Confessions of a Dubious Planner

Story Time

I was interested in scheduling a body comp test for myself. This particular test required showing up without having eaten for at least 12 hours beforehand. So I did what I thought was logical: I scheduled an appointment at 7:30 am two weeks away.

The idea was that I would take the test as soon as I woke up and profit. That is, I would not have to worry about the rest of my day being disrupted.

Come appointment day, my alarm went off at 6 am, as planned, and I snoozed it. It went off again at 6:10, and I snoozed it again. It went off a third time at 6:20, and I stopped it and started doomscrolling. At 6:45, I realized my folly and jumped out of bed, barely making it to the appointment in time. I must confess some dodgy driving may have been involved.

In the moment when I made it to my appointment, all I could feel was relief that fortune favored me. But after the very short appointment, I went down a fun existential rabbit hole: "I suck at time management." "How am I supposed to do anything when I cannot even trust myself to make it to a simple appointment on time?"

And then I had another thought: "It is almost like I have two versions of myself, the planner and the doer, and the doer is hell-bent on sabotaging the planner."

I realized I had this persistent feeling that I was split in two: a planner making promises, and a doer actively sabotaging them. A friend pointed out this sounded exactly like Jonathan Haidt's classic rider and elephant analogy. But looking at my own morning failure, I realized the standard model was missing something crucial.

The elephant was not the problem.

Two Little Guys In My Head

That last thought, the idea that there is a version of myself intent on sabotaging everything I plan, was the spark that set off this journey of introspection. I am not claiming to understand all of human nature, but I have found a useful way to think about this: I have two little guys running around in my head.

The elephant is the doer. He is the part of you that actually operates. He is embodied, friction-sensitive, and affected by sleep, hunger, mood, energy, and environment. He is operating under constraints. In my example, he is the version of me who woke up at 6:45 and drove to the appointment.

The rider is the planner. He is the guy who can strategize, look ahead, and set the direction. He can also be a bit irresponsible, because he is not the guy who executes. He is the version of me who decided that 7:30 am was the most logical time for this appointment.

Dubious Planner

Thinking back to my little story, if the rider is the guy who planned things out, he completely failed to account for the reality of the elephant. The rider scheduled an appointment for a frictionless, perfectly disciplined robot. He did not schedule it for a tired human who relies on snoozing alarms to wake up. The elephant did not fail the plan; the plan, and hence the planner, failed the elephant.

If the elephant shows up to the gym without a workout plan and with absolutely no clue how to use the equipment, whose fault is it? Is the elephant expected to derive modern exercise theory just by seeing what other people are doing?

Or if, come lunchtime, the planner in all his brilliance has decided that today the elephant is going to cook a nutritious and delicious meal, but with no recipe selected in advance, is the elephant expected to earn a Michelin star? Of course not.

We would label all of these as planning problems. It turns out my rider is a dubious planner if he does not account for the fact that the elephant who shows up is not Superman, but just Regularman. Sometimes the elephant is groggy, sleepy, hungry, tired, and whatever other constraints the day brings.

A bad rider says: "Tomorrow I will work out, eat well, publish a blog post, clean, cook, study, and make ten good decisions."

That sounds ambitious, but it usually hides dozens of unresolved decisions. What should I eat? When should I work out? What should I work on first? What counts as success? What do I cut if the day goes sideways?

The elephant gets handed ambiguity, friction, and an impossible checklist. When it inevitably stalls, the rider blames the elephant. But the rider is just a bad manager.

Teamwork Makes The Dream Work

In How to Train Your Dragon, there is an iconic scene where Hiccup and Toothless learn to work together as a team. The satisfying click on screen makes the first Dragon Rider. It works because, as the music swells, Hiccup is not just yelling at Toothless to fly better through sheer willpower. He is actively operating the prosthetic tailfin he built.

Hiccup manages the mechanics, the pedals, and the aerodynamics so Toothless can do what he does best: fly. Hiccup does not demand that Toothless become a flawless, uninjured dragon. He builds a system that accommodates the exact dragon he has.

A good rider does exactly this. He does not ask, "How do I force the elephant to be a perfectly disciplined machine tomorrow?" He asks, "Given the actual Regularman elephant I have, what plan would let him move with the least amount of friction?"

That means fewer live decisions, clearer defaults, smaller success criteria, and less avoidable friction. Meal plans should be pre-decided. The first work block should be obvious. The workout should be planned out. The day should not depend on the elephant rederiving the laws of physics.

Good planning starts from that reality, and not fantasy.

An Alternative Morning

Roll it back all the way to when I booked my body comp test.

The takeaway is not that I am fundamentally incapable of waking up early or showing up on time without rushing. The experience highlighted that my plan was brittle because it relied on an idealized version of myself who could execute flawlessly without any allowance for error or delay.

This scenario is not unique to me. Many people design plans that assume perfect circumstances and do not account for the ordinary variables of daily life. A more effective approach is to recognize typical human limitations and plan accordingly.

For example, instead of scheduling the appointment at 7:30 am, a more realistic plan would have set it for 8:30 am, providing a buffer for foreseeable nonsense. That is not a profound insight. The rider does not need a postdoc in human nature. He just needs to be aware of common human failure modes and plan smarter.

But let's be honest: that puts a neat little bow on things a bit too easily. Realizing that the rider is a bad manager is a useful first step, but it does not automatically fix the system. If I leave it there, I am just handing you another impossible checklist. Managing the rider and the elephant takes more than "planning smarter." In the next post, I will share more about what works for me and how this model kept evolving.