How I Went From Homeless, High School Dropout to Harvard and MIT
And the 3 Things You Should Know About Achieving Your Dreams
“To be nobody-but-yourself — in a world which is doing its best, night and day, to make you everybody else — means to fight the hardest battle which any human being can fight.” — E.E. Cummings
It’s back to school season, and many of us have already started thinking about 2021. If you’re anything like my friends, you’re thinking about what’s next for you and career, and how to make the most of the *dumpster fire* (I mean that in the most loving way…) that is 2020. For many of us, we’re using this time to reset by setting new goals.
We’ve all had big, near insurmountable, Mount Everest-level, goals. I call them BHAG’s — big, hairy, audacious goals. Often, we set BHAG’s after a moment, or in the case of 2020, a year of disappointment when we feel like we didn’t live up to our own standards. For me, that first moment of disappointment came at 17, as my vice principal kicked me out of high school and pointed to her degree, echoing what my guidance counselor had been telling me for years — I would never get a degree because people like me weren’t cut out for school.
Joke’s on them.
Do I sound a little salty? That’s because I am — or I was. If you’ve ever eaten potato salad, chicken, or frankly any food without salt, you know that life without salt is pretty bland. Salt adds flavor to your success journey, and I’m here for the flavor.
Anyway, at 17, I set a BHAG so big, it took me almost 20 years to accomplish it. Along the way, I endured the humiliation of being a square peg struggling to fit into a round hole, navigating life like a game of snakes and ladders. Some days I’d lose (hello, dead-end, telemarketing job!), and other days, I’d win (goodbye, homeless shelter!). In the Subtle Art of Not Giving A F*ck, Mark Manson talks about embracing change by embracing the pain that comes with the process of changing on the journey to success. For me, that meant confronting an education system that had already rejected me. My BHAG was simple: get a degree — but in order to do that, I’d have to face the fear, anger, and discomfort of “traditional” education.
Except, I didn’t.
“The most fulfilling human projects appeared inseparable from a degree of torment, the sources of our greatest joys lying awkwardly close to those of our greatest pains…”
— Alain de Botton
Once I was out of school, I quickly realized the difference between education and learning. Showing up every day from 8am–4pm to take direction from a bunch of adults who have been trained to tell you that you know nothing and will be nothing without their guidance is what many of us lovingly recall as “education”. Conversely, challenging conventional wisdom about the value of an education system that treats young people like empty vessels, devoid of meaningful, lived experience is learning. And once I was out of school, it turned out that I loved to learn.
Within a year of dropping out, I had gone from a homeless, high school drop out to outspoken teen activist and entrepreneur. I taught myself how to code and started freelancing for extra cash (goodbye, telemarketing job! hello, new apartment!). I learned how to speak up around decision makers and throw down with emcees (because hip hop saves lives). I made friends with smart people who taught me how to read municipal budgets, analyze government policies, and call out political double speak. Those smart people became my teachers, and then my mentors, and finally my friends — and I achieved all of this before the age of 21.
Today, I’m a Harvard grad now preparing to do my second graduate degree at MIT. When I’m asked about what it took for me to get here, I realize that everything I ever needed to know about success, grit, and ambition I learned in those years from ages 17–21.
If you’ve got a BHAG of your own, here’s your cheat code* to success:
Lesson 1: Define success on your terms.
There’s a common misconception that success is synonymous with money or fame. Many of our institutions — education, work, etc. — are designed to drive you toward the pursuit of one or the other (or both). However, if you look at some of the most successful people in the world, they didn’t set out to become rich and famous. They set out to be really good at one thing — better than anyone else. Toni Morrison wanted to be a good writer. So, she became an editor to get access to the tools she needed to write. Zuck, for all of his company’s flaws, built Facebook because he wanted to be noticed and wanted the power to notice others. So, he built a network for people who wanted to be seen.
The best way to win is to do it on your own terms. So, create your terms. Define what success means to you and use that to guide your decisions.
Lesson 2: Choose your teachers.
“A child cannot be taught by anyone who despises him, and a child cannot afford to be fooled. A child cannot be taught by anyone whose demand, essentially, is that the child repudiate his experience.”- James Baldwin
It’s hard to learn anything from a person you don’t like or respect. It’s even harder to learn from someone who doesn’t value or respect you. The beauty of living in the digital age is that, with a little time and dedication, you can learn almost anything. But skills alone will only get you so far. So, figure out what you want to learn and then find someone who can teach you.
It’s important to find someone you respect and who respects you in return. They don’t need the official title of “teacher” to teach and you don’t need the official title of “student” to learn. In fact, you don’t even need learn in a classroom. Just orient yourself towards learning and growth — approach all of your professional relationships as a student rather than an expert — and you’ll get all the things education promises to do, but tailored to the learning you specifically need.
If you believe that experience is the best teacher, then turn the world into your classroom and be sure that what you’re learning and who you are learning from are setting you up for future success.
Lesson 3: Go for it. YOLO, fam.
“Started from the bottom, now we here…” — Drake
Thousands of people have dreams of attending the most prestigious educational institutions in the world and never get in — not because they were rejected, but because they never tried in the first place.
In fact, many of us talk ourselves out of BHAG’s because in our minds or the minds of the people around us our goals sound far-fetched and unrealistic.
“I could never get into Harvard. I was a bad student in high school.”
“I could never launch my business idea. I know nothing about business.”
“There’s no way they’d hire me. I don’t have all of the qualifications listed in the job description.”
If you do this, stop.
Stop it right now.
Chances are there’s a little voice in your head interpreting your ambition as danger. In response, your mind attempts to guide you to safety. In this context, “safety” means predictability, which means control — and we all feel safe when we’re in full control of our environment. So, it’s understandable. But understand that BHAG’s, by nature, are supposed to shake up your life. So submit that application, apply for that job, and shake up your life.
Here’s another way to think about it:
Setting an ambitious goal is like riding the world’s tallest roller coaster. It starts slow enough for you to feel like you can manage it and as you begin the ascent to the initial peak and experience that first, stomach-turning, adrenaline-inducing drop, you begin to wonder if you made the right decision. But by then, the momentum has picked up. You can’t quit in the middle of the ride. Jumping off mid-ride is potentially fatal. All you can do is commit and ride it out. So do that. Ride it out. You only live once, and at the end, as your racing heart recovers, and your vocal chords rebound from the shrill screams of petrified fear, realize that the fear you once felt is immediately replaced by feelings of accomplishment the moment the ride ends. You’ll hop off the ride and walk away confidently knowing that you did that.
To borrow a familiar phrase, “Just do it.”
Take My Advice
There are a ton of lessons about how to make it and win against the odds. So, obviously take my advice with a grain of salt. But if you ever find yourself setting a massive, seemingly unattainable goal, with the odds stacked against you and no solution in sight, just remember this: Every goal you achieve brings you closer to becoming who you’re meant to be. This makes BHAG’s essential points of interest on your success roadmap — they help you leap forward and transform into the kind of person you can be proud of. Every win you achieve, big or small, only reinforces that idea. So do what needs to be done and push ahead. It may take you two years or it may take you 20, but you’ll get there. Trust me. I know.
Keep going. You got this. I’m rooting for you.
*There are no real cheat codes. Do the work.
