Kunal Gupta's Blog

How to Unpattern

The apartment was quiet when I returned. The suitcase waited untouched by the door, though I was already unpacking in other ways.

Lisbon was exactly as I’d left it, the soft light through the windows, the smell of the summer heat lingering faintly in the air. Familiarity returned quickly. But something inside took longer to arrive. It was still somewhere up in the mountains.

We had been in a small ski village in Canada last week. My partner, my parents, my sister, my brother-in-law, my nephew. A shared birthday with my sister, and a family vacation folded around it. Time together that felt both rare and full.

What surprised me most was not the scenery, although beautiful and inspiring. It was the spaciousness of being together, uninterrupted. Not by time so much, but by patterns.

Usually, when I’m with family, we gather in someone’s home. And in each home, something quiet and near-invisible takes hold. A pattern. Someone becomes the host. Someone becomes the helper. Someone becomes the guest. I often become tech support—fixing wireless printers, troubleshooting websites, rearranging apps.

But this time, we were somewhere that belonged to no one. A rented apartment with unfamiliar linens, an oddly shaped kitchen, and walls that held no memories. For once, the house didn't tell us who to be.

We shared meals differently. One person would start chopping vegetables while another found spices tucked behind mixing bowls. Someone had already done groceries without being asked. Someone else would quietly wash dishes while a game carried on in the next room. There were no plans. There was no one “in charge.” There was just movement. Exchange. Offering. Receiving.

My nephew, just four and a half, seemed especially alive to it. Curious, playful. His habits didn’t settle in because they had nowhere familiar to land. In this in-between place, he didn’t fall into routines he’d learned at his home or at his grandparents’. He created new ones, and they looked like delight.

That was when I began to notice what had really shifted. It wasn’t just our location. It was something subtler. It was the unpatterning.

There is comfort in patterns. I’ve built many of them into my life here in Lisbon—mornings that begin with hikes, evenings that end with friends. Routines that make the ordinary beautiful. Routines that feel alive and chosen.

But there are other patterns too. Ones I don’t always choose. Ones that choose me.

Returning to my parents’ home can feel like stepping into a costume I outgrew. A version of myself shaped by relationships that once made sense, but now feel slightly out of rhythm. Nothing is wrong. Nothing is uncomfortable. But there is less space to move. Less space to reintroduce myself, as I am now.

Environments have a silent authority. They hold memory. They hold expectation. And without realizing it, I often move to meet them.

Some places invite a self I’ve carefully grown into. Other places summon a self long gone, but quietly preserved in the paint, in the couch, in the dishes we always use.

That’s what made this family vacation different. We were together. But we had left the setting behind. And in that space, a different kind of relating became possible. A different kind of being.

Comfort, without history. Presence, without prescription. Belonging, without blueprint.

I began to wonder what it would be like to travel this way more often. Not just physically, but emotionally. To ask quietly before gatherings what space might allow for a new shape of connection? What setting could allow something unexpected to emerge?

It reminded me that experience is always being designed, even when unconsciously. The environment is part of that design. It sets the stage, even before the first word is spoken.

By stepping outside of our usual frame, a small miracle occurred: the frame did not follow us.

And that is how I learned to Unpattern.

How to AI

For the past few years, I’ve been orbiting the world of AI. I’ve written about it, built around it, and followed it closely enough that its changes feel personal. It’s something I genuinely enjoy, an intersection of curiosity and creation. And like many others, I’ve welcomed small ripples of it into my daily life.

I’ve used chatbots to brainstorm, summarize, rewrite, organize. Each use quietly functional. A little faster here, a little smoother there. But always within the realm of the familiar. AI was helping me do what I already knew how to do. That made sense. That felt safe.

But it also felt… flat.

Faster didn’t necessarily mean better. Just quicker variations of an already known thing. And after a while, I noticed I wasn’t learning much. I was just moving through tasks more efficiently. The shape of the work stayed the same.

Something shifted recently though. Without deciding to, I began using AI in a different way. Not to accelerate what I already understood, but to attempt something unfamiliar. A kind of quiet boundary was crossed. I started using it for things I didn’t know how to do. Things I avoided because I felt unqualified. Or incapable. Or simply unsure.

That openness surprised me.

At first, it was a technical observation. I have access to a tool that knows much more than I do. So why not use it? But the real question became emotional. Why hadn’t I used it this way before?

It wasn’t about function. It was about fear.

There’s a particular discomfort in not knowing how to do something. Not just the not-knowing, but all that surrounds it. Feeling exposed, unqualified, behind. Even when no one is watching, there can be embarrassment. The subtle pull to return to what is known can be strong.

What made the difference now?

I think it was a mix of things. Some practical. Some personal. Over lunch recently, a friend reflected something to me I hadn’t fully named. That to do something unfamiliar requires humility. A softening of ego. A willingness to not have all the answers, or any answers. It requires emotional capacity. Not just time, but energy. Space inside.

