Kunal Gupta's Blog, page 3

How to Start

There is a certain kind of weight that does not show itself on the surface. It lingers quietly, pulling gently at attention. Some days it feels light enough to ignore. Other days, it hums in the background, asking to be noticed.

For the past month, I carried the simple desire to refresh the website for Pivot 5, my AI newsletter. It was a small project. Something I thought about almost daily. Each time I met someone new and wanted to share the newsletter, I found myself pulling up the old site, feeling a small, familiar discomfort. A reminder that there was something unfinished. Something waiting.

I kept telling myself it was a quick task. I kept not doing it.

Yesterday, somewhere between East Asia and Western Europe, sitting on a long-haul flight, I opened my laptop. There was a rare feeling of determination. No fanfare, no special plan. Just a small window of willingness. I connected to the airplane wifi, opened a blank page, and began.

Within forty-five minutes, the new site took shape. Nothing complicated, nothing revolutionary. Just simple, clear, and — for now — enough.

After I hit publish, I closed my laptop and pulled out my journal. I sat with the question: why had this felt so heavy for so long?

It wasn’t that the work was hard. It wasn’t the time it would take. It wasn’t even the skills involved. The real weight had lived elsewhere — in the mind, not the hands.

There is a difference between cognitive load and physical load. Physical effort is easy to spot. Muscles tire. Limbs ache. But cognitive effort is quieter. Decisions accumulate. Doubts pile up. Expectations build until even the simplest task feels like a mountain.

For this website refresh, the cognitive load was heavier than the task itself. Every time I thought about doing it, I imagined all the decisions that would need to be made. What to say. How it should look. How it might be received. Somewhere beneath it all, a perfectionist voice whispered that it needed to be great, not just good enough. That if I wasn’t ready to nail it, I shouldn’t even start.

It is not lost on me how often this pattern repeats itself. The things that weigh the most are rarely the things that require the most physical energy. They are the ones that ask for emotional courage, for the willingness to face uncertainty.

In other areas of life, I have found ways to ease this burden. 

I love attending yoga classes, even though I could easily practice at home. I often work out with a trainer, not because I don’t know what to do, but because it feels lighter to follow. For years as a CEO, and even now working independently, life has required a kind of constant self-leadership. Always deciding, always setting the direction. There is a certain fatigue that comes from always leading, even if only oneself.

Sometimes, it feels good to let someone else guide the way. To follow a recipe rather than invent one. To ask ChatGPT even the most basic of questions, just to lighten the load. To not have to figure everything out alone.

There is a certain conservation of energy that happens when the cognitive load is shared, even slightly.

Starting is often the hardest part. The mind can inflate the difficulty of beginning into something monstrous, while the body waits patiently, ready to act. Resistance grows in imagination, but shrinks in the doing.

The experience on the flight reminded me that conserving energy is not always about becoming stronger or pushing harder. Sometimes it is about creating conditions that make important work feel lighter. Reducing friction. Building systems of ease. Lowering the cognitive cost of beginning.

It also reminded me to have compassion for the parts of myself that hesitate. 

The part that delayed the website refresh was not lazy or careless. It was cautious. It cared about getting it right. Sometimes, delay is not resistance but a quiet form of protection — an attempt to preserve energy for when it might be most wisely spent.

There are no simple answers here. Only open questions. How to recognize when to push through resistance, and when to listen to it. How to distinguish between the heaviness that protects and the heaviness that holds back. How to create more conditions where beginning feels lighter, and more days where the work flows without force.

The energy to live, to create, to move forward — it is precious. Perhaps conserving it is not about holding it tightly, but about learning how to spend it wisely, and how to trust that sometimes, even the heaviest things are lighter than they appear.

And that is how I learned to start.

If you are interested in keeping up-to-date on the latest in AI, subscribe now for Pivot 5, my AI newsletter here: pivot5.ai

How to Anything

For a long time, I believed I could do anything. It was a belief that served me well. It gave me permission to dream. To try. To say yes before knowing how. 

I have long approached the world with the quiet confidence that, with enough effort, energy, or intention, anything was possible.

And then, I tried to do everything.

Especially in business, I fell into that trap—believing that since we could do anything, then we must do everything. 

Why not chase every idea, pursue every opportunity, take on every client, build every product? I told myself it was ambition. I told myself it was vision. But over time, I realized it was noise.

