The Five Year Plan

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. 

  1. 1h ago

    How to Know When It’s Time to Quit: 5 Questions to Ask Before You Leave

    Thank you to Strawberry.me for sponsoring this episode. Get 50% off your first coaching session at strawberry.me/thefiveyearplan. How do you know when it’s time to quit your job, change careers, end a relationship, or walk away from something you’ve spent years building? In this solo episode of The Five Year Plan, Anna breaks down 5 questions to ask yourself when you’re trying to figure out whether you’re going through a difficult season — or whether something is fundamentally no longer right for you. Drawing from her own decision, along with lessons from more than 50 hours of conversations with people who have made major life and career pivots, Anna explores the difference between temporary discomfort and knowing it’s actually time to move on. In this episode, you will learn: How to tell the difference between “this is hard” and “this is wrong for me”Why you should try changing your circumstances before changing your entire careerThe question: Do I actually want the future this path is leading me toward?Why your gut feeling can matter even when you can't logically explain itThe physical and mental signs we sometimes normalize when we're unhappyWhy apathy can be a bigger warning sign than hating your jobWhat it means when you haven't lost your ambition — your ambition has just movedWhy knowing it's time to leave doesn't mean you have to leave tomorrowHow to start making a plan when you know something needs to change Because sometimes the question isn't whether you can keep going. It's whether you actually want the life waiting for you at the end of the path you're on. -------- Sponsors: Thank you to ⁠⁠Strawberry.Me⁠⁠ for sponsoring this episode. Visit ⁠Strawberry.me/fiveyearplan⁠ for 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com ---- Help Plan The Five Year Plan Have a topic you want Anna to cover, a guest you want to hear from, or a question you want answered on the show? Submit here: https://forms.gle/W4xNQhL3Sqxd1WiK7 --- Follow TFYP: Instagram: ⁠⁠https://www.instagram.com/thefiveyearplanpodcast/⁠⁠ Tik Tok: ⁠⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠⁠ Newsletter: ⁠⁠https://substack.com/@thefiveyearplan⁠⁠ Email: anna@thefiveyearplanpodcast.com ---- Timestamps 00:00 Should You Quit 01:55 Season Or Forever 09:41 Track The Patterns 14:00 Try To Fix It 19:19 Do You Want That Future 25:11 Health Warning Signs 28:37 When You Stop Caring 33:47 Make A Quit Plan 36:32 Final Thoughts 00:00 Should You Quit 01:55 Season Or Forever 09:41 Track The Patterns 14:00 Try To Fix It 19:19 Do You Want That Future 25:11 Health Warning Signs 28:37 When You Stop Caring 33:47 Make A Quit Plan 36:32 Final Thoughts

  2. Sep 29

    Gillian Liu: How She Built a $10M Company While Working a 9–5

    Most entrepreneurship stories start with someone quitting their job and going all in. Gillian Liu did the opposite. Gillian is the co-founder of Kiyoko Beauty, one of the largest Asian beauty retailers in North America. She and her co-founder started Kiyoko as a side project in 2021 and grew it into a $10 million business — all while keeping their corporate jobs. In this episode, Gillian shares why she waited nearly five years to leave her 9–5, how keeping her job actually helped Kiyoko grow, and why she thinks we’ve romanticized the idea that becoming an entrepreneur means risking everything. We talk about immigrant parents and traditional definitions of success, fear and financial security, building a business on nights and weekends, knowing when to delegate, and why you don’t necessarily have to blow up your life to build something big. Follow Gillian Here: https://www.instagram.com/hi.itsgillian/?hl=en https://www.tiktok.com/@hi.itsgillian https://www.youtube.com/@hi.itsgillian --- Follow Kiyoko Beauty Here: https://www.instagram.com/kiyoko.beauty https://www.tiktok.com/@kiyokobeauty --- -------- Sponsors: Thank you to ⁠Strawberry.Me⁠ for sponsoring this episode. Visit Strawberry.me/fiveyearplan for 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com ---- The Five Year Plan Instagram: ⁠https://www.instagram.com/thefiveyearplanpodcast/⁠ Tik Tok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠ Newsletter: ⁠https://substack.com/@thefiveyearplan⁠ Email: anna@thefiveyearplanpodcast.com ---- Timestamps: 00:00 Meet Gillian Liu00:47 Childhood Goals01:57 Immigrant Success Mindset03:38 No Entrepreneurs Around05:43 Excellence And Pressure09:07 Resentment To Respect11:10 Biochem To Business Pivot16:16 Kiyoko Origin Story19:56 Bored In Consulting25:33 Choosing A Co Founder27:03 When It Got Real27:54 Mom Becomes COO28:33 Making It Feel Real30:03 Balancing Two Jobs31:54 Toxic Startup Wakeup35:20 Delegation Over Perfection40:57 Why Not Quit Yet46:51 Fear And Monkey Bars49:13 Owning Entrepreneur Identity53:33 Kiyoko North Star Vision54:22 Off Plan Segment 56:51 TFYP Concluding Question