For me, there was also a kind of remembering. I started a company at 20. I had no idea how to build an organization, raise money, hire people. Everything I did, I was doing for the first time. There was a lot I got wrong. And back then, that felt okay. The pressure to be polished hadn’t taken hold yet. Mistakes were expected. Even welcomed.

I think I had unlearned that along the way with success. Grown accustomed to the illusion and identity of competence. The safety of operating inside a box labeled “things I’m good at.” It’s a soft trap. Comfort masquerading as ease. After all, doing what I’m good at feels good. It’s stable, predictable, efficient. But over time, it can also be numbing.

I’ve noticed how rarely I give myself permission to try something I don’t know how to do. Not because the stakes are high. Often, they’re not. But because the fear of failing, of not being good, tugs quietly at the edges. So I stay inside the frame. Efficient. Capable. Stuck.

But here’s what I’ve been discovering.

When I use AI to try something I don’t know how to do—not to polish, but to explore—I find myself feeling something I didn’t expect: satisfaction. Even when it doesn’t work. Especially when it doesn’t work. Because when it doesn’t work, I try again. I ask a different question. I take a screenshot. I probe. I iterate. I learn.

I don’t see these early failures as failures. They’re just part of the process. Like trying a new piece in a puzzle without knowing where it fits. There’s no shame in getting it wrong. There’s only information.

And because AI doesn’t judge. Because it’s patient, immediate and available, it makes the process easier. Not less challenging, but less personal. I can be clumsy without consequence. That feels rare. And spacious.

None of this is really about AI. It could be a person. A book. A blank page.

It’s about something else. Choosing to try to do something I don’t know how to do. To experiment before expertise. To do before knowing how. To allow myself to be not good and to do it anyway. That’s not a technical capability. That’s emotional permission.

And I’ve realized how deeply satisfying that is.

Not because it’s productive or efficient. Not because it leads to something useful. But simply because it expands something inside. A reminder that I am not fixed. That I can try. That I can learn. That I can grow.

And that is how I learned to AI.

How to Unplan

There was a time, not long ago, when booking flights felt like a form of self-care. I would sit with tabs open, measuring layovers like puzzle pieces, lining up departure times with sleep schedules and sunlight. The choices felt precise. Refined. A satisfying kind of order would settle after clicking the final button. The destination was chosen. The plan was made. Some small corner of the future had been neatly put away.

And yet, more and more, I notice how rarely life goes as planned.

It’s not subtle. Looking back on the past few months, three out of every four flights I book, I don’t take. I cancel them. Change them. Move them to a different day, or a different city altogether. The destinations shift. The timelines move. The ideas that once felt so certain become soft around the edges.

At first, it felt like a practical problem. Something to optimize. Better forecasting, clearer communication, more decisive decision-making. But something deeper kept nudging. An unease that this wasn’t about poor planning at all. This was about the need to plan in the first place.

There’s something seductive about having a plan. It gives the illusion of direction, of preparedness, of control. When a flight is booked, there’s less room for doubt. When dates are in calendars and confirmations in my inbox, I can tuck them away. A kind of quiet knowing: I’ve done it. The future is accounted for.

But it never is, really.

I used to believe planning was practical. Economical. That flights were cheaper when booked ahead, that being early meant being smart. It turns out, that’s not always true. Especially in places like Europe, where price protections exist and common routes are well-traveled. Waiting isn’t necessarily more expensive. Sometimes, it’s quite the opposite.

But even when it is more expensive, the trade-off has changed.

There’s a cost to locking my future self in, from the vantage point of today. To deciding where I’ll want to be, what I’ll want to do, before I get there. The emotions I use to justify my plans—the logic of saving money, of protecting my calendar—are often just that: justifications. I find myself talking logic to defend a deeper need for certainty.

And I’ve started to notice how emotional that need really is.

Oliver Burkeman, in “Four Thousand Weeks,” writes that planning is how we try to control the future. I keep returning to that phrase. It makes me smile, partly because of how innocently true it is, partly because of how absurd it becomes once seen clearly. Of course the future cannot be controlled. Not entirely. And more importantly—why would I want to?

What felt like effective travel planning slowly began to feel like something else entirely. A kind of performance. A script that became harder to follow as life’s tempo shifted. I began to wonder if the pattern was pointing to something deeper.

Maybe the canceled flights weren’t mistakes after all. Maybe they pointed to something right.

So much of the inner work I’ve done in the last decade—through meditation, therapy, personal reflection—has been about cultivating awareness. Presence. Closeness to reality. And that decisions made from presence will feel more grounded than decisions made from prediction.

Maybe all these changed plans are not a failure to commit, but a growing capacity to listen. A willingness to say yes to what is happening right now, rather than what was planned.

There are still moments when planning is necessary. Especially when involving others: family trips, group dinners, business meetings. When more people are involved, more coordination is needed. That’s real. But when it’s just me, or just my partner and I, that need softens.

There’s more room to respond to the present. More room to let the present shape the plan, rather than forcing the plan onto the present.

Sometimes that means booking a flight only a few days before leaving. Sometimes that means not booking at all. And sometimes it means changing something that, from a practical lens, "should" have worked, but from a deeper knowing, no longer does.