When everything matters, it becomes hard to tell what really does.

It wasn’t sudden. There was no single moment of collapse or crisis. Just a slow, growing awareness that the energy I was spreading across many things was leaving us with little depth in any one of them. 

I was always moving, but rarely arriving. And the more we did, the harder it became to explain—to myself and to others—what we were really about.

I didn’t want to choose. That’s what made it so hard. Choosing meant closing doors. It meant letting go of ideas that were exciting, even if they weren’t essential. It meant acknowledging that time, energy, and attention are finite. It meant growing up.

We’re often told a story that anything is possible. But what that story leaves out is that everything is not.

That’s the quiet truth at the heart of this reflection.

We can do anything. But not everything.

Tradeoffs are not something I was eager to embrace. For years, I saw them as compromises. As limits. As what happens when things don’t go to plan. But I’ve started to see them differently. Tradeoffs are not signs of failure. They are signs of choosing.

Choosing what to focus on is not a weakness. It’s a kind of wisdom. It’s a way of celebrating and deciding what matters most right now, even if it means setting aside things that also matter—just not right now.

There’s a cultural pressure. The quiet—but constant—messages that more is better. That success looks like expansion. That if I say no, I’m missing out. Falling behind. Thinking small.

I’ve felt that pressure. I’ve internalized it. And I’ve seen how easily it can pull me away from my own intuition.

But there is something deeply grounding in making tradeoffs with intention. In not just reacting to what’s urgent, but returning to what’s essential. In being honest with myself about what season I’m in, what I can hold, and what I need to put down, for now.

It reminds me of pruning. Cutting back not because something is dead, but because I want something else to grow. Tradeoffs can feel harsh in the moment. But over time, they create the space for depth. For clarity. For flow.

These days, I try to make tradeoffs from a place of alignment rather than fear. When I’m afraid, I say yes too often. I chase too many things. I try to prove too much. But when I’m grounded, I can feel what’s mine to do—and what isn’t. And I can make those choices more gently.

Sometimes, I still resist. I still fall into the temptation of doing more. Saying yes to everything can feel good—until it doesn’t. Until I find myself tired, scattered, or unsure of what I’m really working toward. That’s usually when I remember to pause. To step back. To ask a quiet question that has become a kind of compass: what matters most right now?

That question doesn’t give me certainty. But it helps me listen. It helps me notice what I’m holding onto, and what I might be ready to release.

I still believe I can do anything. But now I know that doing anything means choosing. It means being okay with not doing everything. It means trusting that every time I let go of something, I am making space for something else to emerge.

And that is how I learned to anything.

How to Learn

A few minutes after I finished giving a talk on AI trends last week, as the audience began to disperse and the noise in the room started to fade, a young man approached me. 

He was quiet, maybe a little nervous, and had waited until the crowd had thinned before stepping forward. He was the only university student in the room—surrounded by professionals, founders, and technologists twice his age—but he had clearly been paying close attention.

He asked me, simply, “How do I learn AI?”

There was something innocent in his voice. Not the kind of question meant to impress, but the kind that carries the weight of genuine curiosity. The kind of question I might have asked when I was his age. The kind I don’t hear very often anymore.

I asked him what he had been doing so far. 

He told me about a few online courses he had taken, some YouTube videos he liked, and a handful of small projects he had already started building. He was clearly excited—eager to show me what he was working on on his phone, proud of what he had created, even if it wasn’t polished. His enthusiasm was infectious. And it stirred something in me that I hadn’t felt in a long time.

When was the last time I was that excited to learn?

I used to love learning. 

I learned to walk by watching others around me. I learned to speak by listening to the sounds that surrounded me. I learned to read and count and write not because I had to, but because it was all new, and I was ready.

I was open. I was unafraid. I was constantly observing, mimicking, trying. I failed all the time, but I didn’t even notice or label it as failures or mistakes. That’s just what learning looked like. 

The first twenty years of my life were dedicated to learning. That was the purpose of life. Every environment I was in—from school to home to the playground—was designed around the idea that I didn’t know, and that not knowing was okay. In fact, it was expected.

I miss that.

