The Five Year Plan

Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living 06.07.2026 1h 12min

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

Am I Falling Behind? 30.06.2026 35min

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/@thefiveyearplanpodcast⁠IG: ⁠https://www.instagram.com/thefiveyearplanpodcast⁠Substack: ⁠https://substack.com/@thefiveyearplanpodcast⁠Email: annashuyizhang@gmail.com

KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School 23.06.2026 56min

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: @KAYAM403TikTok: @KAYAM403Youtube: @KAYAM403---- Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠Email: annashuyizhang@gmail.com

A Conversation With My Dad: The Story Behind My Story (BONUS EPISODE) 21.06.2026 55min

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

Shawn Kanungo: Accountant to Innovation Strategist — How To Stay Ahead In The World of AI 16.06.2026 57min

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.kanungohttps://www.instagram.com/shawnkanungo/ https://www.youtube.com/@shawn.kanungohttps://shawnkanungo.com/---- Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠Email: annashuyizhang@gmail.com

BTS: I've Been Made Fun of for Starting This Podcast 14.06.2026 50min

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

Kath Smith: Thirty, Flirty, and Thriving — Starting Over in Her 30s After Spending Her 20s as a Caregiver 02.06.2026 1h 12min

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/@kathhsmithhhttps://www.youtube.com/@kathhsmithh

I Love My Job. So Why Am I Struggling? 19.05.2026 42min

They say misery is reserved for those who hate their jobs, hate their careers, hate their colleagues, hate their bosses, hate their hours etc etc etc.... or is it? In this episode, Anna explores a different kind of struggle: what it’s like to genuinely love your job, believe in what you’re doing, and still feel like you’re falling apart underneath it all.The lows hit harder than you ever expected. Your anxiety is through the roof. Your identity becomes completely tangled up in your work. And because nothing is technically “wrong,” it becomes even harder to explain why you’re struggling so much.This conversation is for anyone who’s ever thought: “nothing's technically wrong… so why do I still feel this way?”Links to Articles Referenced: Two Types of Passion Passion Study

Henna Choi: The Life-or-Death Decision to Quit Being a Lawyer 12.05.2026 1h

For Henna Choi, leaving her career as a personal injury lawyer was literally matter of life or death. For years, Henna tried to do everything “right.” She went to law school, built a successful career, and appeared to be thriving in the public eye. But behind closed doors, she was falling apart.In this episode , Anna sits down with Henna to talk about the hidden reality behind her viral “depressed lawyer” videos, her stint working as a barista after quitting law, and being diagnosed with autism in adulthood.Henna opens up about growing up in an immigrant household where success felt non-negotiable, masking her neurodivergence for years, and quietly struggling while appearing “high-functioning” on the outside. She speaks candidly about burnout, depression, suicidal ideation, and the loneliness of living a life that never felt authentic.Follow Henna here: https://www.instagram.com/18hens/https://www.tiktok.com/@18henshttps://www.youtube.com/@18hens

Jules the Lawyer: Corporate Lawyer Turned Famous Person 05.05.2026 57min

How does a corporate lawyer become a famous person? Today, Jules Romano sits down with Anna to unpack the real story behind the transition—from billable hours to building a personal brand on the internet. What started as sarcastic, off-the-cuff videos quickly turned into a loyal following, a public identity, and a completely different career path.In this episode, Jules reveals the parts of her life and story that haven't been visible to the public. Join them as they talk about: burnout, internet scrutiny, and what it's actually like to live the "Hannah Montana" double-life as a lawyer and content creator. Also watch this episode if you want to know how she actually finds her best thrift gems (and how you can too).Follow Jules here:https://www.instagram.com/julesthelawyer/https://www.tiktok.com/@julesthelawyerhttps://www.youtube.com/@julesthelawyer

