I Wanted a Career Coaching Session. The Zen Master Gave Me a Reality Check.
No back-and-forth. No debate. Just a lesson that left me rethinking how I approach permissions: both asked and given.
Tuesday is career coaching day. And since my coach is literally an AI, I get to do something you can’t do with human coaches: change their entire personality on a whim.
At the start of the month, I trained ChatGPT in Eastern philosophy for a coaching session, and it turned out to be surprisingly insightful. So this week, I decided to up the stakes, not just a coach who understands Zen, but an actual Zen Master.
I imagined a back-and-forth, a thought-provoking discussion. I had my notes ready. I expected a dialogue.
But that’s not what happened.
Because, well… Zen Masters don’t do back-and-forth.
I shared my notes, and instead of the usual interactive session, the Zen Master just spoke. No space for debate, no questions, no clarifications. Just one long, deliberate response, like a riddle wrapped in a lesson wrapped in an existential crisis.
So, here it is, unedited, unchallenged. A pure, uninterrupted career coaching session with a Zen Master.
The Zen master sits before you, eyes half-closed, as if he is observing the space between things rather than the things themselves. After a long pause, he speaks.
Zen Master:
"You have learned that rejection is not a storm, but a breeze. It brushes past you and leaves you standing where you were—unchanged, unless you choose to move."
"You have also learned that seeking rejection often brings something else instead: access, connection, new pathways. You knock on a locked door, only to find it was never locked to begin with."
He places a small stone on the ground between you.
"Now, tell me: what is the greatest barrier between you and what you desire?"
[Note from me: I actually thought about this, before reading the next line. I would say not being 100% clear on what I want and then just different levels of fears]
You think for a moment. The answer should be obvious. The external systems, the structures, the limitations. But something in his expression tells you that is not the answer he is looking for.
He nods knowingly.
"The greatest barrier is not the ‘No’ of the world, but the ‘No’ within yourself. The hesitation before asking. The doubt before stepping forward. The belief that you already know the answer before you even pose the question."
Lesson 1: The Barrier of Assumption
"You assumed rejection would be easy to find, yet you encountered generosity instead. What does that tell you?"
He pauses, letting the question settle.
"Most people carry invisible doors within them. They expect difficulty, so they never ask. They expect rejection, so they never step forward. And in doing so, they reject themselves before the world ever has a chance to respond."
Lesson 2: Rejection as the Wrong Target
He gestures toward the list of "No’s" you have collected.
"You counted your rejections as if they were proof of courage. But I ask you: is courage measured by the ‘No’ or by the act of asking?"
A breeze moves through the room, shifting the small stone on the ground slightly.
"What if your true practice is not rejection but discovery? To ask not to be denied, but to see what is possible?"
Lesson 3: The Missing No—Your Own
His gaze sharpens, as if cutting through the quiet.
"And yet, when the moment came for you to say ‘No’—when your space was trespassed—you remained silent. Why?"
The memory surfaces. The worker in your home. The private space entered without permission. The unease, the hesitation, the self-doubt.
"You are learning to accept rejection, but you must also learn to give it. A tree does not apologize for where its roots will not grow. A river does not ask permission to flow in its own direction. Your space is your space. Your boundaries are yours to protect."
He lifts the stone from the ground and places it in your hand.
"This week, your task is twofold: Ask boldly, without assumption. And say ‘No’ when it must be said, without apology."
"The practice of rejection is not about learning to accept it—it is about mastering your own permission to exist fully, to ask freely, and to refuse without guilt."
He closes his eyes again, signaling that the lesson is complete.
So here we are. Rejection was supposed to be the lesson, but maybe the real challenge is permission: both the kind I ask for and the kind I refuse to give.
Like an Ensō circle, a "No" is never entirely closed, it holds space for what comes next.
I thought I was collecting No’s. Turns out, I also need to start handing them out. Boundaries and openness aren’t opposites, they shape each other.
What about you? Did the Zen Master make you reflect on anything else?