Author: Simon

Remote Work, Scheduling and Serendipity

Something I’ve been thinking about quite a lot these days is the role that structure and discipline play in the life of a remote worker, and a downside I’ve noticed to becoming too structured.

I wrote a little about the import of creating your own signals – in some way we can see that through this same conversation, right? We have to make our own signals in order to keep things running smoothly, to ensure we have the discipline or structure to work the way that we would like to work.

There is a definite tension when it comes to the idea of structure and the idea of working remotely: I think personal freedom is a huge part of what attracts people to a remote lifestyle.

I often find when chatting with others who work remotely, that there is a certain sense of reluctance around creating more structure in their day, or in their approach to work. This Post isn’t all about freedom and structure, although I do think that’s a topic 100% worth really taking a bite out of.

For today, let’s take a look at how I think about structure in terms of what helps me work most effectively, and then we can move on to this bigger topic of going a bit too far in terms of structure.

I structure my work time entirely around my calendar (Google Calendar that is) – I move everything from my to-do lists and legal pads to my calendar as quickly as possible. It’s where I keep everything.

If it’s not on my calendar it doesn’t exist.

That’s from Ramit. He and I agree on this one.

Especially when working remotely, having things laid out very clearly, in a structured and time-bound manner, helps me ensure nothing slips through the cracks, and allows me to see what my day will be like without having to check a dozen different places or processes.

It has been working really well, for years now. It’s kept me focused and successful and impactful in the ways that I have envisioned and planned out ahead of time.

As an aside, do you remember Blockbuster video, or other video rental places? I have really fond memories as a kid, high schooler, and even into college, going to the video store and just sort of wandering until something caught my eye. There wasn’t an algorithm or selection mechanism at play, other than the ones in my own mind, I guess.

I watched some awful movies, but also some really great ones, ones that wouldn’t ever show up on my Netflix queue today. This was a little bit of serendipity, a minor act of finding something that I wasn’t looking for.

The same thing happened in public libraries for me a lot growing up. That’s how I first found and read Stranger in a Strange Land, which was my absolute favorite book for decades. In fact, my first tattoo was from another Heinlein book, TANSTAAFL.

Before our last Grand Meetup, I told the newest folks on my team, joining Automattic for their first ever Grand Meetup, that the most important thing they could do was to leave room for luck – to avoid overpacking their days, to leave room to decompress, to engender chance; meet someone new, join conversations you’d otherwise rush by.

For some reason it never occurred to me, at least until now, that this advice is actually very important for everyone who is engaged in remote work, all the time – not just during a once-a-year workcation.

I would argue that not only is it important for remote workers to try to leave time for serendipity, you actually must find and create space for it. Teams and departments and approaches being siloed is bad enough when folks are in different offices – when you’re on different continents, the odds of a serendipitous meeting of the minds at just the right moment, well, it’s unlikely.

If you work remotely, you need to not only leave space in your day for chance, you also need to get out there. You need to ask folks in the design department to lunch – yes, maybe it’s a voice call while you’re eating breakfast and they’re eating lunch. You need to see if your HR rep would join you for a coffee – maybe they’re in a Starbucks in London and you’re having Cheerios in Chicago, but it’s still a coffee!

When we’re not physically close to one another, we lose something without the chance meetings of mere proximity. To recapture this, we have to make time, and make friends.

Get out there and meet someone new.

 

Working Remotely and Getting Weird

Boiled down, the Big Idea of this Post is this: working remotely is awesome because it lets you be much weirder than if you were working in an office, and this makes you happier and more productive.

I’ve spoken before about how working remotely means you lack certain social signals in your day – however, working remotely also means that you don’t have to worry so much about what folks around you think of your behavior – since there are likely only folks around you when you choose to have them around, be it in a cafe or a coworking space or whatever.

Something I have come to deeply appreciate in the remote work environment is the opportunity to run experiments on myself and the way that I work, to become happier, more productive, and a bigger impact agent within Automattic.

I don’t think of myself as a particularly anxious person, but I do think that I’d struggle to pull off some of the things I’ve tried in a more traditional office setting.

When I was working with the Terms of Service team, each day was a bit of a roller coaster – you never knew what you’d run into (but lots of golden cucumber derived medications, oddly), but it wasn’t always the sort of thing that weighed lightly on the conscience. I would often take 2-3 breaks during the day to lay quietly on the floor in Shavasana to still my mind and listen to my own breathing.

When I was first working with a live chat team, I tried working a number of different hourly and daily configurations – four long days, three long days and a few hours here and there the other four days, six shorter days, etc.

Working remotely also allows you to see how other activities can impact your day – for a long time I’d take a break in the middle of my day to go to the gym. I eventually found that my day before the gym tended to be less focused, less productive, so now I get to my local Y at 5AM on gym days – that way I’m home before Mango or the Doc wake up, and I usually get some quiet work done in that post-gym, pre-breakfast window.

