Don’t know your next career move? Start with a map.

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Embracing Ambiguity, Reinvention, and Self-Leadership with Caroline Wanga

A few of us grow up knowing exactly what we want to do. And if we're lucky, it all works out. Most of us aren't really sure. We happen into jobs, explore career paths, try things that don't work, and then change direction and try new things. We get halfway through our careers and realize our passions have changed, or the industry has changed, and we need to reinvent ourselves. It's time for the next move.

But what is the next move? And what if you don't feel like it's open to you? That decision about what to pursue can become paralyzing.

This week, I sat down with Caroline Wanga, CEO of Essence Ventures, and someone whose career path is anything but conventional. Caroline started as an intern at Target, and rose to the C-suite. For a young person, she was remarkably intentional in how she did this. She didn’t climb a ladder; she drew a map. And then she redrew it, again and again. Her story is a masterclass in embracing uncertainty, designing your own path, and learning to trust your intuition even when the world tells you not to.

Caroline shares how she navigated early career ambiguity, how mentors helped her turn “I don’t know” into a strategy, and how she learned to distinguish between her inner saboteur and her inner guide. Her insights are raw, funny, and deeply empowering.

You’ll walk away with a new way to think about your career as a living map you get to draw. You’ll learn how to give yourself grace when you’re unsure, how to seek out meaningful experiences without sacrificing financial stability, and how to build a support system that helps you thrive in the ambiguity.

#WatchWithPremium

We filmed this conversation in our Premium studio, and the full, uncut version is available exclusively to our Premium subscribers. If you’re ready to go deeper, to hear every moment of this powerful exchange, I encourage you to upgrade. It’s worth it. https://lnkd.in/djNtgBdr.

And don't forget 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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