It might cost more in fees. That’s okay. It’s a small price to pay for closer alignment to my reality.

The shift, I’ve realized, is from control to freedom. Not freedom as chaos, but as responsiveness. Gentleness. Trust. The trust that life can be met in real time, not always prearranged. That clarity doesn’t always come months in advance. Sometimes it arrives on the morning of departure.

And in those moments, I’d rather be free than prepared.

The map still matters. But the roads that get drawn now are softer lines. They can be erased. Rewritten. Or simply walked, one breath at a time.

I don’t always know exactly when or where I’m going anymore. But I feel closer to wherever I am.

And that is how I learned to Unplan.

How to Birthday

My sister and I share our birthdays, born just a day apart. Growing up, we celebrated together every year. She’s younger than me, but it never really felt that way, at least not to others. Maybe it was her confidence. Her ease around people. Everyone mistook her for being older.

I didn’t mind. I was a shy kid, the kind who preferred the corners of the room to the center. I liked being near the action but not in it.

Every summer, our parents would host a little garden party for our birthdays. There would be one birthday cake, and we’d blow out the candles together. Friends and family gathered on the lawn, and I remember it always felt festive without feeling overwhelming. What most people didn’t see was that I was hiding behind my sister. Letting the spotlight fall on someone else. And quietly enjoying that.

Being a summer baby meant that school was out during my birthday. A small blessing, in that it saved me from the classroom song, birthday attention, and the inevitable cookies or cupcakes brought in to share. Our birthday parties had more of her friends than mine, but I didn’t mind. I had a few close friends, not many, but enough. What I remember most is the quiet comfort I felt in not having to perform happiness, or celebration. Not having to be seen.

Later, at university, nothing really changed. Birthdays fell between semesters. A moment of stillness that didn’t ask for much. Conveniently placed for slipping by unnoticed. There was a pattern forming. Each year, I found subtle ways to avoid the weight of that particular kind of attention.

But, eventually, the context shifted. I was in my twenties, living on my own, and surrounded by friends who showed their love a bit more loudly. Birthdays became occasions to celebrate in the way everyone else did. Parties, dinners, dancing, drinking, staying out too late. The kind of nights that live loudly and fade quickly. I enjoyed those moments. They were fun. But something always felt slightly out of sync. Like I was playing a part I hadn’t auditioned for. I still showed up, and I liked the version of myself who did. But something was missing.

It was my thirtieth birthday that changed things.

The day before, my sister asked what I wanted to do. Where I wanted to go. What I wanted to eat. Her enthusiasm was genuine. I normally would've answered quickly, but this time, I paused. Something felt different. Over the past year, I had begun meditating, and had started paying more attention to the feelings that surfaced quietly, without reason. What I noticed was discomfort. A kind of pressure that was hard to name. It wasn’t about turning 30. It was about the unspoken expectation I felt to make something of the day. To make it count.

So I told her the truth. I didn’t want to celebrate.

She was surprised. Maybe a bit confused. So I explained that I wanted a quiet birthday. No invitations. No toasts. No decisions about what to wear, what to eat or where to go.

I turned off my phone the night before and decided to fast for the day. Strangely, that made things easier. Fewer things to coordinate, fewer boxes to check, fewer moments to try and perfect. I meditated in silence for three hours that morning and still remember some of the places I went. Memories that weren’t thoughts. Feelings that weren’t emotions. A kind of presence with myself I hadn’t felt before.

Later that day, I went to see my family. We had cake, quietly. It didn’t feel like a birthday so much as it felt like a still point in time. A moment of returning home, not just to the people I grew up with but to myself. I spent the rest of that evening journaling.

When I turned my phone back on the next day, messages flooded in, surprised friends, missed calls. I began replying, one by one. But I noticed that something had shifted. Connecting back to others now came from a place of deeper connection to myself. The reflection came first, the participation after.

That was also the year I stopped drinking, and I suspect looking back, that also made my birthdays more memorable and more meaningful for me.

That spontaneous birthday practice became a ritual. Each year, I would fast for the number of years I was turning. I would turn off my phone. I would meditate for longer than usual, write for longer than usual, and say less than usual. It became the way I reminded myself how to return within myself. I did that for seven years.

And then, I moved to Portugal.

I made new friends. Started a new life. And when my birthday arrived in Lisbon that first year, I felt something I hadn’t in a while. A desire to share. To celebrate, not to be celebrated. To gather people, not to be the center of them. So I rented a boat on the river in Lisbon. Everyone dressed in white. As friends stepped aboard, we collected their phones. We drifted down the river without screens, music playing, food shared, eyes meeting. Laughter. Conversation. Connection.

Somehow I had brought the rituals with me into the gathering. The distraction stayed out, the connection stayed in. The next year, I did it again. More people. More joy. Still no phones.

Last year, my partner surprised me with a trip to the Swiss Alps. It was quieter. Colder too. A summer mountain escape, a few close friends, silent mornings. Again, the outer shape had changed. But I recognized the same feeling on the inside.

