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: