The Boy and the Mountain

The journey of a lifetime.

Hey everyone, it’s Yash!

I originally wrote this piece to formally announce my decision to become a full-time entrepreneur. In the course of writing it, it turned into the most important and difficult work of my life.

It’s a long read, ~30-40 minutes. As you read, I urge you not to compare our stories, but rather to find the seeds within that resonate with you. All of my healing has been an expression of the innate healing potential that exists within all of us.

If you do finish the piece, I’d be grateful to hear your thoughts.

So, nine edits, three re-writes, two “almost” quits, and one and a half months of tears, sweat, and damn hard work later, here we go!

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Preface

It’d just rained, and I walked along the patchwork trail of mud and dirt with my good friends Sid and Alikhan. As we strode along, Alikhan grabbed me and exclaimed, “YO, that mud is moving!” We ran up to the mud patch, got down on all fours, and shoved our faces inches from the ground. I’d been to the Louvre a few months before, and the Mona Lisa didn’t hold a candle to this muddy masterpiece.

I had taken LSD for the first time an hour earlier. The journey began.

The hours rolled by as we traversed Downtown Austin, eventually ending up at a spring-fed pool. As I sat on the banks looking at the water glinting in the midday sunlight, I felt something alien. I hadn’t had a flashback in hours. Where there once was persistent shame, harsh self-criticism, and anxiety, now there was… nothing. I felt ‘here’. I hadn’t thought of Dad, the future, or any of my worries in hours. My eyes teared up in wonder as I turned to Sid and Alikhan and said, “Everything is okay. It’s always been okay. And it will always be okay.” They looked back at me in silence, looked at each other, and burst out laughing. So much for my career as a philosopher.

Eventually, we left the pool and walked towards the city. I barely knew where I was because my mind and body were marinating in the feeling of ‘okayness.’ For 21 years, my experience was chaos until LSD said, “Let there be light.” My entire life had been spent trudging along a never-ending dark forest and suddenly, I was catapulted to the summit of a mountain that I didn’t even know existed. The weather was clear and crisp up there, and I could see for miles. I was in a peak experience, rare, exciting, expansive, and mystical.

I turned to Sid and Alikhan and said, “I’m committing my life to creating this sense of ‘okayness’  for myself.” Alikhan solemnly nodded and responded, “Keep going, man.”

To understand why the light on that summit felt so wondrous, you must understand the dark forest I came from.

Part 1: Falling

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Chapter 1: Two Decades in Hell

*BEEP* *BEEP* *BEEP* I woke up in a panic as my alarm blared, wiping the sleepiness from my eyes. I took a deep breath and winced. Last night, I’d jolted awake to a starburst of pain and the bleary-eyed sight of a balled fist in front of my face. Dad was on another rampage. My body and mind knew the pattern well and instinctually braced for more.

For the first 17 years of my life, my days went something like this: I woke up in dread at what new horror Dad had in store for me, my sister, and Mom that day. I slipped into the bathroom and took every extra second possible in the safety of the locked room, fighting the urge that grew louder every day to end my life. Anything was grounds for punishment, and over 17 years, I’d had all manner of weapons brandished against me - physical, emotional, and sexual. I dressed as quietly as possible, straining my ears to listen to Dad’s tone and determine if that day was a day where I would “know what’s coming,” which was his cruel euphemism for pain. 

In school, I’d count the minutes until the final bell rang and I’d have to go home and enter Hell again. I remember reading about depictions of the Devil in my art history class, remarking how much his face looked like Dad’s. I’d hold my breath as I walked into the house, preparing myself. The days when nothing would happen were the worst because I’d be left wondering what fresh hell he was dreaming up for me. In one instance, I remember Dad striding towards me with a baseball bat, a sardonic smile on his face. Despite the pain in the ensuing hours, I felt relief. At least I didn’t have to wonder.

Dad made sure to give me his daily sermon, which went something like: “You useless piece of shit. I’ll kill you one of these days. Better than leaving your worthless chicken ass alive. Nobody would miss you.” After 17 years of hearing this, I believed him. Many times, I even nodded my head in agreement. He was right. I was a shame to myself and those around me; no one was there to help me.

There were a few times that the truth peeked its head out of our home, like in third grade when I came to school with a black eye. My teacher suspected foul play, but Dad wove a tale about a freak accident where I fell off my bike and hit a curb. He’d convinced us that seeking help was somehow worse than the state of things at home. And worst of all, he’d convinced us that his actions were acts of love.

