Shabnam Aggarwal's Blog

There’s something about my hair that has always felt so central, so fundamental, to who I am. It can make me feel confident and powerful on good days, frumpy and sick on bad days. It can make me go to the gym just before it needs a wash, and avoid walking outside just after a blow dry. It can make me spend hundreds of dollars on products I’ll never use, just for the sake of the dream that I might look like the woman on the front cover of the bottle for an hour or two.

I have had lengthy WhatsApp chats with my girlfriends about their hair routines. The most instagram accounts I follow are about hair. Most Saturdays I wake up and tell my partner, “Today is about my hair.” My hair has defined me since I was a little girl, when my healthy roots shone a dark brown and my wavy long, dry ends, bleached by chlorine and a distaste for head massages involving coconut oil, reached all the way down my back.

When I was 10, I had a sitter named Dominique who was a runway model. She said I had beautiful hair but that it needed a perm to look healthy again. So I permed it. When I was 12, I had a haircut with a South Asian aunty who said I had beautiful hair but that it needed to be blow dried straight to look tamed. So I blow dried it. When I was 15, I read a magazine that said I had beautiful hair but that it needed to be colored to be trendy. So I bleached it. When I was 24, I had a friend who said I had beautiful hair but that the grays were showing and they needed to be covered. So I covered them. By the time I turned 30, my hair was no longer mine.

My hair had become a separate being, a monster that required daily taming, maintenance, touch ups, planning, and care. It ran my life more than I ran it. It was no longer fun. At some point in my late teens, my hair transitioned from being my personal canvas upon which I expressed myself creatively to a burden that held me down.

I worried about what men would think, what my family and friends would think, what my judgmental alter ego would think every time I stepped out the door and my hair was not perfectly coiffed. I worried about photographs people would take and how my stray grays might reflect at the wrong angle, how everyone would know that I was getting older and what it said about me that I had grays at 30. I worried about being in the public eye on my book tour in India and the clicking tongues of Indian women reminding me I was going off-script with my hair.

Then, a year ago, in an act of defiance and rebellion against my own vanity and society at large, I just stopped. I stopped coloring. I stopped straightening. I stopped touching up. I stopped just to see what it would look like, how it would make me feel, what it would do to my self confidence and self perception. I stopped to see who would win the battle between ego and acceptance.

I did not stop caring, though. Over the past year I’ve spent more time on my hair than any year before. I’ve watched as the grays grew longer and demurred as my mom lovingly asked me if I wanted to color it on tour. I’ve smiled as my friends told me they thought it was brave and cried as I looked at old pictures of my colored straight black hair. I’ve tried to believe when my partner told me he liked it, and tried to ignore when my uncle said I looked old.

Some days I love my salt-and-pepper naturally curly hair and other days I tie it up in a bun and try not to look at myself in the mirror. The battle has not been won; perhaps it’s one that will continue on until I’m old.

There will be days in the future, I am sure, when my ego will win and I will give in to looking a certain way, a way I once looked when I was younger, less experienced, and more normal. But for all the rest of the days, I hope I can say, fuck you, hair. You’re beautiful.

When I was ten years old, my mom wanted to go back to work full time. That meant my brother, Yogi, and I would be home alone for a couple hours a day just after school until 5pm when Mom could get home to us. Yogi is five years older than me, which, at the time, meant he was in the prime of his teenage years. After a few weeks of testing this new normal out, it was clear Yogi and I could not be home alone together without getting into a fight, so I asked Mom if someone else could be there with me after school. Mom brought home a girl named Dominique to meet me.

Dominique was breathtaking. She walked in the front door with shiny long black hair, tall and graceful, strong as a soccer player. She sat down quietly at the dining room table in a chair next to mine, smiling, and watched as I finished my homework. She didn’t ask any questions, she didn’t tell me what I was doing wrong, she just watched me as if I was already special and wonderful in her eyes.

Dominique spent the next three years teaching me things, but what I learnt most from her was how to live life without fear. She had an air that traveled with her everywhere she went- as if anything was possible if you fought hard enough for it. The first thing she taught me was to write legibly and beautifully. She taught me to never be scared of heading a soccer ball and to stop saying sorry every time I shanked. She taught me to smile through a fight because nobody could make me feel inferior when I was happy. She taught me to love myself when all I could do was hate myself for all my perceived flaws.

I never asked much about her life, but then one day she took me to her home. Dominique lived on a ranch in Fremont, which was uncommon amongst the families and friends I grew up with. As we drove up to her house, horses galloped beside the car. She took me inside to meet her Aunt and Uncle, who raised her and her twin brother, Andre. Dominque told me she was part Indian and part Italian, but that her parents were no longer in the picture, and she didn’t know the cultures too well, but she wanted to get to know them better one day. She wanted to work in fashion in Italy one day, she told me.

Her life was so different from mine. Her’s was harder and the road ahead bumpy and unpaved- she was caring for me because she needed the money- whereas mine was predestined and cushy, but she filled her life with such a love for adventure; I knew I wanted to be exactly like her when I grew up.

This was the mid-90’s, so AOL was still on dial-up, and life-long email addresses were not a thing yet. So when Dominique left to study in Australia, we lost touch. I would hear her favorite song play on the radio, “I love you, always forever” and my heart would flutter in her memory. I visited Australia a few years after her, secretly hoping I’d run into her somewhere along the way. She was my first mentor, sister, and sherpa, but she had disappeared almost without a trace. She existed only in my memory.

A decade later, during a summer internship in Europe, I decided to backpack through Italy. I started in Venice, which was expensive, hot, touristy, and rude. I was determined to make the most of my intern’s salary, though, so a fellow backpacker and I walked to a grocery store to buy wine, cheese and crackers for lunch. We sat down on the steps of one of the millions of bridges in Venice next to a violinist, and ate our lunch.

