“I’m out,” I said as my longtime friend, mentor and CEO of the company I worked at stared back at me. I honestly couldn’t believe I said it; before this moment, I envisioned the exact situation of how and when I was going to leave playing out in over one hundred different ways. Would he be angry? Would the company think that I was betraying them after all of this time? In terms of a professional career, I had grown up there. From being an intern in 2012, eventually being hired to run social media and community, to starting the Sales team with the CEO and then growing it out from there. I didn’t know what I was always doing along the way, but had the trust, confidence and guidance of both those who managed me and who I managed. And, I couldn’t have been more grateful for it.

When I came in as an intern, I was a recent NYU grad with ripped Vans and cheap shirts I had bought on a visit to India. I was hungry to prove myself, contribute and become someone. The only thing was that I didn’t know how. After three months, as I was getting ready to leave to work somewhere else, I got the opportunity to interact one-on-one with the CEO. He told me that people liked me, but that it wasn’t enough. That they could only afford to pay people who would run through brick walls; kick their motor into a gear they may have not known existed. In short, people who were indispensable. I was taken aback by the conversation, by the brilliance of the man who I was speaking with and the opportunity that was in front of me. My hands were sweating. “This is how I can become somebody quickly. How I can prove my worth to the world beyond anything I’ve done before,” I told myself.  It was then that the light bulb went off in my head, and the fire started to burn in my heart. Becoming indispensable was my only goal.

Previously, I had been waking up at 4am and getting a ride to Manhattan with my mother – who works as a nurse – two days out of the week. But, after that talk, I knew two days wasn’t enough. So, four it was. I would have done five, but I had a consulting job that needed me on call for at least one day a week. Not looking to make the early commute every day, I would crash on a variety of couches including my ex-girlfriend’s, my best bud Q’s and another good friend, Regina’s.

Becoming indispensable was a good goal, but it needed to have action items attached to it. So, I told myself that I would do absolutely anything anyone asked me to do: get coffee, stay late, build something, etc. But doing what people ask of you isn’t enough. So, I began to proactively ask as many questions from anyone I could. “What’s the difference between a project and product manager?” “How do you raise money for a company?” “How do you decide how much each investor gets?” “When does a company transition from building a product to making money?” It may have been a case of “right time, right place,” but my questions were never received with a sigh or a “dude, above your pay grade. Get back to work,” which undoubtedly set me up for success. It was a perfect formula of a curious, insatiable young guy looking to cut his teeth and an environment that was fortunately conducive to what he always sought and where he wanted to go.

At that time, I was living Bedstuy paying $645 / mo for a room only a bit bigger than a closet, located next to the Marcy Projects – shout out to HOV. Fortunately, the only thing that ever happened to me over there was that I got a ticket by the cops for walking through a public park at 8pm…right after two girls walked through without a problem only thirty seconds before me. I won’t make it a race thing…but it was a race thing. Despite the rent being cheap, I couldn’t afford it. I only had about $200 in my bank account when I first moved in, and my parents advised against it. “This is a mistake,” my mother said as I sat next to her the night before I left. I stared into the glow of the lamp on her bedside table. “It may very well be, but I’d rather move out and fail than not try at all. I believe in myself.” So, I lived off of $40 / week and 4-6 egg sandwiches a day (I used to fry them before work, throw them on an onion roll and carry them in my backpack, which gave off a specific and serious stench on the G and L trains during the commute. Apologies if you were an unknowing casualty). And, even though I had that other consulting job, they weren’t actually paying me (they eventually did, but it took about two months after I had been working there). What did this all mean? It meant I couldn’t afford rent for the first few months. It meant I had to crawl to my parents, who don’t come from means themselves, and ask them for the money. Fortunately, it wasn’t met with a “told you so.” Only, “We hope you know what you’re doing.”

