Steph Yiu

What It’s Like To Work, Future-Style


Me riding a square bike in the future. (Taken at the Museum of Mathematics in New York)

I recently started working for a “distributed” company, which is sort of a dream come true for a Third Culture Kid like me. The company that is “distributed” means that it’s scattered across different locations, and everyone works wherever they are. As someone who’s pretty much always had a normal desk job, the transition was pretty rough on me. It’s now been almost three months, and this new gig has completely changed the way I work, and for the better. It has convinced me that more and more companies will be structured this way in the future. Here’s what I’ve learned from working future-style:

1. Focus on the work, not the hours
When you work remotely, it doesn’t matter how much time you spend sitting at your desk — the only thing you have to show for your day is what work you’ve actually gotten done. So, to minimize the time I spend staring at a screen that makes my neck and eyes hurt, I work as efficiently as possible. By setting my own schedule and not having any distractions (i.e. chit-chatting with colleagues), I’m twice as productive than I have ever been.

2. Leave Email Behind
Email blows. Someone once told me that it’s a personal to-do list that anyone in the world can add to. It’s also a black box where information is locked away — no one else can get access to information that doesn’t really need to be private anyway.

At Automattic, we don’t email our colleagues. We use IRC in place of hallway conversations, Skype in place of private meetings or quick emails, and a discussion board in place of department-wide emails and project management tools. I love this so much. By freeing the team of private inboxes, we’ve optimized collaboration. Folks can look up the information they need to see how a project’s going, and someone can quickly step in when a colleague is out on vacation.

3. Document Obsessive-Compulsively
Ever forget what was discussed at a meeting? Or, what a client talked to you about? When you work remotely, it’s essential to write everything down to share with your colleagues virtually. If it’s not written down, it didn’t happen. I’m loving this new habit because the process of writing things down encourages me to slow down, organize and clarify my thoughts before proceeding.

4. Learning Can Be A Slow Process
Learning the ropes of a new job virtually is a painfully slow process. When you talk to someone face-to-face, you get a lot of contextual information, and information is exchanged pretty quickly. When your colleagues are showing you the ropes over chat, you get only what you see on the screen, and the information exchange is pretty slow, since you’re typing.

I thought I was moving at a snail’s pace my first few weeks, but I realized that besides learning the actual material, I was also developing entirely new work habits that I would need to function at my virtual job. My first few weeks were a crash course on how to communicate with your colleagues virtually, how to use the internal communications appropriately, and where to find information in our “virtual office.”

5. I Don’t Need a Physical Office To “Do Work”
One of the most freeing things about working remotely is that I no longer have to cut trips short to make it back to the office Monday morning. During Thanksgiving, I spent the week in St. Louis, working from Jared’s parents’ kitchen counter for a few days. In the winter, we left for a ski trip earlier than usual, and I just wrapped up the work day on my laptop in the car (I wasn’t driving). For Christmas, I traveled to meet my parents in Las Vegas, working from a lounge at the Wynn for a day. I love being liberated from a physical office because I’m more focused on doing my work, instead of getting to the office to work.

6. Set Boundaries, Otherwise You’ll Be Working 24/7
When your office travels with you, you need to set up boundaries. When I was in Las Vegas, my parents were constantly trying to get my attention while I was trying to get work done — it’s hard for other people to understand that even if though you’re around, you’re actually “at the office” working. On the flip side, while I was on a ski vacation, it was really hard for me not to check-in with the office while I was supposed to be disconnected. When working remotely, you have to set boundaries, otherwise you will end up working all the time.

7. Gizmos and Gadgets Are Taking Up My Carry-On Space
Because I am on the road so much, and working from all sorts of crazy locations, it’s incredibly important to have internet access wherever I am. If I don’t have internet, I can’t work. Within two weeks of working at the company, I set up my iPhone with a Personal Hotspot, so that I can tether my laptop to my phone to work from everywhere. Within a month, I got packing cubes and GoToobs to help me pack efficiently and travel comfortably. Within two months, I purchased a mophie for extra battery life on my phone, which kept dying from being used constantly while I was on the road. I never thought I’d grow up to be my dad, but my carry-on is now full of gizmos and gadgets to help me travel and work easily.

