Creative Constraints and Opportunity

From vending machines to AI tutors, how creative constraints drive innovation, learning, and authentic growth.

Hey, Friends! Hope you’ve had a great week. Here’s a little creative inspiration before the weekend.

Exploding Kittens Vending Machine

In a recent interview, Elan Lee, CEO of the smash hit card game Exploding Kittens said this:

Creativity loves constraints.

This was in regards to an idea he had for a publicity stunt vending machine that he wanted to set up at conventions like Comic-Con. The machine would dispense their card game, but there’d also be a random button that for $1.00 would distribute an unknown prize. Such random prizes included:

• Hand drawn art

• Brooms

• Asparagus

• Sombreros

• Toilet plungers

• Bags of rocks

• Watermelons

Hear him tell the story below (at 47:40):

The challenge he faced was in designing such a machine. The spiral dispensers of typical vending machines couldn’t possibly fit the random variety of products he envisioned giving away. So they built it large and crammed an intern inside to dispense the items manually.

An additional challenge they faced when selling produce in convention halls was that, in certain cities, only registered grocers are legally allowed to do so. Their solution? Complete the paperwork in each city to become a registered grocer. It was a surprisingly bureaucratic workaround—but also a perfect reminder: creativity loves constraints.

Technical and bureaucratic constraints that would have otherwise derailed the project forced Elan, and his team, to consider creative ways around those problems. They could have spent countless resources building a “real” vending machine, or succumbed to red tape. Instead, they tried to understand the challenge at its core and found a solution that just worked.

Takeaway: Challenges and constraints might feel like impediments in the moment, but they’re also opportunities to think differently.

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We’re Not Raising Grass

In Harmon Killebrew’s baseball Hall of Fame induction speech, he shares a story about the time when his mother admonished him and his brother for tearing up the grass while playing in the yard. His father stepped in and said this:

We’re not raising grass here. We’re raising boys.

When my kids get messy with their art and accidentally spill over onto the table or intentionally draw on the couch, I remind myself of this quote. My goal isn’t to preserve furniture like my home is some sort of showroom. It’s to raise kids who explore their curiosities, take risks, experience consequences, and develop a confident sense of self.

Yes, they need to learn right from wrong, but developing the motor control to keep their marker on the paper, or baseball on target, only happens through experience, not for fear of doing it wrong.

Creativity, like athletic prowess, is something to be fostered and encouraged. Yes, it can be messy at the beginning, but the consequences of cleanliness means quelling the inclination to explore, create, and improve.

Takeaway: Take pride in each scratch on your floor, ding on your cabinet, and crayon on your wall. It’s evidence of a creative environment.

Bonus: Ryan Holiday recorded an excellent short on this quote here.

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The Proximal Zone

Matt Mannino

recently shared a note on Substack stating:

…The more you write online, the more normal it feels to write online. I lost years of creative output because I was so hung up on sharing it publicly…

See the entire post below:

It’s natural to feel self-conscious about creative hobbies, especially if you come to them later in life. Being a beginner is uncomfortable, and your talent often falls short of your vision at first. You might not be as proud of your work as you’d like to be, and therefore keep it to yourself.

The thing is, growth rarely happens in isolation.

The psychologist Lev Vygotzky, best known for his work on psychological development in children, described the proximal zone of development as “the space between what a learner can do independently and what they can do with guidance from a more knowledgeable person, such as a teacher or peer.”¹

When you share your work online, you broaden the space between those two endpoints by increasing the number of more knowledgeable peers who can provide you with feedback, constructive criticism, and encouragement.

Takeaway: Growth happens on just the other side of your comfort zone.

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Expertise and Credentials

Mike Rohde

recently turned me onto the

Ted Gioia

’s Substack: The Honest Broker. Gioia, a jazz pianist, cultural critic, and music historian recently said this in his piece Who Are the Real Experts Now?:

“Expertise is the credential. The credential is not the expertise.”

Certainly, some professions will always require credentials. I wouldn’t undergo rhinoplasty from someone who figured it out on YouTube, for example, but that modality of instruction is increasingly becoming a viable option for a growing number of fields. The rate of technological change, and its associated professions, greatly outpaces the ability for traditional academic institutions to create preparatory programs for them all. Here are five roles that didn’t exist a decade ago—and for which no university curriculum could have fully prepared anyone:

• AI Prompt Engineer

• Metaverse Architect

• Drone Light Show Designer

• Digital Detox Consultant

• Online Reputation Manager

In a world where we can no longer defer to the degree as a measure of capability, it is perhaps harder to hire for talent and skill than ever before. The other side of that coin, however, is that more opportunities exists for those talented and skilled individuals than ever before. The trick is standing out and letting your work speak on behalf of your expertise.

That’s why I advocate for sharing your work publicly. When you build a body of work and share it with the world, your reputation precedes you and your expertise serves as your validating documentation, not some diploma.

Takeaway: Your diploma will by no means work against you, but equally important to your fancy piece of paper is real evidence of your ability.

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Ten Times Zero

Architect turned writer,

Michael Dean

, recently said this about AI on David Perell’s podcast How I Write (at 23:56):

Everyone who is automating everything from the start is divorced from the fundamentals.

Listen to the full conversation below:

I like to think of AI as having a multiplicative effect. I’m a 10X better coder when I use Copilot to build software. It’s important to note though, I am still a pretty terrible coder, 10X an extremely low number is still a low number.

And guess what 10 times zero is?

When you outsource everything to AI, with no understanding of the fundamentals underneath, you lack the ability to truly evaluate its output. As a teacher, I am especially wary of how AI is used in education. I see its potential as a one-on-one tutor, something which Benjamin Bloom identified as the single most effective way to improve student learning², but the temptation to shortcut that learning by students asking it to do the work for them is strong.

I’m unsure of what the solution will ultimately be, perhaps custom language models that only tutor and refuse to complete assignments. I do know, however, that this is currently an issue impacting students, and it’s one that we need to figure out.

Takeaway: Those who work with young people, or learners of any age for that matter, would be wise to not mistake the end result for the process that led to it.

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Two More Things

I wrote a novella called Windsor Greetings. I’m publishing it here on Substack, and you can check it out here. I’d love it if you gave it a read and then checked back on Tuesday for chapter 5.

Also, if you’re reading this on the Substack app, clicking the like and restack button goes a long way to helping surface this newsletter to other readers. It’d be super cool of you to click those buttons.

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

Until then,

-Mike

1. https://en.wikipedia.org/wiki/Zone_of_proximal_development

2. https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem