Episode 88: Debra Messing

5 Questions With Dan Schawbel

An interview with Debra Messing about how her parents supported her career, how she’s challenged the status quo, staying positive in the face of adversity, the global health crisis, and her best career advice.

Welcome to the 88th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is the star of Will & Grace, Debra Messing. Born in Brooklyn, New York, her family moved to Rhode Island to attend high school, where she acted and sang in musicals. Before pursuing her acting career, she was urged by her parents to attend college at Brandeis University. Upon graduating with honors, she attended New York University’s Tisch School of the Arts. After appearing in the film A Walk in the Clouds, she was chosen as a co-star for the TV sitcom Ned & Stacey, which led to roles in other shows like Seinfeld and Prey. In 1998, she co-starred as Grace Adler in mega TV hit show Will & Grace. The success of the show led to other roles in movies like Along Came Polly, The Wedding Date, and the remake of Dirty Dancing. More recently, Debra reprised her role in the revival of Will & Grace with a ninth Golden Globe nomination and is the co-host of The Dissenters Podcast. I had the pleasure of speaking with her about the impact of Will & Grace on the gay community, which is timely since the Supreme Court just ruled that workers can’ be fired for being gay or transgender.

The 5 questions I ask in this episode:

1. Part of why I was able to pursue my career path as an author, podcaster, and researcher was the support of my parents. How important were your parents encouraged you to pursue your dream of becoming an actress and what advice did they give you during your pursuit?
2. Your new podcast The Dissenters features nonconformists like Glennon Doyle who was recently on this podcast. In what way have you challenged the status quo and what inspires you about others who have done the same?
3. You said that acting is 90% confidence. As both a social activist and actress, you’ve faced criticism, rejection, and obstacles. How do you stay positive, confident, and motivated in the face of adversity?
4. How has your involvement and activism around HIV and Aids in Africa shaped your understanding of the global health crisis we are dealing with today?
5. What is your best piece of career advice?

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