After a particularly brutal few weeks in my senior year of high school, I decided one of us had to go. I had to act before he did.

Between classes, I went to the seediest guy I knew and asked him to meet me after school. Later that afternoon, I told him about my “bad uncle” and asked him how to kill someone and get rid of the evidence. It involved a gun and some very toxic acid. All the necessary materials would cost $900. That night, I quietly emptied my blue plastic Comerica Bank piggy bank and counted the bills and coins I’d saved over the years. It was about $1000.

I had one attempt at salvation.

The next step was to maneuver my way out of the house. Under the guise of getting the mail, I slipped out, nervously fingering the envelope filled with $900 worth of twenty dollar bills. I dropped the money in the mailbox and texted my contact. The hours rolled by… 7pm, 8pm, 9pm, 10pm… and finally, I saw his beaten-up Honda roll up to the mailbox. I anxiously stared at my phone, waiting to hear back for hours. Nothing.

The next morning, I woke up to a text that said, “Abort. They scammed me and stole the money.” I sank in despair. That was it. My saving grace was gone, along with my life savings. I lost.

**

On April 26, 2013, everything changed.

Dad was in a particularly vicious mood. I had a flat tire, and he decided we’d repair it together. I’d never changed a flat tire before and nervously anticipated the pain to come. One of Dad’s favorite pastimes was punishing me for failing at something new. I got the jack out of the trunk and set it up on the side of the car. *BAM* - the first swing landed with a thunderous crash, and my head exploded in colorful stars of pain. Brandishing the metal wrench from the jack kit, he bellowed, “Hey idiot. The jack goes there,” and pointed to a jack point on the car.

After an hour, we finally changed the tire, and I was released. I lay on my bed, cradling my head and wondering how the rest of the night would go. When Dad was in moods like this, the beatings would last for hours, spread across the entire family.

When Mom came home, Dad began unloading on her without hesitation. My sister and I sat on the stairs, clutching each other in terror, fully aware that he had a wrench and could cause some serious damage. Peering around the edge of the staircase, I caught glimpses of Mom’s head covered in blood. Perhaps it was fate, but just before I looked down, she yelled, “CALL THE COPS!”

Reader’s note: My memory gets blurry here. My sister and I ran to my room. One of us picked up the phone, dialed 9-1-1, and hesitated. The other whispered, “Do it,” and pushed ‘call.’ We shut my closet door and told the operator our address in strained whispers, ending with, “Please come quickly. He’s about to kill my Mom.”

My sister and I huddled under the hanging clothes, waiting with bated breath for the longest 5 minutes of our lives. When the police arrived, they walked Dad out in handcuffs. Mom cried as she wiped blood off of her forehead. In one fell swoop, it was over.

**

I’m not exactly sure what kept me alive in the first two decades of my life. The best I can come up with is that I had some internal sense that I had to “keep going.” And that day, I’d won my war with the Devil. All the terror and fear I felt were gone. I was finally ‘okay’.

Or so I thought.

Chapter 2: A Rude Awakening, Courtesy of Jordan Belfort

Four months later, I walked onto campus at Southern Methodist University in Dallas. Looking back at my college years, I always felt out of place. The time that was supposed to be the absolute best in my life was a fetid broth of daily flashbacks, panic attacks, and nightmares. I was miserable and stuck in a tremendous loneliness borne of feeling unseen and unable to share with others. In one instance, I shared my childhood story with a rugby teammate, who remarked, “That’s a horrible story, dude. You shouldn’t share that openly with people because they might judge you.” Another tally in the ‘I’m seriously fucked up’ box.

I attached all my pain to my external world, assuming it was because of impending exams, not getting the girls I wanted, or the existential pressure of entering the “real world.” I entered college convinced that medical school was my next step despite the nagging inner knowing that it wasn’t my path. I tried to appear ‘normal,’ joining the rugby team because I thought it was manly, living in a half-drunk stupor on the weekends, and ingesting every drug that was placed in front of me in a desperate attempt to escape the pain. Finally, my prayers for guidance were answered by the Gods of Hollywood. The Wolf of Wall Street gave me the playbook to happiness - money, drugs, Mediterranean yachting, Margot Robbie! I blissfully ignored the last third of the movie, where his life falls apart. All I needed to do was enter the business world.

So, I did. I landed an internship at Bain & Company, a prestigious consulting firm that was harder to enter than Harvard. “Finally,” I thought, “the good life is here.” But a summer of complimentary business class flights, five-star hotels, A5 wagyu steaks, and flings still didn’t hold the answer. I could hide from it all I wanted, but the pain remained. I had one final card left in my sleeve, and it pointed to Denmark.

