Unlearning

When I woke up that morning, I had no idea everything was about to change forever. I was living in Toronto at the time. The day started with my usual routine: walk to the office, which was down the street; log in; answer a few emails. Between meetings, emails, text messages, and social interactions, there wasn’t much else in my daily life.

It was barely 9 a.m., but the bright sun was spilling in through the big windows of the office. As the sunlight turned my computer screen into a glorified mirror, I found myself in a staring contest with my own reflection. The rest of my team had yet to show up, and in the quiet office that morning, I noticed something different inside me.

I felt bored.

Boredom was a new feeling. Seven years into my business, which I started right out of school, working long hours and long days were the norm. There was always something broken to fix. Now, sitting there with this unfamiliar boredom, I went through a familiar mental checklist.

Over the years, I have learned there are four problems that can arise in any business: 1) a product or service issue; 2) a client, competition, or market issue; 3) a people, process, or talent issue; 4) a cash or funding issue If two of these issues are present, it’s stressful; three, the business outlook is not great; and four, there is no business, and people are fooling themselves. Until that moment, there had always been only one or two things broken in my business—rarely three and never all four. It was always a game of spinning plates: constantly fixing one, thinking everything would be good once it was solved, but then having to solve the next, and the next, and so on.

I used to believe that buying stuff would bring me happiness. I must have wanted to be really happy, because I bought a lot of stuff. That habit might have gone on forever were it not for a romantic crush.

At the time I was traveling frequently to London. On one trip, a woman at a conference caught my eye. We immediately hit it off. We didn’t talk about business, despite the context. She asked me out for a drink in Covent Garden, a popular tourist area in central London. She was “proper” British, and very much on time. I was late, a habit I’ve now accepted. I must have been cute enough for her to tolerate my tardiness, at least for a while. I found myself attracted to her, especially the way she dressed. She introduced me to Reiss, a British clothing brand that had been popularized by Kate Middleton during her engagement to Prince William. Reiss was undiscovered and unavailable in North America, which only added to the allure for me. Feeling courageous, I asked, “Hey, can we go shopping at Reiss together sometime?”

On my next visit to London a few weeks later, we did exactly that. To be honest, it was intimidating to go shopping with a woman I had a crush on. It was like taking a woman out to a fancy restaurant just to impress her. In this case, she did not get an expensive meal—but I got new clothes. No surprise, I walked out of the shopping mall that day with both hands full of Reiss bags.

The pattern was set. Every few months during my visit to London, I made a pilgrimage to Reiss. I even convinced one of the store managers to give me a 25 percent discount under the table. As a visitor, I learned about the sales tax refund trick that saved me another 23 percent. The fact that I now got almost 50 percent off everything was enabling; it gave me permission in my mind to buy anything.

After two years of not buying things, I began to be curious about what the next experiment would be. The first experiment had helped me reset my relationship with stuff. Now I wanted to reset my relationship with my physical space.

Once again, the catalyst happened to be a documentary: this time a series called The Kindness Diaries. The film followed Leon, an Australian man, who was trying to test a thesis that the world is, in fact, kind. This man decided, with no money and no belongings except the clothes on his back, that he was going to travel around the entire world, relying solely on the kindness of others.

First spoiler alert: he did it.

Second spoiler alert: the world is, in fact, kind. The kindness Leon experienced in each episode often brought me to tears. I found the story fascinating. It was the right inspiration, at the right time for me.

The question came as I sat quietly on my sister’s couch, watching the show: What’s my version of this?

The experiment to experience the kindness of others had been done before. I had no doubt people would offer me food and stay from a place of kindness, but I didn’t believe I would learn enough.

I had challenged a belief that buying stuff would bring me happiness. My experiment had proven this was not the case.

Now I wanted to challenge a belief that my physical space is responsible for my happiness. This piqued my curiosity. It felt juicy.

I decided to challenge myself by going “houseless” for half a year as my next experiment with life.

The use of the term houseless instead of homeless is intentional. For me it was a choice, and I recognize that, for many people who are actually unhoused, underhoused, or experiencing homelessness, it is not a choice.

The trip was my girlfriend’s idea, not mine. We were supposedly on vacation on an island off the coast of Mexico—but it wasn’t the kind of vacation I was used to taking. My jet-setting lifestyle meant traveling to New York, London, or Dubai, not a random tiny hippie island off the coast of Mexico. For fear of getting sick, I barely ate anything and prayed every time I took a sip of water.

