Learning to Bet On Myself

“Tell them your story. How you made it here.”

When talking about this first blog post with a close friend of mine, this is what she said. She knew me before the coaching, when I was in the midst of the biggest transition of my life. She helped me feel seen and understood. She helped me bet on myself. So, this one is for you Taina Figueroa.


Born and raised in the gritty West Bronx, I was (and am still) a short, awkward, half Dominican, half Puerto Rican ball of thunder (firecracker some would call me). I was raised mainly by my mother, a single woman born in the Dominican Republic. Together with my younger brother, we lived most of our lives stuffed in a Bronx apartment with my Abuela, aunt, and uncle.

Strong independent women raised me. They taught me to always have enough to care for yourself, and to work hard to provide for your family. Their ultimate value was stability, that what a good life was, and stability can only be guaranteed by money. At times my mother had two jobs. Depending on the season, my Abuela had different hustles. In the summer, selling food. In the winter, recruiting other immigrants and first-generation folk for a local tax agent. This was never fun, but the good life doesn’t guarantee good feelings, only stability and stability demands sacrifice.

My mother (and father) both made it clear that education would be the key to securing the good life for myself. I was to become a professional in something that made money. Having money means you don’t have to struggle. I ran with science, which started as an interest in medicine. Having Dr. in front of my name guaranteed me a good life, right? I started on the road of pre-med, which led me to the Posse Foundation, the non-profit that first recognized me for my leadership. Posse exposed me to the transformative power of facilitation, holding true space for my self growth for the first time. Posse bet on me, they took a chance by saying I embodied leadership. I didn’t even know what that meant.

Pre-med turned into neuroscience, (I could still be a doctor but not have to take the evil that is organic chemistry) which turned into a pursuit of a PhD. It was instilled in me by my immigrant matriarch that at best one could like what they did for a job or career. They almost certainly would never love it. It didn’t matter how you felt, all that mattered was providing for your family. Good job, good money, good life. PhD would allow me to have it all without making the type of sacrifices my parents did. Except I was, only worse, sacrificing myself.

A year into my PhD, I heard “you’re unhappy” echo across the phone. My boyfriend saw in me what I did not want to admit. I didn’t want to admit that this life didn’t feel “good”, and that I was slowly losing who I was for a pipe dream of stability that I wasn’t sure was even real. I pushed down the feelings of discontent. “This process isn’t about happiness”, I rationalized. This is about survival. This was about Dr. Marrero. This was about stability. This is about the good life.

But he heard my ache - the ache that asked what about me, when would it ever become my life? When would I feel joy and good?

Suddenly, I became hyper aware of the fact that my “good” life was never mine - it was a version of what my parents, mentors, and society wanted it to be. I was sold on the dream that I would be living a good, worthy life if I was on that path to doctor. Never did I realize I had never asked myself what I wanted my good life to look like. Never did I realize I even had the ability to ask that question. Never did I bet on myself.

I gave into the ache, I became driven to fill this void with something, that thing that people who loved their work had in their eyes. I was searching for passion. Did I ever feel it before? Did only certain people ever really get to feel it? Was it even real?

I knew it was real - I saw it in my beloved when he performed. I felt it when I was at those Posse workshops and leadership trainings. I felt it when I was amongst those seeking their own reclaiming. While I didn’t know what to do, what my good life was going to be, or even if I could do it, I decided to run with the possibility. I decided it was better to be about something that mattered to me then live as an actor in someone else’s dream.

So the journey began, first by giving myself the permission to take my power back and figure out what it felt like to truly want something. I never knew what it felt like to choose something based on my own desire, to silence the sound of all around me and turn inward. It took practice, patience, and a lot of tricks from self-help.

I knew the type of spaces I wanted to be in, but I didn’t even know if they existed. Leadership was a common theme in my life. The word led me to the places that felt like home, so I used it as a guide. I attended a training that introduced me to an industrial and organizational psychologist. I found myself on the edge of my chair as he facilitated the activities. The whole day I felt like I was playing, I was excited and completely driven to do more. This was passion. This is what I want to do for others

Within less than a year, I moved to the Midwest with my beau and started pursuing a higher degree in learning and organizational change (this time because I wanted to). This time because I knew I wanted to be on this path to home, to passion, in my power. This time I bet on me, instead of the stories about who I should be.

Fast forward to now, I am facilitating workshops and coaching individuals of different backgrounds. I went from following to leading, from being powerless to embodying my power. That’s what I seek to gift others through my work. I was never taught to investigate my inner narrative, but without taking the time to do so I would have never realized I was living as a character in someone else’s story. I wouldn’t have ever bet on myself. I wouldn’t be here.

We all need to take a hard look at our lives to see if the lives we are living are truly ours. This year let us reclaim who we are, what will be our story, and determine what it is to truly want. When we do that, we bet on ourselves, which is the most valuable investment you could ever make.

I wonder, dear reader, how will you bet on yourself?