In my final semester of college, I studied abroad in Copenhagen. I lived a life of extravagance for four months, filled with partying and indulgence. I’d had everything I wanted from my college experience - grades at the top of my class, a job most would kill for, no longer a virgin, mimosas in Chamonix on Monday, cocktails on the Champs Elysees on Tuesday, limoncello in Amalfi on Wednesday. The supercut of that time would make an influencer foam at the mouth.

**

Sid came to visit me over spring break. We sat on the train from Madrid to Barcelona, Spanish wine country whipping by. I barely paid attention. I was miserable, a potent cocktail of loneliness, alcohol, and a burgeoning sense that the Wolf of Wall Street had lied to me. There were no more strategies left. Like a pressure cooker that has run for too long, decades of pain bubbled in my body until I felt like I would burst.

So, I turned to Sid and told him everything. The flashbacks, nightmares, and panic attacks shoved beneath my drunk smiles in the clubs. I’d tried everything that society told me should make me happy, yet I was miserable. I’d upgraded from a rowboat to a yacht but still clung to a life preserver for fear of drowning. Sid listened intently, and I could see a dark cloud enveloping him. We sat silently for a while, stewing in the milieu of what I’d just shared. 

Suddenly, his eyes grew wide and sparkled. He said, “We’re taking LSD.” Three months later, I walked a muddy trail in Austin with him and Alikhan.

Chapter 3: New Dress, Same Devil

A few months later, I started my full-time job at Bain, the consulting firm I had interned with before studying abroad. On paper, the job was amazing. Fortune 500 clients! Learning opportunities galore! Advise CEOs! Get paid a lot of money! Hide your insecurity behind a corporate logo! Okay, that last one wasn’t explicitly in the pitch, but true nonetheless.

It was a rough start. On my first project, I worked 90-hour work weeks, during which my team and I would hide our exhaustion behind masks of professional excitement. I spent 15 hours a day in a conference room that looked like it’d been designed to induce a panic attack. There were no windows, white walls, too many fluorescent lights, and a strong smell of bleach. The only semblance of the outside world was the green pasture of my Windows screensaver.

I’d spent two decades in Hell as a child, and this stretch of work was arguably worse. As an analyst, it was my job to take notes during meetings. Easy enough, right? Except I kept having flashbacks during them, dissociating for 5-10 seconds at a time. The cherry on top was that my manager looked like my Dad. When I saw his face, I was so triggered that I could barely think. I felt completely alone, unable to confide in my coworkers for fear of appearing too ‘broken’ to stay at the job.

Eventually, I was put on a Performance Improvement Plan, which is a nice way of saying that Bain and I were on the fritz. In retrospect, I don’t blame my team or Bain, because to them it looked like I was an angry kid that just couldn’t do the basics of the job.

“I’ll die if I have to keep living like this,” I thought.

**

On a cold day in January 2018, I sat in my apartment wondering what had happened. I naively thought the expansive ‘okayness’ I felt on the summit during my LSD journey had permanently washed away the pain. But the ‘okayness’ was gone, barely a whisper in the wind. Once again, I was back at square one. I reluctantly decided to seek out professional support.

Chapter 4: Cognitive Dissonance and the Case of Purpose v. Venture Capital

A few months later, I sat in my therapist’s office for what felt like the billionth time, diving into my pain. We practiced EMDR, a form of trauma therapy that stimulates the memory transfer process that occurs during REM sleep. Memories came into my awareness in trickles and floods. I opened my eyes, sweat beading down my face, and screamed, “This isn’t working! I don’t want to remember these things. All they do is bring me pain!” My therapist listened intently and said, in her infuriatingly calm manner, “Keep going.” So I kept going, driven by the hesitant hope that I could get back in touch with ‘okay.’

//

I shifted projects at Bain, moving to one with lighter hours. I finally had the much-needed space for my body and mind to integrate EMDR and rest. I leaned into the job and graduated from the Performance Improvement Plan. And I began to enjoy the work, treating it as a puzzle that my team and I would tease apart together.

Over time, I got more responsibility, managing an analyst and owning harder problems. I met colleagues who worked at Bain for decades and had tens of millions of dollars in the bank. They took a genuine interest in me, even offering their personal cell phone numbers so I could contact them if I needed anything.

The excitement was tempered by a budding feeling that I was living two lives: one at work and the one in my therapist’s office working to recapture ‘okayness’ while my friends were at happy hour.

