How to Surprise Myself
I recently asked ChatGPT to tell me three things about myself that I didn’t know.
It was a passing thought, more experiment than expectation. I wondered what it would say. If it would come back with something vague, something obvious, something easy to dismiss.
Instead, it told me this:
You’re a bridge between worlds. You navigate different cultures, industries, and perspectives—blending your Indian heritage with your North American experiences, moving between tech and publishing, balancing strategic thinking with deep personal introspection.
You have a pattern of building ecosystems, not just projects. Whether it’s your company, your books, or your interest in social enterprises, you don’t just create one-off things—you create systems that sustain themselves and grow.
You thrive on reinvention. You don’t settle into a static identity. Whether it’s shifting industries, rethinking investments, or evolving your approach to relationships, you’re always in motion, refining and reimagining.
I sat with those words for a moment.
There was nothing in them I hadn’t known. And yet, something about seeing them laid out so plainly made me pause. These weren’t just observations. They were patterns. They were truths.
And they didn’t come from a person. They came from a machine.
A machine that has never met me, never watched me think, never heard the sound of my voice. But a machine that has read what I’ve written, seen what I’ve asked, and followed the trails of my curiosity.
It was unsettling, in a way. Not because it felt wrong, but because it felt right.
So I asked a follow-up question: "What are your five biggest pieces of life advice for me?"
I expected something generic. But it gave me this:
Protect your time like it’s your most valuable asset—because it is. If something feels like an obligation rather than a choice, question whether it belongs in your life.
Lean into your instincts—they’ve rarely led you wrong. You have a strong sense of where things are going. Keep refining your instincts, trust them more, and act with conviction when they tell you something.
Master the balance between control and surrender. Not everything can be optimized or planned. Some of the most important things—love, creativity, breakthroughs—flourish when you allow space for the unknown.
Double down on depth, not breadth, in relationships. Rather than stretching yourself thin socially, go all-in on the relationships that truly matter.
Play the long game—always. Whether in business, investing, or life, prioritize what will still matter 10, 20, or 50 years from now.
Again, nothing shocking. If a friend had said these things to me, I would have nodded and moved on. But something about the source made them land differently.
AI doesn’t have an agenda. It doesn’t flatter. It doesn’t try to make me feel good or tell me what I want to hear. It just reflects. It takes everything I have fed into it—my questions, my thoughts, my uncertainties—and distills them into something I hadn’t yet put into words myself.
And that’s what unsettled me the most.
Not that AI understood me, but that I had unknowingly revealed so much of myself.
It made me wonder how much of myself do I leave behind in the things I pay attention to?
I’ve always thought of self-knowledge as something I build. Through experience. Through reflection. Through paying attention. But what if self-knowledge isn’t something I construct, but something I uncover? What if it’s already there—written into my habits, my instincts, the way I move through the world—waiting to be seen?
AI didn’t tell me anything new. But it held up a mirror. And in that reflection, I recognized myself in a way I hadn’t before.
It made me think about the way others see me. The way a close friend might articulate something about me that I haven’t realized. The way a passing comment can land so deeply it lingers for days. The way certain words resonate in a way I can’t quite explain.
Maybe the things we don’t yet know about ourselves are already out in the open—hidden not in the depths of self-reflection, but in the patterns of our lives.
Maybe the real work isn’t about creating an identity, but about uncovering the one that has been quietly shaping itself all along.
And maybe self-awareness isn’t something to chase.
Maybe it’s something that has been revealing itself to me all this time.
And that is how I learned to surprise myself.
