On September 1, 2015, I emailed my resignation letter and walked away from my teaching salary, benefits, and gulp…pension.
I may not have considered myself an entrepreneur then, but that was undoubtedly my first day as an entrepreneur.
Quitting my job, but not for the first time.
Throughout my life, I’ve made a habit of walking away from everything to try something new.
I left home at 16 with a suitcase and a dream. Landing my first job at 17 (by telling them I was 18), I spiraled into a stream of amazing—and sometimes not-so-amazing—experiences. At 21, I bought a one-way ticket to Los Angeles and six years later moved back to Chicago. All this with just one suitcase to my name.
And at 35, I quit my career as an educator to start Nerdy Media.
Over the years, I’ve resigned from a number of jobs to pursue various opportunities. But the decision to quit teaching after only 4 years felt…different.
Teaching was the most challenging job I’ve had, one where I somehow figured out what the heck a pedagogy is and for 4 years facilitated learning experiences for over 300 students across four very different public high schools in Chicago.
The weight of guilt lingered long after I made my choice. It wasn’t the salary, benefits, or pension I missed—it was the 60 mischievous, misunderstood, and striving teens who I worked tirelessly to inspire.
My decision was difficult, but it was also well considered. I didn’t just wake up one day and dive into entrepreneurship. I contemplated, debated, and wrestled with the pros and cons—right up until the very moment I clicked send.
But by realizing the strength of my unique skill set, I made the decision to resign and start the nonprofit I’d been thinking about. Being a nerd is an asset I’ve always relied on, one that has been my job stability and one that I felt confident would help me on my new path.
I quit my last job with more than a suitcase to my name, but questions linger: Was it a mistake to quit? Am I chasing a dream?
The same goal, but a different path.
After spending time with Chicago’s teens in a traditional classroom, I founded Nerdy Media, a 501c3 nonprofit, to reach our city’s disconnected youth in a new way.
Nerdy Media is the culmination of my educational and professional experiences. But it’s not just a chance for me to develop professionally; it’s an investment in Chicago’s underserved communities. It’s equipping our teens with the know-how to not only take advantage of opportunity, but to create it for themselves.
More than anything, it’s a business with a mission: to inspire Chicago’s youth and help them develop 21st-century skills for sustainable employment.
Entrepreneurship: lonely, difficult, exhilarating, and worth it.
As the founder and executive director of Nerdy Media, I am what’s called a social entrepreneur. Many entrepreneurs design and market products intended to make a profit. I develop, fund, and implement solutions that address social, cultural, and environmental issues.
When I first started Nerdy Media, social entrepreneurship was a foreign concept among my family and friends, who often looked at my new profession as nothing more than unemployment.
Even without misperceptions like this, the leap into full-time entrepreneurship is lonely, busy, and filled with self-doubt.
The 40-hour workweek? Now 80 hours, plus. Supervisor instructions, progress evaluations, and rewards? Not anymore! After countless bosses delegating countless tasks, I’m now both boss and employee.
Another truth is that entrepreneurship is inevitably full of failure. Nerdy Media endured a number of setbacks and failures until we finally pivoted through self-directed learning into an organization with potential for innovative social impact.
My first 16 months as a social entrepreneur have been challenging, but it’s been worth the effort: within a year, Nerdy Media has evolved from vision to strategy to action and, finally, to social impact.
And the family and friends who once discredited entrepreneurship? They’re now considering their exit plans and seeking my advice.
The challenging yet rewarding lifestyle of entrepreneurship is appealing, but it’s also a long-term investment requiring tenacity to see a return. It’s not glamourous, and it’s not for everyone—but I do believe that entrepreneurship is something that everyone can learn.
If you’re considering a leap into the unknown, I’d like to share three key concepts I’ve learned from my first year as a social entrepreneur with Nerdy Media.
Key lessons from my first year of social entrepreneurship.
1. Life is a tradeoff.
If I had a dollar for every time my mother said, “Life is a series of tradeoffs,” I would own a small island and have decent passive income because she continues imparting this life lesson to this very day.
In fact, when I called my mother to tell her about my plans to leave education and enter the world of social entrepreneurship, I justified my decision with her own words.
To figure out how to make Nerdy Media work as a sustainable nonprofit, I traded off a lot: going out on the weekends, attending my best friend’s destination wedding, and doing countless other small things that added up over the course of a year.
And these days? I sound like my mother: like life, social entrepreneurship is a series of tradeoffs.
In her blog post entitled “The Key to Unlocking Your Happiness,” life coach Laura Coe states that happiness is attained by taking action from the soul. And I take this advice to heart as much today as when I first started on this path.