**

EMDR is successful when you can revisit painful memories and they lose their emotional charge. After a year and a half, things started to click. I revisited a childhood memory where Dad was hitting my sister for falling off a swing set and was able to watch it from my vantage point as an adult instead of getting sucked back into my 8-year-old self. This happened with other memories, too.

Life began to change. My flashbacks and nightmares reduced from five times a day to once a day to once every few days to once a week. I was in a nurturing relationship with a supportive partner who hugged me as I cried after therapy sessions every weekend. I built deep bonds with three friends that I now call brothers. I felt like I had a new lease on life. Finally, the promise that LSD had shown me had started to materialize. I wasn’t on the summit, but the cloudy sky that surrounded it was starting to part and I could catch glimpses of it.

//

For two decades, it felt like I’d lived in a fully opaque cocoon of sorrow, never able to see beyond the confines of the dark forest. But now, the walls of that cocoon had started to become translucent.

As I started to re-capture that sense of ‘okayness,’ the cognitive dissonance between my day job and healing journey grew. It was especially strong during in-between space, like on planes during takeoff and while lying in bed at 11pm with the lights off. In those silent moments, a new question took form: “What would it look like to dedicate my life to creating ‘okayness’ for others?”

**

My first attempt at answering that question took a few years to materialize. I landed a leadership role in Manhattan at a mental health tech startup, and I was filled with a sense of possibility.

After a year of growing annual revenues from $10M to $45M, I stared at my laptop, thinking, “What happened here?” The startup was every venture capitalist’s wet dream - well on its way to a billion-dollar valued “unicorn” and preparing for the public markets. But as I parsed through customer feedback, I saw a different story. One client complained that their therapist was washing dishes during a session. Another said that they lived paycheck to paycheck, and their account was overdrafted because they got triple charged for one month of therapy. And therapists were burning out faster than we could find them. This wasn’t what I’d signed up for.

Dejected, I turned to my partner and said, “I give up. I thought this was the place where I could bring ‘okayness’ to others.”

She smiled, hugged me, and said those magical words, “Listen to those feelings. Keep going.”

**

The cognitive dissonance that started at Bain had grown like an algal bloom on a lake, filling every crevice of my mind until I couldn't ignore it any longer. My inner world was coming to life with a sense of ‘okayness.’ The flashbacks and nightmares had reduced to basically zero, and when I did get caught in them I could reliably pull myself out. In contrast, my outer world was stagnant and I felt like a cog in the machine of capitalism. To truly create ‘okayness’ for others, I had to leave the confines of the systems I’d traversed for almost five years. I had to start my own business.

Chapter 5: Fear Has Joined Your Party

Building a business is easier said than done. A few years later, I started my leadership coaching practice. I saw the green shoots of early success, with five clients and five-figure revenues in the bank, but quickly hit the ceiling of how much I could grow it as a side business. In the intervening years, I’d shifted roles to work in Product Management at an enterprise mental health tech company. I loved the team and work, but when I thought about quitting my day job to work on coaching full-time, my chest constricted with fear.

I was stuck and didn’t know what to do next. In Fall 2022, I learned about a retreat targeted at entrepreneurs who wanted to take bold steps in their lives and businesses. I signed up.

**

I sat in a meadow in the Adirondack forest. Justin, the head facilitator, was leading a “connection circle” with the retreat attendees. I listened as people progressively divulged deeper and more vulnerable parts of themselves to the group. The circle wound itself closer to me.

“If you really knew me, you’d know that I’m going through a breakup.”

Two people away.

“If you really knew me, you’d know that I have no idea what I’m doing with my life.”

One person away.

“If you really knew me, you’d know that I can’t live without my cats.”

My heart skipped a beat as eyes settled on me. I could feel my breathing get shallower. I thought, “Should I be honest?” I was terrified of sharing my story with my closest friends, so the prospect of voicing it to strangers I’d just met the night before was nothing short of a waking nightmare. My eyes darted back and forth, scanning faces around me, my brain trying to predict how people would respond based on prior experiences. I recalled what my rugby teammate told me in college about how people would judge me because of my story. I remembered the pain of sitting through EMDR, my head writhing in pain at the memories I revisited.

And then, I remembered sitting on the train to Barcelona with Sid and the mystical expansiveness of the LSD journey. Buoyed by a hesitant courage, I opened my mouth and spoke.

“If you really knew me, you’d know that I was brutally abused for most of my life. And that I still feel like that little kid on the inside: terrified, hurt, and alone.”

Eyes widened. The silence was so palpable that you could hear a tree growing.