As I stood up to wipe the crumbs off my shirt, I spotted a woman in the distance who looked like an angel. She wore a long fluffy white skirt and had shiny black hair that blew in the wind. It was as if a halo shone upon her. Her back was to me, but I stared at her, waiting for her to turn, confident I was either drunk or hallucinating.

As she turned to face me, I squinted my eyes to focus on her features. She had that same bright and beautiful smile. The same creases in her neck that she hated but I loved. The same grace that I remembered from a decade past. She walked in my direction and although I was still sure it could not be her, I blurted out, “Dominique!?”

The woman stopped at a short distance from me. She had not changed much, but I had become an adult in the time since we last met. She stared, confused.

“It’s me, Shub,” I said.

She blinked in disbelief. “Shub? What? How? What are you doing here?”

“This is my last day in Venice,” I said. “I can’t believe it’s you. It’s been forever. What are you doing here?”

“I live in Italy now. I work in fashion. I am living my dream! This is my fiancee, Flavio. We’re running late to a train, but here’s my email address and number. I want to hear all about you!”

We kept in touch after that. She left fashion and went into early childhood education. Eventually, so did I.

Today, pancreatic cancer took the life from my big sister after months of battle for the sake of her four beautiful children and her husband, Flavio. I was reminded of a handwritten letter Dominique wrote me from her dorm in Australia decades back.

“Now that I’m here, I’m happy to say that I’m having the absolute time of my life in the most beautiful place I’ve ever imagined. I often sit back and smile just because I can’t believe that I’m on a whole other hemisphere than anyone I’ve ever known. The sky is different, the buildings are different, the people are different. I’m living a whole new life in a whole new world. It’s unreal.”

Dominique, I hope you’re living a whole new life in a whole new world today. You were, and will always be, one of my greatest inspirers. I hope I can be a little bit more like you, everyday, and in every way.

I tend to write about my failures because they make me feel human and flawed, and I think we can all connect to that raw and painful feeling of having missed our ideal target at some point in our lives. But once in a while things go the other direction for me and I feel equal parts of surprise and confusion. I think I struggle with owning my successes because I have a major case of impostor syndrome- I always assume that my failures are entirely my fault, but my successes are accidents- which makes me very nervous to write about my accomplishments. What if everyone finds out I’m a fraud?

That feeling makes this post particularly tough to write. As I write this sentence, I still wonder if I’m allowed to feel proud of this milestone in my life. Do I truly deserve this?

I just finished writing my first book. It will be published by Harper Collins in November this year. I’ll be 33 years old next week.

I never thought I’d write a book this early in my life, especially not a book about my life, my work, and my many failures. I had always pictured myself writing a book when I was sixty-years-old, looking back on my career and threading pearls of wisdom and clever metaphors into a riveting best-seller.

I was offered my book deal by Harper Collins 2 years ago. Since then, I’ve met many aspiring and inspiring authors and creatives, and the one question I get asked over and over is, “How did you get your book deal?”

I remember how embarrassed I was the first time someone asked me that question. We were standing in the corner of the communal kitchen used by the Grub Street writers and I was making coffee to help me stay awake late into the evening of my memoir class. A fellow writer approached me and loudly, almost accusingly asked, “Do you have a book deal already?”

I wanted to keep it a secret in this class that I had sold my book. I felt like all the other students were much stronger writers than me, and they had years of experience and various publications under their belt, but I was only one with a deal on the table and a deadline to work towards.

It felt like I didn’t really deserve it. “Why me?” I’d ask myself over and over. “What did I do to deserve this? Everyone else is so much better than me.” The haunting lore amongst aspiring authors is that it’s easier to get into Stanford than it is to get a book deal if you’re a first time, non-fiction, non-celebrity writer. Most writers end up spending years writing a large portion of their manuscript, sending it around to tons of agents, getting rejected hundreds of times, and finally, maybe, finding one agent who is willing to try pitching their manuscript to a handful of publishers. And then, more rejection from publishers until one day, seemingly magically, a publisher picks up their book for a deal.

That was not my experience and for that I felt guilty. I felt like I jumped the ladder or I got lucky and I should have kept my mouth shut because I was going to offend hard working people who wrote, unpublished, their whole lives, while I sat there with all my book-deal-chutzpah without any real writing abilities whatsoever. But then I thought, maybe that’s how we all feel.

I started writing publicly in 2008. I had quit my job on Wall Street, accepted a job in Cambodia, and was feeling nervous and scared. I thought I would lose touch with my friends and family, but at the same time I couldn’t imagine putting the effort in to write people individually. So, after watching Steve Jobs’ commencement address, I grabbed a free blog URL for “Hungry n’ Foolish” on WordPress, and I started a travelogue.

Cambodia was a lonely time for me; minutes on the internet were expensive back then, Netflix and Hulu hadn’t expanded beyond the US yet, and I didn’t know a soul when I first moved there. I spent a lot of time reading and thinking that year. Slowly, I started writing more and more introspective pieces-  pieces about life, my purpose, and meaning. I remember meeting a guy at a party that year who was a journalist. By our third date, he had printed out all of my blogs and brought them with him on our date so he could read highlighted sections of my pieces back to me. That was the first time I realized my words might have the power to move people.

My pieces were often poorly constructed, riddled with grammar mistakes and contained no narrative arc, a bit like this one. I didn’t care, though. I was writing to stay connected and speak my mind, not to win an award or a deal. I wrote because I had an opinion that I thought might be a little bit different from other people’s.

Eventually, I left Cambodia and moved to India to become an entrepreneur in education, but I kept blogging. Facebook, Instagram and Twitter picked up traction and my post cadence diminished, but I wrote whenever I felt compelled to speak up in long form about something that mattered to me.

I gave a few talks on TEDx stages around the world about my theory of change: that failure had become a Grand-Canyon-sized pothole on the road to success that we had learned to avoid at all costs. But instead of taking the long detour around to avoid it, it was time we embraced failure, explored it, and used it to our benefit.

