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Why failing is not what you think

Why failing is not what you think

In this issue: why what got you here won't get you there, how creativity is like navigating the fog of war, discipline vs regret, and the true definition of failure

PJ Milani
April 03, 2025

🤔 INTERESTING

Illustration by milaniCREATIVE.art showing two ladder scenes side by side. The left side, our hero character stands at the top of one ladder, unable to reach the second ladder because the first rung is too high. The second ladder leads to a red diamond above—captioned “What got you here…” The right side shows a second character giving a boost to help our hero character climb the rest of the way—captioned “…won’t get you there,” with an arrow labeled “finding help.” The visual metaphor highlights that progress often requires support or new strategies to reach the next level.

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There are two ladders in your career.

But remember, what helped you climb the first ladder may not be useful in the second.

📐 DESIGN

Engaging in creativity is like building a LEGO set without instructions.

With each new piece, the whole thing warps and twists. You have a vague sense of the shape, but there inevitably is a point where key pieces go missing and you have no idea how to move forward.

The lights turn off and you start running into brick walls that come out of nowhere. This dark void is called “The Zone of Ambiguity,” a temporary but necessary space.

A short clip highlighting the “zone of ambiguity”

The only difference between someone who considers themselves creative and someone who doesn’t is the confidence that the Zone of Ambiguity is a temporary space.

And you build confidence through seeing you can in fact can find your way through. With each rep, that gap between ambiguity and insight shrinks smaller, but it will always exist.

🔮 ENCHANTING

Illustration by milaniCREATIVE.art showing a series of life stages with a title that reads “I’ll be happy when…” as progress bars labeled with different milestones. From top to bottom: a crawling child says “I’ll be happy… when I grow up,” followed by a graduate running with “when I get a job,” then a working adult with “when I retire,” and finally an elderly figure at the end of a final bar labeled “when I…” The last panel is incomplete, symbolizing the never-ending chase for future happiness. The visual critiques the habit of postponing joy for distant milestones.

The Arrival Fallacy

Illustration by milaniCREATIVE.art showing a split image of two staircases. The top half depicts a figure climbing sturdy blue stairs labeled “Pain of Discipline,” reaching toward a red diamond at the top. The bottom half shows a crumbling staircase labeled “Pain of Regret,” with an older figure hunched over a cane, surrounded by debris. The visual contrasts short-term effort with long-term consequences, emphasizing that discipline is hard—but regret is harder.

2 Types of Pain in Life

I used to have this T-shirt I loved in high school from a brand called "No Fear."

On the back it said, "There's nothing in life more painful than regret."

Everything we want has a sacrifice.
Everything we don't want has a consequence.

But one thing’s for sure—the regret of "what could've been" is often heavier than the discipline it takes to change the present.

🧠 ANALOGY

Illustration by milaniCREATIVE.art showing an archer on a cliff aiming at a target on a distant cliff. The top panel reads “This is not failure” as arrows land around the target, but miss it. The bottom panel shows the archer tossing the bow down the cliff and walking away, with the caption “This is.” The illustration highlights that true failure is quitting, not missing the mark—emphasizing persistence over perfection.

Definition of failure

To be clear, no one enjoys failing.
It sucks to feel like you're not good at something.

But there'll always be learning pains. Accept the miss and adjust your aim.

Don't quit before you've given yourself a chance to feel what it's like to get good.

🤓 WHAT I’M READING NOW

“Making Comics” by Scott McCloud

As a follow up from this post highlighting Scott McCloud’s “Understanding Comics” book, I recently bought the whole Understanding Comics trilogy and absolutely love it. I think “Making Comics” is my favorite of the three. So many helpful insights and observations on technical concepts (for beginners and experts) but the images themselves are full of visual strategies that can inspire visual metaphors!

examples of creative visual thinking

how to indicate depth

🔬 AN EXPERIMENT

If you’ve opened your feed in the last week, chances are you’ve seen the “Ghibli-craze” hitting the internet.

I won’t share too much about my mixed feelings on the ethics of AI art (this would probably need a series of its own emails) but I wanted to share a deeply moving tiny experiment for me.

As some of you already know, my father passed away about a year ago, and for about a dozen reasons too complicated to share quickly in an email, I was never able to celebrate his life with anyone.

So I wondered what would it feel like to see the milestone moments in my dad’s life captured in the melancholic, timeless style of Hayao Miyazaki. And I can’t confirm or deny balling my eyes out 😭, but something about interpreting a fragmented, frozen memory through the lens of this artform I love hit me hard.

Would love to know your thoughts: what other interesting ways can we use AI to help process emotions?

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