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Dancing with Structure: The Antifragile Calendar

Photo: Smith’s Illustrated Astronomy, by Asa Smith (1851)

Why Calendars Fail

I’ve had an emotionally fraught relationship with my calendar for many years.

I was able to dodge some of the love-hate rollercoaster from time to time by stripping it down to its simplest use (using it for meetings, and only for meetings); and leaving the rest of it completely blank.

This approach allowed for perfect calendar adherence, which meant that what the calendar said actually mattered. For much of the day, the calendar didn’t tell me what to do; but when it did, it really meant something.

Those fat blocks of blank space, though, between meetings, resulted in a background hum of decision fatigue, opportunity cost, and a grating sense of constantly fighting back against the impossible-to-predict chaos of each day.

I could survive alright in those empty spaces by establishing morning & evening routines, and following some simple to-do-list practices between meetings;

But, still, I had the feeling of life being somehow split: between the near-sacred but sporadic structure that gCal prescribed, and the shifting sea of unformed temporal life-force between, which I was constantly wishing would hold still with the kind of reliability that pre-scheduled meetings did.

As a result, I would inevitably begin to fill my calendar with blocks that I hoped would bring some of that same sweet sense of structure to the rest of my day.

It sometimes started off small (“dinner,” “evening routine,” “writing”); sometimes it took the form of an entire recurring daily schedule, pre-planned, from sunrise to lights out.

Regardless of how much I packed the calendar, one thing proved constant:

At some point, whatever I’d planned wouldn’t end up happening, and life and calendar diverged.

And as soon as life and calendar diverged, whatever the calendar said about the future no longer mattered quite as much.

This experience doesn’t come as much of a surprise. If you have a friend who says he’s going to meet you somewhere at a particular time, and shows up 45 minutes late with no communication, the verbal claims of that friend in the future no longer mean quite as much.

Or if an acquaintance on social media spouts repeated predictions about a grand reveal of cannibalistic cabals at the highest levels of government next week, and the prophesied events continuously do not come to fruition… it probably doesn’t make much sense to pay attention to jack shit anymore that this person posts on FB.

This matters because a calendar is a friend; it is a kind of golem, a technological companion with an impeccable memory who parrots back whatever predictions you teach it.

And, unfortunately: no matter how disciplined, structured, and consistent a soul you may have, your predictions and life will inevitably diverge.

This means that there seem to be two basic options for calendar use:

  1. Keep it mostly empty and useless, containing only meetings where the involvement of another person and the necessary synchronization of two individuals’ timelines holds you strictly accountable, such that what the calendar says remains sacred but sparse;

  2. Or fill the calendar up, and have it slide gradually but inexorably towards utter meaninglessness.

Or, put more succinctly:

  1. immediately keep most of it useless;

  2. gradually make the entire thing useless.


Building a Solution

There is a third option, which took (a) many painful cycles between option #1 and #2, (b) learning the basics of financial spreadsheet management, and (c) an off-handed comment from my wife to come together.

I won’t go into the full history of the system’s genesis here, but will map out a succinct overview of how it works and why, such that you’re fully equipped to try it out yourself.

If you’ve shared any of my calendar pains in the past, it is worth a shot. My life is better when I use this system.


As mentioned above: the failure of detailed calendaring does not result from a lack of discipline.

A detailed calendar’s inevitable decline into meaninglessness results simply from the fact that humans predict imperfectly. None of us is going to escape that element of reality any time soon.

Our failed predictions include those about external events (e.g. not anticipating a time-sensitive call from your bank) as well as those about inner states (e.g. not anticipating that you’re really not going to be in the mood to work on that creative project at 4:30pm.)

The fact of imperfect predictions gives birth to two different principles:

  1. Structure is good (because it helps strengthen our predictive power)

  2. Flexibility is good (because it helps us respond appropriately to life’s unexpected demands)

Calendars by default serve as extensions of the structure principle. This means that they do not serve the principle of flexibility.

And this in turn means that the chaos of life inevitably conflicts with the structure of a calendar. A calendar of pure structure is guaranteed to live in antagonism to the fluidity of life.


The Solution: An Antifragile Calendar

Nassim Taleb is most famous for his invention of the term antifragile. Antifragility is a kind of crowning mode of super-resilience.

