How Wearing Weird Clothes Will Help You Develop Courage and Make You More Grateful

As I walk out my apartment, I text her:

I hope I don’t end up in jail.

I step into my car and begin driving to a nearby Whole Foods in a posh area of town.  I can feel my heart beating faster the closer I get to Whole Foods.   As I pull into the parking lot my mind starts to make up worst case scenarios and my cortisol shoots through the roof.  This is going to be fun.There I am in the parking lot of Whole Food, wearing my pajamas, with basketball shorts over them and a dress shirt to top it off. I feel the wind in my hair, and I walk into Whole Foods – expecting the worst:)

As I walk in I notice a couple of dirty looks, but only a few.  I guess this attire I’m wearing is a lot more normal than I thought.  Maybe people will be wearing this next fall.  I begin to realize that this is not such a big deal.  It’s actually fun.  And that’s the beauty of our thinking; as humans we have a god given gift to make stupid stories in our heads to scare ourselves.  Most of the time these stories just aren’t true.

My mind switches, and I begin to think about my friend reading this text and wondering:

What the hell is Martin up to?

I’m doing my latest experiment.  It’s called Practicing Misfortune, an old Stoic exercise.  The premise is twofold:

1) spend time without what you love and you’ll grow to value it more and

2) spend time with your biggest fear and you’ll become immune to it.

Seneca, the old Stoic Philosopher describes Practicing Misfortune:

Set aside a certain number of days, during which you shall be content  with the scantest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I so feared?… Let the pallet be a real one, and the cloak coarse.  Let the bread be hard and grimy.  Endure all this for three or four days at a time, sometimes for more, so that it may be a test of yourself instead of a mere hobby.  Then, I assure you… you will leap for joy when filled with a penny worth of food, and you will understand that a man’s peace of mind does not depend upon fortune, for, even when angry, she grants enough for our needs”

In essence by Practicing Misfortune one develops a visceral understanding that we don’t NEED what we value most nor do we NEED to avoid what we fear most. This opens us up to great personal freedom.

The exercise works like this:

1) Think about what you value most or fear most.

2) Set up a time to practice not having what you value most or exposing yourself to what you fear most.

3) While you do the exercise ask yourself: Is this what I feared most?

I love this exercise.  I find it extremely effective, but it ONLY works if you do it. This is key.  Nothing works if you don’t do it.

The question I ask myself as a people helper is: how can I structure information so that it is actionable  and so that people actually follow through with it?

The answer comes from BJ Fogg’s Persuasion Lab in Stanford University:

Simple and easy changes behavior.

To qualify what’s considered to be simple and easy:

1) It takes less than 30 seconds to do.

2) It takes minimal effort to do.

The number one reason people fail at implementing a new habit is because they rely on motivation instead of making the new habit simple and easy.

The odds are NOBODY is going to consistently do the Stoic exercise above, because it takes more than 30 seconds and it takes a bunch of effort.

With that in mind, I’ve developed a modern rendition that takes the essence of Practicing Misfortune.

1) Find a habit that you already do every day; that you do without any effort at all. Examples: brushing your teeth, combing your hair, etc.

2) Find something that you over-value.  Examples: success, attention, avoiding failure, etc

3) Ask the following question: Do I really need X?  (X is whatever you are over-valuing)

4) Commit to asking the question from step 3 every time you do the habit from step 1.

This exercise is deceptively simple, BUT again:


It’s taken me 10 years to find that out.

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