Justin took a deep breath, looked into my eyes intently, and said, “You’re a hero, Yash. Your story ignites fires in others. When you’re tapped into it, you are powerful beyond measure.”

The words hit me with the force of an eighteen-wheeler. I wondered, “What might open up for me if I’m authentic with everyone?”

**

A few days later, I sat on the lawn with Justin. “I came to this retreat to connect to a deeper sense of what the heck it is I want to do with my life. I think it’s taking my coaching practice to the next level by going full-time, but I feel stuck in fear of failure.” We dialogued for three hours, but my fear was unshakeable, like a boulder that sat atop a horde of treasure. Justin hacked away at it with every tool at his disposal, barely making a dent in its surface. I looked up at him and sighed with exasperation, “This isn’t working. Nothing we’ve tried has hit so far. My fear is just too loud.”

Justin turned in his chair, now upside down with his feet hanging over the back and head by the grass. “It’s almost like every time we poke the fear, its roots grow deeper.” I smiled wryly. Every hit sank the boulder deeper into the ground, entrenching it.

I stood up and wrung my hands, “I need to take a walk and shake some of this off.”

As I walked away, my thoughts turned sour. “I’m so fucked up I can’t get over my fear.” My mind flashed forward to the scenes of my life as written by fear: giving up my dreams of bringing ‘okayness’ to others, slaving away at a desk, buying a house in the suburbs, 2.5 kids and a dog, and holidays with the family where I’d drown my regrets in alcohol. I looked up. Night had crept into the sky, and the stars looked like millions of tiny spotlights beaming toward me, a universal audience awaiting my next move.

I barely slept that night.

The next morning, I took a walk before our activities started. As I walked the asphalt path toward the forest, I saw Justin sitting in the same chair as the day before. He waved me over and said with urgency in his voice, “I had an idea.”

Groggily, I tumbled into a chair across from him. “Hit me.”

Justin asked, “What if overcoming your fear isn’t for you but for those around you?”

I cocked an eyebrow, my curiosity peaked. “What do you mean, like my friends?”

“Your friends, family, future generations, and ancestors. This fear you feel is potent, we know that.” And then he repeated, “What if this work isn’t for you but for those around you?”

“I’m still confused. I mean, it’s my fear. What does it have to do with other people?”

Justin sat up, “Our ancestors can pass their unresolved baggage to us. It’s called intergenerational trauma. Like, say your Grandma showed her anger by screaming at her kids. Then it's no surprise that your Mom would show her anger by screaming at you. Maybe it’s the same thing with your fear of failure. What if this work isn’t for you but for your progeny?”

I was dumbfounded. I’d never encountered the concept of intergenerational trauma before, and as we talked, a spark flew into the dark void of my fear.

The game had changed. My mind raced as this insight started to re-pattern my stories. “What if my healing was the same as supporting others’ healing? Maybe taking the plunge to build a business to create ‘okayness’ for others meant creating enough ‘okayness’ in myself to change my relationship with fear.”

With fire in my voice, I said, “There’s no way I’m passing this down to my kids. I’m building this.”

Part 2: Deeper

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Chapter 6: “You Thought It Was That Easy?” God Laughs

A few months later, my relationship ended. All the passion I felt for taking the plunge into my business had evaporated, along with any sense of stability or control in my life. I plummeted back into the dark forest. The ‘okayness’ I had been basking in since the retreat was gone.

I catapulted violently, sinking into the cold depths of the parts of myself that I despised the most. My daily routine for months was waking to deep pangs of despair and loneliness, dragging myself out of bed, opening my laptop, and smiling through hours of meetings and work, trying to display some semblance that I had it together. Once that was over, shutting my laptop, ordering takeout from the place down the street, and sitting in darkness, watching TV and crying until I crawled into bed. Shout out to Jojo’s Bizarre Adventure, you’re the best there ever was.

Many of the toxic beliefs I thought had been drowned for good reared their ugly heads once more. It wasn’t just a struggle to live my daily life, I felt lost in how to even exist in the vortex of shame, harsh self-criticism, and fear that surrounded me.

I started working with a new therapist. In a particularly challenging session, I teleported back to one of the most painful memories in my life. I was 12 years old, huddled in a woodchipped nook under a playground slide. The Ritz Carlton wishes it was that sanctuary. I sat there for an hour, crying and repeating to myself, “I wish to be free – free of the world.” My teachers roamed around the playground, distressed and shouting my name for fear of having lost me. As I sat in the therapy session, I’d completely forgotten about my adult self and was living in that moment. I said to my therapist, “I don’t know how I survived that day,” as tears streamed down my face.

