Lived Through This

Finding My Fighting Words: How I Learned to Have Uncomfortable Conversations

I had 50 painfully uncomfortable conversations with strangers to practice being assertive under pressure. Here’s what I learned.

A photo of smaller dinosaur figurines in front of a T-rex figurine.
A photo of smaller dinosaur figurines in front of a T-rex figurine.
Photo: MirageC/Getty Images
The four types of people I encountered at work.

The big idea

In theory, AQ felt easier to improve than EQ. But finding opportunities to practice it was a challenge.

Building the bootcamp

The exercises

The grand gesture

The structure

One of the spreadsheets used to track the exercises. Columns C onwards were filled in after completing each exercise.

Lying on the floor

Starting the day practicing extreme discomfort on the floor. I asked the (at this point, bewildered) barista at the coffee shop to take this picture on the last day of the experiment.

The secret

The important caveat

What Happened

It was grueling

But it worked

Unusual conversation #17: challenge a stranger to an arm wrestle. This university student kindly obliged, warning me that he wasn’t any good at these things. Then he demolished me.

…Sort of

I love building and learning new things.