This year, I’ve celebrated in different ways, with different people. No single answer to what the birthday was, or was supposed to be. Just a moment, really, to notice how much I’ve changed.

I used to think there needed to be a blueprint, a tradition to hold on to. But maybe that’s what birthdays are best at revealing. The gap between who I was and who I’ve become. A part of me still craves solitude. And another part of me craves connection. And they don’t need to be in conflict, anymore. The celebration with self and the celebration with others can coexist, so long as neither asks for performance.

The places have changed. The people have changed. The feelings, too. But each year, the desire is the same. To return, to reflect, and to notice.

Birthdays have become the mirror I forget about until I’m standing in front of it, wondering what’s changed. They help me remember that change is not something that happens once. It’s something that’s still happening. One quiet, invisible shift at a time.

And that is how I learned to birthday.

How to Be Remembered

Recently, I found myself in a quiet corner of the Portuguese countryside, surrounded by twenty-five of my closest friends.

Some who have known me for decades, others more recently. All of them, in one way or another, had walked by my side through different chapters of life. They came from different cities, Sydney, London, Toronto, and New York, to be with me to celebrate my upcoming birthday.

Some had seen me stumble, some had seen me rise. Many had seen me change.

There was light agenda for the weekend. My partner had taken the lead in organizing it, and somehow, the lack of structure allowed space for something far more meaningful to arrive. People connected easily, as if they had been meant to meet, as if the story of my life had been stitched together into the kind of gathering that needed no explanation.

Lately, I’ve been working with a coach on developing a five-year vision. The intention behind it feels simple but daunting: to develop clarity as I enter a new decade, to deepen alignment between where I place my energy and define what truly matters for me right now. One of the exercises in this process involved writing my own obituary.

At first, I struggled. The very notion felt strange. But surprisingly, what unlocked the exercise was asking ChatGPT to write a first draft based on what it knew about me. Reading what it generated created space for me to respond. Not with edits, but with presence. Soon after, I wrote my own version. I shared it with my coach. We reflected that while it captured my own perspective, it felt incomplete.

Not long ago, my aunt passed away. After the funeral, my parents called me. They spoke not about the sadness, but the beauty of the words shared about her. And then they said something that stayed with me: “Why do we only share these kinds of things after someone is gone? They should hear them while they’re still here.”

Back to the birthday weekend away with my friends now. Halfway through the weekend, I made a spontaneous announcement.

I would host my own funeral. A living one.

My friends were surprised, but after a moment of it sitting in, not surprised to hear that I would want to experiment with something like this.

A friend stepped in to facilitate. He split our group of twenty-five into smaller groups. Each group was handed post-it notes and pens and asked to write a eulogy for me. Not from prepared thoughts, but from spontaneous presence. No time to rehearse, only time to reflect and write.

While they wrote, he and I set up chairs for everyone outside beneath a wide patch of sky, with a beautiful view of rolling hills.

After about thirty minutes, everyone was invited into our makeshift space. Music was playing in the background. My partner and I sat at the front. And then, one by one, each group sent one person forward to read what they had written.

Some were funny. Some were tender. Some wrapped kindness in mischief and others unwrapped truths through tears. They spoke about curiosity, calm, and kindness. About presence over performance. One spoke about patience. Another about wonder. There was much laughter, and shared stories I had long forgotten.

As I sat there, quietly receiving their words spoken in past tense, I felt something unexpected.

I felt seen. Appreciated. Held. And also… surprised.

None of the eulogies focused on the aspects of life I spend the most time on. My work, my health, and my relationship. Areas that occupy much of my conscious living energy were barely mentioned. Instead, what surfaced were subtler qualities. How I show up in a conversation. The way I create space. How I listen. The lightness I bring, even unknowingly.

Afterwards, debriefing with a few close friends, I shared that observation. And they gently offered a reframe. Perhaps those domains of life I focus on so intensely aren’t ends in themselves. Perhaps they are means. Means to a more authentic self. Means to deeper connection. That the work isn't in being remembered for any one thing, but in being present with who I already am.

And perhaps friends are the ones who see that most clearly.

Family wasn’t there that weekend. Neither were professional colleagues. My partner didn’t speak. What was reflected back to me came from friendship alone. And there’s a particular honesty in that kind of mirror. It’s where nothing needs to be proven. Where the self can be witnessed without the scaffolding of achievement, responsibility or identity. I felt known in a way that words rarely allow. And what I heard, almost universally, were not just stories, but feelings. Unfiltered, unearned, freely given.

At the end of the ceremony, I stood and gave a brief, impromptu speech. No notes. No idea what I was going to say until I heard myself say it. That I am not just me. I am, in some quiet way, made up of every person here. Every strength, every quirk, every moment of laughter I offer to the world is borrowed or mirrored from someone I’ve loved. I spoke of how each of their reflections helped me see myself more clearly. Not as a static thing, but as a living dynamic being, shaped by others with every passing year.