My girlfriend at the time had convinced me to join her for a yoga retreat which, like Mexico, was something new to me. On the first morning, when a rooster woke me abruptly from deep sleep, it didn’t feel much like a “retreat.”

I felt out of my comfort zone physically and emotionally. I was not looking forward to the days that followed. We rushed downstairs, late—as usual—to the 6 a.m. start. I had no idea what the schedule was and made no effort to find out. The first surprise was that the yoga retreat was in Spanish: a language I did not speak. The instructor said 'respira profundamente' which I mistakenly thought meant 'stand up'. So there I was, the only one standing in a room full of seated yogis. It took me a moment to realize why everyone was staring and then my face turned red, as I quietly sat back down.

We were all seated uncomfortably on the floor. Everyone else looked far more comfortable than I was, sitting cross legged. I adjusted my posture, trying not to disturb anyone but managing to disturb everyone.

The teacher opened with a short tale, in Spanglish, and then explained how to meditate. He first focused on instructing us on how to sit, which I found challenging, and then about focusing all of our attention on our breath or body.

I was spending the evening with fellow entrepreneurs who had successfully navigated the ups and downs of the tech industry we had helped create. As plates of food came and went, conversation flowed from the predictable topic of business to the unsettling topic on all our minds: tech addiction.

I’d spent years uncomfortably addicted to my devices. The irony was clear to me, given that I’d started a technology business. But that was partly why. It's like opening a bakery and developing a sweet tooth you just can't shake.

I was constantly spinning plates in my business, trying to find solutions for every problem, and fixing anything that went wrong. In the early years, I kept three smartphone devices on me in order to demo my business’s products and to feed my tech addiction. Email in particular was highly addictive for me. Even when I tried to be disciplined, I always broke. Email was like walking around with a bag of popcorn, constantly stuffing my face. It was not healthy.

The dangling promise of that dopamine hit, though, was often too much to resist. The anticipation of someone sending me a message led me to obsessive inbox checking, even when there was nothing there.

I couldn’t sleep well.

I couldn’t eat a meal without checking my email.

I couldn’t sit through a date without sneaking a peek at my inbox. Frankly, it made me feel important. I was reacting constantly to the needs of other people, which fed my ego, even if I couldn’t admit it to myself.

But it also felt like work. It wasn’t the individual actions, but rather their cumulative effect. I felt like I was always working.

It was my first solo vacation. My romantic relationship wasn’t in a great place anymore. The experiment with anti-consumerism had recently begun, so had my experiment with committing to meditation. Changes were starting to appear on the surface, as something deep within me had shifted.

I needed some space to process the changes in myself and as a result, in my romantic relationship. So, I went to Costa Rica on one day’s notice for a weeklong vacation. While I had no plan for the vacation, I had a plan to disconnect for the week from my relationship, my business, my devices, and my growing anxiety that something had to change. I landed at the airport, took a cab into the capital city, San José, and walked into a random hotel, where I stayed for one night. Struggling to find vegetarian food with my phone off, I just wasn't feeling the city vibe.

The next day, I went back to the airport and took another flight, a domestic one to the west coast of the country, to a town called Nosara. It was one of the smallest planes I'd been on; the kind where there were only six passengers. When the solo pilot buckled up and moved his seat forward, I suddenly had more leg room.

During the forty-minute flight, the plane was still below the clouds. I could see Costa Rica’s beautiful landscapes and rainforests from up high. The white-haired American next to me, super tanned and wearing shorts, was quick to strike up a conversation with me. He asked where I was staying; I told him I had no idea. He asked who was picking me up from the airport; I told him nobody. I’d take a cab.

It was early December when the question arose while I was meditating one Saturday morning: What will I do for the end-of-year holiday?

My sister had gotten married that year, so she was busy with her in-laws. My parents had their own plans. There was no family gathering or celebration on the calendar. Meanwhile, I’d been traveling every week for business all year long, and the idea of planning a trip or vacation felt effortful and heavy.

During that morning meditation, I found a dose of inspiration. This year, I would experiment with something spontaneous.