Because the next twenty years, for me, were mostly about working. And sure, there was learning in that too—learning how to navigate teams, how to lead, how to manage complexity, how to solve problems. But it was a different kind of learning. It was linear. It was goal-oriented. It was focused on output, on performance, on mastery. The kind of learning that fits neatly into a spreadsheet or a resume.

Through working, I learned how to get things done efficiently, effectively, and reliably. But that kind of learning rarely felt playful. It didn’t feel free. There was always a deadline, always a deliverable, always someone expecting something from me. 

Somewhere along the way, I also developed the belief that I should already know. That being new at something was a sign of failure. That asking questions revealed weakness. That unless I was good at something, it probably wasn’t worth doing. But that’s the lie.

The truth is that learning, by definition, begins with not knowing. And there’s a certain grace in that. A humility. A quiet strength in being able to say: this is new to me. I don’t know how to do it yet. And that’s okay. That’s the whole point.

The challenge, though, is that as adults we become attached to who we think we are. 

I’ve noticed this in myself. I start to say things like “I’m a founder,” or “I’m an investor,” or “I’m a writer.” And each of those statements, while useful in certain contexts, begins to define the boundaries of what I allow myself to explore. If I’m a founder, then I should know how to build businesses. If I’m a writer, then I should be exceptional at expressing myself. There’s less room for surprise. Less room for play.

Back to the student who approached me after my talk. He began showing me a few of the projects he had built using AI—small tools, clever experiments, things he had thrown together using open-source models and APIs. Then he asked me, “Do you think any of these could make money?”

I stopped him. Not because it was a bad question. But because it wasn’t the right one for that moment.

“Why does it need to make money?” I asked.

He looked at me, unsure how to respond. “I guess… I thought that’s what I was supposed to do.”

There was a pause between us. I could see him thinking. I could also see him wondering if he had said something wrong. I filled the silence by reminding him of his original question. He had asked me how to learn AI. Not how to monetize it. Not how to build a company. Not how to become a success story.

I told him to keep building. To keep experimenting. To keep launching new projects—every single week, if he could. Not because one of them might work. But because the act of doing is the real learning. Not the videos. Not the podcasts. Not the reading. Not the articles or courses or conversations. 

His face lit up. There was a visible shift in his posture. I could feel his excitement begin to return, maybe even deepen. “So,” he asked, “if I just keep trying ideas, one of them will eventually work?”

“No,” I said, again challenging him, without hesitation. “That’s not the point.”

The purpose isn’t to get one of your ideas to work. The purpose is to keep learning. To keep pulling the thread of your own curiosity, without needing to know where it leads.

And maybe that’s the hardest part.

As adults, we become so oriented around outcomes. We want results. We want validation. We want our time to feel productive, our effort to be justified. But learning doesn’t work that way. Not the kind of learning that expands us. Not the kind that lights us up. That kind of learning can’t be scheduled or measured

Play is a word I’ve been coming back to more often lately. Children learn through play not because it’s a strategy, but because it’s an instinct. It’s how they make sense of the world. And when I think back on the moments when I’ve learned the most in recent years, they haven’t been when I was trying to learn. They’ve been when I was trying something new just for the sake of it. When I allowed myself to experiment. To explore. To play.

Learning, I’m starting to remember, is not something to achieve. It’s something to return to. Something to remember. A part of myself I once knew well and, somewhere along the way, misplaced.

The student didn’t need a roadmap. He needed a reminder. And without meaning to, he gave one back to me.

And that is how I learned to learn.

How to Write

It started, as many things do, with a question from a friend. One I’ve been asked before, and never answered well.

"How do you write so much?"

For a long time, I would say what many say: just start.

It was an easy answer. A quick way to move past the question. But recently, someone challenged me and I started to wonder if that advice has ever really helped anyone. It’s like telling someone who’s never cooked before to just make dinner. Technically true. But not really useful.

So I sat down. I let the question sit with me. And I began to think about how writing has shown up in my own life.

Writing has been one of the most meaningful parts of my adult life. Not because I set out to become a writer, but because I wanted to find a way to express myself. And for me, writing became the most natural form of expression. For others, it may be music, dance, sport, art, cooking or a myriad of other activities. For me, it’s writing.

Over the years, it has taken many shapes. Blog posts, books, newsletters. But also private notes I have never shared. Simple text messages to people I care about. Journal entries that no one else will read. Each of them, in their own way, is a form of writing.