I’m still integrating what happened that weekend. I’m still listening to what was said. And to what wasn’t. I walked away with a full heart and an open question. What are the things I chase now, that in the end may not matter? And what are the things that matter deeply already, but go unnoticed because they ask nothing in return?

I’ll likely do this again. Not as an event. But perhaps as a practice. A way to pause and ask. A way to make space for reflection not just from within, but through the lives I’ve touched and been touched by. Not to be praised, but to be mirrored.

There are truths about my life I can’t see alone.

And that is how I learned to be remembered.

How to Remember

My birthday is approaching. And this one is an important milestone.

I gave myself the summer to develop a five year vision for my life, as I enter a new decade and chapter. Not a rigid one. Not a plan. Something softer.

For much of my life, I’ve lived with a plan. For fifteen years, I led a company as CEO. I planned in quarters and years. That type of planning was tied to outcomes—concrete, prioritized, trackable. This is different.

The starting point for my five year vision surprised me. It wasn’t a question of what I want to build, achieve, or even who I want to become. It began with qualities. Ways of being. Not in the shape of my accomplishments, but in the shape of my presence. It is about how I move through life, regardless of when or where, or even why.

So I started making a list of qualities that are important to me. It came quite easily. Now I am working with my coach to sift through them to discover which ones are the most important to me right now, and relevant to this next chapter of my life.

In a recent conversation with my coach, we shifted from qualities to something else altogether. A prompt he gave me. A writing experiment I hadn’t expected: to write my own living obituary.

Had it come at any other time, I might have hesitated. But the timing made sense. I’d recently been reminded of the idea by Tuesdays with Morrie, a book that I read many years ago. In it, Morrie, a professor facing a terminal illness, hosts a living funeral. He wanted to hear what people will say about him before he dies. A subtle rebellion against a world that waits too long to speak honestly and lovingly.

And recently, my parents returned from the funeral of my aunt. When they spoke about the experience, they kept returning to one observation: how strange it is that we only seem to say these things after death. Why wait? they asked.

So when the prompt came to write my own obituary, I felt a surge of energy pass through me. I had to do it.

I’ve written every week for this blog for over ten years. I journal several times a week privately. I have written four books. Words are a home for me.

However, when it came to writing my living obituary, my page stayed blank.

It’s easy to write about an experience from within it. It’s harder to zoom out, to see myself from the outside. I didn’t know where to begin. Not because there was nothing to say, but because the exercise required looking at myself differently than I am used to. And maybe that was the point. Looking not out at the world, but across my life. Not forwards in time, but backwards.

After a few attempts, I found myself turning to one of my AI assistants, ChatGPT. I gave it a single line: “As part of a reflection exercise, and knowing what you know of me, I’d like your help writing a living obituary.” I wasn’t sure what, if anything, would emerge.

Six seconds later, a draft appeared.

And I sat back. And I read quietly and slowly about my life.

The words held a mix of familiarity and distance. They were about me, but not by me. There were facts about my life, but what surprised me was how present my hidden desires were embedded throughout. My hopes. My aspirations. My dreams. Not written in the usual future tense where they live in my journal and my mind, but in the past tense. As if they had already happened.

It changed something in me.

Sometimes, speaking about the future feels like building a story we may never enter. But reading that future as if it had already occurred, there was a strange intimacy in that. My ambitions felt less speculative, more lived. They felt, for a moment, like memories.

When I journal, there’s always a sense of reaching, into the unknown, toward something unformed. But here, the past tense created a kind of grounding I didn’t expect. A possibility dressed as remembrance.

Of course, the words weren’t perfect. They weren’t mine. But they gave me something to work with. A clay form. I’ve always enjoyed editing, and this now feels like that. A chance to shape. To soften. To reveal. And in doing so, not just to craft a better piece of writing—but to better understand myself in this moment in time. The prompt pointed not to the end of life, but to the center of it.

It reminded me of how powerful it is to pause and look, not forward or inward, but from the imagined edge, backwards. The things that feel vague become visible. What I’ve value begins to reflect back towards me with more light.

The obituary isn’t finished. And neither am I. But what emerged was clarity.

And that is how I learned to remember.

If you are curious to read it, simply reply to this email and I’ll send it to you.

How to Inspire

For the past two weeks, I’ve been alone in Lisbon.

My partner has been away traveling, and without shared presence or familiar routines to anchor the day, my calendar opened up. There were fewer dinners to prepare, fewer invitations to accept, and fewer movements around the city to make. The stillness wasn’t silent, but it was quieter than usual. And in that unexpected space, something unexpected happened.

It didn’t begin with an intention. There was no plan to retreat or reset. But with fewer inputs from the outside, more attention turned inward. I found myself drawn to a new project—an idea I’d been circling for a little while but hadn’t completely stepped into. It's a different kind of creative effort than this blog, but something about it called for exploration. Slowly, then suddenly, I found myself deep inside of it.

I didn’t think of it as work. In fact, I avoided calling it that. Maybe because I wasn't doing it for outcomes. There was no performance to measure, no deadline to meet, no one else waiting beside me. And yet, I was waking up buzzing, energized, thinking about it, and only it. Not with worry, but with possibility.

