Deanna (Della Cioppa) Colon, Class of 1991

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Deanna (Della Cioppa) Colon graduated with the WHS Class of 1991 and is currently living in Simi Valley, California.

What are you currently up to?

Currently, I am an entertainer wearing many hats including singer and songwriter, television and radio host, actor and vocal coach. I have written songs for Sophia Grace, Cody Simpson, and Charlie Wilson, and have had over 100 film, advertisement and television placements. I have had the privilege to work or perform with Stevie Wonder, Celine Dion, Nick Jonas, Justin Bieber, and Paul Abdul. I’m also a solo artist and one of my songs, “Higher,” made it to three on the Billboard dance charts. Recently I performed at the Radio City Music Hall for the quarter semifinals for America’s Got Talent. The thing about this business is that you have to be self-promoting, self-motivated and self-disciplined.

What is a recent accomplishment that has come from your passions?

I am a body positivity, self-love advocate. When I was younger, there were very few plus size people that I could look up to. Now eyes are opening to the fact that people need to be more inclusive to people of all colors, sizes, abilities, and gender preferences.

Specifically, I am very excited that I was able to participate in Master Chef’s Season 10. Even though I have never worked as a cook professionally, I did grow up in my family’s restaurant and learned from them at home. So with sheer trust and belief in my own abilities, I took the risk to audition. There were months of auditions and tests and interviews. But how exciting to get the call to cook for Gordon Ramsey, Joe Bastianich and Aarón Sánchez and to garner a coveted apron for my homemade ravioli. It validated me as a chef and someone in the culinary world. Since then I’ve been working on pop up demonstrations, in-home lessons, and perhaps a cooking show.

Was there a moment during your time at Winchester High School that led you to pursuit your passions?

High school is really hard, and I struggled at WHS to find my identity and to fit in. People perhaps judged me because I was “the bigger girl.” But during my senior year, my class rallied and signed a petition to have me sing the national anthem at graduation. It was then I finally realized my place, my home, was on the stage. There I felt special, that I had something special to share. Whenever I got behind the mic, that was when I felt loved by my community.

I never intended to go to college. Next to my name in the graduation edition of the Red and Black was “move to NYC to become a singer.” Luckily I was discovered by a talent agent at Berklee College of Music, was offered a full scholarship, and after taking a year off between high school and college, graduated with a degree in music business and management. That moment when my classmates rallied behind me was a pretty huge turning point for me. It gave me the gas to pursue a business that is really challenging, and even harder not to give up on yourself. The entertainment industry is a lot like high school with that need to be in the cool club.

My advice: you don’t have to believe in yourself 110 percent, but you have to believe in yourself enough to never give up. Persevere. The belief has to outweigh the doubt.

What connection do you still have with Winchester?

My parents have only recently put their house on the market and are soon to be Vegas-bound. They have been my primary connection to town. I love that regardless of your relationships in high school, we’re all friends on Facebook now. Social media allows us all to stay connected.

I am also proud of my little town, especially the way they have supported the Doherty family after the loss of Glen, our hometown hero. When I see how the community comes out for races and supports the Foundation, I am reminded of the limitless capacity Winchester has to show love for its neighbors.

Any wishes or advice for current students?

I’m always really saddened by the statistics of suicide and heavy drug use, violence, infidelity, poverty. There are so many horrible and serious worries in this world. But if we were to put all of our troubles out for comparison, we would quickly take our own problems back.

I wish I knew about the power of perspective earlier. Your life is your life, and it is a gift. That perspective would have helped me navigate the hills and valleys of my life. With health and love in your life, you are a billionaire. Those are the things that really matter. There are going to be gray days, but there are sunny ones too. Just hold on and don’t give up. That’s the message.

Find Deanna on Twitter: @deannabombchica, her website: IamDeanna.com, or on Facebook. She also teaches vocal lessons long distance through Skype: lessons@iamdeanna.com.