The Case for Limits: An Unexpected Lesson from Dr. Seuss

In 1960, publisher Bennett Cerf made a $50 bet with one of his authors. Cerf’s challenge was to write a great children's book using only 50 unique words. For context, the author's previous book had used 225. It sounded impossible.

But the author accepted and it took him about nine months to finish. The result was Green Eggs and Ham, written using exactly 50 words. That author's real name was Theo Geisel, but you might know him better as Dr. Seuss. The book became one of the best-selling children's books of all time.

I love this story. Not just because a friendly wager produced a timeless classic, but because it shows what happens when limits force clarity. We tend to spend so much energy fighting boundaries, trying to negotiate our way around them or wishing we had more time, more budget, more freedom. But sometimes the constraint isn't the problem. It's can actually be the catalyst.

So this week, let's talk about the power of limitations—what they actually unlock, why they matter more than we think, and how you can use them to push your own ideas further.

Why Unlimited Feels Stuck

You’d think infinite options might feel liberating. They don’t. They feel paralyzing.

The paradox of choice is real. When you’re staring at fifty paint samples, you don’t feel empowered. You feel trapped. Which shade of white is the right one? What if you pick wrong? More options don’t make decisions easier. They make them heavier.

When everything is an option, where do you even start? Unlimited potential turns out to be its own kind of trap. You need something to push up against.

Parenting expert Barbara Coloroso puts it this way: “Our children are counting on us to provide two things: consistency and structure.” Kids don’t thrive in bedlam. They need boundaries. They need to know where the edges are. It’s not restrictive. It’s clarifying.

The same is true for adults when it comes to work, projects, and ideas.

Without guardrails, everything expands until it bursts. Parkinson’s Law captures this pretty well: work grows to fill the time and space you give it. Give yourself six months to write something, it takes six months. Give yourself two weeks, somehow you get it done. The deadline isn’t just a target. It’s a container.

What Good Constraints Do

I learned this firsthand years ago at my old job, while working on an early version of our site. We wanted to add badges that rewarded users for small wins. The idea sounded simple, but the scope exploded fast: notifications, art systems, profile pages, leaderboards. It ballooned into months of work we knew we’d never finish.

So we shelved it. If we couldn’t do it right, we wouldn’t do it at all.

But the idea wouldn’t die. Users kept asking, and finally I gave our small team a challenge: two weeks. What could we build that still felt fun and rewarding? Not perfect; just good enough to get something worthy out there.

Those two weeks were kinda brutal to be honest. Scope creep was banned. Every “nice-to-have” hit the cutting-room floor. My unusually strict demeanor did not make me popular. When we launched, the first badge was simple: score 100 percent on the U.S. Presidents Quiz to earn the “Quite Presidential” badge. No notifications, no extra pages, no leaderboard…just one small win.

And people loved it. They didn’t care that it was bare-bones. They cared that it existed. Over time we added everything else. That two-week constraint didn’t limit creativity; it launched it.

It also taught me three things about how boundaries actually work:

1. Boundaries force prioritization. When you can’t have everything, you figure out what actually matters. We stopped debating features and started asking, “What’s the smallest version that still feels rewarding?”

2. Boundaries create focus. Every limitation is also an elimination. With two weeks and a tiny team, there was no time for shiny distractions. The limits told us exactly where to look.

3. Boundaries generate discovery. When the “right” way is off the table, you have to get creative. We couldn’t build a full art system, so we made one badge and made it count. It felt like less of a compromise and more of a breakthrough.

Cause ome of the best ideas don’t come from having more. They come from making do with less.

Using Constraints on Purpose

And the good news is that you don’t have to wait for someone to hand you a constraint. You can create your own. Ya know, better living through limits.

Start by setting a time cap before you begin. Pick a deadline that feels slightly uncomfortable. Not impossible, just tight enough that you can’t afford to drift. Two weeks. Three days. One hour. Whatever fits the project. Commit before you start, instead of negotiating with yourself later. And add a consequence for missing it. When Dr. Seuss accepted the fifty-word challenge, he didn’t leave himself an escape hatch. Neither should you.

Next, define what you won’t do. Most projects start with a list of goals and features. Turn that on its head and make a “not list.”

• “This will not have more than three steps.”

• “This will not require new infrastructure.”

• “This will not use more than two colors.”

What you leave out shapes the work as much as what you put in. Being clear on what you won’t build is just as powerful as knowing what you will.

Then, ask better questions. Instead of “What could we do?” try “What’s the smallest version that still works?” Instead of “How do we make this perfect?” ask “What’s the one thing that has to be there?” Constraints turn vague ambitions into specific choices.

You can also reduce resources on purpose. Cut your budget in half. Cut your time in half. Cut your team in half. See what happens. It isn’t about making things harder just for the sake of it. It’s about exposing what’s essential. When you strip away the nice-to-haves, what remains is usually the thing that matters most.

Next, put in limits that make you think more clearly, not just work faster. Good constraints don’t punish. They clarify.

• If you could only explain this in one sentence, what would you say?

• If you had to pitch it in 30 seconds, what would you lead with?

• If you could only keep three features, which three?

These are filters not obstacles.

And finally, ship the smallest version first. Don’t wait until everything is perfect. Launch something tiny, learn from it, and build from there. Our badge system started with one badge. That was enough. It proved the idea, gathered feedback, and created momentum.

Constraints help you get something real into the world faster. And real beats perfect every damn time.

Closing

So, what’s the big lesson here? It's not that constraints are suddenly a delight; they are, as a rule, still very annoying. But the real enemy of creation isn't the limit itself. It’s the delusion that we need unlimited time, boundless resources, and zero accountability to create something incredible.

Dr. Seuss didn’t make magic by doing whatever he wanted. He made it by doing the most he could with what he had.

When you choose a constraint, you trade paralyzing potential for focused action. Limits work because they do three things: they force prioritization, sharpen focus, and spark discovery. They take the easy, predictable solutions off the table and make space for something smarter to show up. It’s the universe giving you a nudge and saying, “Right then, time to be clever. There’s a good chap!” (The universe in this example is British for some reason.)

So this week, don’t wait for the perfect conditions. Pick a constraint. Give your next idea a tight deadline. Cut your feature list in half. Make a “not list” before you touch a line of code or text.

Because the space you work within often matters more than the space you wish you had. And sometimes the difference between stuck and finished is fifty good words.

As always, thanks for reading,
Derek (aka Chief Rabbit)
Oh and have something interesting you think I should write about? You can reply to this email (or any other Chief Rabbit email) to suggest it. 

Oh one more thing…

When I am not writing this weekly(ish) newsletter, I spend time helping people make sense of this wild new AI world. I even gave a talk at Seattle AI Week last week to a packed house.

Since folks keep asking me for more, I’m now offering small workshops that walk through the tools (and others) step by step.

So if AI still feels like alphabet soup or you are wondering why people keep talking about a steak sauce, sign up for the next one. In under an hour, you’ll go from “Where do I even start?” to “Wait… I can actually do this.”

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