Resilience is the ability to stay strong in the face of chaos; antifragility is the quality of getting stronger in the face of chaos.

Too much structure = brittle = fragile;

Too much flexibility = soft = fragile;

A good balance of structure and flexibility = resilient;

A union of structure and flexibility = antifragile.

For a calendar to successfully incorporate the principles of both structure and flexibility, it must do two things:

-to the greatest extent possible, it must become antifragile (in other words, it must somehow unify structure and flexibility, such that the system grows stronger in the face of failed predictions or intentions)

-wherever antifragility is not possible, it must strike an appropriate balance between structure and flexibility, to optimize the resilience of the system.

A map for how to accomplish both of these aims is laid out below.


The System Itself

The central rule of an Antifragile Calendar is simple:

The calendar has to match reality.

This can come about one of two ways:

  1. You can do what the calendar says

  2. You can change what the calendar says.

Neither 1 nor 2 is intrinsically preferable to the other. Both are perfectly acceptable methods of reality-mapping.

Theoretically, you could keep an accurate log of reality by simply entering in what you’re doing in real-time—but this would be a pain in the ass to do throughout the day, so it proves much easier to give advance predictions your best shot.

So this is the whole system: map out your best predictions in the calendar (largely with recurring daily and weekly events), change those events when life diverges from the plan, and then change your predictions for the future based on what actually happens.

The process above, on its own, has the following four effects:

  1. the map and reality constantly re-converge throughout the day after every inevitable divergence—making what the calendar says continue to mean something

  2. daily and weekly predictions grow steadily more accurate, by engaging in a consistent, rhythmic dialogue with real life

  3. your behaviors begin to naturally re-organize as a result of seeing an accurate map of how you’re spending your time (just like financial habits re-organize simply by looking at expenditures each month)

  4. you experience a gentle, externally-generated pull towards your original intentions through the simple fact that doing what the calendar predicted is just a tad bit easier than changing what the calendar says—so you have technological friction aiding your daily intentions, in such a way that willpower is no longer your primary source of adherence to structure

We could end the article right there. That is the heart of the system, and all you really need to know to make it work. Everything else is secondary.

But there are certain considerations and tricks that I’ve picked up along the way, which will accelerate the learning curve and increase long-term effectiveness in some significant ways.

Zero Empty Space

This system only works if you have the entire day—i.e., all of your different activities—mapped out.

Otherwise, you’re working with the equivalent of a financial budget that leaves out specific categories of spending.

Reviewing your calendar and not having things like “mealtimes” recorded is like reviewing your finances without any of your food expenditures recorded. It defeats the purpose.

Initially, this full-stack calendar can look a bit overwhelming.

The best ways to deal with that experience are to (a) include rest periods and “free time” in your predictions, and (b) put “sleep” as a real calendar event—not leaving any blank space at all.

(This second piece might seem slightly counterintuitive with a view to escaping overwhelm; but if your entire calendar is filled, then something shifts in the way you see it. We’re used to empty space meaning something like “freedom”—the easiest way to break that view is to eradicate all empty space.)

Empty space in the calendar can’t exist because an Antifragile Calendar serves as a perfect record of what you’re doing, and you are always doing something.

Weekly Reviews

A cornerstone of this system’s power is a single recurring weekly time to engage in review and refinement of the recurring daily and weekly blocks of the calendar itself.

This can be a 15-minute block, though I like to make it a bit longer to stack in other review activities.

During this review you do three things:

  1. Look at what happened the week prior

  2. Look at what you’ve currently predicted will happen in the week ahead

  3. Change your predictions as you see fit.

That’s it. Don’t worry too much about how best to change your predictions—you’ll try different things over time, and every time you perform a weekly review you’ll get better at it.

For instance: you may notice that your days usually start in reality about 30-60 minutes later than you’ve mapped out, and after the first week you resolve to try really hard to get up when your alarm goes off, so you don’t change your morning map for the next week at all.

After another week of the same thing happening, though, you decide to change your wakeup time in the calendar to 30 minutes later, to help you more accurately map out the rest of your realistic mornings—and discover that all you have to do to make that work is to bump your 30-minute reading block from the morning to the evening before bed, to replace half of your current hour-long “TV + Schmooze” block.

After a week of trying this new wakeup time prediction, you find that it’s significantly more realistic for how your body actually behaves, and you’ve consciously reorganized the day to still hit your major priorities.

(And, most importantly—the calendar still means something.)

If you miss a weekly review, that’s ok—just remove it from the calendar for this week, to show that it didn’t happen. It’ll show up again in the future, and give you another chance to do it.

Even if you used the calendar with no weekly review, it would still be far more powerful than a standard calendar system.

The rhythmic weekly review, though, does have the potential to significantly increase the system’s power—so if you were to treat any single event in the calendar as relatively sacred (so that it at least happens, even if it doesn’t happen at the time you intend), I’d recommend making it this one.

Two final notes on weekly reviews:

  1. Since the system is built on recurring daily and weekly blocks, you should be able to do a solid job comparing “predicted” to “actual” by looking back at the recent week and comparing it to the week ahead. But if you want to get more precise, you can take a screenshot of each week in advance and store it in a folder on your computer to compare to the week’s record once it’s done.)

  2. Each weekly review + refinement is your chance to resolve any overlaps or gaps in the week ahead. (If, for instance, a meeting’s been scheduled during your usual afternoon work block on Tuesday, you can break up or shift that work block to accommodate the meeting.) You want to be able to head into each week after your review such that if you did exactly what the calendar said, you wouldn’t have to adjust a single thing in the calendar, and would always know with 100% certainty what you predicted you’d be doing.


I’ve experimented with different degrees of precision in logging the reality of what happens (to the nearest 1 minute, 5 minutes, 15 minutes, and 30 minutes).

I’ve concluded that a 15-minute scale of precision provides the right balance of flexibility and structure. This means that you use 15 minute increments in the calendar, and round to the nearest 15 minutes whenever things deviate.


  • don’t create calendar events smaller than 15 minutes. Events can be 15, 30, 45, 60, 75, 90 minutes… etc.

  • if you go 7 minutes over or under on something, you don’t have to change what the calendar says.

  • if you go 8 minutes over or under on something, you do have to change what the calendar says.

This gives you 7 minutes of breathing room before you have to change the calendar, which is a realistic amount of time to deal with the natural ebbs and flows of each day.

This keeps things relatively tight, while helping prevent the resentment that might otherwise accrue from having to change your calendar every time you go a few minutes over on a task.

(It also has the benefit, in Google Calendar specifically, of allowing you to change the event with one mouse click-and-drag on a laptop.)


Perhaps the biggest question in first mapping out your recurring daily or weekly predictions is “how specific should I be.”


Do you block out “7:00-9:15 morning routine”?

Or do you block out “7:00-7:15 shower and get dressed; 7:15-7:30 breathwork; 7:30-8:30 meditate; 8:30-9:00 journaling; 9:00-9:15 to-do list” as 5 different calendar events?

The answer is simple:

It doesn’t matter. Try to strike a solid balance between generality and specificity, and refine it over time during your weekly reviews.

If you’re consistently confused by how long a particular block of tasks takes, then it could be useful to break it down into smaller blocks to see what’s going on.

If you’re getting annoyed by having to check and adjust your calendar in between the items of a relatively consistent morning or evening routine, then it probably makes sense to chunk them together into a single event.

If you’re going into vacation or retreat mode, and don’t want to track how you’re spending your time, no problem—just block off the entirety of those days and call them “vacation” or “retreat.”

Ultimately: your level of specificity doesn’t matter. Do your best to strike a reasonable balance, and it’ll improve over time simply by using the system.

Interaction With Other Systems

If you use a task management system, habit-tracking software, or even simple to-do lists, you can think of them as “hanging off” the central structure of the calendar.

This means putting dedicated blocks of time in the calendar for going into those systems and processing them.

Again, the level of specificity that you choose to go into with this is a matter of personal preference and experimentation.

For example:

Some people like to have dedicated blocks in the calendar called “Process emails” (I don’t—I just have blocks called “Process Tasks,” and have emails as a recurring daily item in my separate task management system);

Some like to distinguish in the calendar between specific projects, or between “business tasks” and “personal tasks” (also not something I do);

Some like to integrate Cal Newport’s “Deep work” idea by having a two-hour block at the start of the day where they work on their most important project;

Some like to integrate David Allen’s Getting Things Done method by having time blocked off to process different inboxes. (Though David Allen famously discourages extensive calendar use, a lot of his methods turn out to fit quite well with an Antifragile Calendar).

