The 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.
Podcasting since 2026 • 3 episodes
The Five Year Plan
Latest Episodes
The Career Advice That Ruined My Life
This piece of advice is one that I guarantee we've all heard before. But when I tried following it, here's what happened: I developed a romanticized view of what my career should be I had unreal...
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Season 1
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Episode 3
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27:26
Why A+ Students Struggle In the Real World
Work hard in school. Get good grades. Land a good job. As long as you do those things, you'll set yourself up to live your happiest life.... Right? Well, Anna followed that formula to a tee: got good grades, went to the best l...
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21:03
Starting The Five Year Plan: What's This About Anyways?
Anna thought she did everything right. Built the resume. Followed a path. Checked all the boxes. And yet, at 28 years old... she's completely lost and confused, with big question marks about her career. Did she pick the wrong path? ...
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Season 1
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Episode 1
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8:22