It felt more like play—like the kind of play I remember from when I was twenty and building my business for the first time. Where the effort comes not from pressure, but from imagination.

Some days, I’d spend hours entirely focused. No phone. No notifications. No email. No stock market. Well fed, well hydrated, and alone with my thoughts. Books piled beside me. YouTube videos queued up. Podcasts paused mid-sentence so an idea could be written down. It was deep work, but also deep learning. Probably the deepest I’ve gone in years.

What surprised me most was not the clarity or the quality of attention, but the energy.

Despite sleeping less, exercising irregularly, and spending less time socializing, I didn’t feel depleted. I felt the opposite. Inspired. Body, mind, heart, and spirit—aligned and alive. Not sustainable, maybe. But also not necessary to sustain forever. Sometimes a sprint is what’s needed. Not to escape life, but to remember a part of it.

The satisfaction didn’t come from anything completed. It came from showing up. Not half-heartedly or cautiously, but fully. There’s something rare these days about giving something everything—not as sacrifice, but as self-expression. To try, just because it feels good to try. Without calculating if it’s worth the time, or whether it will amount to anything. Nothing was owed to it, and yet something inside wanted to keep giving.

Learning like this is harder now than it used to be. Maybe because it feels less urgent. Or maybe because it requires more humility. Being a beginner takes effort. It asks for presence. But when that effort is made not toward mastery, just toward curiosity, the reward isn’t a result. The reward is the trying.

When I would share this burst of energy with friends—when I’d talk about what I was building, what I was reading—I kept hearing the same word back: “inspired.” It made me pause. I hadn’t set out to inspire anyone. That wasn’t the point. But something in how I was living those days had a ripple effect. Not in grand gestures. Just in the quiet way a person lights up when they’re deeply engaged. And how, somehow, we notice.

I’ve experienced this from others before—watching someone follow what moves them, and feeling a subtle ignition inside. Energy transferred without intention. Without knowing. The most inspiring people in my life never tried to be that. They simply were.

At the start of each year, I choose a word. A one-word intention, like a quiet promise to myself. In past years, it's been words like open, space, build, flow. This year, the word was inspire.

Until now, it hadn’t really landed. I hadn’t felt it in a way I could describe. I’d journaled about it. Thought about it. Wondered whether I had chosen the right word. But after these two weeks, something clicked. Not all at once. More like an unfolding. The connection between feeling inspired, and inadvertently being that for others, finally made sense.

None of it happened through striving. That’s the part I keep returning to. The inspiration came through immersion. Through permission. Through less structure, and fewer demands. Less of everything, really—except intention.

And that is how I learned to inspire.

How to Low Stake

A few weeks ago, my aunt passed away.

It was unexpected, yet not surprising. That strange space where the heart is broken open but the mind quietly nods. In the days that followed, we gathered—some in person, others from afar. There were phone calls, shared stories. A mixing of grief with gratitude.

In the quiet that follows loss, emotion makes way for a softer kind of thought. Not strategic planning, not goal setting—just a murmur of something deeper. Something simpler.

A family member said something that's stayed with me: “We all end up in the same place.” There was no drama in her voice, just calm. “We come with nothing, we leave with nothing.” A reminder I’ve heard before, and forgotten before. But in that moment, it felt less like advice and more like gravity. A truth that didn’t require agreement—it simply was.

A few days later, I went for a long walk with an old friend in Lisbon. We hadn’t seen each other in a few years. He’s around my age, maybe a few years older. He walked me through his cancer diagnosis from two years ago, and the many moments of not knowing what would come next. He told me about the strength he had found and the grace he had grown into, uninvited.

When I asked how this experience had changed his perspective on life, he smiled and said what I had just started to touch myself: “Most things aren’t that important.”

That sentence keeps repeating itself.

Most things aren’t that important.

But my mind is good at making most things feel that they are important.

There’s a habit I’ve noticed—one that lives quietly in my day-to-day. The gym session missed and turned into guilt. A stock market trade made, not for the sum of money but for the illusion of control. A late reply to a message, a small tiff in a conversation, or a dinner reservation gone wrong—each one has the potential to feel like more than it is. Like something is at stake. As if a single choice could jeopardize the entire direction of a day, or a life.

There are moments, looking back, where the intensity I felt simply doesn’t make sense. The pressure to finish something. The need to be understood. The desire for things to unfold exactly as imagined. I remember days when, after not meditating “well”, I felt like my entire self-discipline unraveled. As though one “poor” practice erased a decade of showing up.

And yet, there is so much—almost everything, really—that is actually low stakes.

The disappointment of a meal. The annoyance of a flight delay. The frustration of a weak Wi-Fi signal. The uncertainty of a video call that doesn’t load on time. The inconvenient timing of an invitation. The mood shift after a lost sports match. The entire evening revolving around a show on Netflix.

None of it really matters.

But it can feel like it does. I’m slowly seeing that feeling and reality do not always hold hands.

There’s a quiet liberation in remembering that. A freedom made not of apathy, but of perspective.

