If you’re afraid to look bad, you’ll never be an effective leader.

Tyrian purple was an expensive, fashionable color in Ancient Rome during the 1st century BC. It could only be produced from tens of thousands of sea snails found on the coast of Tyre (hence Tyrian) in modern-day Lebanon. For that reason, it was the Rolls-Royce of colors, and only the richest, most powerful people could wear it.

The tunic was a type of clothing that was also in style at the time. Worn by almost everyone, it was the fashionable standard—much like blue jeans or a white dress shirt today. Not wearing a tunic was considered unthinkable, much like wearing a belly shirt to church today.

But there was one man in particular who frequently went against the grain of the time. Cato the Younger, a Roman senator during the era of Julius Caesar, was known best for his staunch integrity and his courage to stand against Caesar himself. He was immune to influence, bribes, and corruption. Later referred to as “the perfect Stoic” by Seneca for his unflappable reputation, he frequently chose NOT to wear the customary Tyrian purple tunic of the wealthy and powerful. Instead, he would walk around in darker clothing—entirely out of style. Why did he do this? Wouldn’t a Roman senator have been above the petty business of rejecting social norms? He did it so that he could train himself to only be ashamed of things that were truly worthy of shame.

Think about yourself for a moment. What are some of the things you’re concerned about? Appearance? Your check engine light? Behavioral norms? What’s for dinner tonight? Voicing your thoughts? Rent? Take stock of your worries over the course of a week. You’ll notice that most are really not worth the agony. Sure, you always want to look presentable (optics matter, as we’ll discuss in a later essay). You want to behave in accordance with someone who is trustworthy. You want to monitor your beliefs to ensure they are founded upon reason and truth. But taken too far, and these things can morph into what amounts to unhealthy and unnatural self-consciousness. The human mind has only so much bandwidth, and if you are preoccupied with social approval, how can you possibly do your job at the highest level? How can you possibly lead other people who are looking to YOU to set the standard, the tone, and the direction?

I’ve always had a knack for doing uncommon things. I walked 500 miles across Spain on a whim. I occasionally ask for a discount at Starbucks for no reason. In college, large groups of kids would wait for the “walk” sign at the empty intersection on Lancaster Avenue—I liked to cross anyway and chuckle as the rest would follow. In middle school, I liked the look of Hawaiian shirts, so I bought a few and would wear them for no reason in the dead of winter. The Hawaiian shirt was my “purple tunic.” I never knew why I insisted on doing socially or fashionably awkward things, but now I see the value in them. When I’m running a restaurant staffed with 80% college kids, I’m not worried about petty judgement. I’m entirely focused on the job at hand. When I’m taking on a challenge of 100 leadership articles in 100 days, I’m not worried that some will judge me. I take pride in going against the grain, and it has gifted me the freedom to lead with principle, not popularity.

Your ability to practice discomfort on your own terms will set you free. As a leader, you will face more uncomfortable situations than you prefer, so why not train yourself to be ashamed of only those things worth your shame?

So, ask for a discount when you go to Starbucks. Cross the street when there are no cars coming. Wear a Hawaiian shirt for no reason. Or wear a Tyrian purple tunic.

Channel your inner Cato. Practice discomfort on your own terms. Because when discomfort and humiliation inevitably find you, you’ll be well prepared to handle it.

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