An interview with Alyssa Milano on how her family influenced her career, how to overcome the fear of rejection, when she decided to be a political activist, how to stay true to yourself instead of conforming and her best career advice.

Welcome to the 29th 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 actress, political activist and podcast host Alyssa Milano. Born in Brooklyn, New York, to a fashion designer mom and film-music editor dad. She began her career at the age of 7 when she auditioned for the national touring company of Annie. She was selected from over 1,500 other girls for one of the top parts. During the tour, her and her mother were on the road of 18 months. Then, when they returned, Alyssa appeared in several television commercials, off-Broadway shows and eventually landed an agent. Milano made her film debut in the coming-of-age drama Old Enough, which won First Prize at the Sundance Film Festival, then had her big break as Tony Danza’s daughter on the sitcom Who’s the Boss? Since then, she’s had other famous roles including on Melrose Place, Charmed, Wet Hot American Summer: 10 Years Later and her latest, Netflix’s Insatiable. Her latest project is her podcast called Sorry Not Sorry, where she tackles social, political and cultural issues as she speaks to key figures.

The 5 questions questions I ask in this episode:

How did your family influence and support your early career?
How do people overcome the fear of rejection in your industry?
When did you decide to become a political activist?
How do you stay true to yourself instead of conforming?
What is your best piece of career advice?

Follow Alyssa’s journey:

Episode 29: Alyssa Milano