If I could do it all over again, I would have practiced my negotiation training and calmly replied in my best FM DJ voice, “You’re from Chicago?”

I hate getting sidetracked. Whenever I learn something new, I try to practice that new skill. But someone or something always seems to appear out of thin air to distract me like a jelly donut brigade parachuting into a fat camp. 

Then, I spend days or even weeks ruminating before unlocking the hidden lesson.

Instantaneously, a reel posted by a whiskey influencer on Instagram transported me back to a recent personal experience when I experienced confidence dilution.

“While barrel proof is more expensive, you control the dilution by altering the amount of water that goes into the glass. Doing so gives you a better sipping experience because you can dial in the flavor profile based on your preferences.”

After completing a two-day Mastering Negotiation with Tactical Empathy workshop in Downtown Los Angeles hosted by The BlackSwan Group, I decided to stay for the weekend. The city of Angels has undergone quite a transformation since I moved away in 2016. A mini-vacay would allow me to absorb the transition and practice my newfound skills before embarking on my journey back to Tokyo. 

I made plans to tour the Los Angeles County Museum of Art and catch up with friends on Sunday afternoon. After strolling down the hallway, I entered the elevator to head down to the first floor. 

Standing confidently with my hands on my hips, I wore blue wool flat-front straight-fit trousers, a custom alligator skin belt peppered with gold flake details and matching buckle, a grey cashmere turtleneck sweater, black tassel loafers, and an olive green mini diamond-patterned Moncler puffer jacket. Outfits like this make me feel great when I go to the museum because it’s a solid middle-ground between a suit and athletic wear. I never considered my unique sense of style might be a bit much for Downtown LA on the weekend.

Standing in the elevator was a tall, athletic man with caramel skin wearing grey baggy sweatpants, an oversized T-shirt, and white sneakers, staring down at his Iphone. 

As always, I tried to initiate a conversation. 

“How’s the weather outside today?” 

He scoffed disapprovingly and proudly proclaimed, “I’m from Chicago. And in Chicago, we wouldn’t be wearing all that...” With a wave of his hand, he pointed at me and grinned subtly. Then he made a “psh” sound, like Ed Bassmaster in one of his YouTube comedy skits… 

My classic casual chic was too much for the era of athleisure. Clearly, I was out of pocket in this guy's mind, and he’d let me know.