“I’m going to show you a picture. Don’t overthink what you see and just answer these three questions.”

She flashed the first picture on the Zoom screen.

“The first question is,” she explained, “What happened before this scene? The second question, is what is the person currently feeling? And the last question, what happens next?”

“This is strange,” I thought to myself. But I’m not one to back down from a challenge so I played along and tried my best to answer sincerely.

What happened before?

A child is at a bus stop coming home from school. There are delays and he has no idea when he’s going to get home.

What is the subject feeling?

He’s frustrated that there are so many steps outside of his control to get home. He’s jealous that the other kids have it so much easier — they just get picked up by car. He’s starting to get scared as dusk approaches which means more unsavory characters both at the bus stop and on the bus itself.

What happens next?

The bus eventually comes. He takes out his homework and starts doing it to kill time. He wants to be a good boy. He stays small on the bus to not bring attention to himself. He gets home and has dinner. He doesn’t discuss the delay with his parents.

I was trying out a new coaching modality, this one focused on Attachment Strategies. Openly discussing my feelings and emotions was a relatively new practice for me. I grew up in an emotionally neutered household. There was a lot of love, but it was practical. My dad expressed his love with a perfectly polished knife that cut succulent and sweet mango cubes for my sister and me. He waited until we were full before eating the deformed leftovers and sucking on the pit. Not once did he ask us for one of the good pieces. My mom ran a chore-free household — we were relieved of cleaning dishes and folding laundry — with the tacit agreement that we’d use that extra time to study.

We knew we loved each other, but we never said “I love you.” I only started saying it to them in my 30s, after losing my friend Lauren to breast cancer. They’d reply with a squeamish look and an awkwardly cute one-liner like, “Yes” or “Us too.” Things got a bit dicier when it came to “bad emotions” like sadness, anger, fear or shame. And I can count on one hand how many times I saw my parents cry (only when my mom’s father and best friend died). As a kid from the 80s, expressing feelings was frowned upon and I was regularly told to “stop crying” — and dutifully complied. There was the occasional spanking (dad) and face slap (mom). All of this felt quite normal.

As an adult, I put all those uncomfortable emotions into a steel vault and buried them deep inside my soul. When they’d start to flare up — either in response to a mistake at work or self-loathing from going pre-maturely bald — I’d find a way to numb it. Two regular numbing tools were workaholism and alcoholism (the “isms”). But my coping repertoire was quite refined and expanded into doomscrolling, pornography, dark chocolate and even meditation (what’s known as spiritual bypass).

When I quit Wall Street, the same internal whisper that said “this career ain’t right for you” also said “you should really get to know yourself.” That set off a decade of uncomfortable introspection. I worked with life coaches, therapists, mediation teachers, marriage counselors, trauma healers and even a practical philosopher. When I started this journey inward, I had a simple goal: to be happier. I quickly realized that this parsimonious reduction of the human experience into a single word (“happy”) was not only was a disservice, but totally hoodwinked me from seeing life’s bigger purpose. At the most primary level what did happiness even mean? Was it the experience of pleasure? Feeling loved? Hitting goals? Embracing your mortality? Or was it a reductive process — the elimination of sadness?

There’s an argument to be made that I ditched the corporate grind just to become an hippy navel gazer. And over that decade of introspection, some peers would lob in passive criticisms such as:

“What if there’s no answer to what you’re looking for?”

“Are you going inwards as an avoidance technique?”