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The Eisenhower Shuffle: How to Beat Perfectionism For Good

An Eisenhower Matrix depicting perfectionism in the important and not urgent zone.

I am ashamed to admit that my most precious ideas sit unpublished in my drafts folder.

But they do. Some of them have been drafts for years.

These ideas wander the universe: listless and unfinished. Their immaterial shadows haunt my folder of Documents. On repentant afternoons, the ideas tail me through the streets—and I scamper into crowds to lose them again.

These are my most pivotal ideas. I wish I had set them free. But alas, I am a perfectionist.

The Eisenhower Matrix of perfectionism

If you’re a perfectionist like me, breathe a sigh of relief. If I’ve figured out a way to finish projects despite myself, chances are, you can too*. I’ll show you how. Let’s start with perfectionism. 

Perfectionism is the (implicit) belief that something should either be done perfectly, or it should not be done at all.

And nothing can be done perfectly. So, perfectionism makes it hard to finish anything at all.

Typically, this means that projects most prone to being erased by perfectionism are those that are most important—because they appear the most worth doing perfectly.

Perfectionism also greatly handicaps projects that are never due—it’s easier to wait for a time when things can be done perfectly, so we never start.

The greatest victims of perfectionism then, sit on the top right corner of this stripped-down Eisenhower Matrix (a popular time management tool I’m adapting to make my point):


An adapted Eisenhower matrix depicting perfectionism as the important and not urgent box.
An adapted Eisenhower matrix by the author.

The money is in the top right corner.  

Projects in the dark green box—important but not urgent tasks—tend to have the greatest value to you but aren’t yet being demanded of you by the world. Actions such as writing a book, spending meaningful time with your family, or learning something new, fall into this category.

Because these tasks are important and not urgent, they are the most likely to be cannibalized by perfectionism. And it’s an awful shame too. Because the actions that have the greatest potential to transform your life fall in this box.

What other task could? The stuff in the “not important” boxes don’t matter. And while the important and urgent tasks (such as work) are significant, they come with built in accountability. So it’s likely you’re already getting them done, even if it’s a struggle.

It’s the important and non-urgent things then, that are most underdone. And so, by learning to finish these tasks with consistency, we open the door for immense long-term transformation in our lives.

And to do that we need to beat perfectionism.

Beating Perfectionism is about Cheating the Matrix

Since perfectionism afflicts the important and not urgent, the best way to beat perfectionism is to move important and not urgent tasks to a different box. I’ll call this the Eisenhower Shuffle, because its fun. There are two ways to do it: make it more urgent, or make it less important (go small).

1. Make it Urgent

Set a strict deadline with a harsh, unavoidable penalty for missing it.

If you needed to fix perfectionism in this second, this would be the way to do it. The harsher the punishment, the more likely this is to work.

Here is a popular way of applying this:

Give a certain amount of money to an accountability partner. If you do not get the task finished by a specified deadline, ask your accountability partner to dispose the money in a way that hurts you.

This is an example, but you can make up your own way too.

It’s important to pre-decide what “finished” looks like. Otherwise, the perfectionist in you will find a loophole to leave projects incomplete. This means your work should ideally be submitted or published or in some other way taken out of your hands for it to count as finished by deadline.

This technique (unlike the next one) can feel punishing, but it works. Use it if you need it.

2. Go Small

Going Small: Altering a project to diminish its perceived importance in your mind, while achieving as much of original aim as possible.  

Going small works by making projects appear less important. Here’s how I go small: I write shorter articles. I write more self-contained ideas. I write about things that I have less to say about.

To go small systematically, you can set artificial constraints for yourself. Directives such as: “keep it under 500 words” or “finish it in one sitting” can work well. Again, if you’re having trouble keeping yourself honest, find someone else who will keep you accountable.

Illustration by the author

Going Small is trickier than making things urgent because it requires a subtle mindset shift.

But there is a powerful philosophical reason to Go Small: recognizing that you are not as important as you once thought is one of the fundamental opportunities for growth for any human being.  

Learning that your problem, your project, and your life as a whole are not so important is liberating. It frees you to do better work while also making you more considerate. Most importantly, recognizing your own insignificance allows you to be truly, and childishly, happy.

I would think of Going Small as less of a productivity technique and more of a mental attitude to fall into. When bitten by perfectionism, you can remind yourself:

“There’s nothing wrong if this project doesn’t turn out perfect. It is not so important after all, and neither am I!”.

By Going Small with your projects, you will be preparing to do so in life as well.   

Should You Really Be Okay with Putting Out Imperfect Work?

Both these strategies—make it urgent and make it smaller—risk making your projects worse. And I understand if you’re apprehensive to dive in. It’s worrying to give up your standards as perfectionist: that’s the one thing we have!

Our worries are unfounded. For, finishing projects makes your work infinitely better. This is not hyperbole: as a proportion, one is an infinite improvement on zero.

Here are 3 reasons why finishing projects, however imperfectly, is fantastic:

1. Testing Solutions:

Imagine you’re a writer and you just can’t figure out a way to connect two important scenes or ideas.

Perfectionism will tell you not to publish yet because you don’t have the perfect connective sentence. But what if you had to publish today? You’d find a way.

It wouldn’t be perfect, but it would be your best timed effort given the constraints.  

By putting this effort is out there, you give yourself the chance to try different solution the next time you have the same problem and must publish. And then again, the next time.

As you repeatedly search for solutions, you will start to notice that some solutions are better than others. These will then become a part of your toolkit as a writer.

Soon, you will brandish these solutions instinctively in your writing. Others will think: “She’s a natural. I could never write like that.”


The further hope is that in all this publishing, we will also be learning the meta solution of finishing pieces. I can’t attest to this yet. But perhaps the more you finish pieces, the more you start believing in finishing pieces and the less of a hold perfectionism has on you. 

Certainly, some parts of the process can only be practiced by finishing some pieces. In these at least, finishing pieces makes you better each time. 

2. Landmarks in the Map of Your Mind

Finished pieces act as landmarks in the map of your creative and intellectual life. This is how much I hated productivity in August 2020. This was my best take on habits last month.

Finished pieces are time capsules to your best timed efforts at a particular period of time.

When you constantly tinker with an idea without ever trying to put it out in a finished way, the only version of the idea that you can do justice to is the one in your head right now.   

Yet, your most recent take on an idea isn’t necessarily your best—and its never the complete story. By finishing pieces, you allow your thinking to evolve while having an articulate record of your thoughts on the subject in a previous time.

You’d be surprised. Once you’ve forgotten about them, your past projects can be spectacularly informative for your present self. But only if you finish them first.

3. Moving On

Finally, finishing pieces is about setting the proverbial skeletons free.

Ideas are wonderful, but perfect ideas aren’t perfectly wonderful. If kept to yourself, perfect ideas feel like a curse. They’re unlived potential and give off a musty, attic smell. They weigh on you.

By finishing your work—however imperfectly—you allow yourself to move on. Though it is never as good as it was in your mind, at least you’ve had your say.

And now you can go on to say something else. Something honest. Something fresh. Something even less perfect; something even more you.


 

If anything is perfect about the internet, it is the possibility of coming across ideas that thrill you. I hope my email list can be that place for a community of thinkers and readers who share in my delight of ideas.

If that sounds like you, check out my email list.

 


 

* Sometimes perfectionism is a symptom of more serious mental conditions such as anxiety  and OCD. If this concerns you, consider speaking to a mental health professional.