The Perfection Paralysis Problem 14.04.2026 35min

You’re not stuck. You’re just scared of picking wrong.In this episode, we're talking about the perfection paralysis problem—the reason you hate your job but haven’t applied anywhere, the reason you’ve been “thinking about” starting something for years… and the reason doing nothing somehow feels safer than doing the wrong thing.From overthinking Netflix choices to comparing a $100 mic to a top podcast in the world (yes, I did that), this is a brutally honest breakdown of how perfectionism quietly keeps you exactly where you are.If you’ve been waiting for the right moment, the right plan, or the right version of yourself—then you gotta listen to (and watch!!!!) this episode.Sources:The Jam StudyPsychology Today: Three types of Perfectionism Three Types of Perfectionism Paper (Hewitt & Flett)Share Your Story: ⁠The Confessions Vault ⁠Tik Tok | Instagram | Substack Email: annashuyizhang@gmail.com

Maggie Arai: Law Student Turned 4x Founder 07.04.2026 1h 5min

In this episode, Anna sits down with Maggie Arai—former law student and aspiring intentional human rights lawyer, turned 4x founder and social entrepreneur—to talk about what it really looks like to walk away from a path that made sense on paper, but didn’t feel right in practice.Join them as they talk about: The difference between being disliking something because it's hard vs. disliking something because it's wrong for you. The pressure of sunk costs The less glamorous side of entrepreneurship that people don't often talk about and social media rarely portrays The loneliness epidemic and how the commodification of convenience has fundamentally shifted our ability to form meaningful and long lasting friendships with those who matter the most. Check out Founders who Give a F*ck: https://www.fwgaf.com/Share Your Story: The Confessions Vault TikTok: https://www.tiktok.com/@thefiveyearplanpodcastIG: https://www.instagram.com/thefiveyearplanpodcastSubstack: https://substack.com/@thefiveyearplanpodcastEmail: annashuyizhang@gmail.com

The Shame of Burnout 31.03.2026 31min

Burnout is not a character flaw. So why does it feel like one? In this episode, Anna talks about the part of burnout that we often don't address —the quiet, creeping fear that you’re the problem. That you’re not resilient enough. That you're not cut out for the life you worked so hard to build. Join Anna as she reflects on: Why burnout feels like a personal failure (even when it’s not)The unspoken pressure to “handle it” in high-achieving careersHow your childhood quietly set you up for thisThe difference between being overwhelmed and being fundamentally misalignedAnd how to start letting go of the shame of burnout without blowing up your entire lifeIf you’ve ever felt like a failure for "not being able to handle" the life you chose, this episode is for you. "The Boiling Frog Syndrome: A Metaphor for Burnout" Article: https://www.psychologytoday.com/ca/blog/lessons-from-a-burnt-out-psychologist/202406/the-boiling-frog-syndrome-a-metaphor-for-burnout Share Your Story: The Confessions Vault TikTok: https://www.tiktok.com/@thefiveyearplanpodcastIG: https://www.instagram.com/thefiveyearplanpodcastSubstack: https://substack.com/@thefiveyearplanpodcastEmail: annashuyizhang@gmail.com

Chef Nathan Ng: From Neuroscience to the Kitchen 24.03.2026 59min

He's cooked for Taylor Swift. Jennifer Lopez. And almost became a neuroscientist? In this episode, Anna sits down with Nathan Ng - sous chef at TOCA inside the Ritz Carlton Toronto - who walked away from the "perfect" academic path as a neuroscience student at the University of Toronto to chase something far less certain... and at times, more brutal. This is less of a polished success story and more about what it actually looks like to choose a different life. Join them as they get into: What it really takes to drop out of the best university in the country at the age of 18 when everyone expects you to stay The weight of immigrant expectations and what happens when you don't follow them The uncomfortable truth about the commodification of Chinese cuisine Being an Asian chef in elite, European-dominated kitchensThe "open secret" of substance abuse in the hospitality industryShare Your Story: The Confessions Vault TikTok: https://www.tiktok.com/@thefiveyearplanpodcastIG: https://www.instagram.com/thefiveyearplanpodcastSubstack: https://substack.com/@thefiveyearplanpodcastEmail: annashuyizhang@gmail.com