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.

 

4 thoughts on “Remote Work, Scheduling and Serendipity

  1. Great post! You reminded me of the days when I’d go to the local video store (I’m old enough to remember the pre-Blockbuster days, when you had lots of mom-and-pop video rental stores!) without a specific movie in mind, and I’d walk out with whatever looked interesting. Some were definitely duds, but most were actually great for Friday nights with the family or a few friends.

    1. There is something special to that experience, right? Finding something that you weren’t looking for? I feel like the Dutch must have a word for it 🙂

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