Without giving it much thought, I called up my friend Jen. I didn’t know Jen super well, but we’d kept in touch since our university days and recently connected when she was visiting New York. She was top of mind.

“Hey Jen,” I said nervously. “I want you to pick a place for me to go alone on vacation for the holidays—and not tell me where.”

There was a long pause on the other end of the line. “ Are you serious?” she asked. “Yes,” I said. “You don’t have to do it, but I thought of you. I wanted to ask if you’d be game.” Another long pause. “ Are you sure?”

Again, the answer was yes—and that she was free to say no. Silence. I sat there, patiently waiting for her response.

Finally, it came. “Okay,” she said. “I’ll do it.”

Then she hung up, and I decided to get on with my day.

An hour later, Jen called me back. “I only have one question for you,” she said. “What’s off limits?”

I smiled. This was clearly the right friend to pick for this experiment. Thinking out loud, I said, “I don’t want to end up in prison. And I’ve got a bad knee.” That was my way of signaling: Don’t send me to Machu Picchu. Lastly: “Nothing to do with drugs.” That was it. Three restrictions.

I was back in Toronto, having moved out of New York. I didn’t know how long I’d stay in Canada, but I sensed my next experiment was imminent. There was a growing desire deep within me to leave North America. Or rather, to leave my North American life and identity and challenge myself with something new.

Choosing where to move was not an easy decision. I found myself drowning in options for a few weeks. Hours were spent going down internet rabbit holes, reading travel blogs and expat stories, and asking friends for ideas. The information was endless. Anywhere was possible.

A sense of overwhelm set in. I noticed how big of a distraction this decision was. I was dreaming about it at night, so during the day it was impossible to concentrate on much else. The rest of my life had been put on pause. Now I can see I was experiencing fear. Fear of making the “wrong” decision. Fear of regret.

Unsure what to do, I gave myself some space. I would not think about it or talk about it for a few days. I assumed that, after this break, I would either still want to move—or abandon the idea altogether. This momentary mental break was the best thing I could have done. It may feel counterintuitive, but when faced with a problem, I like to stop trying to solve the problem and instead take a break.

It works. This has been my experience time and again. The clarity surfaces once I turn away. Something deeper within me, or bigger than me, is often the source of this clarity. Day three of my mental break coincided with my birthday. I woke up and sat in my traditional three-hour continuous birthday meditation, a ritual that has stayed with me for nearly a decade.

I grew up with very few close friends in grade school and high school. I could count on one hand the number of close friends I had until the age of sixteen. The first reason was that I was quite shy and socially anxious. I was not socially awkward but felt nervous in social situations. I learned how to hide it well. I would hide behind my intellect, sticking to topics I was confident about. I would hide it by becoming curious about the other person, having learned that people love to talk about themselves when invited to. The second reason was that I have a large extended family, and we were very close growing up. There were always so many people around, I didn’t feel the need to get out of my comfort zone socially. Once or twice a week, the house was packed and noisy. Dozens of cousins, aunts, and uncles sharing meals, opinions, and laughs. My parents were social creatures and had countless family friends, mostly of Indian origin, like us, living in Ottawa, Canada.

The third reason was my sister. She was a blabbermouth and loved the spotlight. I unknowingly took a lot of comfort and safety in hiding behind her. Since she always took the lead and showed initiative in social situations, I did not have to do very much. The turning point came at seventeen. Despite my shyness, I managed to get elected for student government every year in middle school and high school, then student council president in high school. On the first day of school of my final year, I had to make the morning announcements from the principal’s office. My shyness and social anxiety came through that morning as I nervously read from the piece of paper the principal handed me. After the dreadful four minutes were over, the principal turned to me and said, “This isn’t going to work.”

This chapter could easily be titled How Not to Work. I have a lot of experience with this. My first time working in business was at the age of six. My sister beat me—she was five when we both joined our parents in the family businesses. Our parents were struggling to get their start in Canada as immigrants who had moved from India weeks before I was born. My father was always an entrepreneur, having tried many different ventures in his teens and twenties.

Once he found his stride, he finally landed on something that worked: retail stores. Specifically franchises of Canada Post, the national postal service. That is where I got my start in business. I am grateful for the early exposure my parents gave me. It shaped my confidence and conviction that, one day, I could start a business. And I did, multiple times. In my teenage years, I had a few attempts at various businesses. Some worked; most didn’t. The businesses could have been called nonprofits: they lost money, despite my humble attempts at the age of thirteen. But what mattered more was that I was encouraged by my parents every step of the way.