  3. Sep 22

    Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself

    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 went from policy analyst to stand-up comedian, what it was like becoming a beginner again, and how she eventually knew it was time to leave her 9–5. We talk about bombing, perfectionism, sexism in comedy, and why sometimes the only way to figure out what you want is to be willing to try something you might fail at.------ Follow Hilary here: ⁠https://www.instagram.com/hilaryhendersonn ⁠https://www.tiktok.com/@hilaryhenderson https://www.youtube.com/@hilaryhenderson -------- Sponsors: Thank you to Strawberry.Me for sponsoring this episode. Want to partner with us? anna@thefiveyearplanpodcast.com ---- The Five Year Plan Instagram: https://www.instagram.com/thefiveyearplanpodcast/ Tik Tok: https://www.tiktok.com/@thefiveyearplanpodcast Newsletter: https://substack.com/@thefiveyearplan Email: anna@thefiveyearplanpodcast.com ---- Timestamps: 00:00 Meet Hillary Henderson01:36 Ten Years Ago Dreams03:51 Policy Passion Reality Check07:25 Comedy Roots Early Life09:48 Post Grad Cliff Content11:49 Learning Stand Up Basics14:05 Turning Down Ottawa Job17:19 First Open Mic Story21:09 Grinding Mics Content Sales22:57 Burnout Tipping Point26:24 Sexism In Comedy Industry30:55 Handling Being Undervalued31:58 Control What You Can33:03 Bombing Defined33:45 First Bomb Lessons35:27 Lawyer Court Bomb37:03 Shame Versus Mistakes39:13 Perfectionism And Drafts40:23 Starting The Podcast43:26 Becoming A Beginner Again48:38 Reps Stress And Burnout50:16 Comparisons And New Careers52:34 Smash Or Pass Game55:46 Five Year Vision

    Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself

  4. Jul 6

    Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living

    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. If you've been waiting for the "right time" to start living, this conversation is your reminder that tomorrow is a promise none of us are guaranteed. ---- Special note from Anna: Guys.... this is the final episode of Season 1. Thank you for being part of an incredible first season. Whether you've listened to one episode or all of them, I can't thank you enough. Stay tuned for Season 2 this fall!!! --- Follow Janine here: IG: @janineilya TikTok: ⁠@janine.ilya Youtube: ⁠@janineilya ---- Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠ ⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠ Email: annashuyizhang@gmail.com

  5. Jun 30

    Am I Falling Behind?

    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

  6. Jun 23

    KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School

    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 ---- Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠ ⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠ Email: annashuyizhang@gmail.com

  7. Jun 21

    A Conversation With My Dad: The Story Behind My Story (BONUS EPISODE)

    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

  8. Jun 16

    Shawn Kanungo: Accountant to Innovation Strategist — How To Stay Ahead In The World of AI

    For years, we were told there was a "golden ticket" to success: become a doctor, engineer, accountant, or software developer and you'll be set for life. But what happens when that golden ticket disappears? This week, I'm joined by innovation strategist, bestselling author, and global keynote speaker, Shawn Kanungo. We talk about growing up in traditional immigrant households, learning to stop worrying about what other people think, and why the most successful people aren't necessarily the smartest—but the most curious. Shawn, who started his career as an accountant, shares how the death of his father changed the trajectory of his life, the concept of building your identity "room by room," and why he believes we're living through the most exciting time in history. We also dive into AI: why so many people fear it, why most of that fear comes from misunderstanding, and how anyone can start using these tools today and become the most dangerous person in the room. If you've ever felt pressure to follow a certain path or wondered how to stay relevant in a rapidly changing world, this episode is for you. Topics discussed: Growing up in a traditional South Asian householdWhy there is no longer a "golden ticket" careerPortfolio careers vs. staying the course Why the most successful people explore before they exploitAI, innovation, and the future of workKnowing when to persist and when to quitBuilding an identity "room by room"Follow Shawn: https://www.tiktok.com/@shawn.kanungo https://www.instagram.com/shawnkanungo/ https://www.youtube.com/@shawn.kanungo https://shawnkanungo.com/ ---- Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠ ⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠ Email: annashuyizhang@gmail.com

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About

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. 

Information

  • Creator
    Anna Zhang
  • Years Active
    2026
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © Anna Zhang
  • Show Website
    The Five Year Plan

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