Did I know what I was doing? Yes and no. I didn’t know whether my internship would actually lead to a job, if I would start making money, or if I’d need to move back home. But what I did know was that I had more energy than most people I met. That I knew (for the most part) when to shut up and listen, and that I wasn’t afraid to look someone in the eye and pretend that I was unblinkingly sure of who I was and what I could offer.

Eventually, I was hired to run the company’s social media profiles, as a Community Manager, and started to receive a salary (money, yes!). Social media was easy for me. It was a formula of creativity + emotional quotient + speed. And, when I wasn’t coming up with new posts, I was learning how to be more agreeable than combative through responding to customer service inquiries. Shortly after becoming the Community Manager, I was told that I had to actually create a community; a global group of power users who we would give free swag to, use for focus groups and ask to help get the word out. I teamed up with our database architect and began to scour our internal data to see who our top users were each day. Then, I’d shoot them an email and invite them to join the program. Somehow, it worked! We grew the program to 150+ individuals all around the world who were in love with, and wanted to support, what we were doing.

A few months later, senior leadership decided that it was time, as most companies would and should, to make money. It was then that I was tapped to start the Sales team. The only thing was that I had no idea what I was doing. Had I ever sold anything before? Sort of. I was used to selling the idea of anything I was passionate about e.g. the old-school T-mobile Sidekick (I had almost every version), H&M clothing (I honestly still love it today), traveling, Yerba Mate, etc. Passion is a double-edged sword for me. I can use it to fully get behind and promote something, but sometimes it goes too deep, to the point where the distinction between myself and the thing that I’m in love with is lost, which can be dangerous when you’re moving at a pace so fast that any concept of identity can easily come untangled. And, it eventually did. But back to the story.

My Sales training was one of the most intense experiences I’ve ever had. I was thrown a mile off the shore (of where, I don’t know?) and was forced to figure it out. I remember sitting in the center of the office hoping to dear God, Allah, Brahma, Tao, Zeus and any and every other deity that no one would pick up the phone. Obviously, people did. I remember the first time someone picked up. It went like this:

(Ring ring)

Prospect: Hello?

Me: Um, yes. (Clearing my throat) Hello.

Prospect: Yes, how can I help you?

Me (whispering now): Um, yes. I’m looking to speak with (prospect name).

Prospect: Yes, this is he.

Me: Well, I’m calling from (company) and we were just featured in (local newspaper).

Prospect: And?

Me: And I wanted to tell you that we can help you.

Prospect (now laughing his head off): Oh yeah? Please, tell me how.

At this point, I could hear that he put me on speaker and was bursting into a raucous laughter with his partners or whomever was on the other end. He eventually told me to “fuck off” and hung up.

So, what did I do? Did I “Fuck off?” To him, yes. But, I fortunately had the guidance of my mentor and many others to help me figure it out. The marbles in my mouth began to fall, call by call, and I fell into a rhythm. We eventually hired more salespeople, and it was apparent that my early skill was more in bringing large deals to the table than actually closing anything beyond a couple hundred dollars or thousand dollars (first deal I closed was a school for $500 – woohoo!).

I owned this new role and became so fluent with the pitch – the “yes behind the no,” skirting rejection and navigating the tumultuous waters of a sales call – that I would put my phone on mute and shoot the shit with coworkers as the person on the other end of the line would continue talking. I didn’t feel as though I needed to listen to what they were saying because, in my opinion, it was all the same. Now, if I ever saw a rep doing this today, it wouldn’t be a pretty sight. But, I was an immature guy in my early twenties who felt like conquering a Sales call was like Christopher Columbus arriving in the Americas, pillaging the indigenous people’s villages and resources and destroying them with disease. The Christopher Columbus analogy is a bit extreme, but you get it. I was having the time of my life.  

