TL;DR:

I thought I knew "myself." Turns out I didn't.


Long Version:

For most of my life, I was shaped by everyone and everything around me. I achieved what I was supposed to achieve. I became who I was supposed to become.

Then, going into my last year of college, my crush didn't want to be with me. I had everything I believed would make me "enough"—the resume, the looks, the charisma—and it still wasn't enough.

I fell apart.

Late one night, I wrote in my journal: "Why? Am I not enough?" That question broke something open. For the first time in my life, I stopped running from my pain and just sat with it. I let myself feel the inadequacy, the shame, the fear I'd been avoiding for years.

And something shifted. Beneath all that pain was a quiet knowing I'd never noticed before — a sense that who I actually am has nothing to do with what I achieve or who wants me. I started discovering the difference between who I'd been performing as and who I actually was.

But things were already in motion. I'd signed an investment banking offer before any of this happened, so I graduated torn — excited for what felt like freedom, but dreading the life I'd committed to without knowing myself.

On my first day as an analyst in New York City, I looked around the office and thought, "Is this really it?" Everyone told me I'd made it. I felt lied to.

I spent six months in hell. I'd wake up every day and have to perform as someone I wasn't. Smile in meetings. Pretend to care about pitch decks. Go through the motions while feeling like I was betraying something essential in myself. I felt utterly helpless.

On December 12th, 2021, during a bus ride back from Boston, I finally asked: "What the fuck am I doing with my life?"

Three months later, I quit.

Since then, my life has been shaped by one question: What feels alive? Not "What should I do?" or "What will impress people?" but "What does my soul want?"

That question led me to creative work, solo travel, coaching, San Francisco. To the people who've become my chosen family. It's brought me back to myself again and again — not to some fixed destination, but to a way of being that feels like home.

Maybe that's what this whole human thing is about. Not figuring ourselves out once and for all, but learning to come home to who we've always been — and helping each other do the same.

Now

🎨 Creating

Writing about what's alive on Substack

Intimate conversations on YouTube

❓Questioning

  1. How can we be more ourselves more of the time?

  2. How is this in service of a whole life?

  3. How can we create (in-person) containers for transformation?

📚 Reading

A Wizard of Earthsea

Anam Cara: A Book of Celtic Wisdom

Essentials of Mahamudra: Looking Directly at the Mind

❤️ Cherishing

The sun breaking after a rainy day.

A light rain while the sun shines — the gentle caress of drops blended with the warmth on your shoulder.

Walking through a torrential downpour with friends.

Watching a lizard nom a bug.

Daily gratitude and check-in with one of my close friends.

Almond croissants. Always.

Uninterrupted nights of sleep.

Showering off a New York City summer.

Staring at other people's tattoos while riding the subway.

Smiling at babies.

Saying hi to birbs and street kitties.

Naps.

My parents speaking in Chinese.

Calling my grandmother.

Seeing friends from different parts of my life connect.

🎨 Creating

Writing about what's alive on Substack

Intimate conversations on YouTube

❓Questioning

  1. How can we be more ourselves more of the time?

  2. How is this in service of a whole life?

  3. How can we create (in-person) containers for transformation?

📚 Reading

A Wizard of Earthsea

Anam Cara: A Book of Celtic Wisdom

Essentials of Mahamudra: Looking Directly at the Mind

❤️ Cherishing

The sun breaking after a rainy day.

A light rain while the sun shines — the gentle caress of drops blended with the warmth on your shoulder.

Walking through a torrential downpour with friends.

Watching a lizard nom a bug.

Daily gratitude and check-in with one of my close friends.

Almond croissants. Always.

Uninterrupted nights of sleep.

Showering off a New York City summer.

Staring at other people's tattoos while riding the subway.

Smiling at babies.

Saying hi to birbs and street kitties.

Naps.

My parents speaking in Chinese.

Calling my grandmother.

Seeing friends from different parts of my life connect.

Dennis Xiao

Living the Questions

Where I write about what's alive in my life

Copyright © 2025 Dennis Xiao. All rights reserved.