HeyJaredThe Five Year Plan
A podcast about all the "five year plans" that did not go according to plan. From lawyers turned comedians, to neuroscientists turned chefs, come join Anna in exploring the craziest career pivots and the ups, downs, and uncertainties of being in your 20s and 30s.
- Indexed episodes, last 90 days
- 2
- Latest publication
- Sep 22, 2026
- Audience
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- Earliest in this view
- Jul 6, 2026
Latest episodes
Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself (opens the original)
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Most of us spend years working toward a career before we ever find out what that career actually looks like day-to-day. In 2021, Hilary Henderson, a stand up comedian, was working a desk-job as a policy analyst when she had that realization. Hilary studied international development and economics, earned her master’s in public administration, and built a career in policy — only to realize the life she had worked so hard for wasn’t one she actually wanted. In this episode, Hilary shares how she we
Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living (opens the original)
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In January 2025, Janine Ilya fell into a week-long coma. Against all odds, she woke up. But she couldn't walk, couldn't speak properly, and had lost much of her memory. She had to relearn everything—from taking her first steps to rediscovering who she was. This isn't just a story about surviving. It's a story about what happens when you're given a second chance at life—and how coming face-to-face with death changes the way you think about time, ambition, relationships, and what really matters. I
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