I spent an entire summer slaving over a hand-drawn 15-second animation for a book trailer that got 139 views. The book it was promoting sank like a stone. I was left feeling like an idiot, frustrated, angry, resentful. Why didn’t this work when I put everything I know into it? 

It all started out so fun. I had never made animation before, but the storyboard sprang almost fully-formed into my imagination. I thought, this is going to be so cool, it’s going to be a viral hit. It might even be bigger than the book!

I did not stop to consider that this trailer was intended for a book coming out from a mainstream French comics publisher, in France, where there was no tradition of book trailers. There was no marketing plan to use this asset. The publisher took it and basically shrugged. Slapped a generic music track on it and put it on YouTube.

I actually really enjoyed the process of making this thing. I learned a lot, and I like how it came out. But I spent months on this instead of paid work or setting up book events (or my children!) with a dream that it would do something it was not designed or set up to do.

And, unfortunately, the Wile E. Coyote feeling of racing towards a goal that turns out to be a mirage and ending up over a cliff was all too familiar.

The podcast that’s supposed to sell books but takes over my life and doesn’t move the needle.

The textbook that’s supposed to launch an educational empire but never pays a dime past its advance.

The graphic novel that’s supposed to get me a screenwriting career.

I’ve been an author, cartoonist and now coach for 30 years, and my history is littered with massive, high-concept projects that were fundamentally misaligned with what I needed out of my work—even when they were excellent in their own right.

But no matter how often it happened, I kept being caught by surprise. And I’ve seen this pattern derail my creative clients over and over.

It took years to solve the puzzle. The answer finally came via Annie Duke’s book, Quit, from an unexpected source: Google X.

The Monkey and the Pedestal

Astro Teller, who works at Google X (what they call their “moonshot factory,” where they come up with wild ideas and try to make them work) created this metaphor to put a spotlight on a mistake he saw his colleagues falling into.

It goes like this: Imagine you have a genius idea: You’re going to put a monkey who juggles flaming torches on a pedestal in the town square. Now: How much time should you allocate to building the pedestal?

The answer is clear: almost zero time—at least until you know the monkey can juggle fire.

Pedestals are straightforward. You know how to build pedestals. Also, building pedestals feels like progress.

But training monkeys to juggle fire? If you can’t do that, the pedestal is worthless.

The rule Astro Teller suggests is to spend at least 80% of your time on training the monkey first. If you can’t make progress on that hardest, most uncertain part, kill the project before you sink too much into it.

Pedestal-building is the pattern behind most creative business failures.

For Astro Teller’s projects, the pedestal part might be building a website, or making a mockup, or branding.

However, for experienced creatives, the idea of a “pedestal” is dangerously misleading, because it sounds simple and boring.

That’s why I like to call this idea the Monkey and the Monument.

The idea of a “monument” starts to suggest what creatives actually often do, when caught in this trap.

Pedestal Monument work for creatives might be:

• write the novel
• create the journal
• build the course

This is real work that requires skill, training, and vision. It’s work you’re genuinely good at.

The problem isn’t that monuments are trivial. It’s that monument work does not train the monkey.

And if your plan still hinges on a flame-juggling monkey, you can build the most elaborate monument to your genius the world has ever seen, and it’ll still fail.

The real question you need to ask is: Which part of my project actually determines whether it succeeds?

There are two kinds of work inside most projects

Monument work:

• Known, legible, skill-based work you’re excited to do.
• You understand the steps. Progress is visible.
• Often impressive from outside.
• Not fake, not trivial, but also not success-determining.

Monkey work:

• The risky work with unknown outcomes.
• You may not fully know how to do it yet.
• Progress may be hard to track.
• Feedback is delayed or external.
• Actually determines whether the project works at all.

One important clarification: while in this context it might look like it, this is not actually an “art vs business” division. It’s known work vs. success-determining work.

For mid-career creatives, the creative production is usually the monument. Because as challenging as that work might be (writing a book is no joke!), you know the process. You’ve written before, you understand the steps. You might struggle, but the work itself isn’t mysterious.