Writing doesn’t have to mean publishing. It doesn’t have to mean performing. It doesn’t even have to mean being read. It can be a quiet act. A way to make sense of what’s going on inside. A way to turn a vague feeling into something that can be seen or understood.

I understand why writing can feel hard, especially for adults. In school, we learned how to write in order to get a grade. We wrote for a teacher, followed a structure, and moved on. We didn’t learn how to write for ourselves. We didn’t learn how to write in a way that was connected to our identity. And we certainly didn’t learn how to write for a wider audience, or how to build the confidence that comes with doing so.

As adults, writing begins to show up again, but in different ways. In texts, emails, reports, presentations. On social media, in bios, in captions. The stakes feel higher. The audience is wider. The expectations are louder. There’s a real fear of being judged. Of being misunderstood. Of being remembered for the wrong thing.
The pressure to be perfect can be overwhelming. If it’s not good, don’t share it. If it’s not perfect, don’t start. And so, many people don’t.

I used to think that writing was the hard part. But over time, I’ve come to see that writing is not the hard part. Thinking is the hard part. When I sit down to write and feel stuck, it’s usually because I haven’t done the work to think something through. Or, more honestly, I haven’t allowed myself to feel what I need to feel.

When I’m clear about what I believe, when I know what I want to say, when I’ve taken the time to sit with an idea or a feeling—then the writing flows effortlessly. The writing takes care of itself.

We all think differently. For some people, clarity comes through conversation, through engaging with others. For others, it comes through solitude, through quiet reflection. For me, it comes in the empty spaces. When I’m in the shower. Driving with no destination. Walking without my phone. Cooking a meal. Cleaning the apartment. These are the times when I notice ideas surfacing from within me. Not because I’m doing nothing, but because I’m tuning into myself

These spaces are often dismissed as unproductive. But they are full of insight. When the noise fades, what’s left is a chance to hear something that’s already there. Something waiting to be heard.

Writing hasn’t changed my life. Writing has helped me change my life. It has helped me see and understand myself more clearly. Hear myself more honestly. Trust myself more deeply. It didn’t happen all at once. But over time, writing has become a way for me to stay close to what matters. A way to remember who I am.

So when I’m asked how to write, I no longer say: just start. Now I say: make space.

Make space to think. To feel. To listen. That’s where writing begins. Because the words are already within. They just need a way out.

And that is how I learned to write.

How to Make Friends

Two WhatsApp messages came in last night, both unprompted, from friends of friends who are moving to Lisbon and asked me an innocent question, "how do I make friends there?"

The question stumped me. Not because I don't know what to say, but because it can't be said over a few sentences in a text message.

Making friends is not a logistical, practical item, like say where to find healthy vegetarian food, or how much health insurance costs, or which yoga studio should I try.

It is a deep question that requires first going inwards before going outwards.

As I sat there on my couch at night, I put my phone aside and began to reflect.

In the past few weeks, I have been traveling and connected either in-person or over the phone, with close friends across different chapters in my life and continents in the world. From Sydney and Lisbon, to San Francisco, New York and Toronto, to London and Singapore, I look back at my recent interactions with friends with fondness and gratitude.

The process of making friends as an adult begins with deciding to make friends. That decision has tremendous consequences and implications.

This decision requires sacrifice. To treat friendship not as a luxury for when time permits, but as essential as sleep, as food, as exercise. It means sometimes choosing a coffee with a potential friend over an extra hour of work. It means showing up to gatherings and events, when exhaustion begs me to stay home. It means vulnerability when all my adult instincts push toward self-protection.

The structure of adult life is inherently isolating. We no longer have the ready-made social pools of classrooms and dormitories. The casual daily interactions that spark connection have been further eroded by remote work culture—no more impromptu lunches with colleagues or conversations waiting for the elevator.

I felt this acutely when I first started working remotely five years ago. The freedom was intoxicating, but something vital was missing. The spontaneous human moments that punctuated office days disappeared. My world narrowed to scheduled video calls and carefully crafted text and voice messages.

What I've learned through setting up a home, and by proxy, a life, in New York, Lisbon and Sydney, is that adults must create the conditions for friendship that once happened naturally. This is not a passive process—it's architectural. I have needed to build the structures that foster connection rather than waiting for them to appear.

Adult friendships haven't happened in the margins of life for me—they happen only when I carve out space at the center.