8. Staying Healthy Is Harder
When I worked at the Test Kitchen, I was on my feet all day. I either walked, biked, or bussed to work, I ran up and down the stairs all day between my department and the kitchen, I bounced into different departments to check in with my colleagues, I packed and shipped goodies to bloggers constantly, and I booked it into meetings because I was always a minute late. Nowadays, I take a train into my co-working space, or walk upstairs to the home office, and then I’m pretty much seated all day. Jared and I got matching Fitbits for Thanksgiving and he’s constantly doubling my walk score without even trying. I’m also noticing that my shoulders ache more than they ever have before. Needless to say, fitness is now something I have to pay close attention to. Besides my regular yoga-and-dance-class pseudo-regimen, I’m considering running another half-marathon next year, or getting a personal trainer to whip my ass into shape.

9. It Can Get Really Lonely
As if it weren’t already obvious to everyone who knows me, the Myers-Brigg test defines me as an extrovert, someone who “gets energized by being around people.” Being alone at work has probably been the hardest adjustment for me so far. Some days, when I work from home instead of the co-working space, the only person I’ll talk to all day is Jared. On these days, I get pretty stir-crazy, and a little sad. In the last few months, I’ve been more pro-active about going to dance class, running errands or bugging friends to for breakfast, lunch, coffee, dinner, game night, pasta night, drinks, just to get out of my head, away from the screen and feel more like a normal human being. And think this better — I shouldn’t be dependent on work for social interactions, and I’m encouraged to spend more time with my friends.

10. Being In Control Rocks
Working remotely isn’t for everyone, and it’s definitely taken me a while to adjust to it. But, I love being in control. I can plan out my schedule, my location and my work day to what works for me. If I don’t like something, I can change it. It’s made me more proactive about finding ways to improve how I work, and I’m learning how to be better at it every day. I’m also getting lots of great advice from my colleagues, since everyone has gone through this before. Basically, it means that as long as I put effort into improving it, working future-style will only continue to be more and more awesome.


  1. Awesome write-up, Steph! I found #9 on your list particularly interesting. I definitely noticed that you are an extrovert :) So I am curious about your strategies to tackle this. Do you spend much time on the phone, and does it help? I found that having even a short voice conversation with a colleague or a client was energizing and “unstuck” my thinking when I worked from home.

    I’m an introvert, and working in an open space office a couple of years ago sucked the life out of me to the point that I had no energy or desire to go out after a day in the office. The first couple of months of working at home (my previous job was also at home) were a hermit heaven for me, but then I started getting itchy, and now I’m at the point where hanging out with other people is something that I active pursue and put on my priorities list.

    Regular in-person meetups are also very refreshing – so glad that Automattic organizes them, will definitely try to get to more of them this year.


    • Thanks for reading! I used to work in a very social office atmosphere, where I would get lunch, dinner or drinks with my colleagues on a regular basis — so switching to working remotely has been a big change. To tackle the loneliness, I just make sure to plan a lot more lunches, dinners, drinks, etc. with friends. I really enjoy this because it means that I actually make time to spend with my friends, we do fun things together, instead of relying on my work environment to satisfy my social needs.

      And, I totally agree — I really value seeing my colleagues in person, and am looking forward to more meetups :)


  2. Dan

    I wish that more employers would see the corresponding benefits of each of these. The most obvious ones that come to mind are minimal overhead costs, no office space to lease, the potential of a multi time zone support offering with resources distributed across a country, not to mention a really great perk to grant employees at virtually no cost


  3. jerome

    Everything sounds amazing except for the loneliness part. I couldn’t live without people to goof on all day. Seeing everyone’s faces means a lot to me.


  4. So much awesome in this post. In my experience, #5 is the most powerful, by far, though I’d argue #6 is less about boundaries and more about living/working in a constant flow between both work and play.


    • Thanks for reading! I think people handle #6 very differently — there are some folks who prefer having a constant flow between work and play, and I am really envious of that trait. For me, I can’t properly unwind or relax unless I’m completely unplugged so I really need clear boundaries. Maybe this is something that will change as I get more used to working remotely — we’ll see!


  5. I’m a avid reader of Matt and Tim Ferris writings, so is nice to see that working at Auttomatic is cool.

    For me, the #8 is the worst part. I’m a illustrator and web-designer, so I work all day seated.