I took a detour from business for nearly a decade, as I got more interested in student politics and youth leadership. Little did I know the skills I would learn running organizations through high school and university would give me the foundational skills for leadership and management in business.

The technology business I started at twenty-one and led as Chief Everything Officer for fifteen years became the defining chapter of my professional identity. I felt I had been training for this role for the earlier fifteen years, starting at the tender age of six. As Chief Everything Officer, I learned a lot about how not to work. I made every mistake one could imagine. I ran out of money a few times. Missed payroll twice. Hired and fired countless people. Burned out multiple times. Burned out my team, including close friends. Upset clients. Lost clients. Disappointed investors. Disappointed myself. Despite a rollercoaster of a journey, I learned only one thing about how to work: to not overly identify with it.

One morning, while I was staying in my parents’ home in Toronto, I was rushing to prepare a morning smoothie for breakfast. I had the morning ritual down to a precision sport. The defrosted frozen fruit, the perfect amount of almond milk, the hemp, chia and flax seeds, the amount of time the blender would be on. Not being in my kitchen though, that morning I miscalculated the power of the blender and the size of the container. I had to run it for a few extra seconds. And that threw off the rest of my morning, it seemed. My dad turned to me in the kitchen and innocently said, “You look like you’re in a rush.” Without hesitation, without even looking his way, I snapped, “Yes, I have to go meditate now and I’m hungry.”

It was only once I walked upstairs to my sister’s old bedroom—which I had commandeered as my makeshift meditation studio—and sat down in her chair that I caught up to the irony of my response.

As I shared with the meditation group I was leading on Zoom that morning, the rushing to meditation and yoga classes was a classic New York phenomenon: unique to the hustle and bustle of the environment, and one I had experienced far too many times to admit. The desire to optimize the mundane and squeeze efficiency out of the boring routines was how I had found greater meaning. Now I’ve learned that rushing to slow down had less to do with New York—and more to do with me.

The morning started off like none other.

I woke up naturally with a smile on my face. My bedroom in Lisbon is pitch black, thanks to blackout blinds, and without any clocks or natural light, I have no concept of time. This is intentional.

As my eyes opened, I softly said out loud to my voice assistant, “Hey Google, what time is it?” The voice responded, “10:36 a.m.”

In what felt like a fraction of a fraction of a fraction of a second, I calmly observed to myself how I had already missed four meetings.

And then I became curious, still lying there in bed in my pitch-dark bedroom. Has this ever happened before? I wondered, and drew a blank. I could not think of a single example of when I had slept in this late.

I slowly got out of bed, went into my bright sun-filled living room with a sweeping view of Lisbon, and picked up my phone. Without even checking text messages, Whatsapp, email, or my missed calls, I said to my other voice assistant, “Hey Siri, call Ricardo.” The ringing stopped as Ricardo answered the call, not with a Good morning or Hi, Kunal, but with a shameless, “ Are you alive?”

“Yes.”

“You slept in,” he said to me, with full confidence.

“Yes.”

“Okay, don’t worry, I’ve rearranged your schedule. How long until you can make it to the office?”

“I’ll be there in twenty minutes.”

“See you soon.”

And just like that, I proceeded with my day. Without tension and anxiety. It was only then that I realized what had happened. My body, having just returned to Lisbon from New York the day before, had adjusted to New York time.

My favorite cartoon as a kid was DuckTales. Not only were the voices of the main characters (Huey, Louie, and Dewey) funny but there was often a scene of Scrooge McDuck swimming in a swimming pool full of gold coins. I found it funny every time the brother ducks did something to upset the uncle. It usually involved him losing his coins. Growing up, I associated being rich with having a lot of money. The word “currency” had one meaning: money. But over the years, I’ve found myself developing a far more personal—and more valuable—relationship with the concept of a currency. What I am discovering is that, unlike the currency used to trade money, I have my own unique currency in life. Everyone does. This currency influences what I do far more than money does; it also influences what I avoid. Like any currency, it is meant to be exchanged. My experiment with what it means to be rich has changed what I seek and desire to feel wealthy.