Friendship occupies territory that nothing else can fill. Not family, not romantic partnership, not professional relationships.

Sitting across from a friend in a café in Sydney, I found myself sharing thoughts I hadn't even admitted to myself. There was nothing at stake—no family dynamics to maintain, no relationship stability to consider, no professional reputation to protect. Just the clean air of connection for its own sake.

I've observed that family relationships come with tribal expectations—patterns established decades ago that can be beautiful but also limiting. Romantic partnerships carry the weight of shared life management. Professional connections must always honor certain boundaries.

But friendship—true friendship—creates space for exploration without consequence. For authenticity without calculation. For growth without an agenda.

After fifteen years as a CEO, I understand the difference profoundly. Professional friendships, while meaningful, exist within constraints. They're contextual by nature. True friendship transcends context—it follows no organizational chart, honors no hierarchy, serves no purpose beyond itself.
This isn't to diminish other connections. Rather, it's to recognize that friendship fills gaps that nothing else can. Gaps that, left unfilled, leave us incomplete.

Making friends as an adult follows a consistent equation: initial effort + consistent investment = compound returns.

The first stages require the most energy. Every interaction feels deliberate, sometimes awkward. Every invitation carries the risk of rejection. Every conversation requires presence when it would be easier to retreat to the comfort of established connections online.

I remember feeling exhausted after my first few weeks of friendship-building in Lisbon. The constant introducing myself. The stretching to remember names and details. The showing up to events where I knew no one. It felt like pushing a boulder uphill.

But something shifted around month three. Invitations began to flow both ways. Conversations developed continuity. Inside jokes emerged. The boulder that once required my constant straining began to roll with its own momentum.

This is the secret that few discuss: friendship has a tipping point. Invest enough consistent effort upfront, and eventually, the relationship begins to generate its own energy. The challenge is that most adults give up before reaching this inflection.

Looking at those Whatsapp messages again, I realize there's no simple answer to give. No three-step process. No list of meetup groups or apps or venues.

Making friends as an adult isn't about finding the right locations or activities. It's about becoming the right kind of person—one who has decided that connection matters enough to rearrange life around it. One who is willing to make the initial investments of effort. One who understands that meaningful relationships don't just happen to adults—they are built, deliberately and patiently.

The research confirms what experience has taught me: nothing contributes more to wellbeing than genuine connection. Not career success. Not financial security. Not even physical health. We are, at our core, social creatures whose nervous systems regulate best in the presence of trusted others.

I look back at my phone now, ready to craft a response to these two people who asked me how to make friends. I see that in the time I spent staring out over my balcony and reflecting on what to say, I had received a few new messages—someone from Lisbon checking in, someone from Sydney extending an invitation, someone from Toronto continuing a conversation from days ago.

This is the momentum of friendship at work.

And that is how I learned to make friends.

How to Five Years

This past week marked five years since that collective pause. The world stopped, held its breath, and in that stillness, something had shifted within me.

Looking back now, the contrast in my life feels stark.

My New York City life moved at a relentless pace. My days were filled with meetings, evenings with networking, weekends with recovery. Just to do it all again. 

Breathing in subway air and ambition in equal measure. Running, always running. Toward what? It wasn't really clear to me.

My identity felt solid then. Entrepreneur. My business card said it, my introduction at parties confirmed it, my schedule demanded it. It was comfortable in its discomfort. Known in its exhaustion.

Then everything stopped.

In the quiet that followed, realizations emerged within me. Not immediately, but gradually, like plants slowly breaking through an old concrete patio. Thoughts that couldn't be heard in the noise before.

What existed beyond the life I had constructed? The identity I had so carefully built might not be the only possible one for me.

The first changes I made were practical. Location. Daily habits. A move across an ocean, that wasn't meant to be permanent.

Now my life unfolds between Lisbon and Sydney. Between ancient cobblestones and oceanside beaches. Applying lots of sunscreen has become my daily ritual, replacing the morning rush for the subway.

The shift in my surroundings has brought a shift in my perspective.

My conversations now happen in accented English, with many non native English speakers as friends, whose journeys to this moment took paths entirely different from mine. 

Their stories and viewpoints reshape my understanding of life in ways impossible to predict. Foreign accents that once registered to me only as different now carry nuance, history, identity.

