The Art of Imperfection: Why Early Work Matters

Creative risks today spark future breakthroughs. Learn how early struggles shaped great artists and why embracing imperfection fuels innovation.

A digital collage I made in Photoshop

Hey friends! The Midwest flirted with spring last week, only to dust us with snow again. Not to worry. My creative embers are still burning hot. Let’s get into it.

Crummy Today, Brilliant Tomorrow

I recently read a great piece by

K. Woodman-Maynard

titled Crummy Art By Exceptional Artists. In it, she examines the early work of Georgia O’Keeffe. She makes the argument that it’s in O’Keeffe’s lesser-known, earlier pieces that she was experimenting with ideas that would later make her a household name. In those early paintings, the ideas aren’t, as Woodman-Maynard puts it, “fully clicking,” but there are traces of what those ideas would become.

Woodman-Maynard encourages the artists and cartoonists whom she coaches to “experiment freely,” just like O’Keeffe, even if that work never finds an audience. It’s through experimentation that a seed of an idea can germinate and blossom later.

Woodman-Maynard included an example of her own experimentation, republished below with her permission. In the first image on the left, a 15 minute diary comic, she unexpectedly found herself using the branches of a tree as panel borders—a device she later used in her Tuck Everlasting graphic novel which debuts in the Fall of 2025.

If she had waited for divine inspiration to strike, or had set out to make the perfect sketch before putting pen to paper, the branch-panel-borders concept may have never found her, and she wouldn’t have created what she says is her favorite spread in the book.

To Support Woodman-Maynard, consider subscribing to her publication and purchasing her Tuck Everlasting graphic novel.

Takeaway: It’s hard to predict where creative experimentation will take you, but that’s kind of the point. Much like O’Keeffe’s early works held traces of her future brilliance, creative risks today can spark unexpected breakthroughs tomorrow.

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Hell Yeah!

I’ve previously written about Derek Sivers’ concept of Hell Yeah, or No, a decision making heuristic which says if your answer isn’t hell yeah, then it should automatically be no. The great illustrator

Lewis O’Brien

recently put out a graphic that promotes this concept.

It features a carnival style high strike machine with a mallet and striking target. The high striker’s vertical axis is filled with “No” at every level—except for the very top, which reads “Hell Yeah!” As a teacher, I love when a simple picture says what would otherwise take several paragraphs to explain.

In a world where everything seems to be competing for your attention, you need to guard it or someone else will decide for you.

Takeaway: Next time you find yourself doom-scrolling or letting Netflix autoplay another episode, pause and ask, “Would this even register on my high striker?” If not, maybe it’s time to pick up the mallet and aim higher.

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Matters of Taste

One of the reasons I’ve felt compelled to write this newsletter is to try to figure out what the future will look like as AI radically changes everything. Many predict this shift will surpass both the transition from an agrarian to an industrial economy and from an industrial to a knowledge-based one.

As a career and technical education teacher, who’s ostensibly tasked with preparing students for what awaits them after high school, it’s something I think a lot about.

The future still looks blurry around the edges, but insights from startup thought leaders are starting to sharpen my vision. I keep coming across a common theme that centers around the idea that as computers continue to become better at the types of things that were solely in the domain of human capability, what you ask those computers to do, in other words creativity and matters of taste, will become increasingly important.

Designer, speaker, and entrepreneur Cameron Moll, recently Tweeted the following:

Willing to bet my career on this: When the AI dust settles there will remain an evergreen need for taste & style at the hands of a professional, the ability to judge with your gut, methodical work at a slower pace, typographic mastery, and so much more that we do as designers.

This rings true to me. Over the past year or so, I’ve used AI extensively in a variety of ways. To name just a few, AI tools have served as my:

• Research assistant

• Sparring partner for ideas

• Copy editor

• Designer and Artist

• Computer programmer

• Unlicensed therapist

Every week I learn of some other way AI can amplify my abilities. The change is more rapid than anything else I have ever seen in technology, and there’s no sign that it is slowing down. As new AI tools are added to humanity’s toolkit, human potential, for better or worse, appears to be increasing as well.

While the risks of an AI-driven dystopia exist, I remain optimistic that we’ll steer toward an age of abundance, fueled by unprecedented creativity and innovation.

Takeaway: There is no roadmap to the future. We’re making it up as we go. If you’re at all interested in where it leads, it’s important to understand the tools that will help chart its path.

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What You Learn

In a recent interview, Nick Bilton, author of Hatching Twitter and American Kingpin, shares spicy behind-the-scenes stories of Silicon Valley’s most famous companies. Towards the end of the interview, he gives advice on writing stating:

One of the things that frustrates me about Silicon Valley, and the tech bro culture, is that everyone is trying to optimize their life for the most number of seconds for this and that. What they don’t realize is that some of the greatest things that they will learn is [sic] from the things that have nothing to do with what they do.

While the phrasing is a little clunky, the advice is a great reminder to not lose the forest for the trees. Bilton explains how he took up the piano at 45. Now 48, he is far from a concert pianist, but he can reasonably play pieces by Frédéric Chopin.

To his surprise, he discovered that composers are really storytellers. Their language being musical notes instead of the written word. Today, he sees the influence of learning piano in the screenplays that he writes.

Takeaway: Serendipity sometimes outweighs productivity.

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Make it Right

Life hack: if you’re curious about a new podcast, scroll to the December episodes. You’re more than likely to find a best-of episode from that calendar year. If you don’t like what they’re putting down, you can pretty safely skip the less-than-best-of episodes too.

That’s exactly what I did with the Rich Roll Podcast at the end of 2024. I haven’t yet “rolled” (sorry) his show into my regular rotation, but I did like much of what I heard, and I’m one step closer to becoming a subscriber.

One thing in particular stood out to me on the topic of decision making (at 20 minutes and 3 seconds). Ellen Langer, professor of Psychology at Harvard University said this:

Rather than waste your time being stressed over making the right decision, make the decision right.

This is certainly good life advice. There are too many unknown unknowns to be able to properly assess the counterfactual events that could have transpired. What is within your power, however, is how you react to given outcomes. Creative endeavors are more often met with rejection, failure, and indifference, than acclaim.

It does you no good to ruminate on what could have been had you made some other decision. That decision was made. It happened, and there is no undoing it. You can learn from it though. You can collect your errors, your mishaps, your foibles, and blunders, and let them guide you as you hone your craft, find your voice, and iteratively improve as a creative.

Takeaway: By definition, creative slop must far outweigh the work that earns high esteem. Accept that, and keep creating.

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One More Thing

Good things are better when shared. If you liked this, it would mean the world to me if you sent it to someone who might like it too.

I’ll see you in your inbox again next week.

Until then,

-Mike