For months, I showed up to therapy and felt like I was getting nowhere. I banged my head against a wall of pain over and over again, hoping to break through it and instead finding that it was thicker than I could have ever imagined.

One day, I broke through.

It was mid-February 2023, on a sunny and cold day. I sat on a cushion in my bedroom with my therapist on Zoom. Eyes closed, I saw myself as a little boy and felt his pain. Except this time, something had changed.

I said, “This feels… different. It’s more like a movie that I’m watching in my head. I still feel like adult me.” My therapist asked me if there was anything I wanted to say to the little boy. “I want him to know that I love him. I want to give him the biggest hug he’s ever had.” As I repeated the words to him, he stopped crying, wiped his tears, and looked up at me curiously. I kept beaming love and good intentions at him, and slowly, he transformed. His body unfurled, and he stood up. He spread his arms and legs, soaking up the light and love he so desperately wanted. And then he turned his head upward at me, beaming the biggest smile I’d ever seen. I wiped the tears from my face, looked at my therapist on the screen, and said, “I feel whole.”

**

We continued to explore and grow that sense of wholeness for the next ten months.

One day, as I sat on my bed and shut my laptop after finishing a therapy session, a wild thought crept into my mind: “The time has come. There’s no more hiding from my fear of failure.”

My fear was the same one that Justin and I had discussed in a meadow on retreat a year ago. For most of my life, I sprinted away from it as fast as I could. Now, with my evolved sense of wholeness, I’d developed tools to meet it, accept it, and address its core. Nonetheless, these tools would only temporarily abate its effects and the fear would always come back, screaming at me to take the safe route.

In the session we just finished, I told my therapist that I felt caught in repeating cycles of faith in myself and fear of failing. My inner world felt like two stars circling themselves while ripping each other apart with their gravity, a dance of beauty and chaos that led to one natural result.

She listened intently, sighed, and said, “You may never be rid of this fear permanently, but at this point, you know how to manage it when it shows up. Sometimes, there’s only one way left to confront the thing that scares you. You do it scared.” My mind blue-screened, dumbfounded at what she had just said.

After I regained my composure, I thought, “Of course. There’s no other answer.” I had saved up plenty of money. I had traction in my business. I had a newfound sense of wholeness in my body. There was no more therapeutic progress to be made.

I raised my eyes to meet my therapist’s and said, “I’m complete with psychotherapy for now. There’s only one thing left to do.”

I was ready to face my fear in real life.

**

Two months later, I quit my day job to focus on my dream of bringing ‘okayness’ to others. C-Suite executives confided in me that they were envious of my leap and had their own entrepreneurial dreams.

After just a single day of elation, I sank back into fear. Some thoughts I had: 

“What the hell did I just do?”

“What do I tell my family?”

“If this crashes and burns, I’m going to be homeless!”

I calculated how much ramen I could buy if I spent every dime I had. It was a lot of ramen.

I’d spent one year and four months building the courage to act on the revelation I’d had on retreat in the Adirondacks. It was a messy, painful time that brought me to a deeper intimacy with my inner world.

But I still couldn’t shake the fear of failure. The opportunity to build my own business was in the palm of my hand and I still wanted to load it into a catapult and sling it as far away from me as possible. I was utterly stuck, and the tens of thousands of dollars I’d spent on therapy, coaching, retreats, and psychedelics didn’t hold the answer. My quest for ‘okayness’ was dead in the water.

Chapter 7: In Me and Not Mine

My partner and I had planned a trip to India, and I figured a vacation would allow me to forget that I’d exhausted the energy of one hundred burning suns on my healing and had almost nothing to show for it.

I’ve always had a tortured relationship with my Indian heritage. When I visited as a child, my family and I would make our way through hordes of people to a taxi that would take us on a two-hour-long, harrowing drive that would make an Apollo astronaut piss themselves in fear. Then we’d scuttle about from one relative’s house to another, sitting in living rooms, squatting to poop, and feeling hot, sweaty, and stinky all the time. I associated India with everything bad that Dad was, disgusted by the culture that allowed a person like him to exist.

On this trip, my partner and I decided we wouldn’t visit any of my family and instead explore the country. We began in Kerala, a South Indian state known for its natural beauty. We disembarked the air-conditioned plane cabin into a swelteringly hot summer day. “Here we go again,” I thought.

