Explorez tous les épisodes du podcast The Five Year Plan
| Titre | Date | Durée | |
|---|---|---|---|
| The Executive Coach to CEOs: Why Getting What You Want Can Leave You Unhappy | Rachel Barbaro | 20 Oct 2026 | 00:57:33 | |
You’ve worked hard, checked the boxes, and built a life that looks good on paper. But you still find yourself thinking, “Is this really it?” How do you figure out what’s missing—and what to do next? In this episode, executive coach Rachel Barbaro joins us to unpack why achievement doesn’t always translate into fulfillment and how to get clearer on what you actually want. Rachel works with founders, CEOs, and senior leaders across banking, law, healthcare, and tech, helping them navigate burnout, career pivots, and the pressures of high achievement. We explore how to distinguish a difficult season at work from a sign you want something different, why familiar unhappiness can feel safer than change, and how to recognize when you’re pursuing someone else’s definition of success. We also talk about building a personal board of directors, creating more room for joy, and taking a next step when you have too many interests—or no idea where to begin. --- Follow Rachel here: Linkedin: https://www.linkedin.com/in/rachelbarbaro/ Instagram: https://www.instagram.com/rachelbarbaro/ — Sponsors: Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com — The Five Year Plan Instagram: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: anna@thefiveyearplanpodcast.com --- Timestamps: 00:00 Meet Rachel Barbaro 00:49 The Sunday Scaries 02:26 Ego Versus Intuition 03:37 Redefining Success 04:15 From Corner Office 07:11 Kids And True Self 09:56 When Goals Disappoint 11:54 Dip Or Sign 14:48 Six Month Check 17:46 Control In Toxic Jobs 22:24 Find Your Purpose 24:16 Purpose When Lost 27:13 Interview Them Too 28:36 Asking About Culture 29:15 Interview Recon Tips 30:38 Unhappiness vs Existential 32:43 Setting Conditions for Joy 34:59 Phone Boundaries Focus 38:22 Fear of Change Loop 42:32 Burnout Body Signals 47:11 Highest Leverage Priorities 49:09 Coach Me Rapid Fire 52:59 TFYP Question | |||
| The Nurse Who Built Graze Anatomy: How to Re-Start Your Life And Pursue Your Passion | Sophia Cong | 13 Oct 2026 | 00:55:57 | |
Most people don’t walk away from a stable career they actually like. Sophia Cong did. Sophia is a former nurse and the founder of Graze Anatomy, one of Toronto’s leading charcuterie and grazing companies. What started with Sophia making charcuterie boards out of her home while working 12-hour nursing shifts has grown into a business serving clients like Chanel, Sephora, Google, Microsoft, and Tiffany & Co. In this episode, Sophia shares why she left a nursing career she was good at to pursue something more creative, how she tested and validated Graze Anatomy before quitting, and why she waited until the business matched her nursing income for three consecutive months before going all in. We talk about immigrant parents and traditional definitions of success, the guilt of walking away from a career you spent years building, starting over without feeling like you’re starting from zero, working for free to learn a new skill, turning a side hustle into a real business, navigating the uncertainty of entrepreneurship, and why Sophia believes “the more you do, the luckier you get.” ---- Follow Graze Anatomy Here: ---- Sponsors: Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session. Want to partner with us? ---- The Five Year Plan ---- Timestamps 00:00 From Nurse to Founder 01:46 Do You Feel Successful 04:42 Childhood Dreams and Roots 06:20 Immigrant Expectations 09:39 Why Nursing Wasn't Enough 13:30 Creative Outlet Food Blog16:42 Breaking Into Food Styling 19:50 Learning for Free Mindset 21:16 First Charcuterie Breakthrough 24:00 Turning Orders Into Business 27:08 Passion Versus Burnout 28:17 Sponsor Career Coaching 29:39 Quitting Nursing Benchmarks 31:01 Validating With Feedback 32:24 Balancing Two Jobs 33:26 Origin Of The Name 34:31 Graze Or Nay Game 36:53 Fear And Skill Building 39:20 New Stress Tradeoffs 42:16 Slow Seasons Mindset 47:00 Big Clients And Reviews 50:28 Working With Your Spouse 52:31 Protecting The Relationship 54:45 TFYP Question | |||
| How to Know When It’s Time to Quit: 5 Questions to Ask Before You Leave | 06 Oct 2026 | 00:39:26 | |
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:
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 | |||
| $10M Founder: How She Built a $10 Million Company While Working a 9-5 | Gillian Liu | 29 Sep 2026 | 00:59:40 | |
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 | |||
| Policy Analyst to Viral Comedian: She Turned Down a 6-Figure Job to Pursue Stand-Up Comedy | Hilary Henderson | 22 Sep 2026 | 00:58:15 | |
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 | |||
| Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living | 06 Jul 2026 | 01:12:13 | |
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 | |||
| Am I Falling Behind? | 30 Jun 2026 | 00:35:53 | |
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 | |||
| KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School | 23 Jun 2026 | 00:56:33 | |
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 | |||
| A Conversation With My Dad: The Story Behind My Story (BONUS EPISODE) | 21 Jun 2026 | 00:55:39 | |
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 Jun 2026 | 00:57:54 | |
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:
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 | |||
| BTS: I've Been Made Fun of for Starting This Podcast | 14 Jun 2026 | 00:50:21 | |
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:
This 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 Jun 2026 | 01:12:22 | |
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/ | |||
| I Love My Job. So Why Am I Struggling? | 19 May 2026 | 00:42:42 | |
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: | |||
| Henna Choi: The Life-or-Death Decision to Quit Being a Lawyer | 12 May 2026 | 01:00:26 | |
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/ | |||
| Jules the Lawyer: Corporate Lawyer Turned Famous Person | 05 May 2026 | 00:57:14 | |
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/ | |||
| The Perfection Paralysis Problem | 14 Apr 2026 | 00:35:31 | |
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: Psychology 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 Apr 2026 | 01:05:33 | |
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:
Check out Founders who Give a F*ck: https://www.fwgaf.com/ 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 | |||
| The Shame of Burnout | 31 Mar 2026 | 00:31:48 | |
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:
If 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/@thefiveyearplanpodcast IG: https://www.instagram.com/thefiveyearplanpodcast Substack: https://substack.com/@thefiveyearplanpodcast Email: annashuyizhang@gmail.com | |||
| Chef Nathan Ng: From Neuroscience to the Kitchen | 24 Mar 2026 | 00:59:31 | |
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:
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 | |||