Danger's rules for working remotely

11 Jul 2015

At the time of this writing I’ve been working full time in the Square San Francisco office for about four years. The culture here relies on high-bandwidth interpersonal interactions and working in close physical collaboration. Some of my colleagues, when they work from home for a day or two, will return to the office and say they’re happy to be back because home “has too many distractions”. Others can’t wait to get home and away from the distractions of the office to focus.

My career in professional software started when I was 21 and until I joined Square 8 years later I only ever worked remotely and with flexible hours. The first three or so years I struggled to keep a schedule and stay on task but I eventually found a system that works for me really well. So well, actually, that when I joined Square my productivity took a hit as I tried to adjust to the distractions of a communal working space. Here are the rules that I developed for myself over most of a decade to make remote, flexible work more productive than being physically close to my colleagues.

Rule #1 Dress up

One of the side-effects of going to an office that we tend to miss is that it forces us to look and act respectably. When you dress well you’re going to feel good. It’s not just for other people - it’s something you do for yourself.

One of the oft-lauded benefits of working from home is the ability to work naked or be in your underwear or pajamas. The fact that you can do this is great. But this should be exceedingly rare. Because the moment it no longer feels special to work in your pajamas you become a human who lives in your pajamas. It’s a self-image you have to spend energy fighting against if you want to feel professional.

I once founded a company with a partner and worked for a full year on it without ever seeing him or any of the rest of our company in person. Everything was over the phone, email, chat, or laggy, low-fidelity video chat. It worked great. But it also meant that I could have spent 12 full months wearing nothing but the same greasy clothes and forewent every form of personal hygiene until I cried myself to sleep every night in a sweaty ball of self-disrespect.

So don’t skimp on nice clothes and a good morning bathing routing. You’re not doing it because somebody else expects it of you, you’re doing it because you’re a professional and you’re good at what you do and you should look good doing it - even if the only person who sees you is yourself in the mirror.

Rule #2: Don’t touch your computer until you go outside once

This is both the hardest rule to follow and the easiest. Years ago I had a morning workout routine that saw me at the gym at 7am. Once I stopped going so early I just began work that much earlier. And then I started hating every day because I’d wake up and immediately open my email. There were a few days where the sun had set and I was still in bed, furiously trying to do something that seemed really urgent.

Maybe you don’t need this rule but I am a person of extremes. So, to keep myself from forgetting about the unfathomable wonder of our planet, I go outside – even just to walk around the block – before my email gets a chance to eat me alive. As a side effect this forces me to also put on clothes which, if I want to keep them clean, forces me to shower.

Rule #3: Initiate relational connections

The Square SF office has some 600 people all in one giant room. This is amazing when you want to make friends out of your colleagues; there are so many people around that it’s really easy to start a conversation.

But even having so many lovely people all in the same place every day isn’t enough to prevent loneliness. Building a relationship requires more than “Hi, how are you? I’m fine” with a hundred different people each day - it takes initiating vulnerably and sharing your real self with someone.

The difference between how this works in an office or remotely is only in the very first step. If you see someone while walking past their desk then you might stop to chat. If you’re remote you have to go initiate a chat. You can do this without having a work-related question, without any particular topic to discuss, solely for the purpose of building a relationship.

One-on-one meetings serve this function but so do watercooler-style chat rooms and end-of-week Google Hangouts where everybody in the team joins and just plays around with putting on funny hats and sharing jokes. Getting past that first step – just saying you want to connect with somebody – is the only distinct skill needed to work remotely.

Rule #4: Record your daily accomplishments

An unfortunate truth of office work is that we evaluate the output of our colleagues and reports by how much time they seem to spend at work. If they’re in the office before us and leave after us we say they’re hard workers. And if we don’t see them for two weeks we assume they’re at home marathoning Netflix.

In my opinion this creates work cultures where there’s no distinction between the cost of the work and the value. The cost is how much of your time and energy and willpower and emotional investment it took to perform a task. And the value is how much competitive advantage and/or profit was provided to the business. Your company should seek to minimize its costs and maximize value, right? Which would mean minimizing how much of employee time is spent at work doing non-valuable things. And maximizing what each person produces.

Sadly, if you don’t provide a clear story about the value you provide you’ll be measured by the cost you incur working. If you want to prove your value to your colleagues/lead/clients you need to actually communicate what you’ve accomplished. Not what you’re working on – your accomplishments. When your face isn’t visible your output neds to be. I did this for years and it allowed me to find tasks that took only an hour but would provide a full day’s value. Then I could either take off the rest of the day or, more likely, work on things that I wanted to do that I knew wouldn’t have a direct visible output.

When I first started managing a team at Square I set up an iDoneThis.com account that asked each of us the same question every evening: “What is different in the world because of your work today?” I like this question because you don’t get to say how you spent your time. I don’t care how somebody I’m paying spent their time – I care what they accomplished. And I’m not interested in providing an incentive structure that rewards worthless, hard tasks.

This is one of the great liberations of remote work – you can just think about the value. What have you actually accomplished today? Is your client/customer satisfied? If so, you did a great job, even if you did it in 15 minutes.

Rule #5: SPINE

Several years ago a close friend pointed out to me that it was obvious to him why I’d get depressed during the work day. He introduced me to a silly acronym “SPINE” that represents the things you need to get each and every day.


A full night’s sleep, no exceptions. If you report to me and you didn’t get enough sleep the night before I’ll ask you to take an afternoon nap. We’re about as useful working while sleep-deprived as we are driving while sleep-deprived: You can do most of it fine but you’ll miss a few details and that can make all the difference.


This might be reading a book or dancing to music. It might be sex or going to a movie. Whatever you do for pleasure, do at least one of those things every day.


We need intimacy with someone every day. Parents who’re stuck at home with little ones understand this best when they realize they’d chop off an arm for a single adult conversation. Just being close to someone who understands you whom you can understand makes a world of difference. I believe this is something that needs to be scheduled in alongside work stuff at a very high priority.


One of the great advantages that Silicon Valley-style startups have is that they provide healthy food to their employees. In my time at Square I’ve seen people look healthier a few weeks into joining the company thanks to the food.


When I was first dating my ex-wife we’d plan a day together and she would ask “But when am I going to get exercise?” I was baffled the first few times because she had just exercised the previous day, why’s she doing it again? After a while that question burrowed into me and I started asking it, too. Between 2006 and 2009 I lost 50 pounds and transitioned from being a non-runner to finishing a half-Ironman. Yeah, this is me all braggy-braggy but it’s true and it’s because I made exercise a daily thing, not a sometimes thing. Walking totally counts. So does dancing. Anything where I move my body.

These rules could be distilled into just two: Take care of yourself and take care of the needs of the person who’s paying you. If you do that then there’s no reason you can’t make your job happen in a hammock on a beach somewhere.

Please if you found this post helpful or have questions.