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The Five Year Plan

The Five Year Plan

By: Anna Zhang
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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.

Anna Zhang
Career Success Economics
Episodes
  • Am I Falling Behind?
    Jun 30 2026

    This week, Anna dives into one of the most universal - and quietly terrifying - questions we ask ourselves: Am I falling behind??

    In this solo episode (and the second last episode of Season 1!!!), Anna unpacks where "feeling behind" comes from, why high achievers are especially vulnerable to it, and how to redefine success when your life doesn't follow the timeline you imagined.

    Special shoutout to the listener who submitted their story to the Confessions Vault and inspired this entire episode. Your fellow planners are rooting for you!!


    Share Your Story: ⁠The Confessions Vault ⁠

    TikTok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠

    IG: ⁠https://www.instagram.com/thefiveyearplanpodcast⁠

    Substack: ⁠https://substack.com/@thefiveyearplanpodcast⁠

    Email: annashuyizhang@gmail.com

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    36 mins
  • KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School
    Jun 23 2026

    Kayam Khalfan is a recording artist with more than 20 million streams worldwide, has toured internationally with Jay Sean, opened for Pink Sweat$, built an award-winning startup, completed two degrees with distinction, and is heading to law school this fall.


    In this episode of The Five Year Plan, Kayam shares how a missed school bus led him to audition for his school's production of Aladdin and fall in love with music. He also shares how navigated being mocked for pursuing music in high school, and why he believes the most successful people are often "delusionally optimistic."


    Follow Kayam here:

    IG: @KAYAM403

    TikTok: @KAYAM403

    Youtube: @KAYAM403

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    Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠

    ⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠

    Email: annashuyizhang@gmail.com

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    57 mins
  • A Conversation With My Dad: The Story Behind My Story (BONUS EPISODE)
    Jun 21 2026

    In 1999, my dad made a decision that changed the course of our family's life forever.

    At 29 years old, he was a rising star chemical engineer in Shijiazhuang, China. He had the career he had always dreamed of, a young family, and a clear path ahead of him. But after realizing that the future he'd spent years working toward wasn't the future he wanted, he made a choice that shocked everyone around him.

    He packed his bags, left behind his family and friends, and moved across the world to Canada—alone. He didn't speak the language. He didn't understand the culture. He had no job, no connections, no family, and no clear plan for what came next.

    In this special episode, I sit down with my dad to talk about the risks he took, the sacrifices he made, and the unexpected twists that brought our family to Canada. We discuss ambition, reinvention, immigration, regret, resilience, and the moment he realized that success meant something different than he once thought.

    This is the story behind my story.

    Thank you, Dad.

    ---

    Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠

    ⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠

    Email: annashuyizhang@gmail.com

    Show More Show Less
    56 mins
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