“Your calendar is horrible.”



For years, this is what I heard from people trying to schedule time with me. They weren’t lying. I had virtually no gaps — at least from what they could see — for them to book meetings over. All they saw was a sea of events, a nonstop barrage of useless blocks of time. And some of the time, I hate to admit that they were probably spot-on. At times my calendar was truly horrible, and a lot of what was on there was pretty useless, even to me.

That being said, there’s been a lot of talk about Focus Time and Deep Work in the past several years, which paints a bit of a binary: that meetings are bad, and free time for me to go into a cave by myself is good. This mentality is furthered by Paul Graham’s “Maker's Schedule, Manager's Schedule” from 2009, which places a lot of emphasis on the benefits of reducing meetings and spending more time on more “productive” activities.

Taken to the extreme, we might be arguing that the best schedules have…nothing on them at all.

However, while my slammed calendar was sometimes an indicator that I was oversubscribed, unfocused and deeply underwater, that wasn’t always the case: often, my busy calendar actually indicated that I’d optimized my time around my priorities and that all of my time that week was going to be spent on those things. In fact, as someone would try to book time with me and lament “Your calendar is horrible”, I would respond “Yep, it sure is. I’m spending my entire workweek on priorities A, B, C, and D with the key people I need to get that shit done. Let’s try to meet next week.”

Be busy...for the right things

My perspective on this is simple: a busy calendar isn’t by itself bad. A busy calendar with intentionality, that is, isn’t bad. A busy calendar with no intentionality, however, most certainly is. In other words, if you’re filling up the 40-50 office hours that you have each week on the things that are truly important and defending your time to work on that stuff, your calendar is assuredly going to be busy. Busy, but not horrible. If you’re a victim of your calendar, though — if you just relent to the deluge of meetings that come your way and don’t think of the schedule as actual blocks of time that are dedicated to your priorities, you’re going to be hurting every week.

Another take on this comes from Mike Monteiro’s excellent article, “The Chokehold of Calendars”:

People rarely schedule working time. And when they do it’s viewed as second-tier time. It’s interruptible. Meetings trump working time…By handling events as something we work towards and need time to produce things for, rather than as disruptive singularities, and by respecting that work time as something associated with a goal we achieve a calendar that shows both those meetings, now less inane, and the time time necessary to do the work that will make those meetings successful.

In other words: as you’re planning your week, don’t try to just book "working" time. It's unfocused, and it's not clear what you're doing with it to others, so they see it as interruptible. Alternatively, if you own your calendar and align events to your goals, you're suddenly changing the entire paradigm: it's not "working time vs. meetings", but rather "useful meetings vs. not useful ones."

Yes, take the time you need for solo work. Yes, spend time making things. But if you’re a manager (hell, even if you’re a maker), chances are you need collaboration points with other smart people to make progress on your priorities. Make useful meetings that advance the important stuff. Make meetings that people walk away from inspired and invigorated (imagine that!) instead of energy-sapped and demoralized.

You’re going to be busy, and your calendar will probably still be slammed: ideally, though, it’s for the things that matter. And next time someone says “your calendar is horrible”, you can say “I made it this way, and I love it.”

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