As time went on my success grew directly proportional to the success of our company. We were hiring more and more people, achieving our goals and celebrating in a way that I sadly don’t think I may ever experience in a professional organization again. I was making money now and felt like the world was honestly my playground, which was good for me but not those I was closest to. It was this whole feeling of being on the top of the world, like no one could touch me, that allowed me to throw myself fully into the job. Into positively impacting and developing the lives of those who I directly managed, into building an organization that mattered and into rising up in my own profession. During a performance review, I was once told, “Go as far as you can until someone or something stops you.” Advice I took to heart.

“I’m going to be a big success, and no one is going to stop me. Not even you.” These were the words I used to say to my ex-girlfriend, who I lived with for eleven months during the rise in my career. She loved me unconditionally, but I didn’t know what I had or what to do with it. I put work before her time and time again and never tried to hide it, which led to endless fights, shouting matches and one of us inevitably in tears. I would come home around 9 or 10 at night and just crash without so much as a “hello.” Meanwhile, she would get home earlier than me and either make food or want to go out, and I would just shrug it all off with, “I’m tired. I’ve had a long day and you can’t even begin to understand.” Right now you’re probably thinking, “What an asshole!” Yes, I was. This neglect stretched to my family, who only lived about an hour by train from me, but whom I would only see every three or four months. I used to be exhausted and screen my mother’s calls. Voicemails began to pile up: “Hey hunny, just calling to see if you’re okay. I haven’t heard from you in days. I was hoping I’d catch you right before you went to work. I’m your mother, remember? Please pick up.”

I felt like a speeding bullet. Like I was moving so quickly and could cut through any obstacle: girlfriend, friends, family. Instead of seeing them as equals and allies, I looked at them as impediments to the life I wanted to live. Instead of opening myself up to them, of being that joyous, hungry guy with the ripped vans and cheap Indian shirts, I changed. I was still the life of the party, but in a different way. In a more destructive way. I didn’t take care of myself, ate horribly and had little regard for anything that didn’t directly contribute to the work I did. All because the interior of my personal life didn’t match with, and (at least I believed) had no bearing on, the exterior of my professional world. They were two distinct places and times like yesterday and today. A second in the past, a second in the present and a second flying in from the future. I made new friends, adopted a new family and cared more about picking up a call from a work colleague than an old college friend or brother. Is this how life is for most people at this stage? Maybe, but I don’t think so. As I said, passion is my affliction. My silent motivator and slave master. I wasn’t a slave to any man or money. I was a slave to my passion. But, the thing is is that a slave who’s well-fed and comfortable rarely realizes that the chains that jingle and jangle at his wrists and ankles aren’t the latest generation’s form of jewelry. They’re boa constrictors that tighten their grip the more you slacken your own will, thoughts and intentions of your heart.

Where did this go? Well, where do you think it went? Did I miraculously loosen the grip of the boa constrictor of my passion, start coming home earlier, reciprocating the love of my girlfriend and my family while continuing to grow my career? If you think that’s what happened, I should borrow the two words that my first prospect told me and tell them to you. My girlfriend and I split; I renewed my expensive 1BR apartment in the Lower East Side alone (more money, right? I must’ve been able to afford it, right? Psh), and continued to push away my family and old friends while only making an appearance when I felt like I absolutely had to. This went on for 2-2.5 years.

The wild thing is that when you’re in the thick of an illusion, or a dream, you rarely know it. Think about Plato’s Allegory of the Cave. Friends would sometimes call a sit down and try to talk sense into me, but I would just lash out at them and say they didn’t know an iota of what they were talking about. I was, for all intents and purposes, generally successful for my age. Fancy title, some money in the bank, respect from many others in and beyond New York City. I sewed these patches of comfort together into a quilt of ignorance, making me think that I really had it all. But then, the question that I had always been most afraid of began to pop up into my head. “Is this your purpose? Should you actually be doing this?” I would shout back at it (in a mentally sane way, of course…I think), and I would say the same thing I’d say to friends who I didn’t work with. Who I believed truly didn’t understand. “You don’t know what you’re talking about! I’m at the TOP OF THE WOOOOOOORLD!” But, the roar of the voice grew louder. The questions multiplied like mice in heat (I don’t know if “in heat” is appropriate here, but you get it). And, I had slowly and excruciatingly realized what had happened. I was breakdancing alone on the figurative dance floor of life when the music had shut off a long time ago and all of my non-work friends and family had gone home. Sort of like this without the jaw-swinging.

