Uploaded May 2025 | Updated September 2026, 3 days ago
What does it take to make a bold career pivot after decades of doing the expected? This week, the multi-talented Anna Kendrick joins Jessi in the studio to share her journey from acclaimed actor to first-time director, offering invaluable insights for anyone thinking about making the leap into something new. Anna shares the story behind her directorial debut with Netflix’s Woman of the Hour, a true-crime drama. Watch Woman of the Hour on Netflix now, and tune in to hear how Anna Kendrick is embracing the next chapter of her career.
Tune in for Anna’s take on:
•The courage it takes to step out of your comfort zone
•How to follow your intuition when making creative decisions
•Dealing with imposter syndrome
•Learning to lead
Subscribe to the #HelloMonday newsletter for more on building a work life on your own terms. bit.ly/HelloMondayNewsletter
#hellomonday
#annakendrick
#careerpivot
0:00 Intro
2:48 Anna talks about struggle to break into Hollywood
6:19 Anna talks about how she learned to change course in her career
8:52 Becoming a director of Woman of the Hour
12:17 Being both the main character and director
15:26 Anna talks about new skills she learned as a director
18:10 How Anna handles feedback and reviews
19:41 Anna talks about what drew her to direct Woman of the Hour
21:24 Anna talks about her goal for the film
24:16 Anna reflects on personal thoughts and preparing for film
26:03 Anna’s career path moving forward
27:45 Conclusion
What does it take to make a bold career pivot after decades of doing the expected? This week, the multi-talented Anna Kendrick joins Jessi in the studio to share her journey from acclaimed actor to first-time director, offering invaluable insights for anyone thinking about making the leap into something new. Anna shares the story behind her directorial debut with Netflix’s Woman of the Hour, a true-crime drama. Watch Woman of the Hour on Netflix now, and tune in to hear how Anna Kendrick is embracing the next chapter of her career.
Tune in for Anna’s take on:
•The courage it takes to step out of your comfort zone
•How to follow your intuition when making creative decisions
•Dealing with imposter syndrome
•Learning to lead
Subscribe to the #HelloMonday newsletter for more on building a work life on your own terms. bit.ly/HelloMondayNewsletter
#hellomonday
#annakendrick
#careerpivot
0:00 Intro
2:48 Anna talks about struggle to break into Hollywood
6:19 Anna talks about how she learned to change course in her career
8:52 Becoming a director of Woman of the Hour
12:17 Being both the main character and director
15:26 Anna talks about new skills she learned as a director
18:10 How Anna handles feedback and reviews
19:41 Anna talks about what drew her to direct Woman of the Hour
21:24 Anna talks about her goal for the film
24:16 Anna reflects on personal thoughts and preparing for film
26:03 Anna’s career path moving forward
27:45 Conclusion