My currency is inspiration. Inspiration is what I love to receive, and try to give. For example, when I moved to New York, I was drawn to the city, as it inspired me with the feeling that anything was possible. Wherever I live, I like to feel inspired by my space. The people I feel the closest to also inspire me in their own ways. Some are inspirational by how they share themselves with me. Others encourgage me to do what I dream to do. And others inspire me by simply being themselves, unconsciously modeling qualities and traits I wish to cultivate in myself.

When I think about the many items that have overstayed their welcome on my to-do list, the emails I haven’t responded to in weeks, or the stretches I know are good for my tight shoulders that I still manage to avoid, I see clearly that none of these inspires me. They feel effortful; I do not have any currency to trade in them.

In London on a Friday evening, I made a choice on a whim: to have dinner alone at a busy restaurant—without my phone in hand. As I sat down, taking in my surroundings, the bustling energy of the place inspired me. I was content to be alone and observe the people around me. But then the couple sitting next to me struck up a conversation. We were soon sharing food and laughter. I was touched by how kind, fun, and grounded they were. They made me feel like a part of their world, and I felt grateful for their warmth. My aloneness allowed me to notice things and appreciate people in new ways. It was a reminder of the beauty and connection that can be found in unexpected places. I finished my meal before they did and got up to pay. An experiment was brewing in my mind.

When speaking with the waitress, I asked her to charge me for the table next to me and not tell them until after I’d left. She was surprised. She assumed I wanted to pay for the table on the other side of me, where four young women were having dinner. But I said no. The couple. The waitress was touched by the action. We even added dessert, with a candle on top. I don’t know what they were celebrating, but assumed they’d find something to celebrate.

As I walked out of the restaurant, a wave of energy flowed through me. Then I started to tear up. These people had opened their evening to me, sharing their dinner, their conversation, their true selves. Though I wouldn’t get to enjoy their reaction to my experiment, it was pretty easy for me to imagine it.

When I lived in New York, my parents came for a visit that will forever be remembered. We went out for fancy meals at fun restaurants around the city, and they completely took over my apartment, fixing all the things I didn’t even know needed fixing. We had a great time. Until the energy took a drastic turn.

We learned that my uncle, who lived just outside the city in Staten Island, had just been moved to hospice care. He was eighty-five years old and had lived a life rich in meaning and purpose. A real pioneer in the family, he moved from India to the United States in his thirties with absolutely nothing. Building the kind of life fairy tales are made of, his generosity and kindness had been felt not only by our family but by the entire community. We went to see him. I felt nervous on the ride over. I knew it would be the closest I’d ever been to death as an adult. The last time someone passed away in our family, I was a young teenager.

My uncle was resting in a small room on the lower level of the building. It was quiet and peaceful, without much inside it—only a bed, a few chairs, a couch, a small flower vase. The sliding door to the backyard was open. We heard the birds chirping and felt the cool air blowing through the screen door. Fall sun drenched us in soft light. It felt like a waiting room between this world and the next.

And as I sat there with my dying uncle, it inspired a short poem. I wrote it on a piece of paper and taped it to the wall beside him.

Over the course of my lifetime thus far, I’ve had the privilege of meeting many highly accomplished people who inspired me. But one in particular has been the most inspiring person I have ever met for a range of reasons.

He walks through the world without any fear. He climbs mountains for the sheer joy of the challenge, focused on the journey, not the destination. For him, life is not a series of transactions; it is a series of experiences.

He is unconcerned with how he looks. If he has bedhead, bad breath, stains on his clothes, or holes in his pants, none of it matters to him.

He does not care what others think about him. If he is in a crowded public space or in his quiet bedroom, he speaks with the same tone and uses the same vocabulary. He truly loves everyone he comes across, unconditionally. He will smile at strangers without hesitation, although he can be a little shy at first when seeing someone new. He will quietly examine the person to see if it’s safe for him to engage—and then engage without holding anything back.

He knows how to express his needs and wants clearly and does not stop until he feels that he’s been heard. In this way, he is at peace and does not store any resentment. He is infinitely curious about the world. In each new space he enters, he likes to inspect every corner, every button, every object, every person.

He is always open to hearing what you have to say and will always tell you what he thinks. There is no guessing where you stand; he will make it clear.