When I built my third startup, a few online publications asked me to write pieces for them- pieces about female entrepreneurship, edtech, failure and India. I didn’t always get approached, sometimes I reached out to pubs to see if they wanted a piece- usually they did not- but since my writing was free, sometimes they said OK.

Then, one day an editor from Harper Collins sent me an email. She said she had seen my talks and read my blogs about startup life, female entrepreneurship and failure and wanted to know if I’d be interested in writing a full book on the idea. That’s how it happened.

We spoke on the phone, met up in person, emailed ideas back and forth, and within 3 months I had a signed contract in my mailbox.

I remember when I was fundraising for my startup around that time, I would read articles in TechCrunch about stupid business ideas with idiot founders who had raised millions of dollars when I could barely close a few hundred thousand. Why not me? I thought to myself.

The hard thing about hard things (c/o Ben Horowitz) is that it’s never 100% clear why certain people succeed and others fail. It’s not necessarily because I’m a worse entrepreneur that I failed and other entrepreneurs succeeded. It’s definitely not because I was a better writer that I had a book deal and other writers didn’t (yet). Sometimes it’s luck or serendipity or timing. Sometimes it’s earned and deserved, and sometimes it’s not.

At the end of the day, what does it really mean to deserve something? Maybe I blogged and spoke and marketed myself so much that a book deal was inevitable. Maybe my editor was searching for someone else and google gave her me on accident.

It’s 3am. I’m still up. I’ve been staring directly into the bright rectangular light coming from my phone as I lay on my right shoulder, holding the phone at just the right angle so that the screen doesn’t flip to landscape mode. My thumb joint hurts from the constant flicking, up down, left right. I can’t feel my right arm anymore, so I roll my body over to my left side. Why can’t I sleep these days, I wonder.

I posted a photograph of my boyfriend and I at a wedding today. I look good in the picture, and it’s been a while since I posted a photo, so I know Facebook will up-rank it on the News Feed algorithm. I also posted it on Instagram, and then I put up a cute series of videos and photos of us at the wedding on Instagram stories. I posted something snarky on Twitter with a great hashtag, too. I even got a mention on LinkedIn from someone mildly recognizable. That makes it five places I need to watch.

I keep pulling the screen down with my thumb and holding it there until the app refreshes the data and gives me my nugget of joy: a new like, heart, or view. Someone’s seen it. I want to know who it is. The new name gives me a jolt of happiness and pride- a feeling of having won. When I see their name, I imagine myself as them, seeing my post, and I think I know what they must be thinking.

An ex-boyfriend’s new girlfriend watched my story, she must be thinking about how much prettier and happier I am than her. A female entrepreneur who’s raised more capital than me retweeted my tweet, she must be wondering if I’m wittier and more successful than her. A cute boy I had a crush on in college liked my post, he must be thinking about how he missed out on all of this perfection. A cousin that’s my age saw my story but she didn’t like my photo, and since I didn’t watch her story, she must be jealous of me.

I have won. I am winning.

I keep telling myself to go to sleep, to turn it off, to stop checking, but every time I click the bright light off and see a dead black screen on my phone, I feel sad. I don’t question why it makes me sad to stop refreshing five different feeds every two or three seconds, I just tell myself that a few more minutes won’t change anything. It’s not like I’m going to get a full 8 hours of sleep at this point, anyways.

I know what the Like Arc looks like, and I’m pretty sure, by this time at 3am, these posts have all hit their Like peak. The Likes per minute should start to dwindle soon. When the time between each view and each Like starts to get longer, that’s when I know the show is over. Now, it’s just the slowpokes and stragglers who will come along to peak their head in the door just to see what all the fuss was about, but the main crowd has come and gone and the time has come to pack up and head to the next show.

Upon reflection, I think this Facebook post has done well with 103 likes in the first 30 minutes, I wasn’t sure if I looked good at the wedding but now I’m sure; I must have looked great. That outfit rocked.

But the Instagram stories only had 30 viewers, what happened? What went wrong? Did I use the wrong photo? I go back to the post. I check the first story, I play it over and over again until I conclude that the problem must have been the hashtag. I used the wrong hashtag. I should have put a location pin on it. More people’s feeds would have gotten it. Ugh. That’s annoying. It was a good series of stories. Now barely anyone’s seen that great humble-brag photo of me in my bikini. Can I post it again in another story or will it be too obvious?

I tell myself that this obsession with the number of people who have seen my “work” is not unhealthy- this is part of my personal marketing strategy, I tell myself. I have to build my brand, and people have to follow, like, share, and repost me for my brand to grow. This is what determines how well books will sell, the agent tells me; your platform, your influence, your brand. Without that, no one will care about you. No one will buy you.

I haven’t spoken to 90% of these people in my life, though. How do they know who I am? What I care about? What I really stand for? Am I writing this book for them or for me? How do I build a brand, a platform that truly stands for something, when all I can think about in the middle of the night is how many Likes and Views I got in the first hour of a post?

I can’t think about all this right now, I tell myself. It’s almost 4am and I need to sleep, I need to get up and work on my book tomorrow, and not think about the likes on my latest post.

I thumb the screen down one more time, someone’s posted a new photo. Wow, she looks great. Where is she? Bali? Ugh, I want to go to Bali. Her hair is so shiny. My hair sucks. I love that hashtag, too. Funny, catchy, humble-braggy. And that puppy over there! So cute. Damn, that yoga pose is hard. I wish I could do that. And she’s a boss, too- her company sold for millions last year. This girl is living the life. Why do I suck so much?

The battery on my phone is down to 1%. I fumble around in the dark for my charger like a drug addict that dropped her last pill.

The irony is not lost on me. I want to throw my phone out the window, but instead I plug in, lay back and thumb down one more time.

Just one last hit.