My professional identity has transformed too. From entrepreneur to now investor and author. From creating a single business to supporting many. From telling one story to telling many. Less doing, more reflecting. Less building, more connecting.

But the deeper shifts happened beneath my surface.

I learned to hold my ideas, identities, and attachments more lightly. I discovered that letting go creates space for something new to emerge. I found that curiosity leads to places certainty never could.

Perhaps the pandemic offered me a rare permission slip. Permission to question everything. Permission to release what no longer fit. Permission to begin again without explanation or justification.

In the space between what was and what could be, possibility took root within me.

The lesson from the past five years isn't about my specific choices—Lisbon or Sydney, investing or writing. The lesson is about curiosity itself. About approaching change not as a threat but as an invitation. About moving toward uncertainty rather than clinging to the familiar.

Looking back now, gratitude surfaces within me. For the circumstances that created space for my change. For the people who appeared at exactly the right moment, offering perspectives I couldn't have sought out intentionally. For the courage to follow my curiosity even when my destination wasn't clear.

Five years. So much change in my life, and yet it feels like just the beginning to me now.

The next five years will no doubt bring more change. More growth. More letting go. More discovering.

That's the unexpected gift from these past five years. Not the specific changes themselves, but my capacity to welcome change as it comes. To greet the unknown not as a threat but as teacher.

And that is how I learned to Five Years.

How to North Pole

All I could see was white, for hours on end.

This was while on a recent cross-continental flight, over 16 hours, that took a route across the top of the world, crossing the North Pole.

As it was daytime, and I had a window seat, I couldn't help but stare effortlessly out of the window. A white blanket of snow covered the earth as far as the eye could see. Occasionally, jagged ridges of ice caught the sunlight, like shattered diamonds against the endless whiteness.

While the plane was traveling at a high speed, everything seemed to slow down at that moment though. A peacefulness washed over me—not the forced calm of a meditation practice, but something more spontaneous and genuine that rose from witnessing something so untouched.

I realized I was staring at a part of the world rarely seen by anyone. It was completely uninhabited—by humans, animals, or vegetation. It was empty but full at the same time.

Emptiness often suggests absence, yet staring down at the vast white expanse, I discovered a different kind of emptiness—one full of presence, not absence.

I pressed my forehead against the cold window, watching ice formations that had existed long before human eyes gazed upon them. The landscape wasn't waiting for anyone's arrival. It simply was—perfect in its self-contained existence. Without concern for anyone else.

Somewhere between cloud and ice, I recognized something of myself in that landscape. A flicker of wonder came alive in me, followed by an unexpected desire to carry its profound peacefulness back into my cluttered life.

How often I had mistaken my own quiet spaces for emptiness. The digital world has trained me to equate activity with value. My attention fractures across dozens of apps, hundreds of websites and messages. The complexity compounds in my digital world until my mind resembles an overstuffed storage unit—everything is there but nothing is found.

Yet thirty-five thousand feet above the earth, that snow-covered expanse made a compelling argument for having less, not more.

Time behaves differently over the North Pole. The usual markers disappear. Just the curve of the earth wearing its white cap, indifferent to the human constructs of hours and minutes.

I checked the time and was surprised to find that two hours had passed. There's a certain peace in touching, even briefly, something that operates outside my usual frantic rhythm.

I also felt small against that immense whiteness. Properly small.

The humbling vastness reminded me of my place in the world—not diminishing my importance but contextualizing it. A relief washed over me—the pressure of being the center of my universe momentarily lifted. It was a strange but welcomed feeling: becoming smaller made me feel more.

From thirty-five thousand feet, patterns emerge that remain invisible at ground level. Wind had sculpted the snow into ripples that only revealed their natural and perfect geometry from this height.

I thought about how perspective transforms my understanding—how stepping back from my life helps reveal patterns I can’t see when pressed up against my daily existence.

As I continued staring out the airplane window, I began to wonder about what might lie beneath this immaculate surface, as there is more depth that meets the eye. 

Similarly, the parts of myself I rarely acknowledge—these are my personal North Poles. Regions unmarked on my mental maps. Regions I fly over but seldom explore.

My deepest creativity lies in these untouched regions. My most authentic self exists in this interior space that lies beneath the surface.