The best part of working remotely for a company that understands the import of results over butts-in-seats is you’re able to fit your work to your own ebbs and flows, rather than trying to fit yourself into someone else’s understanding of what The Work should be or look like.

My current schedule would absolutely get me in trouble in most traditional workplaces – a lot of the work that I do doesn’t look like work – it looks like going for walks or staring at a whiteboard or reading a book. It also doesn’t look like a regular work schedule – can you imagine pitching this during a job interview?

Well, I’ll put in an hour, maybe 45 minutes on Mondays, Wednesdays and Fridays between 6AM and 730AM. Tuesdays and Thursdays it’ll be a little more. I break for breakfast and picture books every day for about two hours.

I’ll be around-ish for most of the day until maybe 4:30, 5PM, although I won’t be at my computer or even really available for some unpredictable amounts of time.

I’ll also work on the weekends sometimes, but not always. But sometimes.

It would be a hard sell! But, this setup isn’t random or the result of whim; it’s the result of literally years of experimenting on the way I work, the times I work, when and how I approach each part of my day and each of my responsibilities.

Whether you work remotely or in a more traditional workspace, give some experimentation a try – you never know what might help you make a leap forward 🙂

 

Efficiency is Behavior

Working remotely and leading a remote team is not always so different from doing that same work locally. Many of the challenges are similar, if not exactly the same.

One thing that’s been on my mind a lot, and if you work in any sort of revenue-driven enterprise, it’s something you think about a lot as well, is the idea of efficiency, and how we can create more efficient situations.

I find a tension exists between traditional operations management ideas and approaches to efficiency gains (calculate throughput, build a sensitivity analysis, reduce waste) and my own approach to leadership, which is a sort of mix of servant leadership and hopeless romantic labor reformer.

That tension is the natural pressure that exists between the idea of employees, Workers, as a numerical input into a larger system (the average Subway sandwich maker can produce one point four sandwiches every five minutes. Reducing that to one point three would represent etc etc, just an example) and the belief that every person has creative value, that the folks working closest to the problem (the sandwich) are those most qualified to solve that problem better, or faster.

I’m not the first person to see this tension – we can read the massive acceptance of and growing excitement about Lean as an antidote to this very tension, if we’re generous, since we can see in the Toyota Production system great empowerment of what you’d call line workers to identify problems, repair, and improve their own Work.

There is a difference between efficiency on a spreadsheet (or, even worse, a Powerpoint presentation) and efficiency in action.

My team is fairly small – it’s me and eleven Happiness Engineers – and for us, efficiency is behavior. It’s actions – it’s not such a fungible idea, it’s not a board room topic. It’s about doing something One Way or This Other Way, and seeing which gets better results in the same amount of time – or the same results in less time, then going with it.

If you’re leading a team, especially a smaller team and double especially if you’re leading a remote team, you must recognize that efficiency comes from behavior, and by testing and changing behavior.

We will never get more efficient with a poster with a quote from Deming under a high res photo of a  fighter jet. The only way we’re going to get more efficient is by trying out new stuff, and chucking it if it doesn’t work.

That means leaving room for failure. That means kicking out the sacred cows and rejecting dogma. There is enormous value in reading and in discussing and in building spreadsheets – don’t get me wrong, I love spreadsheets – but all of those things have to result in action, in trying some shit out.

Otherwise, it’s just air, it’s just value locked up inside your head, and we’ve been over that.

Try something new today. Sleep one less hour. Sleep one more hour. Don’t check your email. Turn off Slack. Listen to one song on repeat.

Going from Abstract Goals to Measurable Results

A few posts back I wrote about how important it is to think about results when you’re leading a remote team.

The TL:DR was that whether your team is remote or local,  clear, measurable expectations up front, ideally through consensus. Those expectations should come with a set of results that everyone agrees will have the desired outcome, results that help move bigger pieces into place, help to create impact toward a larger objective or outcome.

It turns out that these results are the trickier part of that equation – we very frequently, as humans, have personal and professional desires that don’t fit that neatly into check lists or “improve 10%” style goal sheets.

I’ve spoken to a few folks about this since creating that post, so I’d like to dip into this idea with a little more depth, if you’ll allow it.

Results are measurable, but they are only indicators.

OK, Simon, what does that mean?

I’m going to borrow from a friend of mine here, Bryce Boratko. I met Bryce when I was working in Providence, RI – I had three jobs at the time, one at a bakery, one at a community college, and one at the newly-opened Crossfit Providence.

Bryce was a former chef, having worked in Michelin starred kitchens, turned really extraordinary strength and conditioning coach. He was coaching at Crossfit Providence, and I remember a conversation that I had with him around that time.

I was talking with him about how I enjoyed Crossfit because it was a kind of exercise that mimicked my sport at the time, rugby. I liked that it made me better at rugby, or felt like it did.