“He keeps asking me what’s wrong. I wish I knew, but I don’t. I don’t know. So I make something up to keep the monsters at bay. I feel so unhappy. I feel empty inside. I feel lifeless. I fear what the future holds for me. I fear the dismay with who I have become. I fear the anger and yelling and hateful words that come out of my mouth when I’m talking to myself. I fear for my sanity. I fear for my composure. It feels as if I know I am walking into a fire, I know it will burn me, and I know I will come out scarred. Yet, I keep walking back into it, like an addict to her dealer.

I yearn for a place to call home. Why can’t I find one?

I sometimes find myself thinking about how I might hurt myself just to see if anyone would notice.

I feel unsafe, unsupported. I feel like I’m falling. I have no identity.

Who am I, truly, when stripped of all the people around me? I am nothing, nobody.

When was the last time I was happy?”

-Notes from my journal, 2011

At the time I wrote these words in my journal, I was in a loving relationship, I had a job, I was physically healthy, and I had built and run one startup business in education technology in India. I was a success on the outside. I was crumbling on the inside, though. I had fallen into a deep hole of desperation, and while I didn’t know how to identify it at the time, I was severely depressed.

When I look back on those painful months in 2011, I see the girl writing those words in her journal as if she is a child I’ve just met. I walk over to her as she writes, and give her an all-encompassing hug. The kind of hug where two bodies meet, melting into one another, holding the pain and sorrow, giving everything they have. I want to give everything I have to that lost little girl.

Back in 2011, a couple weeks after I wrote those words to myself, by chance, by luck, or by cosmic design, I was asked to speak at a TEDx event about my startup experience and my theory of change. My theory was that our ingrained fear of failure holds us back from trying new things, from tackling big obstacles, and from challenging and changing the world. I believed we needed to teach ourselves, and our children, to embrace our fear of failure in order to overcome it. I believed this was the only way we, as a generation and as humankind could achieve our greatest potential.

Only, I hadn’t considered a different kind of failure in my theory of change. At the time, I was outwardly successful by most Indo-parental metrics, but inside I had completely failed to listen to myself, to understand myself, and to love myself. In the midst of this failure, the fear I felt for the next one was debilitating. I was convinced I had nothing valuable to say, and that I didn’t deserve this honor.

A few days later I called up the organizer, having memorized what I would say. I had to convey to her that I was the wrong choice, that she had made a mistake, and that she should find someone else to give the talk.

As I waited for her to pick up her line, I listened to the first three brring-brring’s as if each one had its own story to tell. After each one’s story, there was a long pause, as if every story needed a moment of doubt, a moment of reflection, a chance for introspection. During the third pause, a weak voice in my head whispered, “Hang up now. You can do this. You are capable.”

I wasn’t sure that the voice was right, I didn’t know if I could do it and I definitely did not feel capable at the time. I knew it was a huge opportunity though; to throw it away would be foolish.

I relented, and I put the phone down. After hanging up, I got a pen and a blank sheet of paper, and I started writing down everything I was good at. The list was short at first, but slowly, it grew to fill the page. I taped the list up on the mirror in my bedroom at the height of my face, making it impossible to look at myself without looking at the page. This list would become my daily affirmation- I was worth something. I was good at some thing. I had something to say.

Over the next couple weeks, I prepared my talk. I rehearsed it hundreds of times, recorded it, sent it to friends and family, and requested feedback from anyone who would offer me some. I was still confident I would bomb the talk, either by forgetting everything I had rehearsed, or by fainting on stage. The audience was expected to be 1,000 people, the largest I had ever spoken in front of. But I was going to try.

The night before the talk, I stared at myself in the lengthwise hotel mirror. Something looked off. I could see my face again; my affirmations were gone. Oblong shaped O’s made dark circles around my eyes, as if they were protecting me from something. I tied my thick black hair back in a high bun. I pulled a tiny bottle of concealer from my toiletry bag and poked my face all over with the tip of the brush. Then I colored inside the lines. Maybe this is how they came up with the name for this stuff, I thought. I finished and surveyed my work. Passable, I thought.

I scanned the room behind me in the mirror. It was the nicest hotel room I had ever stayed in. Everything was the color white; the throw pillows atop the bed sheets, the writing desk with the writing pen, the lampshades in front of the curtains, the trimming around the mirror. I could hear the faint fading sound of children giggling just beyond the door in the hallway. The plush cream-colored carpet under my feet felt like stepping on teddy bears’ bellies. A eucalyptus scent wafted through the bathroom door, so strong I sneezed.

“Oh no,” I said.

I sneezed again. And again. And again. Allergic tears formed at the inside corners of my eyes, threatening to invade and destroy my house of cards. I took a deep breath in and held it on the way out. My cheeks puffed up, making me look like a geisha sumo wrestler squaring off against herself.

I fell backwards towards the bed and started to laugh hysterically. If someone were watching me from a room across the hotel courtyard, they would have thought I had lost my mind. Maybe, in some sense, I had.

When I got up on stage the next day, I immediately blacked out. Then, as if emerging from a coma, that same voice in my head caught the right pitch and screamed, “COME ON. LET’S DO THIS.”

I came to, and I gave my speech. I made a few mistakes, and a couple of my jokes fell flat on the audience, but all in all it was one of my proudest moments. Not because it was a fancy TEDx event or because my content was groundbreaking, but because it was the hardest thing I have ever had to convince myself to do in my life.

Afterwards, I called my boyfriend, broke up with him, and moved back home. I found a job I loved, in a city I wanted to explore, and I went on to build two more startups and raise two rounds of venture capital totaling half a million dollars over the next six years. Not only that, I actually learned to listen to and love myself again.

If nothing else, I can honestly attest to the fact that depression happens to most of us at some point in our lives. Depression is the least racist, the least classist, the least picky, and the least avoidable of mental health struggles in the human race. It’s also one of the hardest to identify. I’m reminded of the story of the frog in a pot of boiling water, but it’s a stupid story because who really cares about frogs that much?

