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

After three decades of playing similar roles, a Hollywood talent attempts a career pivot

I don’t envy people who find career success early in their lives, especially the kind of success that brings them spectacular amounts of public attention. I’ve interviewed so many of these folks over the years. They are people like soccer star Abby Wambach, or NFL player Vincent Fuller II, or Arthur Brooks. Today we know Arthur as an accomplished author, but did you know that until he was in his early 30s, he was 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?

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Take Anna Kendrick. She was nominated for a Tony Award for her very first Broadway performance, when she was just 12. She has pretty much worked ever since, and she’s distinguished herself as master of comedic timing with an incredible voice. I will always think of the 2009 film Up in the Air in which she starred opposite George Clooney. My kids, by contrast, will always think of Poppy in the Trolls movie (2016)—and Trolls World Tour (2020)—and Trolls Band Together (2023).

This success is the context to my conversation with Anna. It’s the thing that follows her, that can’t be and shouldn’t go unrecognized. But Anna is in a vulnerable career moment right now. She turns 40 this summer— that’s nearly three decades of playing similar roles, of letting others make the calls about how those characters show up. She’s ready to try something new, to be somebody new. In fact, she’s trying.

In this conversation, we dig into what it has taken for Anna to launch her directorial debut, a film called Woman of the Hour. The movie is her first effort at stepping into a new role, and she feels vulnerable. She straight-up says this, and also we can hear it as she describes how she got to this spot, and what’s at stake for her.

Here are just a few of the things we talked about:

• 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 resume

• 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 keept thinking about this one thing Anna said as we sat down, and then again in our conversation. I leave it with you:

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

Also, this episode won a Telly!

I’m proud to share that Hello Monday with Jessi Hempel has won a Bronze Telly Award in the General—Video Podcast category! Specifically, the award recognized video we created for this episode featuring Anny Kendrick. The Telly Awards honor excellence in video and television across all screens. Established in 1979, they recognize standout work from creators around the globe—from broadcast networks to independent creators and branded content. Our entire team of editors and producers is honored to be included among this year’s winners.

And: what exactly is happening with jobs?

If you don’t follow LinkedIn’s chief economist, Karin Kimbrough, you should. She’s really good at helping to decode what may be going on with employment based on LinkedIn’s Economic Graph. That’s the name w use to describe all the data on LinkedIn. You know, 1.2 billion members. 69 million companies. 140,000 schools.

Karin recently posted about what she’s seeing right now. Yes unemployment remains stay at 4.2% and the Bureau of Labor Statistics jobs reports continues to post solid gains. But LinkedIn’s Workforce Confidence Index reveals that peoples’ confidence they’ll be able to find new jobs keeps dropping (particularly among Gen Z). Meanwhile, hiring is down nearly 7% year over year. Financial Services is the only industry with increased hiring.

This is the information I’m watching as I program Hello Monday for the year. It’s why so many of our shows this year are pragmatic and aimed at equipping all of us with the skills to compete in an increasingly tough job market, to make it up as we go in service of remaining both relevant and satisfied in the future.

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