The calendar takes its tax

8:30am to 9:00am – Team stand-up. / 9:00am to 10:00am – Budget review. / 10:00am to 2:00pm – Be inspired.

“I wasn't planning on marching into the abyss, but someone added it to my calendar.”

If this Substack had an early nemesis, it would be Paul Graham.¹

But every once in a while, mixed in among his “empirical” “analysis” of policies he doesn’t like and his tweets about his industry fraternity brothers, he happens on a good idea. Twelve years ago, he wrote about one: the schedules of makers versus managers. The post argues that managers are most productive when their days are full of meetings, but makers—engineers and writers, in Graham’s examples—need large chunks of uninterrupted time to be productive.² To do their work, Graham’s makers need both focus and a kind of warming up: They have to load a bunch of ideas into their heads and settle into their task. It takes a while to get into this state—and a single interruption can snap you out of it. 

I’d propose an addition to Graham’s theory. Making something often requires two phases: a generative, creative one, and an editorial one. When writing or building a presentation, this generative phase is finding the thread of your argument or story; when doing analysis, it’s exploring the problem and allowing yourself to be taken by curiosity and unexpected results. I assume it’s also there when painting a picture, or writing code, or making music, or developing a recipe, or doing a host of other creative activities. 

Both the generative and editorial phases require time and focus, and neither are possible if your calendar is full of meetings. But there’s a key difference between the two. Given a few hours of free time, you can always be productive in the editorial phase. With space and a first draft to build on, you can always perfect and polish. This implies that you can schedule editorial work. Put sufficient time on your calendar, protect it, and the work will get done. 

This isn’t true for the generative phase. You can spin your wheels for an entire day (or decade) and produce very little. Cliché though it may be, creative work requires a creative spark—and sometimes, you just don’t have it. You can try to kickstart it—by reading, by jacking yourself up on caffeine, by going for a LindyWalk™³—but you can’t plan it or put it on your calendar. Inspiration will visit you when she chooses.

Meetings are catastrophic when you’re searching for this spark. Knowing there’s a meeting around the corner keeps you from grabbing on to a fleeting idea and seeing where it might take you. Instead, we try to bottle it by taking a quick note, failing to realize that the thing to capture was the motivation of the moment, not the content of the concept.

Worse still, if we do find ourselves in a creative sprint, meetings eject us from it, an alarm clock expelling us from a dream. And like a dream, that particular bit of imagination may be lost forever. Next time we fall asleep, we’re unlikely to return to the same one—if we’re able to dream at all.

It’s a tricky problem. On one hand, we have to have meetings. We can’t all flee from them the instant we become possessed by a rogue thought. Company calendars are delicate webs of dependencies, strung between people and conference rooms and time zones.⁴ Agitate one strand, and the whole thing can tie itself in a knot. 

On the other hand, our current conventions are entirely backwards. While productive, generative work can’t be forced, meetings are the exact opposite. If the pandemic has taught us anything, it’s that we can load ourselves into a meeting at any time, in any state, from any prior commitment. And yet, our default is that meetings are the fixed objects on our schedules, the obstacles everything else—every other bout of productivity—has to work around.

This is especially problematic in a remote-first world. Without drive-by meetings and casual in-office conversation—which can be disruptive to creative work, but can also be politely turned away, sometimes simply by wearing headphones and looking ornery—nearly every interaction requires a meeting. This further checkers our calendars, blasting even more potholes in our creative pavement—potholes that, once placed, we dutifully drive over. 

In this context, Graham’s recommendation to protect time for inventive work is somewhere between incomplete and misguided. A better approach would build in creative slack by allowing people to decline meetings when they’re in a generative flow.⁵ Yes, that may periodically disrupt some meetings. But consider the other side of the equation.

By making meetings the fixtures in our days, we have to schedule time to be creative. If those moments aren’t productive—which they won’t always be, even if they’re guarded blocks of focus time⁶—we end up grinding through generative projects, stretching a task that could take hours if it were done in the right moment into one that takes days or weeks. In this scenario, despite sometimes appearing productive, we’re actually wasting massive amounts of time in a diluted, frustrated slog.

Not only is it expensive, but we also do a worse job. Nothing lowers your standards more than trying to wring results from a dry stone. “I want this to be good” erodes into ”I want this to be done.”

Moreover, people who fight this battle long enough end up demoralized and exhausted. Like someone who hates getting up early forcing themselves to go on morning runs, those who push through creative tasks in the wrong moments learn to blame the work as much as the context in which they’re doing it.

Of course, we can’t postpone every meeting, and we can’t entertain every creative flight of fancy. There are times when meetings are urgent, or someone’s role in one would make their absence from it unacceptably disruptive. But surely we can rebalance the scales away from their current extreme, in which the only excused absence from any scheduled engagement is another scheduled engagement. Surely we can do better than crucifying creativity on the calendar's cross. 

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What does this have to do with data? In general, not a lot. This Substack won’t always be about data.⁷

That said, as Emilie Schario reminded me last week, data jobs are creative jobs, and we’ll do better work if we embrace this. When arranging our calendars, we should give ourselves the blocks of time that Graham argues for—and more importantly, try to protect the moments when we’re rapidly unwinding an analytical problem. Just as the term “ad hoc” changes what it represents, our schedules alter our work styles. A packed calendar can foreclose our ability to be, or even see ourselves as, creative.

This is particularly true if our roles become more cross-functional—more purple, more of a melting pot. Being in the room where decisions get made is great, and data teams should aspire for that kind of representation in important conversations. But every meeting comes at a creative cost. Constant collaboration is admirable, but it isn’t free. 

1. Followed closely by concise, direct writing and aeronautical eels.

2. “Maker” is Graham’s word. I’m not a fan. Terms like maker lean into Silicon Valley’s obsession with entrepreneurs and those seen as doers, often in contrast to people presented as administrative pencil pushers free riding on makers’ hard word and ingenuity. It’s a loathsome frame, both in its self-serving moralizing and its cultish fetishization of The Entrepreneur over the people who prop them up. In reality, everyone works on both creative and administrative tasks, and is sometimes a maker and sometimes a manager.

3. Overextending one interesting idea into an entire brand of schlock theories and trademarked merch? Very Lindy.

4. Google Calendar, the original DAG. Although, technically, I guess it’s just a G.

5. Shout out to Matt Knopp, whose own post about slack served as the original inspiration for this post.

6. When I block off focus time, I’ve found it useful to have both generative and editorial work to do. I typically start with generative work, but fall back to more reliable editorial work if the moment—which may last thirty minutes, a couple hours, or the entire day—isn’t right. The worst way out of a creative block, I’ve found, is through. 

7. If you’re only here for diagrams of data stacks, tough patooties. Among the things in the published archive, Clubhouse, Barry Bonds, and stonks. Among the things in my drafts folder, Pitbull, “the marketplace of ideas,” and luggage.