Our job in this journey is not to avoid depression. It’s to make sure we have the right sized safety pins, operational navigational tools, and enough pads of paper in our survival kit to ensure we get through the storm in tact, with our heads held high, ready to take on the next one.

(Originally written for the “It’s OK to Talk” Campaign by PHFI)

The first day after was the hardest. The questions kept lurching towards me like a swinging punching bag filled with sand. I bobbed and weaved as quickly as possible. I threw my left jab out to keep us apart. I answered the hard swings with a right cross, putting my weight behind it, swiveling my hips, keeping my head low and protected from the next one.

I knew other people who had gone through this before. Strong, courageous, resilient people. They made it look easy. They handled the details, closed the coffin, and walked away. They never looked back. “It’s the only way,” they said. “You have to move forward.”

I had called a friend when things started looking terminal.

“It looks like cancer,” I whispered.

“You have to pull the plug.”

“I’ll find a cure.”

“You’ll kill yourself too, in the process. There’s nothing left for you to do. You’ll feel better if you do it now.”

I was sure he was wrong. I was sure, if I looked hard enough, if I called the right people, if I held on a little longer, I would find the answer. At every passing, failing moment, I wondered if I could at least delay the outcome, buy myself some time. If I had time, things might start looking up, and if things started looking up, I could manage a survival.

I could only see 2 feet in front of me, as if I was driving down the winding Rishikesh mountains with a heavy, deep set fog all around me. My high beams were useless, and the brakes were worn out. People kept honking at me to speed up or move aside, but I was too scared to make any sudden movements. I had no idea what the destination looked liked, but I was sure it would have the hollow feeling of wreckage and loss.

I didn’t know I had already become the empty shell of a once passionate, strong, and excited young woman. I had spent months trying to find a solution, coming up short every time, wondering what I was missing. Maybe there was another way to look at it. Maybe if I pulled myself away from it for a little while, I would come back renewed and refreshed. Maybe if I put more hours in, worked harder, smarter, faster, I would change the outcome.

But nothing worked, and I was completely spent, way before it was over. The day it ended, the day I pulled the plug on this thing I had created, I cried until my eyes swelled shut, as if bruised after a fight.

I had shut down my startup, fired my teammates, and lost my investors’ money.

In between dodging the questions swirling in my head the following day, I felt a weight lift off me, as if my hands and feet had been shackled by iron and chains. Then, almost immediately, the weight was replaced by a deep sense of guilt. I had let everyone down. It was all my fault. I had wasted so many people’s time, money, and faith. Faith that I could do this, faith that this was an issue worth worrying about, faith that there would be success at the end of this road.

For the next few months, I slept 10 hours a night, and rarely changed out of my pajamas. I had nothing to think about. What appeared like a vacation was actually a prison I had locked myself inside of. A prison in which I was the inmate, the guard, and the warden.

It wasn’t until 5 months later, when I was sitting next to a 10 year old kid named Nico, working out a math problem, that I realized what was happening. Nico and I had been working on his math skills for a couple of months together. He had been flagged as a special needs child early in his schooling, and I was assigned to his classroom as a volunteer tutor. When we blazed through a packet of math problems one Friday, his teacher asked him if he wanted a break or a challenge. He responded with gusto, a challenge. I was delighted and impressed. The next Friday, Nico and I sat together in the back of the class to learn decimals. Nico, ever the courageous young boy, approached the new topic with confidence. As he got going, though, he got stuck.

“Why,” he asked, “is 4/10 equal to 0.4 but 14/10 isn’t equal to 0.14?”

“You tell me!” I challenged him.

“No. I cant. I don’t get it.” He rubbed his face and slammed his forehead down on the desk.

I was stunned, and confused. The paper under his eyes turned into small, round rippled waves, blurring the ink on the page.

“What happened?” I asked.

“I messed it up. I cant fix it. I’ll never get it.” His voice quivered into the desk as the tears gained momentum.

“It’s not your fault, buddy. We’ll get there, just be patient with yourself.”

He couldn’t stop the tears, and our time was coming to an end. His teacher waived me over to the entrance to give him some time to cool down.

As I left the class, I felt as if a hot spring of realization had opened up before me, begging me to jump in. I had avoided the call, assuming for so long it was the voice of Sirens beckoning me, as Odysseus, to false promises and imminent demise.

Have patience, stop blaming, and give yourself a chance. There was life to be found after death. I just needed a kid named Nico and a tough math problem to bring it all back together again.

I’m laid flat on my back on the fake wood floor in the middle of our office staring up at the disgusting ceiling fan that hasn’t been cleaned in over a year, watching a large clump of dust spin around and around, gathering momentum, teetering further to the edge by the second. I have a deep sense that when it falls, it will fall directly on my face, because that’s just my luck these days, and I wont be able to do a thing about it: I literally cannot move.

Moments before, I had stooped down to pick up one of the 20 liter water bottles to replace the empty one that had been sitting there untouched for hours. My gregarious, absent minded team of 20-somethings apparently hadn’t noticed there was no drinking water on a sweltering June day in New Delhi, in an office that lacked a reasonable air conditioning system.

Little known fact: I am a trained boxer, a marathoner, and I’ve had two major surgeries from soccer injuries. So when I stooped to replace the water bottle, I naturally assumed that I had the wherewithal to carry it through. What happened next was perhaps the most embarrassing moment for an able, barely 30 year old, entrepreneurial, feminist, and egotistical person. I threw my back out.

At the time my office was filled with a scrappy team of young people that cut necessary corners and took big risks because that’s what startups did to survive and get ahead of the competition in those days. We each had the kind of passion for making our “end users” happy that most companies could only dream of. We truly wanted to make kids happy, and we believed each of us, in one way or another, actually were.

Most of us had unfulfilled childhoods ourselves. We had nutty, loving parents who sent us to pointless classes with boring teachers who could not care less about the subject matter. We hated school and exams and college and the whole conveyor belt that dictated so much of our lives. We wanted more and better for ourselves and for other kids out there, and we thought we saw a path to giving it to them.

