Scheduling Chaos

A cure for routine-induced boredom

“The Disintegration of the Persistence of Memory” by Salvador Dali (

A life lived in the cocoon of thoughtful routine is both rhythmic and fulfilling. I’ve come to appreciate such benefits lately in my own efforts to adopt more of a “planner” approach to life. It’s mostly great, but there’s one issue:

Routines are so predictable.

Yeah, I know that’s kind of the point. Still, it’s the reason why I quit the majority of the routines I impose upon myself. If I have to do everything at the same time everyday, am I a human or a machine? OK, maybe that’s dramatic. Let’s take a step back.

Personal schedules and routines are good for us for myriad reasons, but the most important in my opinion are:

  • lessening the anxiety caused by uncertainty and lack of structure
  • feelings of accomplishment for following-through on our promises
  • it’s easier to isolate where things are going wrong, when things go wrong

Sounds great, right? What’s to dislike about that? If you’re the sort of person who, without the guarantee of familiarity in nearly all aspects of your life, spirals into unhealthy habits, rumination, or depression: perhaps nothing. If you’re perfectly fine waking up every day with only the bare minimum of a plan and a smile: perhaps everything.

But if you’re in the middle like me (like most) then you might benefit from a healthy mix of freedom and routine — of chaos and order.

Chaos can be immensely fun if you have a high enough risk tolerance and a safety net.

There are thousands, maybe millions, of articles, books and videos about routines. The options are practically endless. There is an entire branch of engineering — Industrial Engineering — that deals with how make better processes. The issue here, then, is how to properly wield chaos.

Properly wield chaos — haha, what am I a wizard? (I wish) But seriously, I don’t know the name of any five-step techniques, overpriced seminars, or academic jargon describing how to harness the good side of chaotic living. Orderly lifestyles — like those of soldiers, scientists, judges, and athletes — are heralded. Yet the chaotic lifestyles we’re most familiar with are self-ruinous rockstars and violent criminals. Chaos gets a bad rap.

So, what is the good side of chaotic living, then?

Glad I asked. It’s this: chaos can be immensely fun if you have a high enough risk tolerance — meaning the prospect of succeeding entices you more than the consequence of losing scares you — and a safety net. In essence, if you aren’t scared to fail and you have a plan to survive when you fail, then the thrilling wave of adventure is yours to ride.

This looks like startup founders bringing a new idea to a competitive market, or you investing a nontrivial portion of your savings in that same fledgling startup, hoping for a blow-up. This also looks like taking a psychedelic drug to get new insight on your psyche. Or even just transparently flirting with a stranger without (gasp) the pre-ordainment of a dating app.

In each of these endeavors, there is a clear risk of something going sideways — either financially, psychologically, or socially — and this inherent risk scares a lot of people. That could explain why business, investing, psychonautics and dating are dominated (in the sense of high performance) by those who we typically characterize as bold.

In some cases, people acting in the spirit of chaos are acting with outsized courage, but I think the bulk of their boldness can be attributed to their trust in a solid foundation to fall back on — that could be money, the emotional support of family and friends, or competence — and the resultant confidence that they’ll end up just fine in the end.

Our world would be uninspiring and slow-moving if not for those Wielders of Chaos. We’d be more stable, probably, but we’d also be scared of the unknown; we’d be twitchy, untested. Humanity needs both forces, order and chaos, to engage in a delicate dance with each other.

Now let’s revisit my earlier dramatic question: If I have to do everything at the same time everyday, am I a human or a machine?

What I’m really asking here is, “If I must live only with Order, have I lost my humanity?” The short answer is yes, but the complicated answer is that my question is rigged. Who said a routine must necessarily set ablaze the red carpet on which chaos wants to strut?

I’ve assumed that routines drain the chaos from life, when in actuality, they provide the safety net above which chaotic living can fly freely. Based on my own surmising from earlier, a baseline routine for my week, day, morning or night need only fulfill three requirements — lessening anxiety, inducing feelings of accomplishment, and providing structure. Beyond that, I do not need to live deterministically — utterly predictably — like a machine.

chaotic scheduling in action

Here are some ways I might let loose some chaos within the helpful confines of my personal routines:

  • Instead of writing for the arbitrarily long time period of 2 hours every day, I can seek to complete a full thought within that time — then use the remainder to explore another activity of my mind’s intrigue.
  • Rather than scheduling every meal time, I can set a daily nutritional goal and seek to fulfill ad-hoc it as I go about my day. I’ll admit, this is difficult, but snacking instead of big-mealing helps a lot.
  • I can schedule time for media consumption — an intentionally vague prescription— then I can make the decision whether to read, listen to a podcast, or watch something, based on how I’m feeling at the moment.
  • I can use the “loose change” minutes at the end of the hour to do small, but cumulative tasks. For instance, if I finish an activity ten minutes early at 11:50, I might do some quick Duolingo lessons, fold some of my laundry, continue a podcast or reply to texts. Or just relax for a bit.
  • Relatedly, I shouldn’t feel the need to make everything last the whole of the scheduled time! Sometimes it makes sense to stop when I’ve learned enough, accomplished enough, or thought enough. Time for a solo dance party!
  • When scheduling personal projects, I can favor priorities over granular tasks. I can maintain a backlog of granular-level tasks, but unless a granular-level task has a due-date, I need not schedule it more than a few hours in advance. My brain might be better prepared to design a character today, than to write a scene, for example.

The underlying theory behind all of these scheduling tweaks is that routine lays the groundwork for each day, while an allowance of flexibility and malleability makes every day feel like a brand-new adventure. At least for me, who has ten million things that interest me but only a few precious moments in which to try them, these are happiness-inducing adjustments.

Discipline is essential. But I’m a conscious human being — chaos is in my nature. Yours too.

I used to build code, now I build fictional worlds ✍🏾. | My favorite word is ‘paracosm’.

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