Happiness is not about everything being perfect according to other people—it’s about finding what you want and acting on it. And if you want to be a social entrepreneur, it means understanding the tradeoffs you’ll have to make, and then committing yourself to making them for the long haul.
2. Challenges must be embraced, not rejected.
Some call it drive, some call it persistence, but Stanford University psychologist Carol Dweck calls it a growth mindset.
What exactly is a growth mindset? It’s the belief that learning and taking on challenges increases your abilities and improves your chances for success.
In her book Mindset: The New Psychology of Success, Dweck explores two types of mindsets:
- Growth, in which problems are embraced as opportunities to learn.
- Fixed, in which avoiding failure (and, thus, problems) is prized
It turns out that a growth mindset is absolutely key to social entrepreneurship—something I learned the hard way.
For me, 2016 was the year of “no.” I rang in the new year optimistically writing grants, started receiving rejection letters in March, began cold calling to pitch our first program, and ended up with exactly zero opportunities throughout the summer.
But what my commitment to a growth mindset means is this: they may be saying “no,” but I hear “not yet.”
3. Flexibility isn’t optional.
So what happens when Plan A just isn’t cutting it? What happens when your first, second, third, and fourth grant letters aren’t accepted?
The first grant rejection letter was a blow to my self-esteem…for about 5 minutes. I realized that when plan A fails, you can’t take it personally—but you can pivot.
In fact, Plan B, C, D, X, Y, and Z are the tools for innovation.
Receiving criticism and feedback—even in the form of rejection letters—is a gift. People taking the time to identify opportunities for growth or to give you recommendations for improvement reflects an interest in your success.
Oftentimes, entrepreneurs dedicate themselves tirelessly to a vision until they believe it’s perfect, and they get offended when an experienced set of eyes pokes at the holes. (And trust me, there are always holes.)
Instead of worrying or feeling hurt, I welcome these opportunities as a time saver. Insights from experienced people save both time and resources, letting you adapt and refine your process until you finally hit that successful Plan Z.
As famed businessman and philanthropist Andrew Carnegie said, “No man will make a great leader who wants to do it all himself, or to get all the credit for doing it.”
Flexibility means letting go of unrealistic standards, embracing change, and accepting help in all its forms. After all, the freedom to say “I don’t know” is simply another opportunity to know.
Looking forward, not backward.
Every entrepreneur has a unique set of abilities and personal story. Risk takers like Steve Jobs, Elon Musk, and Madam CJ Walker relentlessly pushed innovative ideas to market and evolved industries that resulted in stronger economies.
To me, entrepreneurship represents the desire, opportunity, and decision to take action. And Nerdy Media is my action toward happiness—not just for me but for teens throughout Chicago. It’s a practice in embracing challenges, listening to criticism, and pivoting for innovative sustainable growth.
In sharing this experience, I’ve realized one thing for certain: it’s time to stop contemplating the pros and cons of a job I quit over a year ago and truly embrace the journey of a social entrepreneur.
Sharing my story through Nerdy Media’s workshop, Wearing the Crown.
As demonstrated by the reaction of my family and friends, taking the risk to pursue social entrepreneurship is a bold statement.
But I believe that quitting a job and launching a nonprofit reflects my passion for professional growth and is a significant step toward my goal of building up our marginalized communities, which is needed now more than ever.
Chicago’s underserved youth are navigating a stigma of failure. They were the children left behind by the educational system, our politicians, and the media—and now they’re tasked with countering the negative perceptions forged by those same institutions.
As a social entrepreneur from Chicago’s south side, my story is a powerful illustration of the opportunities that our youth can—and should—have.
Drawing from my own experiences and the key concepts of social entrepreneurship, Nerdy Media’s first program, Wearing the Crown, takes a social and emotional approach to empower Chicago’s youth to realize their potential.
An activity-based workshop, Wearing the Crown is designed to engage and inform Chicago’s disconnected youth, equipping them with a 21st-century perspective of the modern job market.
Through discussion, games, and other interactive activities, the workshop covers several key employment-related topics:
- Acquiring transferable skills
- Transforming those skills into careers
- Understanding the economic realities of today
- Developing sound financial decision-making for higher quality of life
At the end of the workshop, youth participants declare their best skills by writing them inside crowns that they wear proudly.
Wearing the Crown is a resource for organizations to strengthen employment readiness programming, the first of many initiatives on my path to a sustainable nonprofit that pushes for real and innovative change.
I hope you’ll join me as I continue developing Nerdy Media and reaching Chicago’s disconnected youth. I’d love to hear your opinions, experiences, and advice.