**

A few days later, I waded through a sea of green tea plants, surrounded by verdant mountains and waterfalls. We were in Munnar, high up in the mountains. I stopped in my tracks and looked around. I was halfway across the world from my house, experiencing a beauty I’d never quite felt before.

A week later, we walked through a gate adorned with intricate layers of semi-precious stones. On the other side, I saw the white onion dome of the Taj Mahal peek out of the horizon. Our guide Lucky remarked, “It took thousands of craftsmen twelve years to build the Taj.” Once inside the cavernous tomb, I looked upward at the hundreds of thousands of glittering stones laid in homage to Mumtaz Mahal and felt a sense of déjà vu, wondering, “Were any of those placed by hands that shared my blood?”

Feelings of ‘home’ and connection to my people stirred within my body.

At the same time, I started to see that the patterns and fears that ran my life also existed in the people of India.

At lunch one day, my partner and I sat at a table waiting for our dosa and sambhar. I noticed that our driver Prasanth was sitting alone a few tables down from us. It felt odd to be distanced from him now, so I motioned for him to join us. His face grew red, and with a sour expression, he shook his head “No” in obvious discomfort.

I felt hurt. We’d spent 15 hours a day with him for the last week, sharing our histories, laughs, and music tastes. I also understood – it’s a traditionally Indian cultural thing to defer in social hierarchies. I did the same thing with people I thought were ‘better’ than me.

A week later, Lucky, my partner, and I sat in the car talking about life. Lucky was a goofy guy with a big personality, so it was surprising when he said, “I don’t really love guiding, but I’m good at it and it brings in the money.” I inquired further, “So what would you do if you could do anything?” He looked into the distance and his voice became small, “Well, I’m married and have two kids. I’m 45 years old and have high blood pressure. My father had high blood pressure and died of a heart attack at 55. Same thing with my grandfather. So I figure I have ten good years left.” As he told us his expectations for the future I could see the vigor drain out of his body, leaving a lifeless husk behind. My partner and I shared horrified looks. He glanced at us and instantly put his joyful mask back on. With a lilt, he said, “Oh, you both are young. You live a different life in America than I do here. Don’t worry about me!”

I felt my stomach twist over itself in discomfort. Lucky was convinced that he had no control over his life, and more so that I couldn’t understand him because I was American. Just when I started to feel at home, I was pushed away.

**

After two weeks in India, I sat on the plane home reflecting on the trip. I’d visited many times as a child, but this time was different. I felt connected to the land and people, fascinated by the beauty and culture I experienced. And I felt a strong discomfort from a paradox that surfaced. I carried the same patterns of deference and fear as Prasanth and Lucky, even though I lived 8000 miles away. I was them and they were me. Yet, they treated me as an ‘Other.’ This wasn’t a new feeling for me, I grew up brown in a predominantly white world and felt like an ‘Other’ for most of my life. Hours later, the discomfort still hadn’t gone away and I fumed with confusion and anger at why it bothered me so much. My head began to ache with pain so I looked outside the window to distract myself.

We floated over the Indian Ocean on a cloudless night. As I looked at the cosmos reflected in the glassy water, my mind went back to a memory of a similar night in the Adirondacks. Retreat felt like an eternity ago. My mind flitted through memories: staring up at the starry night sky before a sleepless night; sitting in the circle, sweating bullets about sharing my true experience of life; sitting in the meadow with Justin trying to lift the boulder of my intergenerational fear.

My eyes widened with insight: “The paradox of carrying the same patterning as Indians, yet being treated as an ‘Other’ in my homeland bothers me so much because it denies the truth of my experience. Even though I was treated as an ‘Other,’ I certainly don’t feel like one. I also can’t deny that I grew up halfway across the world from Prasanth and Lucky. What if the reason our patterning is the same is because it has intergenerational roots?” In a flash, I saw the impact of my immigrant lineage.

Despite a rich spiritual and cultural heritage, the story of India has been rife with subjugation, repeated colonization, and stratified social hierarchies. It’s in every Indian’s lineage. It’s the story of my parents and their ancestors. It’s the story of Prasanth and Lucky. The immense pressure of societal and familial expectations crushed their dreams like peanuts in a hydraulic press. From the moment they were conceived, their lives had been mapped out for them: specific careers, specific social obligations, specific rituals, specific marital pressures, and even specific lifespans.

As if that wasn’t enough, Indian immigrants have even more suffering layered onto those hardships, facing modern forms of subjugation like moving to a new country with no community and an immigration system designed to keep them subservient and terrified of the threat of deportation. 