In my example earlier of my animation project, I had never done animation, but I knew how to draw, I knew Photoshop, I knew lots of animators who could help. Most importantly, the overall process of learning to animate was something I was confident I could grapple with, even if it would be difficult.

By contrast, the “how exactly does this help me sell my book?” was a total unknown, and the pivot point for success for the project as a whole (as opposed to the animation alone).

For me, as for many creatives, it’s audience/demand/economics that’s the monkey, because that’s the success-determining factor. Why? Because of the Expectation Filter you’ve got for this project.

If you’re developing a course with the expectation that you will sell it for real money, then the monkey isn’t building the content, even if you’ve never done that before. It’s selling the course and having actual students to teach. If you create a journal that you want for people to use, people need to buy it and use it.

Just keep in mind that in some cases, the monkey and monument map to the opposite categories (you have demand, and delivery is the bottleneck).

That’s why it’s crucial to identify the monkey and the monument for your specific project

Why does working on the monument first fail?

It’s pretty clear that monument work does not train the monkey. It doesn’t matter how excellent your work is; it does not automatically resolve the unknown part of the project.

And, worse, as you invest more time, you can get caught up in the sunk costs fallacy, where you feel a greater and greater emotional commitment, but still have no clear path to success.

Astro Teller’s insight is that if one condition determines success, most effort belongs there first, not eventually. Creatives often get caught up in magical thinking, that if the work is good enough, somehow people will notice and the monkey will start juggling fire without you having to do anything.

When we face that idea head on, we know it’s wishful thinking. But of course there’s a lot of cultural mythology, and just enough survivor-bias starlet-discovered-at-the-lunch-counter stories of effortless fame to keep us hoping we’ll be the lucky ones.

But wishing is not a life plan.

Ask yourself: Am I spending most of my time on what determines success, or on what I already know how to do?

How to tell if you’re building a monument while ignoring your monkey

The Monkey and the Monument Diagnostic

Write your answers quickly.

1. What outcome am I expecting this project to produce? (money, audience, career leverage, creative completion, validation). Before you even get to the monkey problem, you need to know what job you’re asking the idea to do. I covered this idea in more detail, with lots of examples, in this article about expectation filters. If you can’t pinpoint the outcome you’re hoping for, check that out first, and come back here to continue. 
2. What must be true in the world for that outcome to happen? These are your success conditions. Ex: Someone (or many someones) must buy, someone must care (and what do you mean by that?), this must be in front of someone specific/a large audience (be specific about what this means).
3. What is currently least known, least proven, or most uncomfortable about those success conditions? (For a paid course, the least known part might be ‘Will people actually pay $X for this?’ Building the course content is difficult, but known. Testing demand is the monkey.)
4. Am I spending most of my time on solving that question, or elsewhere?

If answer to #4 is “elsewhere,” you’re probably building another pedestal.

What to do once you’ve identified your monkey

The instinct is usually to ask, “Am I capable of training this monkey?” That’s another trap. It’s likely to lead to a fast “No,” because monkey work is scary by definition: far outside your comfort zone, and may rely in some ways on external factors. That makes it risky, which of course is the point. That’s why we’re trying to surface it early.

The real question is about consent, not capability.

You can decide to tackle it, test it, try it. That’s completely up to you. Therefore, when you get a gander at your monkey and get spooked, take a beat and think: Do you consent to train this monkey?

The 80-20 Monkey Test

1. What do I need to learn to see if this is viable?
   • New skills: copywriting, sales conversations, tech platforms
   • New information: Does demand exist? Who’s my actual audience? What do they pay for this?
2. Do I consent to the work this outcome actually requires?
3. Do I want this outcome, knowing what it really demands?
4. Am I willing to spend 80% of my effort there first—before building the monument?

You can answer questions 2-4 with a resounding NO if you prefer. That’s entirely up to you! Or, you can decide YES, and start taking action accordingly.

Choosing to redirect, redesign, or walk away early will save you massive amounts of work and disappointment. It’s the strategic choice.

Find your monkey problem now, before you’ve spent years building a shining edifice that never serves your purpose.