He nodded, and said, “What do you want to get out of working out here?”

I said, “I want to get stronger!”

He kept nodding, “Ok, how will you know when you’re stronger?”

And I didn’t have a great answer for that. I’d been going to the gym for a long time, since junior high school really, with this abstract objective of becoming a stronger version of myself.

Through conversations with Bryce it became much more clear to me that what was more important was understanding what would indicate to me what being strong meant to me. It turned out to involve heavy back squats – but that’s a story for another day.

I could never put a number on what it meant to be a stronger version of myself – what I could do was look at where I was at that moment, and a place where I could say with certainty that I’d moved in the right direction.

I knew if I could lift X weight, Y number of times, that I was moving in the right direction. These small, measurable outputs were indicators of a larger change taking place.

This is important – small, measurable steps will always be more effective than large, abstract goals.

Javascript is different than lifting weights, Simon.

Well, it is and it isn’t, right? Any Big Goal that feels hard to put a number to is abstract in the same way. As a leader or as an autodidact or as anyone who wants to get better, being able to break your big, abstract goals into measurable, actionable results is key to your success and your team’s success. Here are some examples of Big Goals:

  • Learn JavaScript
  • Become a better team lead
  • Get a dream job

None of these goals are going to take well to quantification. What you can do, more productively, is ask yourself: what would indicate to me that I’m moving in the right direction?

Another great question to ask during this process is, “What would someone who already is a great team lead / JavaScript developer / dream job-holder be doing right now?”

Through this kind of questioning we can break our Big Goals down into more measurable next-steps, smaller results that indicate that we’re moving in the right direction:

  • Submit 10 pull requests to an open source JavaScript project before July
  • Create a survey for folks on my team so I can measure my progress month over month
  • Cold email 20 people with the job title I want and offer to buy them coffee

Results are the bricks. Your goals are the house.

Going from here to there, whether “there” is a personal goal (“Be Stronger”) or a business goal (“Get More Customers”), requires steps, steps that you can look at and check off a list and say to yourself, that’s done. What’s next? 

Working Remotely Means Making Your Own Signals

My first job out of college was with AmeriCorps – I was a community organizer in Binghamton, NY, working on something called the Binghamton Neighborhood Assemblies Project.

The Neighborhood Assemblies were a series of small direct democracy experiments, based in each of the cities voting districts. It was a fulfilling way to spend time, and was exactly what I needed to dive into after giving graduate school a try.

The community organizer gig didn’t have what you’d call much of a set schedule – our office was based out of City Hall, and we came to get to know the signals of the rest of the building.

When we heard the planners head out to get lunch, it was around noon. When we could hear the local alternative radio station, playing through tinny boombox speakers, it meant folks were gone for the day, and the janitor was doing his job. When the hallway lights went out, it meant we were the last ones in the building, and probably time to start thinking about heading home.

It’s been the same for all of my jobs – small signals that indicate where you are, how your day is going, what time it is. In cafes there were early morning customers and late-day duties – you didn’t mop the floor until an hour before closing. Signals.

Working remotely, especially if you work mostly from home, lacks these signals. There aren’t other folks around who present regular patterns of behavior and expectation that you can build your own day around. There isn’t an entire building’s ebb and flow that you can float along with.

There are pros and cons to this – it allows you as an individual to find your own best way, your own ideal schedule and timing, in a way that being mandated to a particular place at a particular time would preclude. It allows for a lot of this kind of experimentation, in fact.

Having no signals can also allow for, or in some way legitimize, the inclination for a lot of tech workers to put in just one more – one more ticket, one more pull request. This is how you end up working far into the night, really letting your work overflow the bucket you had set out for it.

This is a con – a lack of exterior signals, of social signals, may lead us to overwork, to burnout, to unreasonable expectations of ourselves.

It leads us to the question so common among remote workers – “How do I know when I’m done?”

The answer is, naturally, whenever you decide you’re done. It’s the deciding that’s tricky.

So, the remote worker has to create these signals for herself: through experimentation and weighing of options, to create signals to indicate the end of the work day.

You could construct signals to indicate the beginning of your day, when to take lunch, etc – but I think most important for your mental health is finding a way to put a punctuation at the end.

I’m lucky insofar as The Doctor and Mango tend to get home around the same time every day, so I have a nice bookend to my work. I know about when they’ll be home, and I don’t pile anything time-sensitive or must-do in that calendar slot. When I hear the car in the driveway, I quit Slack, I close my laptop, and that’s it.

It’s very freeing. If you’re working remotely and have not yet built yourself some type of end-of-day signal or ritual, I totally recommend it.

It could take any format – maybe you have your computer set to play a particular song at a particular time. Maybe you have a certain last task every day, and you follow it up with a walk around the neighborhood. Maybe you use IFTTT to flash your office lights at 5PM.

Signals are important. When we work remotely we are lucky enough to build our own.