When I remind myself something is low stakes, I don’t abandon effort. If anything, I feel more curious. More grounded. I allow space for surprise—to be delighted, even.

And what I notice is that on the days I bring that mindset into what I do—whether it's walking into a meeting or ordering a meal—something shifts. I feel more present. More available to life. Less burdened by outcome. There's space for joy to enter, because I’ve stopped blocking the way with anxiety.

The pressure has softened. And in that softening, I can still care. But I no longer have to carry.

These recent brushes with mortality have been hard. And yet, I hold deep appreciation for what they’ve opened. The way they rearranged my perspective without asking permission. The way they trimmed the excess weight of so many imagined crises.

This reflection is a way to remember. A kind of ritual integration. An attempt to stay close to the clarity that only seems to emerge when life itself interrupts the illusion of control.

There is no neat conclusion. Just a clearer horizon. I am inspired to continue to remind myself that things are more often than not low stakes, versus what my mind tries to convince me to believe.

And that is how I learned to low stake.

How to Istanbul

We landed late at night. The taxi from the airport wound through streets we couldn’t see, only feel. The city was there, somewhere beyond the taxi window, but hidden in darkness. There was no sense of arrival, only motion through a place that had yet to appear.

It wasn’t until the next morning that Istanbul revealed itself us. We woke up to the call to prayer echoing loosely across rooftops. My eyes opened to narrow streets filled with cafes, mopeds, clusters of people speaking languages I didn’t recognize. The air carried the scent of warm bread and strong coffee. Something in me softened. We were somewhere entirely new, though it hadn’t been felt until just then.

We hadn’t planned anything. No itinerary, no must-sees. Just a spontaneous impulse followed through with. We had booked only two nights at our Airbnb, unsure if we would want to stay longer. Seven days later, we were still walking those same cobblestone streets.

That first breakfast stretched for three hours. A spread of dips and olives, cheeses I couldn’t name, three kinds of eggs. Flavors that challenged what breakfast was meant to be. I told my partner, without hesitation, that it was one of the best breakfasts of my life. But it wasn’t just the food. It was the presence. And no one else at the cafe was on their phone. It felt like a different world. The way time felt wide enough to hold wonder, without rush or measurement.

We spent the day wandering. Through shops filled with colour and texture and familiar things that felt unfamiliar in their setting. Through crowds that sounded like stories and smells that lingered. In Lisbon I had thought I had experienced cafe culture—until I saw Istanbul, where every second storefront offered some slowing of time, some invitation to pause.

At some point, we found ourselves at the Hagia Sophia. A vast, cavernous peace held within stone. The building is 1,500 years old. Originally a cathedral, now a mosque—and at one time, the largest cathedral in the world for over 1,000 years. It had been standing for longer than I could fathom. Time had written itself onto the walls. Cracks, stains, chipped mosaics. But none of it diminished the beauty. In fact, it added to it. The age didn’t distract. It brought reverence. A quiet respect for things that last not in spite of time, but because of it.

Later that evening, we booked a small boat tour—impulsively, like everything else that week. The guide spoke perfect English. Only a few of us were aboard. As the boat moved along the Bosphorus, the sun dipped behind the skyline, scattering pink and gold across the surface of the water. We listened to stories about the history of the city while watching it flicker between old and new. In that moment, I felt both suspended and grounded. Drifting, but fully present.

It was all unexpected. Not just the beauty of the city, but how safe, calm, and nourishing it felt.

On the way to the airport before the flight, I had called my parents. They had been to Turkey many years ago and offered warnings of safety out of habit. Be careful. It may not be safe. There might be discrimination. The words weren’t new. They echoed the vague anxieties that often accompany places we do not know. Too foreign, too unfamiliar, too uncertain. My own hesitation came not from experience but from the stories I’d heard, the coverage I’d seen, the way places get flattened into headlines and hearsay.

But the Istanbul I experienced bore no resemblance to the one I had imagined. In its place was something vivid, generous, and inviting. Nothing matched the map in my mind. And that was the gift.

It left me wondering: what else have I misunderstood? What places, or people, or possibilities have I quietly put to the side—not from knowing, but from fearing? What stories have I accepted without living, filled in with artificial color, faded by distance?

Last night I read something in a book about how we’re all like cameras. We arrive in the world with blank film. As we move through life, we capture images—moments, impressions, conversations—that shape what we believe about the world. Some of the pictures are clear and vibrant because they’re our own. Others are faint and washed out, taken not by us, but handed down: secondhand photographs of places we’ve never been, people we’ve never met, lives we’ve never lived.

The more I thought about it, the more I started to see this trip not as a vacation, but as a new photo—one I hadn’t taken yet. One that replaced the old picture I had been carrying, unbeknownst to me. And the remarkable thing was not that the real Istanbul was different from what I imagined. It was that I had finally given myself permission to look for myself.

Sometimes, it’s not about collecting more pictures, but about changing the ones we already have. Releasing the images built from warnings, letting go of inherited shadows, creating space for surprise. What we believe can have more to do with what we’ve been told than what we’ve seen. And the only way forward is to see for ourselves.