This cultural trauma stretches far into the Indian diaspora. The CEOs of some of the largest technology companies in the world – Google and Microsoft – are Indian immigrants. Some of their most talented employees, also Indian immigrants. But they’re not the founders. Almost none of us have the mindset to support taking on that much risk.

As the plane crossed over Europe, a radical reconceptualization of my world formed.

I realized that my cultural and ancestral roots held the answer to why my fear of failure and risk aversion were so strong. These patterns were the results of centuries of collective trauma of Indians around the world. I thought these traumas were my own, but they had been passed down to me for generations. They existed in me but were not mine.

The plane landed in Austin. I walked off a different man than the one who boarded.

Part 3: Beyond

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A few weeks after the trip, I attended a retreat in California. As I sat in a psychedelic trance, an image of Dad’s face formed in my mind. I braced myself. When this happened in the past, I reliably spiraled into a bad trip.

But the bad trip never came. Instead, I felt a deep sense of ‘okayness’ that grounded me. I saw Dad’s ancestral lineage projected behind him like an infinite hall of mirrors. Then, Mom’s face came in, followed by her ancestral lineage. At that moment, I understood. In some way, it wasn’t Dad and Mom’s fault. They were acting out the intergenerational traumas of our Indian ancestors, just like Prasanth and Lucky had. Something whispered, “Give them love,” and I felt a powerful surge of compassion directed at them.

After almost thirty years of holding hatred and rage towards Dad and Mom, I’d found my first tracks of forgiveness. I don’t absolve them of responsibility – they were fully formed adults who had control over their actions and could have changed them, but it wasn’t all their fault. Hatred and rage were given to them and me but were not ours.

**

For most of my life, I was convinced that my mere existence was unlovable and shameful. My childhood had fucked me up beyond repair, I couldn’t tell anyone because it would alienate them, and I was lesser than others for being brown and not white.  At 17, I sprinted away from these feelings as fast as possible, seeking refuge in any cove that could shelter me from the typhoon of pain inside. I was the farthest thing from ‘okay.’

For years, I sought the answers outside of myself, convinced I could find ‘okayness’ in jobs, new forms of therapy, retreats, psychedelic experiences, or by starting my own business. None of that worked.

Eleven years later, I’ve realized that ‘okayness’ is my core. Traumas, beliefs, ancestral pressures, and societal expectations layer on top of that core, hiding it, as layers of dust caked on top of an old family heirloom hide the treasure beneath. There is nothing to run from because my core lies within, waiting to be unearthed. My work lies in living into that by sharing my story authentically and building an inner capacity to hold myself in wholeness.

On a recent visit, Alikhan and I played pickleball in Austin. While driving back, we passed by the muddy trail we had walked on the LSD journey nearly a decade prior. Alikhan remarked, “You’re so much more ‘you’ than when we first met. It’s like I’m meeting the real Yash for the first time.”

I don’t feel ‘okay’ all the time. The old patterns are still strong, cemented in place by decades of life experience, but I feel deep cracks in their foundations.

Epilogue: The Boy and the Mountain

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The boy paused on the path, turning around to take in his surroundings. The dark forest lay thousands of feet below him, extending for miles. He remembered the years he spent trudging through it, treading lightly and peering around tree trunks to watch for danger beyond. How eternal it had felt then. Now, from his vantage point on the mountain, he could barely make out the details of a single tree.

With each step on the path, the boy shed layers he’d been carrying through the forest for years. They were no longer needed and he felt lighter and stronger now, suffused with a sense of purpose.

He turned around and looked upward. He could see the summit in the distance, shrouded by clouds. The boy sensed the path wouldn’t always be easy and well-defined. It certainly hadn’t been so far. But, as he gathered himself for the next step, he quietly hoped that the path would extend two steps farther.

He smiled. It would be a long trek to the summit. The journey would be worth it.

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Thank you to all the brothers and sisters who walk this journey alongside me: Jeremy S, Madeline J, Sid G, Alikhan K, Cedric G, Jen C, Kelly Y, Dave S, Emma S, Mike T, Justin M, Aaron C, Ross S, Luke T, Siri C, Rikki G, Teddy M, Cat W, Teddy D, and many others.

Love to Mom and Mana, whose support has given me the courage to do this work.

Huge thanks to Jeremy Scharf, my close friend and brother. Your support and feedback helped me transform this writing from a mess of thoughts into the most important work of my life (for now 😉).

Yash facilitates transformational retreats and helps founders, leaders, and teams get unstuck and operate with more energy as an executive & leadership coach. If this piece intrigued you, drop him a line!

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