Anna Kendrick has earned our applause. Now she is asking for our trust.

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Anna Kendrick Talks Career Reinvention, Imposter Syndrome, and Finding Her Voice

I don’t envy people who find career success early in life—especially the kind that brings them spectacular public attention. I’ve interviewed many of these folks over the years: soccer star Abby Wambach, NFL player Vincent Fuller II, and Arthur Brooks. Today, we know Arthur as an accomplished author and thinker, but did you know he spent his early career as a professional French horn player?

People who achieve early success often face a similar career crisis, no matter their field. They slow down… or grow older… or get bored. They need change. But once you’ve been rewarded for being one thing, the world rarely encourages you to become something else. It wants more of what you’ve already done well.

So how do you grow into someone new—when everyone’s still applauding the old you?

Take Anna Kendrick. She was nominated for a Tony Award for her very first Broadway performance—at just 12 years old. She’s worked nearly nonstop since, earning a reputation for her sharp comedic timing and incredible voice. I’ll always think of her in Up in the Air opposite George Clooney. My kids? They’ll always think of her as Poppy in Trolls (2016), Trolls World Tour (2020), and Trolls Band Together (2023).

That’s the context for my recent conversation with Anna. Her success follows her—inescapable and well-earned. But now, on the cusp of turning 40, she’s in a vulnerable moment. After nearly three decades of playing the roles others gave her, she’s ready to try something new. She’s not just thinking about it—she’s doing it.

In this conversation, we talk about what it’s taken for Anna to direct her first feature film, Woman of the Hour. This is her first step into authorship—into becoming the kind of creator who gets to shape the whole story. And yes, she feels vulnerable. She says so plainly. And you can hear it, too, in the way she talks about how she got to this moment and what’s at stake.

Here are a few of the things we explored:

• What it means to grow when the world wants you to stay the same
• The power of listening to your intuition, even when it contradicts your résumé
• Why imposter syndrome often gets louder when you try something brave
• Learning how to lead for the first time
• Redefining what success means—to you, and only you

I’ve been thinking about something Anna said—she said it early on, and again as we wrapped up:

“If I get out of my own way, I will know what to do.”

Maybe that will stick with you the way it’s stuck with me.

Be sure to check out Office Hours!

We’ll be taking this conversation to Office Hours this week. I will go Live from the LinkedIn News Page to chew on the episode’s ideas with you. You can find us right here on Wednesday afternoon at 3pm EST.

Hello Monday is LinkedIn News’ weekly podcast about the changing nature of work—and how we must change to keep up. It's hosted by me, Jessi Hempel. Subscribe to the show's newsletter.

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