At that point in my life, I felt a bit like Vincent in the movie Gattaca (highly recommend it if you’ve never seen it). It’s a world in the not-so-distant-future where the idea of weeding out the genetically inferior for the superior is commonly practiced and accepted (Hitler, anyone?). Vincent (played by Ethan Hawke, if it helps to picture it) is labeled as an “in-valid,” because his parents didn’t do any genetic engineering to produce him. He’s projected to only live until he’s 30.2 years old and believed he will suffer many life-threatening diseases. Conversely, his brother, Anton (played by Leron Dean), was genetically engineered and has the prospect of a perfectly happy, healthy and successful life. Vincent eventually meets someone named Jerome (play by Jude Law) – a previous swimming star, with impeccable DNA, who’s unfortunately become paralyzed – and gets him to give him samples of hair, fingernails, dead skin, etc., so that he can apply for a job in the prestigious Gattaca Aerospace Corporation (he’s always wanted to go to space) under the guise that he is Jerome and not his inferior, in-valid self. He eventually runs into his brother, whom he hadn’t seen in a decade or two, and it turns out he’s now a detective. He knows what Vincent has been doing, in posing as someone he’s not, in order to get ahead in life. And, he plans to bring him into the authorities. But, before he does, he challenges him to a race in the ocean. When they would race as children, Anton would always kick Vincent’s ass. But, this time, as they swim far out into the distance, and a thick fog begins to surround them. “Vincent! Vincent, we have to turn back!” Anton says. But, no. Vincent doesn’t want to turn back. “How are you doing this?” Anton asks with a mix of desperation and awe. The natural reactions one has when witnessing the alchemy of the impossible becoming possible. “Because I never held anything for the swim back,” Vincent triumphantly replies. Vincent, despite the world labeling him as inferior and incapable of doing and being more, achieved the life he wanted all on his own. He decided to tell the world the two words my first prospect told me. And, he never saved anything for the swim back because he was willing to risk it all to reach the seemingly unreachable.

“I’m out,” I said as my longtime friend, mentor and CEO of the company I worked at stared back at me. I honestly couldn’t believe I said it; before this moment, I envisioned the exact situation of how and when I was going to leave playing out in over one hundred different ways. But, part of me was beyond being concerned about what others would think. Over the past few years, I had changed. I had, like Vincent, taken on so many new labels from the world I inhabited, and I wanted to break free of them. Did I know what I was doing? Yes and no. A week later, I was jobless. I didn’t know what I wanted to do, but I knew that I had to travel and take time to focus on rebuilding myself into the person I wanted to become. Fortunately, a few weeks before I left the company, a friend from high school reached out to me and said:

Hey! I’m not sure what your schedule is like within the next few months but I’m heading down to Costa Rica.. and I just wanted to send you an open invitation! I’m not sure if you’ve ever been, but I heard there’s so much to explore and learn down there. I have a two bedroom on the beach close to Quepos, so if you have time definitely come take advantage!

A case of “right time, right place?” Maybe. But, after leaving the company, I didn’t sit around waiting to ponder whether it was the right or wrong move. I looked at my savings, purchased a one-way flight to leave for Costa Rica a month later and began to tie up loose ends in New York City.