How you decide to divvy up your systems is, again, up to you. The most important thing to keep in mind is that it will likely change, over time—and not just change, but actually inevitably improve, as a result of your weekly reviews.

Just make sure that any other systems you do use “hang” from specific recurring blocks in the calendar.


While this element is partly dependent on the calendar software you use (I use Google Calendar, but it’s not for everyone):

If you have the option to color-code specific types of events, I recommend doing so.

The categories you choose are up to you, but even if you use as simple a set as “Productivity,” “Personal Routines,” “Family and Friends,” and “Romance”—

Having these types of blocks organized by color turns each calendar week into a clear visual schematic of how you’re spending your time in each area. It’s a small detail, but it increases awareness of how you’re living your life.

Rest and Play

One of the most common mistakes when diving into this system is to create an insanely unrealistic map of your intended life that includes no periods of rest or personal nourishment.

Thankfully: the system itself will take care of this fairly quickly. You’re going to take breaks in the middle of the work day even if you don’t plan to, and you’re going to have to record them every time they’re more than 7 minutes long. You might watch TV at some point in the evenings rather than filling out a comprehensive 60-minute daily review process you made for yourself.

When these things happen: they are perfectly within the bounds of the system. Just record them, in the calendar, like you would anything else; and begin to take those needs into account every time you update your predictions on a weekly basis.

Eventually, your calendar will stabilize into a more-or-less rhythmic routine that actually prescribes periods of rest, as well as periods of fucking around—because those periods are required to get your best work done outside of them, and to live a balanced and well-resourced life.

Alarm Clocks

For certain calendar events (particularly work blocks, workouts, or other activities without a natural stopping point), you’ll find it very useful to set an alarm on your phone for 5 minutes before you intend to stop.

This allows you to immerse fully in the activity without constantly checking the time; and when the time does come when you’d anticipated switching tasks, you can then decide to follow the calendar, or extend the calendar block of what you’re already doing as a deliberate choice while shortening the subsequent activity’s block.


We’ve touched on this already, but it bears repeating because it’s the hardest psychological shift most people experience when diving into Antifragile Calendaring:

There is no problem whatsoever with deviating from what the calendar says.

You are not failing the system. You are not compromising your integrity. There is zero need to berate yourself. There is zero need for any shame.

All you have to do is change what the calendar says, to the nearest fifteen minutes, to make sure that the calendar still matches reality.

That’s it. The only “punishment” is the very slight pain in the ass of adjusting the calendar. You don’t have to add anything to that, internally or externally. It works on its own.

Honestly: if you have a calendar that mapped out every hour of every day, and you did somehow manage to follow it to a T, you’d probably be ignoring important elements of your life.

Living skillfully means living in dynamic responsiveness to the shifting demands of each day, as well as to the shifting landscape of your own body and heart. Structure is important, but trying to tyrannize your life into a single consistent shape with no room for flexibility is unhealthy and counterproductive.

This system provides complete structure while also providing genuinely limitless flexibility—in such a way that the structure becomes more and more intelligent over time.

There is no problem whatsoever with deviating from what the calendar says. In fact: doing so is the lifeblood of the system.

Make It The One Thing

There is, still, a small element of discipline needed to use this system.

That’s an inescapable part of any structure, and an irreplaceable part of any life well-lived.

But the discipline required here is simple, gentle, and centralized. The only discipline needed is the discipline of ensuring that the calendar matches reality.

That’s it. It takes 10 seconds (and close to zero physical effort) to change a calendar event on your computer or phone, or it takes 0 seconds to do what the calendar already says.

If you try this system, I recommend treating it as the foundation of everything else. All other systems you use hang off the calendar. Time is the central element of daily life, so it makes sense to treat the tool of time management as the central tool of life management.

Don’t commit to doing what the calendar says; don’t commit to any grand adherence to an ideal daily vision for yourself. Just commit to ensuring that the calendar matches reality. That’s it.

Everything else will naturally—and, over time, inevitably—follow.

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