As the plane continued its arc across the sky, I pressed my palm against the window one last time, feeling the cold seep through the glass.

To recognize that the rarely seen parts of the world, like the rarely acknowledged parts of myself, aren't empty at all but full of meaning. All I have to do is pause and look.

And that is how I learned to North Pole.

How to Bali

Spending the past week in Bali, and like most places visited on vacation, it didn’t take long to notice the obvious—the palm trees, the beaches, the warmth in the air. But what stayed with me wasn’t the scenery. It was something quieter, something that didn’t call attention to itself.

One afternoon, while walking through a small village, I stopped in the middle of a busy street. I hadn’t meant to, but something caught my eye. The gates to a traditional Balinese home had been left open, revealing an intricately carved temple standing inside.

It was beautiful, but what struck me wasn’t the temple itself. It was its placement—right there at the front, effortlessly integrated into everyday life. Not hidden away in a quiet room, not reserved for special occasions. Just there.

It was striking, this natural coexistence of spirituality within the ordinary. Growing up in the West, spirituality often felt compartmentalized—something reserved for specific days, special ceremonies, or particular places of worship. Here in Bali, it is constant and present, quietly part of every day living.

The scooter narrowly missed me as I stood there, staring at the temple, the driver offering a gentle smile rather than the expected frustration.

No horn, no shouting, just a slight adjustment of course before continuing on. This happens daily on Bali's roads—a beautiful chaos that somehow functions with unexpected grace. Narrow streets built for one direction somehow accommodate two. Sidewalks appear and disappear without warning. Traffic signals exist mostly as suggestions. By all conventional wisdom, this should create constant tension, yet the opposite occurs.

In Delhi, drivers would lean heavily on their horns. In London, there would be structured outrage. In New York, colorful language would fill the air. But here, the chaos breathes with its own peculiar calm. The traffic moves like water finding its path, each vehicle sensing the others without rigid rules dictating every movement. There's an unspoken agreement to make space, to yield when yielding makes sense, to flow rather than force.

Bali exists in contradictions that somehow aren't contradictory at all.

Ancient stone temples stand beside sleek cafés serving flat whites. Traditional ceremonies with elaborate offerings occur next to digital nomads typing on MacBooks. A ceremony might temporarily close a main road, and everyone simply adjusts without complaint. Time stretches and contracts depending on what the moment requires, rather than adhering to strict schedules.

The concept of "either" feels foreign here. Instead, there is "both"—a capacity to hold seemingly opposite things with equal regard.

Every morning, small offerings appear everywhere—tiny palm-leaf baskets filled with flowers, rice, and incense. They rest on sidewalks, at entryways, on dashboards, at intersections. By afternoon, many are swept away or stepped over, yet the next day they appear again. The offerings aren't precious in the sense of needing to be preserved. Their value lies in the daily practice, the consistency of attention, rather than the permanence of the object itself.

This steady rhythm of small, intentional acts creates a different relationship with time. Each day contains these moments of pause and recognition. The mind isn't constantly pulled toward some future outcome or achievement. Instead, there is a gentle anchoring in the present—not through elaborate methods or dedicated retreats, but through these tiny consistent acknowledgments woven into ordinary activities.

One evening, watching the sun set at the beach, it occurred to me that what feels most striking about Bali isn't any single aspect but rather the ease with which apparent opposites coexist.

Work doesn't struggle against rest; they flow into each other. Technology doesn't battle tradition; they complement one another. Spirituality doesn't compete with practicality; they inform each other. The sacred doesn't need protection from the mundane; they are understood as parts of the same whole.

There's no need for rigid boundaries between categories of experience. The mind that created such distinctions can also allow them to dissolve.

Back home, my life often feels sectioned off into discrete areas that rarely touch. Investing stays in its lane. Health and relationships occupy designated times. Deeper questions about meaning or purpose get their occasional moment, usually when something disrupts the normal patterns.

This compartmentalization isn't inherently wrong. Structure creates clarity, efficiency, focus. Yet something is lost in this careful separation—a certain richness that comes from allowing different aspects of life to inform and transform each other.

Perhaps harmony doesn't require sameness or careful sorting. Perhaps it emerges naturally when we stop insisting that different elements of our experience must remain distinct and separate.

