The flag of Chicago is widely regarded as one of the best city flags in the United States, perhaps in the world. It is certainly one of the most popular. You’ll find the flag of Chicago printed on t-shirts and mugs, tattooed on local musicians, and flying along streets, over rivers, and above doors throughout the city.

The flag has three white bars and two blue stripes. The white areas represent the three main sides of the city: North, West, and South. The blue stripes stand for the north and south branches of the Chicago River flowing into Lake Michigan. In the center of the flag, there are four red stars symbolizing historical events in the city like the Great Chicago Fire.



Vexillology is the scientific study of flags. The flag of Chicago received stellar 9.03 out of 10 rating from the North American Vexillological Association and was ranked 2nd out of 150 city flags by flag experts known as vexillologists.

Let’s talk about why vexillology and good flag design can teach us an important lesson about life.

vexillology chicago illinois photos
The American flag and the flag of Chicago fly in front of a building in downtown Chicago.

How to Design a Beautiful Flag

“A 3×5 foot flag on a pole 100 feet away looks about the same size as a 1×1.5 inch rectangle seen about 15 inches from your eye. Try drawing your flag on a rectangle that is 1×1.5 inches. You’ll be surprised at how compelling and simple the design can be when you hold yourself to that limitation.”

-Ted Kaye, vexillonaire

If you wanted to design the best flag possible, then you would want to think creatively. Your first thought might be to give yourself as many possibilities as possible. “Give me a blank slate. I want tons of colors and a huge poster board to design this on. I want space to be creative and let my imagination run wild.”

What you actually need, however, is a 1×1.5 inch piece of paper. Placing this simple constraint on yourself actually makes your design better.

You see, flag designs that often look good on paper fail in the real world. A design that looks good in the pages of a report is often confusing and unrecognizable when it is flapping in the breeze 100 feet away.

What makes the flag of Chicago so compelling is its simplicity. If you were to draw the flag of Chicago on a 1×1.5 inch piece of paper, it would still look like a good design. The same principle can be applied to our everyday lives. We often assume that we need more resources when a carefully constructed constraint would deliver better results.

The Carefully Constrained Life

The power of well-chosen limitations extends far beyond flag design and vexillology. Imposing simple constraints in our own lives can lead to well-designed and more effective lives as well.

Here are a few examples from my own experience:

As an entrepreneur, I saved up $10,000 before I started my first business. This money was my constraint. I had to learn how to create products, market my business, and live off of that money until I became profitable. This constraint forced me to start an online business, reduce overhead, and—after a few years of other projects—build this website.

As a traveler, I pack ultralight and often travel for 2 weeks with just a 19-liter backpack. This tiny bag is my constraint. It still amazes me how little I actually need when I’m on the road. Furthermore, my small backpack required me to find the most useful and effective items for my needs. It didn’t just make my travel lighter, it made my travel better.

As a writer, I set a publishing schedule of every Monday and Thursday. This bi-weekly deadline is my constraint. Has it always gone smoothly? No way. Sometimes I don’t feel like showing up, but I still do. And because I have religiously kept this publishing schedule, I have some very popular articles to show for it. Genius only reveals itself when you show up enough times to get the average ideas out of the way.

We usually assume that constraints are the things that hold us back from what we want, but well-placed limitations can make us better, not worse.