My parents weren’t thrilled about the choice, but remembered what I said years ago when I packed up and moved to Bedstuy. “I’d rather try and fail then stick around and do nothing.” The thing is that it’s not like I have a trust-fund, bonds or appreciating assets in my name. My father left Iran in 1976 before the revolution, moved to England where he met my mother, and then they moved to New York City. He worked as a courier for a Japanese company and made $3 / hour. His boss would give him $10 to take the taxi for important deliveries, but he’d check his watch, pay the dollar or so for the subway and then pocket the rest. It was this work ethic that allowed him to rise in another company and become Head of Logistics, going from making $3 / hour in the early eighties to making six-figures two decades later until the company went bust. My mother, conversely, left Jamaica when she was 17 to study nursing in England. They managed to come from relatively nothing by our American standards and build a life for five boys while supporting their families abroad. The point is, your boy doesn’t come from a place where I can live off of mommy and daddy. What I was given were two role models who would get up at the crack of dawn, commute for 2.5 hours one-way (in the case of my father) and all because they did what needed to be done. I may have no longer had a job, but I had, and still have, this sense of hard work coursing through my veins.

I was in a daze for the first two weeks after I left the company. My energy (the energy I’ve always depended on) dropped to an absolute low. My curtains were closed for 85% of the day, and I only went outside for basic necessities. I was confused, had a high level of anxiety and didn’t know what to do with myself. Picture two hands firmly pressing on each other by the palms – sort of like you’re praying really hard. I was one palm and the professional world I lived in was the other. The identity of one couldn’t exist without the other holding it up. So, I fell. But, it was then that I returned to my old friends and my family to pick me back up. Despite having pushed them away for the past few years, they were still there when I needed them most. And, new people either stepped into my life or reaffirmed their presence in it by being there for me to lean on. I didn’t deserve any of them, but there they were.

So, did I tell the story perfectly as it happened? Probably not. But, here I am. In a cafe in Costa Rica, telling you probably much more than I should. What I want to communicate is this: If you’re in a scenario that feels like you’re not living into your purpose, you are not alone. Take the necessary measures to improve your situation. You can do it, you really can. And, like Vincent, don’t save anything for the swim back. You’ll make it.


If you liked what you read, there will be more! Be sure to subscribe here to follow along. Any comments, questions (the good, the bad and ugly) are welcomed. You can also find me on Instagram, Twitter, Facebook, Snapchat (by far, the most entertaining of the channels @gourdmasterflex) or shoot me an email.




  1. Good writing as always Mateo.There is something very cathartic about ‘ putting it all out there’. I love and respect you for being your authentic self.

  2. OMG!!!! With my cup of Saturday morning coffee gone cold I sat enraptured in the reading of the best story of a young man who has reclaimed his life before it’s too late. Not in a negative sense but with an awareness that few have ever discovered or had the courage to act on. Though circumstances may have been the barrier, I can raise my hand and say that’s what I should have done or how I should have reacted on my journey. Certainly some of the sentiments expressed were my experiences, thoughts and barriers but I never acted on them. To be able to learn several lessons from this young man is absolute satisfaction to see that this generation is not settling for the status quo. I am very very proud of you and is confident you will continue to do well.

  3. This is awesome – really enjoyed reading it. Your candidness is both inspiring and admirable.

    I watched Gattaca sometime in middle school as part of a class and I hadn’t thought about it again until this post… Brought me way back.

    Best of luck in this new chapter and thanks for the late night inspiration here in Singapore.

  4. WHOA!!! I can’t even formulate the words to describe what I just read. It was a roller-coster of emotions that are still unfolding and I can’t wait to hear more about your journey and learn about who you become as you become him. Thank you for sharing your story, Mateo. This is just the beginning. PS This is one of my MANY favorite quotes in this story: “I sewed these patches of comfort together into a quilt of ignorance, making me think that I really had it all.”

    1. Thank you so much for reading, Raven. I appreciate your incredibly kind words, and am even more appreciative of being able to move you through my own story. I hadn’t read the piece in a while, and your favorite quote remembers why I’m doing what I’m doing. So, thank you for the inspiration. Excited to see your journey unfold, as well!

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