We were still just kids at heart. We played pranks and threw parties and showed up late for meetings, but we also loved to work hard and like a team. On the rare occasion when we disagreed on something, the whole office went tense and cold. Most days, though, you could hear bubbling music and roaring laughter emanating from our windows, pouring into the windy streets of Shahpur Jat, enveloping innocent bystanders with the optimism and excitement of a startup with audacious dreams.

Those were the good days. In the beginning, the bad days were few and far between, and they were easier to write off. An investor just didn’t understand what moms really needed. A mom was just being too picky for us to really help her and her kid out. A partner was just asking too much from us, it wasn’t worth our effort anymore. When we took a step back and added all the bad days up, we could tell something was wrong, but it wasn’t obvious exactly what it was.

Was it our team? Was it our product? Was it our market? Was it our investors? Was it me? Was it our geography? Was it the photo on our homepage? Was it our number of retweets per day? All of a sudden, the barometers that once told us how we stacked up to our peers were no longer available to us, and we missed them. We yearned for that SAT test that would tell us our score and give us a sense of what our future looked like. But none existed.

All we had to go on was what the pundits told us: You’re not making enough money fast enough. It was the same line I had heard all my life from my father. “You should be doing something more with your education, you should be growing faster in your career. Why do you care so much about the kids in the villages in a country you barely know?”

It was a good question. When I tried to answer it, I came up short. Sometimes, I thought it had to do with my mother’s response to wasted food, “Do you know how many children are starving in India, while you waste your daal like it’s no big deal?” It was the guilt I felt for being lucky and privileged. Sometimes, I thought it had to do with my father’s childhood, “You know when we were kids we would gather around our small stove in Kenya while my mom would serve each of us hot roti before she fed herself.” It was the fascination with a challenging life spanning 4 continents in under 20 years in the search of prosperity, whereas mine had been spent in 1 house in the same suburb in the same state my entire life, in the search of good SAT scores and college acceptance letters. Sometimes, I thought it had to do with my brother’s childhood, “You know how easy you have it? It was different for me. They always wanted me to be something I’m not.” It was the pain I felt for my hero, in not being able to save him. It was all the heroes out there that could still be saved.

The one thing I’ve discovered after building companies for 8 years in India, is that I am not truly an entrepreneur, not in the stereotypical sense at least. A true entrepreneur builds a business with the goal to make enough money to survive and thrive. The money never mattered much to me, it was never the end goal, nor even in the top 5. It was always just a conduit to reaching more kids. To saving more heroes and their dreams. This might sound like some Mother Teresa crap, but I promise you, it’s not. It’s senseless not to care about money.

I often found myself saying what needed to be said, and doing what needed to be done to get access to the money that would help us reach more kids. I was trying to cheat the system to accomplish my own selfish goals. I didn’t actually care how much profit the business made, or how much of it went in my own pocket. What I wanted was different. But in the end, I cheated only myself.

I pursued a path that seemed like an easy win: I loved to work hard and grow people and build products. It made sense to be a CEO, but I hated being the CEO the entire time I was. I would drive myself crazy reading thousands of articles about how to be a great CEO and how to build an incredible culture and how to grow a viral product. I would second guess every single decision I made and doubt myself around every corner of the way.

To build a successful business you have to be confident you are doing the right thing for the right reasons. It’s a fine balance and not one that I found successfully or for any extended periods of time. I would change the story I told myself, depending upon what day it was and who I had spoken to recently.

It was exhausting. I had lost my true north because I was pointing at so many other stars pretending we were going in every other direction except our own. By the time I realized it, I was staring up teary eyed at a dirty ceiling fan and the world had forced me to stop moving at all.

The hardest part about being an entrepreneur was overcoming my own fear. Fear of judgement, fear of being wrong, fear of failure. The hardest part about failing as an entrepreneur was admitting I failed, and figuring out what I’d do differently next time.

I have failed.

I’m still not sure what I’d do differently next time, or if there will even be a similar next time. But for now, I am happy just to have tried and for the opportunity to have failed.

Thank you for giving me that opportunity. Here’s to the next one, whatever it may be.

Let’s do this, 2017.

Recently I was playing with a pen on an airplane, clicking it open-closed-open-closed over and over when I had a vivid flashback of a bloody finger. I should state, for the record, I am the kind of airplane seat neighbor you want to suffocate after being stuck with in a metal can flying around at rapid speeds above the earth for 5 hours. I have crazy nervous ticks and I completely disregard people’s personal space by snoring in their face or spilling tiny plastic bottles of red wine in their laps. I am well aware of this fact, but make no claims nor maintain any hope I will ever fix it. I wear it with self-loathing pride, like those football fans who wear their team paraphernalia even after the star kicker was charged and indicted with second degree murder.

Once, on a trip from France to the US, I was feeling peckish pre-flight so I grabbed a baguette and a small pound of cheese from a friendly man at a nearby café. The cheese I happened to grab was that awful cheese that tastes delicious but makes you want to throw up at the mere sight and smell of it. It’s the same cheese that I would give my right arm for on rainy days when there’s only fresh vegetables left to eat in the refrigerator.

I board a large plane that begins taxiing to take off when the stewardess asks if I’d like a light meal post-departure. I tell her I’m all set with my cheese, recline my chair into the unexpecting man’s lap behind me and tear open the wrapping on my unbelievable pound of cheese. I start munching on it like a mouse that hasn’t had a meal in 2 weeks, crumbs everywhere, and it’s at this precise moment that I notice exactly 5 people pinching their noses and staring at me with disdain. The old French man sitting to my right asks if I’m enjoying my meal. I don’t speak French sarcasm, so I say yes and offer him a bite. He looks like he’d rather die. I go on munching, Alice lost in Cheeseland, and eventually fall asleep while drooling on the man’s left shoulder.

