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10 Questions with... Simon Cataldo!

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Simon Cataldo, a REALITY participant, is Founder and President of Harlem Lacrosse and Leadership (HLL). HLL is a school-based nonprofit organization that provides academic intervention, leadership training and lacrosse to at-risk youth. Simon recently launched an Indiegogo crowdfunding campaign to raise money to expand his organization to include programming for girls.

1. What inspires you to get out of bed every day? The possibility that I can do something to change someone’s life path in a positive way; the possibility that if I don’t, an opportunity will be lost. 

2. What three hashtags would you use to describe yourself? #hopeful #relentless #Jewish

3. What projects are you working on now? In my capacity as President of the Board of Harlem Lacrosse & Leadership, the 501(c)(3) nonprofit I founded during my time as a Teach for America teacher, I lead our geographic expansion and fundraising efforts. I am also currently the Managing Editor of the Virginia Law Review. In that capacity I am in charge of our production and the business side of running the journal. In my spare time, I try to keep up with my law school classes. That last endeavor has been less than successful as of late.

4. What projects would you like to be working on in 5 years? I came to law school hoping to become a prosecutor of organized criminal activity but the success and growth of Harlem Lacrosse & Leadership has tempted me to devote my professional life to the organization. Next year I will be clerking for the Honorable William Kayatta on the First Circuit Court of Appeals. After that, I will decide on a next move. Whatever I am doing in five years, I want to be making it easier for a child to grow up in a world that is safe, happy and filled with opportunity.

5. What it is the biggest risk you’ve taken, personally or professionally, and how did it pay off? Staying in Harlem for a third year (TFA is a two-year commitment) to launch Harlem Lacrosse & Leadership was one of the biggest risks I’ve taken. No one had tried to do what I wanted to do (school-based, full-day, year-round intervention and lacrosse training). I had no fundraising experience or corporate experience—all I knew how to do was teach, coach and tell a good story. Turns out the last one was all I needed to get enough support to get us off the ground. Staying for that third year was the best decision I ever made. I learned how to lead and listen to both kids and adults. I found myself by founding an organization that inspired—and continues to inspire—people I respect and love.

6. Where do you go to find community? Many places, but the REALITY community has been a powerful and enduring touch point for many areas of my life. Probably most important, it is within that community that I am reminded to pause, reflect, reboot and plan for the future. Additionally, I am reminded that I am Jewish, and that I am surrounded by other Jews who have similar aspirations to my own in terms of the change we want to see in the world. Finally, there’s something about knowing there’s a group of people out there who will support you as long as you keep pressing on and making change that is indescribably valuable.

7. Where do you go to find solitude? I grew up in Concord, Massachusetts. There is a quiet spot, not visible from any buildings, by the Assabet River in West Concord where I go by myself two or so times a year and think about what I want to do with my life.

8. What is one change you would like to see in your lifetime? It’s a big one. I want every child in America to grow up with the true and tangible ability to reach her full potential as a person and a professional. That’s not the country in which we live today, but it can and should be.

9. Who is your hero? I have four. Jake Klein, Joel Censer, Sasha Klimczak and Wyatt Melzer. They are the Program Directors for Harlem Lacrosse & Leadership and they do the most amazing work I have ever seen, day after day, under difficult conditions. They don’t just care about those kids—anyone can say that—they transform children’s life paths, and it’s the most beautiful thing I’ve ever seen.

10. Rock, paper or scissors—and why? Paper. Because you can write a thank you letter on it.

Read more about Simon's work in his guest post! The Schusterman Philanthropic Network is proud to empower emerging leaders to explore their values, identity and new ways to strengthen their communities. We believe that as we work together to repair the world, it is important to share our diverse experiences and perspectives along the way. We encourage the expression of personal thoughts and reflections here on the Schusterman blog. Each post reflects solely the opinion of its author and does not necessarily represent the views of the Foundation, its partner organizations or all program participants.