There’s something about a spontaneous trip that creates intimacy, not only with a place, but with our own perceptions. Without plans, we notice more. Without expectations, we feel more. And when we allow a place to reveal itself on its terms, rather than ours, we’re reminded of how much there is beyond the edges of what we think we know.

In many ways, the journey wasn’t just to Istanbul. It was out of a story I had quietly accepted. Out of assumption. Out of caution. And into wonder. There are fewer things more disorienting and more necessary than being wrong in the best way. It’s a reminder of how alive the world is when we let it be different than we expected.

Sometimes, all it takes is a call to prayer at dawn, a plate full of olives, and a boat at sunset to remember how little we know—and how beautiful that can be.

Istanbul felt like a beginning. And maybe it was.

And that is how I learned to Istanbul.

How to Progress

This past week, I received the results of a health test I took a few weeks ago. Nothing alarming or urgent, but something showed up—something that had also showed up a few years ago, that I had thought was behind me.

At first, I managed to keep calm. I feel good physically. The data says one thing, but my lived experience says another. So I focused more on what I was feeling than what I was reading.

For about one day. Then something shifted.

The calm gave way to unease. The unfinished business of this health marker began to loom larger than I had expected it to. Despite all the work, despite the improvements I’ve noticed in my energy, strength, clarity—despite the consistent effort—it was still there. And, with it, a quiet question: Why isn’t this fixed yet?

That question soon became a feeling I recognized. Frustration. Anxiety. A familiar tightness that used to arrive with report cards as a child. The feeling of scoring 98%, but being preoccupied with the missing 2%. Noticing what hadn’t been achieved, rather than what had.

It surprised me. Not because the feeling was new, but because I thought I might have outgrown it.

The expectation of perfection, it turns out, doesn’t retire peacefully. It lingers. Disguises itself. Sometimes it speaks quietly, in the background. Other times, like this week, it steps forward and takes the mic.

I’ve noticed this voice before. It shows up in places beyond health—in relationships, in work, in the expectations I didn’t realize I was holding. And what it often brings with it is tension. Not just in my body, but in the way life feels. Everything narrows. Options reduce. There’s a right way and a wrong way. A good outcome and a bad one. Progress becomes binary: pass or fail.

And that’s when my energy starts to drain. That’s when I hold back from trying new things, from taking risks, from allowing myself to be surprised. Because if perfection is the standard, then trying becomes a liability.

That’s also when the most joyful parts of my life—the lightness, the spontaneity, the play—begin to lose their colour.

I’ve been wondering why this happens. Why the default is so often toward judgment, even when I think I’ve moved beyond it. And I suspect part of it is the residue from years of being measured. Schools framed learning as achievement. Work rewarded outcomes. Health became something to be quantified, tracked, improved. In all those environments, the lesson is clear: better is good, but best is safest.

And so something in me continues to chase “best,” long after the reason for doing so has faded.

But this week invited a different kind of reflection. As I journaled yesterday morning, I saw, with quiet clarity, how far I’ve come—not in terms of results, but in depth of care. I noticed how conditioned I still am to measure progress by what’s unresolved, rather than what’s being tended to. And I felt, in that noticing, an invitation to see differently.

To see the daily choices—the early mornings at the gym, the quiet stretches, the red light therapy, the food prepared with intention—not as transactions toward perfection, but as demonstrations of self care and love. And when framed this way, something softens. I begin to feel more of the satisfaction I often bypass. I begin to see all the effort not as a means to an end, but as something worthy in itself.

This shift isn't unfamiliar—but it still feels new every time. Moving from judgment to curiosity. From closure to openness. From wanting control to accepting care.

It’s the difference between asking, “Did this work?” and wondering, “What is this teaching me?”

There’s something beautiful in that wondering. Something human. And less machine. It doesn’t arrive with answers, but with space. And in that space, growth happens—even when “results” do not.

This softening isn’t just inward. It echoes outward. The more I practice accepting the effort in myself, the more I begin to notice it in others. I find myself focusing less on how others measure up, and more on how they show up. Whether it's my partner, friends, colleagues—there’s a gentler gaze available. One that sees intention even when initiative falters. One that sees care even when outcomes vary.

It begins to form a kind of loop. Recognition of humanity feeds compassion, which in turn, allows more of that humanity to be seen. Less pressure. More space.

It’s not a final destination. I know the next time I receive a test result like this one, I may still feel the reaction. There may still be a moment of comparison, disappointment, desire for certainty. But maybe—hopefully—it will be softer. Less sharp. And maybe I’ll spend less time in that narrow space before remembering that my journey is not about perfection, but about progress. Not about being done, but about being here.

There’s a quiet kind of achievement in that.

The kind that doesn’t show up in test results.

The kind that takes root slowly—in the way I stretch in the morning, in the way I breathe before I react, in the way I remember to be kind when it feel I should not be.

And maybe the most perfect we can hope to be… is to keep going.

And that is how I am learning to progress.