Anyhow, as I said, I was recently playing with a pen on an airplane when I had a vivid flashback of a wrinkled finger and oozing blood. I had been clicking the pen open and closed, open and closed, for hours. I don’t know what it is about pens that click but I just love the way the pen feels and sounds when it clicks closed. The unique combination of frustrating everyone around me with the feeling of having accomplished something so minuscule yet so powerful really gets me going. I almost never use the pen in any meaningful way, but the entertainment ensues.

The finger from the bloody finger flashback belonged to my grandmother. She was my father’s mother. She was my father’s protector, my father’s cheerleader, my father’s voice, and my father’s deepest sorrow. She lived for my father’s happiness. When I was a kid, she stayed with us for many years in the guest bedroom on the ground floor of our house. She slowly deteriorated from an able, vivacious mother of 8 to a struggling, suffering grandmother of 22. She was the centrifuge to our family. I had no idea at the time, but she was the glue that held us together, the pin that kept forcing us to hang out, the love and home that we all shared and respected and admired.

My grandmother was a literal badass. She raised a crazy number of children, in absurd circumstances across 4 continents, and did it without any of the recognition we expect today like when our first kid takes a shit for the first time and we proudly post the video on Instragram amassing hundreds of likes. Hashtag #parentingskillz.

When my grandmother got older, she developed diabetes. That crazy woman loved her sugar like an alcoholic loves cough medicine. She had lost all her real teeth and yet she’d make me sneak her a cookie or a mithai when no one was looking, and for a while I was thus convinced I was directly responsible for her death.

Part of the process of dealing with diabetes in the 90’s involved a kit with a long cylindrical device that you’d slot a fresh needle into with every use. You’d click the needle open and prick the patient with this device. Blood would immediately gush out from their finger, and you’d have to capture some of it on a tiny piece of plastic. Then, you had to slide that plastic piece into this little electronic gizmo, wait for a few minutes, when the gizmo would proceed to tell you what the patient’s blood sugar level was. For a 10-year-old, highly sheltered, and spoon-fed child, it was just about as scary an experience as one could get. Even though my blood sugar was fine and this device was solely intended for my father’s mother, I was chronically mortified someone was going to kill me with this device.

My parents were the kinds of parents that loved to put their kids in uncomfortable and difficult situations just to “see what happens”. It was their way of ensuring we’d never become secure, overconfident or sane individuals.

So one sunny California day, Dad tells me to grab my things so we can go see Grandma. We head out to her house, he hands me her blood kit, and says, “Go take Grandma’s blood levels.”

I looked at him with horror, but my father was not one to take talkback lightly, so I bowed my head and considered my options.

It was at this moment I first wondered what failure meant. On one hand, I knew I could not shy away from the task without causing disappointment and frustration. On the other, it seemed clear to me that if I failed, a lot of people would be very angry with me and I may even cause physical harm to my sweet dentured grandmother.

This choice between disappointment and deep emotional and physical pain completely debilitated me. I lived for moments of triumph and success. I loved seeing that sparkle in my father’s eye when I accomplished something difficult. I yearned to hear him boast about my brilliance at parties with his friends. What would happen if I failed? Would I fall from grace in his heart? Would I lose my longtime standing as favorite child in the house? Would people whisper about me behind my back?

In hindsight it was a relatively innocuous ask. The device was built such that you really could not do much more than draw a few ml of blood from someone, and there was almost no way to mess up the reading. That was not the point.

Often, regardless of how small or large a challenge is in comparison to the greatest challenges people face in the world, in that precise moment we’re faced with making the decision of what to do next, of how to proceed, it feels like the hardest, scariest, most daunting decision we’ve ever had to make. It is not possible to have perspective in those moments, nor should we expect to. When we’re faced with a challenge for the first time in our lives, a challenge that requires a clear and timely decision based on a limited set of facts and information, we tend to do one of three things on impulse: we freeze, we run, or we fight.

The hard part when we’re scared is staying calm, believing in ourselves, and proceeding forward with both caution and confidence that we can do it. It’s the road less travelled, the road hidden beneath the leaves, the road we must find and embrace.

I did not manage to take this road, that day. I froze, threw a fit, and ran out of the house crying and accusing my dad of child abuse. It was one of my finer moments in my life.

I did, however, happen to run a huge staple through my own finger using an industrial sized stapler a few weeks later, realizing not only does such failure result in dismay and anger, but it can also cause confusion and laughter as well as pain and humiliation. After the initial shock and embarrassment, the emotions dissipated and we all went back to our normal lives.

What stuck with me though, was that this inane, goofy failure gave me the confidence to tackle the immense fear of killing my grandmother with a pen. Had I not overcome that fear, nor built the confidence to tackle the challenge head on, I may never have discovered my passion for helping those in need.

This unique triumph over my fear of failure happened on accident. I did not intend to hurt myself or to instill fear in my parents’ hearts. My theory, though, is that we each have a Zone of Proximal Resilience we are willing and able to take on. When we are in the Zone, we feel nervous and excited, we feel fear and intrigue, we feel both able and unable at the same time. Our instinct in the Zone is to protect ourselves, to shy away from the challenge, to go the easier, safer route.

I believe we must tackle the challenge, build our risk tolerance, and grow the confidence to go further and become greater beings over time.

I believe we all face challenges in life that feel insurmountable. At times we’ve chosen them, and at others they’ve been handed to us. Life hands us lemons when we least expect them and when we would really prefer not to have them at all. It’s in those moments we become filled with fear and we are asked to make big decisions that will affect the lives of ourselves as well as the people we love and care for. The only way we can truly create delicious lemonade rather than cower from salted water and yellow balls is by learning first how to cut and squeeze lemons, tasting the water as it sours and sweetens, and finding the right recipe to quench our thirst as we tackle life’s challenges head on.

