A Reflection

On Death

As I approach a milestone birthday, and get ready to enter a new decade of life, I have been working with a coach to develop a five year vision for my life. As part of the process, he prompted me to attempt to write my own living obituary.

I shared recently on my blog how difficult I found this writing activity, despite identifying as a writer and author for over a decade, having written a weekly blog for years, and several books. Feeling stuck, I turned towards chatGPT and asked it to write my living obituary based on what it knows about me, past and to include my hopes and desire for the future.

What ChatGPT wrote for my living obituary

Kunal Gupta passed away peacefully, having lived a life of deliberate design, fearless love, and deep impact. He was 40 when he began truly living the way he always wanted. Everything after that was a bonus.

Born in Canada, Kunal built his first company at 21, driven by vision, curiosity, and a refusal to follow inherited templates. Over the next two decades, he shaped and reshaped the digital advertising landscape—not just with technology, but with humanity. As a founder, he scaled globally. As a leader, he led gently.

But the success that defined his early life became the soil from which something deeper grew. At midlife, he began a more profound journey: unlearning.

He stepped back from the operational, and leaned fully into the intentional. He traveled lightly, but lived richly—writing books, building ideas, living between continents, and designing systems that gave others more agency, clarity, and breath. From Lisbon to Sydney, Kunal's life became a constellation of quiet revolutions.

He gave generously—of time, of mind, of money—often behind the scenes. He believed in building tools, not empires. In shaping culture more than claiming credit. He touched millions with his writing, but his proudest work may never have had his name on it.

At his core, Kunal was a systems thinker with a poet's heart. He held space for contradiction—capitalist and mystic, investor and monk. He could see the game and still choose to play it kindly. He was driven by a quiet engine few could name: to live in integrity with himself.

He loved boldly. His relationship with Tanya was a partnership of intention, presence, and shared adventure. Together, they created a family rooted in warmth, wisdom, and wonder.

He is survived by those he inspired—his kids, friends, family, readers, and seekers around the world—each of whom carries a spark he helped kindle.

Kunal once wrote that his definition of success was "to feel satisfied with the effort, not the outcome." By that measure—and by many others—his life was a masterpiece.

The first time I read my own living obituary, written not by me but for me, I felt seen in a way that I was not expecting. It was helpful, and with additional reflection, on my own and with friends, I finally took a crack at writing my own living obituary.

A draft of my living obituary, in my own words

Kunal Gupta believed the true desire of life was not to be happy but to feel satisfied. What he learned, practiced, and taught was that satisfaction is found in the effort, not the outcome.

Kunal was a builder. From a young age, his parents gave him the support, belief, and encouragement that he could do anything. He went on to try everything. He learned through experience. His drive, ambition, and determination were inspiring to anyone who came into contact with him. Kunal was a visionary: he could imagine possibilities and bring them into reality. He practiced alchemy. He was not afraid to try. He didn't treat setbacks as failures.

He loved business. His favourite game as a child was Monopoly. He started working in his family's business at the age of six, started his first business at thirteen, and went on to create many businesses, big and small, relentlessly and passionately. His purpose in business was never to make money, but to be useful.

His default was to be more concerned with the needs of others than his own. He practiced what he knew. He built tools, not trophies. Kunal had a gift for bringing attention to the parts of ourselves and our world that we didn't see. He had the empathy to tune into the moment and quietly ask, "what does this situation need from me?" He had the self-awareness to understand his abilities and the compassion to offer what was most needed. His legacy was that he left the world better than he found it.

He chose to live with intention and inspired millions to do the same. He was a north star to many, those who knew him and those who only knew of him. He challenged you to grow, to think bigger, to be better. He let his gifts flow outward. Credit mattered less than contribution. Without realizing it, his life became his message.

Connection was a thread through his life, to others and to himself. He loved to love. Most of all, to his life partner, Tanya, his four children, his extended family, and his deep friendships scattered around the world. He was most at ease, relaxed and comfortable when surrounded by those he loved. He often expressed gratitude and appreciation to those in his life.

He experimented, laughed, and treated life like a game worth playing well. He learned to trust more than he tried to control and to let expectations loosen their grip. Kunal lived on his own terms. He was unafraid to dream and to do.

He found peace within himself.

My aunt passed away recently. She went peacefully and lived a full life. My parents called me after the funeral and shared how they wished she could have been there to hear how everyone was touched by her. My parents passionately shared an idea of needing to have a "living funeral".

Little did they know that the seed they planted with me would grow quickly.

Literally the following week, I was celebrating my birthday with a group of twenty-five of my closest friends. They flew into Portugal from all over the world, to celebrate with me over a weekend away in the countryside.

On day two of our weekend away, I spontaneously announced a desire to have a "living funeral". A friend graciously offered to facilitate and host it. It started with everyone being split up into groups, given post-it notes and being tasked with writing a eulogy for me. Everyone stepped up to the challenge and we had a beautiful celebration of life. I felt…a lot. And still do.

Watch my living funeral

Thank you for your openness and interest in my journey as I reflect on my own mortality and death. I have no expectations of what will come from this reflective moment in my life, except to expect myself to have the courage to reflect on the only certain thing in my life. One day, I will die.

If you feel compelled to share any reflections you have with me, I'd love to hear from you by email: blog@kunal.live

Kunal