    Try buying some exercises magazines (like Women’s Health) and do two sets: a light set, for before working, and a heavier, for the end of the day. Is great to burn the stress. ;)



  6. Scott Berkun

    I worked at Automattic from 2010-2012 and my book about the experience comes out fall of 2013. Many folks go through an adjustment period – I’m sure your coworkers on the awesome VIP team will have good tips for you. Thanks for this write-up – it reminded me of a few things.

    One question for you regarding #9: Do you find days where you’re more social online helps? I found there was a large psychological difference between hearing the voice of co-workers vs. just typing in chat. But I’m wondering if for you there are some fundamental things about sharing physical space with people that you require a minimum amount of to feel ok?


    • Hi there! Congrats on your book, I’m looking forward to reading it!

      About your question — I think I’m still figuring this out. I’m the kind of person that prefers being in a group of people than being by myself. I’ve never lived alone, and I loved having roommates before moving in with my boyfriend last year. So right now, no amount of online interactions can replace my need for real social interactions. Maybe this will change — it’s only been a few months for me, after all.


  7. Bashing email seems all the rage these days, but personally I find IM far more of a disruption to my personal and team productivity, especially when our waking/working hours do not overlap. Shared mailboxes and threaded mailing lists work very well with a bit of discipline and proper configuration.


    • I agree that IM can be disruptive. If you were in an office, you’d notice that your colleague is wearing headphones and is “in the zone,” and that it probably isn’t a good time to bother them. Virtually, you can interrupt them at any time you want, since you don’t really know what they’re up to. I haven’t really figured out how to handle this yet, besides going “Invisible” on Skype when I really need to focus.


  8. loberg roofing

    That picture looks like so much fun! I think IM is the worst when I’m working, its certainly a distraction having a blinking application at random times in the day that needs your attention.


  9. Really excellent post, Steph. I’m pretty new to the remote work environment too…and figuring out what works best is definitely an ongoing process.

    The two points that most struck a chord with me were:

    #2: Email: Totally agree. It blows! Not only has Automattic dispensed with a lot of my work related emails – but it has completely done away with “email clutter”…all of those emails you get when you work in an office: “Cookies in the Kitchen”, “Re: Cookies in the Kitchen: Thanks!” “Re: RE: Cookies in the Kitchen: You’re welcome!” When I got busy, these emails piled up and eventually overwhelmed…like weeds in a garden..which is really discouraging. Trying to stay on top and delete all this stuff is a soul crushing exercise that I no longer have to deal with.

    #10: Control: To me, the biggest freedom is choosing your own working hours. I didn’t function at my best on a traditional office work schedule: 8+ consecutive hours of work, sandwiched between personal/eating/sleeping time. My best work schedule was college: wake up, class, lunch, gym, class, send email, class, dinner, homework, go out, email, read, sleep..smaller but more intense chunks of productive time, spread out over an entire day (9AM – 3AM). Not surprisingly, with almost complete freedom from “office hours” my work schedule now closely resembles my old college schedule (minus all that time spent on shenanigans, of course…).


    • Great feedback, Paul! I’m so glad I wrote this post because it means I get to hear about everyone else’s experiences working in a “distributed” manner. It makes me feel surrounded by a community of people who have all gone through similar experiences — it’s nice to know that this strange adjustment period is not just me :)


    • Scott Berkun

      Before you guys joined there were a few P2 threads about how different people manage their time and the adjustment (re #10). It’s possible they’re linked in the Field Guide. If you can’t find it let me know.


  10. Richard

    I’m joining the crew in 2 weeks from today, woot! Thanks for this writeup, it’s good to have even more info on what’s coming up for me. Thanks for tip #3, I’ll have to watch that one; I look forward to #10, yay!; and as for #6, I can already see the dangers of “working 24/7”; I ‘m constantly checking things to see what’s up, in preparation for my 1st day. It’s fun times, BUT I won’t be able to do that forver, I will definitely need to watch that and make sure to disconnect!


  11. Thanks for this blogpost, very interesting! You should visit Ravensbourne College in London. They implemented this concept pretty much throughout the whole building and their employees can work from home too, of course. Just one point I do not agree upon is “3. Document Obsessive-Compulsively”. I prefer to not write down too many things while listening – because listening and understanding is an active process that would be distracted by writing everything down. I agree, that it is necessary to remember what happened and it can be hard to agree upon the content especially in group work. However, I would prefer another solution.. e.g. recording via video / tape.


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