We first met when we were just kids. She was a little older than me; I was nervous she could see right through me. I had a hard exterior back then, a sense of entitlement with a touch of masked anger. I built a high wall with a mote around my heart, and she knew it right away. She could tell I was hiding childhood wounds, overcompensating for them with the ardent stamina of a cactus in the desert. We were fast friends, meeting often, prodding one another with difficult questions about our past, our worlds and the future. Secretly, I wanted to know what her plan was, and how I might factor in. She wanted to know if I was really going to stick around and see this through together. We knew we’d be battling generations of expectations. We knew our lives together would make people mad. We made a blood pact that day that we’d find a way to overcome it all, and preside over the mess.

I told her back then that she could trust me. That I was here to stay and that I’d never give up. To be honest, I never expected to fall so deeply in love. I never expected she’d get under my skin, that she’d scale the wall, and build a bridge to my heart. I never expected her to introduce me to her children nor for me to love them like they were my own. I never expected for this to take over my heart and soul, but she did. We’ve been together almost a decade, and it’s been amazing and terrible and perfect and horrible at once.

Above all, it’s been the hardest years of my life. I’ve never felt so incredibly optimistic about anything. Nor so utterly shattered. We had one of those relationships that never made any sense to onlookers. We’d oscillate from love to hate within hours. We’d take solace in how far we had come, how much we had achieved together, but then we’d fall back down again when we realized how far we had left to go together. How, in the larger scheme of things, we had accomplished so much less than we had hoped.

We realized we had been incredibly naïve that day. Like a small kitten jumping from her first windowsill, we assumed if we leapt, the ground would catch us and we’d survive. We saw the world in black and white, and we were overzealous. We challenged ourselves to tackle issues none had solved before. We consoled ourselves with the fact that we were different, we were unique, and we wanted to change the world.

We chose a finish line for ourselves and set out on our journey together. We saw it all. The lushest forests and the darkest slums. The snowy mountaintops and the windowless prisons. The 50 story buildings and the sad preschool-cow-sheds. We lived life fully together and gave it everything we had.

But then I cheated on her. I turned my back on her for a brief moment, distracted by something in the distance, and I let go of her hand. A motionless light captivated me, drawing me nearer and nearer while the light grew dimmer and dimmer. I became obsessed with the light, refusing to take my eye off it, no matter what she did to try to bring me back to her. I couldn’t stop myself, and she couldn’t either. We knew it was the beginning of the end, back then, but we refused to admit it. We kept trying to mend our broken love with Fevicol and tape but it wouldn’t hold. We couldn’t hold.

She knew it first, but I was the first one to say it out loud. It’s over. We’re too far-gone. We aren’t happy anymore. We’re burnt out and ready for something new. We’re tired of fighting and crying and blaming and losing. It’s no one’s fault, we agreed. It’s just the end. One day, maybe we’ll meet again. We’ll pass each other and stop for a moment to reminisce about what once was. Maybe we’ll smile and laugh at the beautiful memories we had together. We’ll cry about the mess we made and embrace because it was so perfect once upon a time.

The scary part is tomorrow. And all the tomorrow’s after that. When we’ll wake up without each other beside us. We’ll go about our morning without the smiles and smells and laughter and we’ll rebuild our lives in each other’s absence. It will hurt like the moment you open your eyes after a train wreck. We got so used to each other just being there, to everything working out between us, to relying on each other for deep and true happiness.

Honestly, she probably won’t even notice I’m gone. She’s stronger than I am. She’s used to this, she’s seen it before. She’s older and wiser and has had many more lovers than I. She figured I would desert her eventually, when it got to be too much. She expected this might happen one day. I guess I never realized it would hurt this much to accept that she’d be fine without me. I never thought I would become the shattered mess.

India was never mine alone, but I was hers’ completely. I love you India, and I will miss you. You gave me everything. You made me the person I am. You were the worst and the best and the most beautiful, most infuriating lover I have ever had.

Until our next affair.

P.S. Soon I will embark upon the next phase of this adventure, in a new country, a new city, with renewed vows and a fresh take on education, children and poverty. I deeply admire and respect all the incredibly committed people I’ve met along the way in India working to alleviate poverty and fix the education system for kids out here. I will miss you dearly and cannot wait to see the change you will undoubtedly make in the world. Thank you for giving me the opportunity to serve and to learn. I will be back one day, I promise.

“History is hard to know, because of all the hired bullshit, but even without being sure of ‘history’ it seems entirely reasonable to think that every now and then the energy of a whole generation comes to a head in a long fine flash, for reasons that nobody really understands at the time—and which never explain, in retrospect, what actually happened.” -Hunter S. Thompson, Fear and Loathing in Las Vegas, 1971

It all comes down to fear. Fear of judgement. Fear of loneliness. Fear of meaninglessness. Fear of failure. Fear of the unknown. Fear of death. So many decisions we make are based in fear. Sometimes, if we’re lucky, it’s the good kind: the kind we recognize and grab on to because we know that’s where the true stuff lives. Because it feels like the first time we got on our bike without training wheels and rode all the way to the end of the street with bated breath knowing we might fall…and we crave that. But more often, it’s the terrible kind: the kind that pushes us to be safe, to blend in, to force others out, to give up.

Why do we give in to fear? Why do we allow ourselves succumb to it? Did we look past it once? Did all our worst fears come true? Did we decide then, that we would never let ourselves be fearless again? That we would sacrifice our freedom, and everyone else’s, for the sake of our hyper-sterilized, pre-planned, self-contained life? Can we be sure that’s any better?

The fear can only protect us for so long. The fear will turn us against one other, and eventually it will turn us against ourselves. It will degenerate our society and hold us back from the future our children clearly deserve. Our kids need change. Our kids need freedom. Our kids need each other.

We need to ask ourselves how we can save each other, how we can love one other more fully, how we can support and empower each other to rise up and achieve greatness. How can we rid ourselves of our small ounces of fear, for the sake of each child’s future, rather than our own selfish salvation?

Fearlessness is today’s most valuable charitable donation. Give freely.