Preparation’s Siren Song

Estimated Reading Time: 8 Minutes

In my last post, I shared how I learned the stages of preparation and use that breakdown to maximize its utility. If you haven’t read that post yet, this is a direct follow-up, so I recommend checking it out first:

Short on time? Read the distilled version on my SubStack here:

The Greek myth of Odysseus tells the story of our sailor hero, Odysseus, who sails past a group of sirens, mermaid-like creatures that sing a song so beautiful that sailors who hear it can’t help but steer or dive toward them, causing them to crash in the turbulent and rocky waters from which the sirens sing. Odysseus, wishing to hear the song, commands his men to fill their ears with wax and tie him to the mast, not releasing him under any circumstances until they safely pass. His plan works, and Odysseus safely passes by.

In the face of new projects, we often face our own siren song: perpetual preparation.

As a quick refresh, the post covered three types of preparation: mechanical preparation, the necessary preparatory actions to complete a task, lubricant preparation, practicing using a machine so its basic functions become automatic, and parallel preparation, getting other tasks out of the way so fewer resources are being pulled from the task at hand.

One of the most famous adages of preparation is attributed to Abraham Lincoln:

“Give me six hours to cut a tree, and I will spend the first four sharpening the axe.”

Abraham Lincoln

It’s a great quote and places a high value on taking time to prepare. In reality, however, we rarely find ourselves here. Lincoln describes a very simple scenario that, indeed, needs preparation, but it leaves much to be desired. Let’s look at three scenarios, starting with Lincoln’s described here.

Scenario 1: “You have six hours to cut this tree. Here’s an axe and a sharpening stone.”

Just from the instructions you’ve now been given, you may realize some of the flaws in Lincoln’s analysis of preparation. Lincoln presupposes that he’s been given an axe and a sharpening stone. What’s more is that Lincoln was a very skilled axeman; he helped build his family’s homestead! This is a great adage on preparation, but it’s only most applicable when we’ve done something frequently. Lincoln would take one look at the tree and know roughly how many swings it’d take him, how sharp the axe would need to be, how many strokes against the sharpening stone it’d take to sharpen the axe, and everything else necessary to complete the task. He says very confidently that he knows it’d only take him two hours to chop it down. I don’t even know how long my laundry will take half of the time – Lincoln was an expert in his craft! What if that’s not the case?

Scenario 2: “Cut this tree.”

What a vague set of instructions! When am I supposed to have it done by? Do I get an axe? What about a stone? How do I know if I’m able to chop down this type of tree? What if its wood is stronger than I think?

We’ve all seen this one. We have dream projects with no deadline, often waiting for something to force us into it. Unfortunately, this usually means that the forces that led to it are that the tree had already grown so big that it fell on our house. Or, just that the tree never falls and we never cut it. Home renovations, eating healthier, starting an exercise regimen, writing a novel, going back to school, cleaning our room (guilty). We wait on the “perfect moment” or something to jumpstart us, and the perfect moment never comes, or what jumpstarts us is what we wanted to prevent in the first place.

This is where we typically see perpetual preparation show up first. Perpetual prep waits in the cracks between the stages of normal preparation. It traps us, making us think that we aren’t ready to move on to the next stage, changing our process in a way that looks like this:

It moves us in circles, making us feel like we’re making progress when, in reality, we’re wasting our efforts swimming in a whirlpool. It can trigger this in one of two ways:

Probably the less common method is through the effect of partial performance psychology, in which the brain receives some reward for an entire project by only doing part of it. If, as a kid, I decided to clean my room, I’d probably go tell my parents, and they’d say how wonderful an idea that is and how proud they are of me for taking initiative. I would then think to myself, “Man, that is a wonderful idea! I did take initiative! Look at me go.” Then, you’d find me five minutes later playing video games with an equally dirty room, because I got the dopamine and the praise without doing the work.

The more common method is through never enough psychology. Because the instructions are so vague, we feel like we never have enough information to move on to the next phase, leading us to do endless research, buy endless products that are supposed to help, talk to endless people, but eventually we reach a dead end of things we do to prepare. At this point, people frequently give up and say, “I’m not cut out for this.” Even worse, some people convince themselves that they’re still working toward it, but never move forward.

This is the siren song of preparation, luring unlucky sailors to their demise. We can, however, like Odysseus, sail safely on by tying ourselves to something stronger.

Let’s look at our last scenario.

Scenario 3: “You have 6 hours to cut down this tree. Good luck!”

Here, we are given a strict deadline, but we have no axe, we have no stone, and we’ve never even cut down a tree before. I’m sure if this were the case, Lincoln wouldn’t have spent the first 4 hours sharpening an axe – he didn’t even have one yet!

Six hours changes the picture of our preparation a lot now. In this scenario, there’s so much to do that we can’t afford to spend too much time on anything. We still can prepare, but most of that time will actually be spent chopping the tree, either because we’re new and need longer, because we need to learn good form and the only way to do that is practice, or because we need to know if our axe is sharp enough and need to test it. If we sit and think about what the best way is to chop down the tree for the six hours we’re given, the tree isn’t just going to fall down.

It’s very possible that six hours wouldn’t be enough time, but it’s also possible that it is. That’s what makes the deadline so motivating: we see a world in which we can meet it, but we need to get moving! Then, once we’ve done it, we will look at our work and know how much we’ve accomplished. Even if we fail, we are now far better at chopping trees than we were six hours ago.

“To achieve great things, two things are needed: a plan, and not quite enough time.”

Leonard Bernstein

Although we frequently get deadlines for things we don’t want to do (on it, boss!), we often don’t put deadlines on things we do want to do: writing a novel, hiking a trail, getting fit, picking up a new hobby, etc.

To push ourselves, we need to frequently attempt to make it into the next phase and not let ourselves get caught on trying to be “perfect” before moving on. The great thing about preparation is that it’s a cycle – it never ends, so we can continue improving even while moving forward, as long as we spiral up instead of around. We need only to be sufficient to progress, just enough.

Tying Ourselves to the Mast

To get past the song, we need to tie ourselves to our own mast, not allowing us to steer the ship off course. This works as a sort of growth check, making sure that we move on to the next phase if we’re ready. It’s putting the axe to the tree to see if it’s sharp enough instead of staring at it and wondering.

This can take form in many different ways, but a very simple method I’ve learned from Arnold Schwarzenegger is a “what, when, where” technique. Arnold frequently recommends in his newsletter for us tell ourselves what we’re going to do, when we’re going to do it, and where we’re going to do it. The how comes naturally after this.

For each phase of preparation, we can set a deadline for ourselves that says, “On this date, I’m going to this place, to test this project.” Then, decide on a metric that will tell you if it’s sufficient to move on or not. If it is, move on! If not, decide on another deadline and test it again. Take a swing at the tree and decide if your axe needs sharpening, but don’t sharpen it into oblivion just because it can be sharper; you’ll whittle the axe into nothing.

Although the song of “almost ready” is sweet, we must tie ourselves to the mast and sail onward.

What’s something you’ve been working on that needs a growth check? How are you going to test if you’re ready to move on?


“For which one of you, when he wants to build a tower, does not first sit down and calculate the cost, to see if he has enough to complete it?” Luke 14:28 (NASB)


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