The Five Year Plan

Anna Zhang

5.0 (1)
Careers

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.

3d ago

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
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
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
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
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
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
Jun 14

BTS: I've Been Made Fun of for Starting This Podcast

This is the first episode of its kind where I'm pulling back the curtain on what it's really been like to build TFYP over the last three months—from waking up at 4:45 AM, to balancing podcasting with a full-time career, to dealing with criticism etc etc. In this episode, I'm answering the questions YOU GUYS sent in: this past week: 1) What is one thing that has shaped me into the person I am today2) How I balance law and podcasting3) Whether I've faced negativity from the legal community4) How I've booked guests as a brand-new podcaster5) Public speaking, confidence, and self-criticism6) The biggest lessons I've learned about myself through this processThis episode is about more than podcasting. It's about believing in something before anyone else does—and having the courage to keep going even when people don't understand what you're building. ---- Share Your Story: ⁠⁠⁠The Confessions Vault ⁠⁠⁠ ⁠⁠Tik Tok⁠⁠ |⁠⁠ Instagram⁠⁠ | ⁠⁠Substack ⁠⁠ Email: annashuyizhang@gmail.com
Jun 2

Kath Smith: Thirty, Flirty, and Thriving — Starting Over in Her 30s After Spending Her 20s as a Caregiver

Most of us grew up being fed this idea that our lives have to be figured out by the time we’re 30 — house, spouse, kids, stable job, the whole checklist. But today’s guest, Kath Smith, dispels that mythical timeline. At 26 years old, Kath became a full-time caregiver to her then-boyfriend after he suffered a traumatic brain injury. She cared for him over the next 4.5 years as he underwent 66 surgeries. Then, after nearly 12 years together, the relationship ended. Suddenly, Kath found herself “starting over” in her 30s — rebuilding her identity and learning who she was again. In this episode, Kath opens up about what it was like to put her life on pause to become a caregiver in her 20s, going back to school and becoming an HR intern at 29, and everything in between— all while building a platform as a full-time content creator. Kath also shares why she now creates content about being 33 and figuring life out in real time: to remind people that there is no "deadline" for building a meaningful life, that you are never “too old” to make a change, and that some of the best chapters of your life can begin later than you expected. Follow Kath here: https://www.instagram.com/kathhsmithh/ https://www.tiktok.com/@kathhsmithh https://www.youtube.com/@kathhsmithh

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.

Creator

Anna Zhang
Years Active

2026
Episodes

15
Rating

Explicit
Copyright

© Anna Zhang
Show Website

The Five Year Plan