My last night in Bali, I found myself again in traffic, this time as a passenger watching the dance of vehicles negotiating a roundabout with no signals or rules beyond an unspoken understanding. Motorbikes, cars, pedestrians, even a few chickens—all somehow finding their way through without collision. No single path was identical, yet all were flowing toward their destinations.

It seemed, in that moment, a perfect metaphor. The harmony wasn't created by forcing everything to follow identical paths but rather by allowing each to find its own way while remaining aware of the whole. The contradictions were never really contradictions at all—just different expressions of the same life, moving in its own perfect, imperfect way.

And that is how I learned to Bali.

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.

How to Cliffnic

I recently had a picnic on the edge of a cliff.

Getting there required a drive along a dusty, unpaved road, winding further away from anything familiar. The car kicked up a trail of dust, the valley below slowly revealing itself through breaks in the trees. 

Upon arrival, the first order of business wasn’t unpacking food or finding a scenic spot to sit. Instead, it was putting on a harness, tightening a helmet strap, and signing a liability waiver. A small but symbolic act—releasing control for the unknown, agreeing to participate in whatever might unfold.

A fear of open-air heights has lingered for as long as I can remember for me. Over the years, exposure therapy has taken many forms—skydiving, cliff jumping, zip-lining—each one an attempt to outmatch fear with action. 

Yet, standing at the edge of this cliff, the same familiar pulse of anxiety surfaced in my stomach. A quiet but persistent discomfort. My mind already constructing escape routes, calculating distance, anticipating outcomes that weren’t real. It’s strange how the body can feel perfectly safe while the mind insists otherwise.

The invitation for us was simple: sit down, breathe, and enjoy a meal. A blanket was laid out, a picnic basket opened, small vegetarian and gluten-free bites placed between us. Everything about the moment was ordinary, except for the steep drop inches away. My body remained grounded, but my mind flew. 

At first, the experience was quite unsettling. My edges of awareness sharpened. Every shift in weight felt exaggerated. My thoughts wandered to worst-case scenarios, mapping out every possible misstep. My mind, resistant to stillness, pulled in all directions. It was a reminder of how easily fear creates its own reality, even when my body is entirely safe. 

Then, something changed. Not suddenly, but gradually. 

The weight of silence began to press into the moment. The valley stretched endlessly below, unmoving. The air settled. Breath, once shallow and rapid, deepened. Shoulders softened. Body temperature cooled. There was no dramatic realization or forced effort—just the slow release of tension, as if my mind had finally grown tired of resisting. 

The presence of nature became more noticeable. The way the sky opened without boundary. The way the wind moved with its own rhythm. The way the rock beneath provided silent, unwavering support. It felt like an invitation for me to stop holding on so tightly. 

The vastness of the space no longer felt threatening. Instead of being on the edge of something dangerous, it felt like being in the center of something still. The cliffs, the valley, the sky—they weren’t waiting to be conquered. They just existed. And so did this moment.

Memories of past height-defying experiences surfaced—not in the usual way, as a point of comparison, but as a contrast in intention. Those experiences were about overcoming fear through force, rushing toward discomfort as a means of proving something. This moment, by contrast, wasn’t about conquering anything. It was about being with what was there. Not resisting the fear, not pushing it away, but letting it exist without letting it lead.

My mind still tried to resist. For a while, there was a battle—an instinct to pull away, to hold onto tension, to prepare for a fall that wasn’t coming. But as my body settled, my mind slowly followed. 

Sitting there, a quiet clarity emerged: reality is perfect as it is. 

It will continue to shift and evolve, in its own nature and time. Nothing needs to be forced into change. My mind often operates as if things must be fixed or improved before they can be accepted, but sometimes, acceptance is the very thing that allows change to unfold. The lesson was subtle but undeniable—life is always moving, but not everything requires intervention.

It made me think of other moments, other times when resistance has made things harder. How often my instinct is to push against what is uncomfortable, to try to mold reality into something easier to hold. But reality doesn’t need to be gripped—it only asks to be witnessed. 

Nature knows this well—the wind moves without resistance, the valley stretches without effort, the rock remains still without grasping. Everything follows its own rhythm, unbothered by how it is perceived. 

Eventually, the picnic ended. The same path was taken back, the same car ride returned, the same dirt road stretched ahead. But something felt different. Perhaps nothing had changed at all. Or perhaps everything had.

And that is how I learned to cliffnic.