? If so, leave them in the comments, I’d love to hear about them!

7 Comments on “I’m about to start working remotely, and it’s sort of freaking me out”

  1. I’ve been working remote/virtual for over 13 years and love it. It’s the best and most awesome situation to be in. Recently I stayed on a small island in the Pacific for two months to try it out and it worked well. Now with VoIP phone technology and cloud based computing you can create a company and have people all over the world work at it, and be only a 3 digit extension away from a conference call. Now with Google+ Hangouts, face-to-face can be achieved in the meeting sense with up to 15 people. I have a dedicated office at home, with a metal door that blocks outside sound, even the doorbell, which I probably rig that to my desktop. Equipment wise I’ve created a super system of six monitors, and stand-up desk, which I’m using right now. I have a 7.1 surround system and LCD projector if I want to take a brake and watch something or really pound the tunes. It’s a very comfortable setup which I accomplished a lot.

    Now, I’m going to take it to the next level and become a perpetual travel hacker for the next few years and travel the world and go and work in different areas of the world every few months. I’ve really had to break off and start using my laptop, which I just bought a new Mac with the 15″ retina screen, vs. the old 13″ 1280×800 screen which was never enough to do what I do in my day. So with my equipment reconfiguration I’m confident I can stay at the same productivity and live within a small travel footprint. The IP phone which was a pain to drag around is now replaced with an iPad and bluetooth headset. Technologies like RescueTime are a great administrative aid to keep track on remote employee performance. I think life will be pretty good, not much will change other than my GPS coordinates.

    Utilizing the remote working strategy saves a ton of overhead which allows the savings to be allocated towards epic lifestyles, like the nomadic CEO. I’m really excited!

    • Robby Macdonell says:

      Wow! Sounds like you’re really making the most of it. The sound system / soundproofing reminds me of something I missed while working in the office – the ability to unashamedly rock out to whatever music I want to. 🙂 Thanks for the inspiration!

    • Daniel Rico says:

      Well, thats awesome, Im trying to do the same here in Mexico, but work culture its different, for now I just work only fridays at home… haha baby steps!!


  2. Tim says:

    Since I have been working remotely with you at RescueTime I may have some tips. I’m not a morning person either, but you make a great point of a ‘wasted day’ when you do start work late. My solution is to wake up, not early, but not late. About 7:30-8:30 works for me. I’ve allowed my schedule to shift around a few hours depending on my girlfriends work schedule, which is great, but sometimes the schedules can’t match, and that is where it gets challenging for me.

    There have been a few days where distractions poke at my productivity level, but I’ve found that comes from my work goals being left undefined. Using RescueTime you get a concrete value on what you’ve done for a day, and that allows you to answer “Have I given an honest days work?” without guess work and the goals and alerts can really let you know that.

    Which brings me to your point that our team is fairly spread out, but from my perspective I’ve felt like part of the team prior to day one. Google Hangouts have certainly helped bring our virtual office closer but the atmosphere matters. I predict the only thing you will miss about Seattle is Seattle, the office is here, and there.

    • Robby Macdonell says:

      That’s real good to hear! I think answering the “honest day’s work” question was a missing piece the last time around. If I knew there was more to do, I’d just keep churning on it. Obviously that’s a recipe for burnout, so I gotta get over that. Here’s a good post about it on the 37signals blog: http://37signals.com/svn/posts/3180-a-good-days-work

      “The only thing you will miss about Seattle is Seattle” is really well put. 🙂 I’m going to miss a lot about the city, but the day to day work stuff probably won’t change very much at all. Except my standing desk, I’m going to miss the hell out of my standing desk.

  3. Roger Wolgemuth says:

    Being part of the RescueTime family, and working remotely, there are a couple of things I have found. (I should add that I work in Atlanta with my brother, so my situation is somewhat different.)
    1. Structure is crucial. For me anyway. The flexibility of a work-anywhere IT job is great and one of my favorite things about the job. But it would be easy for me to be all over the place time-wise or fall into bad work habits if I didn’t impose some kind of a scheduled plan for getting stuff done. You don’t have the same proximity of peer encouragement/pressure, so you need to create it.
    2. Getting out of the house, also crucial. I could work from home – I have a second room I don’t use for much else where I could work comfortably, but this would make me absolutely stir-crazy. Coffee shops are one solution. I find office space helpful as work isolation – a flexible, part-time solution there would be nice.
    3. Social environment. I think it would be quite challenging moving to a new place where your only immediate network of friends/acquaintances was online. Fortunately, Robby, it sounds like this is already in place for you and I think that will help immensely.
    Good luck with your move! We’re looking forward to having you in the south.

  4. Ben says:

    Hey Robby, I was working from home a few days per week at my last company, and really loved it, so now I’m doing consulting/contracting 100% from home, and currently working with a client who is in New York, but with most software development happening in Seattle (I’m in Portland, OR these days).

    Since my house generally has 1-3 young kids in it, I close my door and put on headphones and that’s enough to let me focus 100% on my tasks. Some days I bike over to a coffeeshop to do some work, but usually only for a couple of hours at the most–my (standing) desk at home is just more comfortable and it’s easier for me to get in the zone in my own space. But even at home I move around a bit, sometimes moving to a couch to do heavy research. The laptop is super easy to move around at home because it’s almost entirely wireless (just power & headphones, though I could go bluetooth if I were motivated).

    The folks I work with are very flexible about times for getting together, with communication moving between email and Skype as needed. I think that as long as you stay engaged and excited about what you are working on, being remote works out pretty well (for me). When I was in the office, I could rarely get more than 1 straight hour of concentration before a coworker came by with either an interesting question or idle chitchat (both valuable, really, but also both concentration-breaking).

    All that said, I do sometimes have nights where I’m working after dinner, but since my work environment is so portable, I can finish up my work while sitting on the couch with my wife (who, to be honest, has a laptop on the couch in the evenings more often than I do).