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How risks are like being stranded on a boat

How risks are like being stranded on a boat

In this issue: what you forget when assessing risks, how to overcome creative "disappointment of outcomes," why it's impossible to do everything at once, and a friendly reminder about the effort behind what we see.

PJ Milani
March 04, 2025

🤔 INTERESTING

Illustration by milaniCREATIVE.art comparing the risks of making a change versus staying the same. On the right, a person stands in a leaking boat labeled ‘Risk of staying the same,’ symbolizing a deteriorating situation. On the left, a stable boat is nearby, but sharks in the water create the ‘Risk of making a change,’ representing the fear of transitioning. The image highlights how both choices carry risks, but staying in a bad situation can be just as dangerous as taking a leap.

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Change is risky, but so is standing still.

Most of my career, my whole identity was “Mr. Milani”—
A high school film & animation teacher.

Now I love being a teacher. But whenever students asked, “What are you making?” I froze. Teaching creativity, yet creating nothing of my own, left me feeling like an imposter.

And then the pandemic hit—and confronted me with a scary question: If I can’t teach, then who am I?

One night as I journaled about my need to start creating, I had déjà-vu. So I flipped through old notebooks and found the same words—written 11 years ago!

“I need to at least start.” (oof)

It seems when you stand in a leaky boat long enough, you stop noticing the water.

So doubts and all, I took a leap—and, yes, I stumbled right into the sharks. 😂
(No one gets it right the first try)

The lesson: when you procrastinate a decision, you’re still making a choice to stay where you are.

If you’ve been wanting to make a change, maybe it’s time to test the waters.

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I only wish I had found it sooner.”
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↳ Translate your ideas into visuals!

📐 DESIGN

My approach to “staying creative”

↳ The simplest hack to overcome “disappointments of outcome” when you post online.

🔮 ENCHANTING

Illustration by milaniCREATIVE.art showing the challenge of balancing time across different aspects of life. The top section displays a full glass labeled ‘Your Time’ and four empty glasses labeled ‘Work,’ ‘Partner,’ ‘Family,’ and ‘Friends.’ The bottom section shows the time being poured out, partially filling some cups but leaving others empty, with the caption ‘It’s impossible to fill all the cups, even if you give all of yourself,’ symbolizing the difficulty of distributing your time evenly.

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Friendly reminder: You can't fill every cup (and that's perfectly okay).

Work demands your focus
Your partner needs quality 1-on-1 time
Family deserves your presence
Friends want you to show up when it matters

The more cups you try to fill:
↳ Faster yours runs empty
↳ Longer it takes to fill back up.

You can’t give 100% to everyone, every day. There's always a trade-off.

❝

You can have it all. Just not all at once.

Oprah Winfrey

🧠 ANALOGY

Illustration by milaniCREATIVE.art comparing success in the spotlight versus the effort behind the scenes. The top panel, labeled ‘What we see in the game,’ shows a basketball perfectly swishing through the hoop. The bottom panel, labeled ‘What we don’t see before the game,’ displays multiple failed shots hitting the rim, backboard, or missing entirely, emphasizing the unseen practice and perseverance required for success.

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Hard work won’t guarantee victory, but it WILL guarantee improvement.

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🤓 WHAT I’M READING NOW

“From Strength to Strength” by Arthur C. Brooks

I only have a handful of books I re-read and re-listen to because they keep me grounded in reality and purpose. “From Strength to Strength” by Arthur C. Brooks is one of them.

I consider it a must-read book for anyone over 40. The subtitle says it all: “Finding Success, Happiness, and Deep Purpose in the Second Half of Life.”

Lots of golden nuggets in the book, but this is one of my favorites:
“Satisfaction comes not from chasing bigger and bigger things, but paying attention to smaller and smaller things.”

And of course I had to visualize my favorite piece of research:
As we age, we shift from fluid intelligence to crystalized intelligence. Critical to be aware of the value of both if you work in teams.

Illustration by milaniCREATIVE.art depicting the two types of intelligence: fluid and crystallized. A performance vs. age graph shows ‘Fluid Intelligence’ peaking around age 25 before declining, while ‘Crystallized Intelligence’ increases over time. A figure is shown making a leap from fluid to crystallized intelligence, symbolizing the transition from problem-solving abilities to accumulated knowledge and wisdom.

One of my favorite ideas: The 2 types of intelligence

Fluid Intelligence

Illustration by milaniCREATIVE.art depicting crystallized intelligence and the ability to connect patterns over time. The left circle, labeled ‘At age 25,’ shows a sky full of scattered stars. The right circle, labeled ‘By age 50,’ connects the stars into a structured diamond-shaped constellation, symbolizing how experience enhances pattern recognition and deeper understanding over time.

Crystalized Intelligence

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