My why

Setting out to find our whys

In March of 2019, a man named Trip Vest and I set out to find each other’s “whys.” We followed the process outlined in the book Find Your Why a “how to” explainer of Simon Sinek’s famous golden circle concept from Start With Why.

We interviewed each other for hours. First at a Kava shop in San Francisco, then at my home in Oakland, and ultimately over Zoom (before it was cool). Trip and I already knew one another, but not very well. That turns out to be a plus for this exercise. We didn’t have any notions that could bias our analysis.

The goal is to listen stories of contribution and impact. What does the speaker feel called to do? What gets them out of bed in the morning? What do they avoid? What drains their energy? Don’t just listen to the words. Listen to the melody of the emotion behind the voice. It’s a surer indicator their feelings.

We took a week to synthesize the results.

The results of the exploration

My contribution

The impact it brings

What, How, and Why

What I do. Uncover the unusual (everything) and show people what’s possible (everything).

How I do it. By sharing words of encouragement and coaching and instruction.

Why I do it? To help others illuminate self-imposed limitations so they can live authentically.


First, principles (“School is a place of business.”)

You love to philosofy and move into deeper ideas. You yearn for authenticity and glow when talking about principled people. You’re pained by inauthenticity. You see minimalism as a form of authenticity and principles as a form of minimalism. The bullshit of the façade doesn’t interest you. You have a passion for learning–but you get bored once you understand the basics. You also need to share everything you’ve learned.

Fascination for unusual folk (“People are strange.”)

You’re a junkie for unusual folk. You have a deep appreciation for all sides of someone, the whole person. You love talking, in one-on-ones, to find what is unusual about others, probably so you can feel comfortable being weird yourself. You appreciate people who live unapologetically as themselves; characters who follow their unique drives. In one sense, you admire their freedom. But in another, you admire them because these folks live according to the values and principles they have outlined for themselves.

Show others what is possible (“Never say I can’t.”)

You want to show people what is possible. You believe that school//work/life is a place of “funny business” to paraphrase your eighth grade teacher. You don’t feel the constraints that other people do. You are ready and willing to challenge the status quo when it no longer serves you. You believe that anything is truly possible. You do not accept what you’re told. You challenge assumptions. You’ve chosen that life is the thing you want it to be.

Become yourself by serving others (“Only speak the truth.”)

You love when you can be yourself. When you don’t have autonomy you feel constrained. You crave permission to be yourself. You are most yourself when you are in service of others. You light up when in service of others. You want to help, you love to give advice, and you want to actually change lives. Personal validation is fuel to you. Sometimes validation is a signpost to what is meaningful and important. That said, you are easily flattered. You like people who like you—and you want to be someone who is liked.

Make ’em laugh (“Life is a place of comedy.”)

Why do anything if it doesn’t matter? You want to make an impact in two main ways: help people do what’s right and help people be themselves. Validation is one way you know you’ve made an impact and laughter is the most immediate, unambiguous feedback you can get. It is the tangible feedback of joy. For you it’s a way to serve that’s uniquely you. To make people laugh lets you be yourself. When you make people laugh, it shows them that anything is possible. The most impossible thing in a tragic world is finding humor in it.

🙏 Much gratitude to Trip Vest.

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