Anna Zhang

The Five Year Plan

About the show

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.

Newest episodes

How To Be Ambitious Without Burning Out

Nov 10, 2026 43 min

First, a little gift for you: Here is the exact Weekly Planner Template I use. You can download it for free and use it too :) This topic was HIGHLY requested by you. Reminder that if you ever want to submit a topic, question, or story, you can do so via the Confessions Vault . In this solo episode of The Five Year Plan, I’m sharing 5 practical tools you can use in your day-to-day life to remain ambitious without burning out. Each tool is drawn from academic research, my conversations with my past guests, and my own personal experience as a lawyer turned creator entrepreneur. We get into: Rethinking the to-do list that leaves you feeling behind Scheduling rest before you’re exhausted Choosing what to prioritize when everything feels important Using the 100/80/done rule to decide what deserves your best effort Finding an “unproductive” hobby purely for the joy of it ---- Sponsors: Thank you to Strawberry.me for sponsoring this episode. Visit https://strawberry.me/thefiveyearplan to get 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com --- IG: @thefiveyearplanpodcast TikTok: @thefiveyearplanpodcast Newsletter: https://thefiveyearplan.substack.com/ Email: anna@thefiveyearplanpodcast.com

Dr. Noam Raiter: The Price Women Pay in Traditional Professions

Nov 3, 2026 57 min

Dr. Noam Raiter is a family doctor and content creator challenging the idea that taking your career seriously means giving up the other parts of yourself. What started as a creative outlet during medical school became a second career—despite warnings that posting about fashion, makeup, or even vacations could undermine her future in medicine. In this episode, Noam shares how being diagnosed with a brain tumour at five shaped her relationship with medicine, why she questioned becoming a doctor after years of working toward it, and how she found a way to pursue both medicine and content creation without choosing between them. We talk about the pressure to make your job your entire identity, burnout in high-achieving environments, navigating social media as a professional, the double standards women face around appearance, overcoming the fear of being judged, and why having interests outside your career can make you better at your job. Plus, why Noam still doesn’t know what she wants to be when she grows up—and why she sees that as a good thing. --- Follow Noam Here:Instagram: @noamraiterTikTok: @noamraiter --- 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: @thefiveyearplanpodcastTikTok: @thefiveyearplanpodcastNewsletter: substack.com/@thefiveyearplanEmail: anna@thefiveyearplanpodcast.com --- Timestamps: 00:00 Meet Noam Raiter 01:08 Childhood Personality 02:37 Brain Tumor Diagnosis 04:34 Why Medicine Matters 06:49 Doubts In Med School 09:59 26 Hour Shifts Explained 11:24 Med Culture Shock 12:46 Burnout And Creativity 15:32 Starting On Social Media 18:09 Professionalism Fears 19:53 Doctors Lawyers And Identity 25:26 Podcast Origin Story 26:06 Career Coaching Sponsor 26:47 Why She Kept Posting 30:32 Fear of Employer Backlash 31:51 Handling Peer Criticism 36:13 Hidden Curriculum Expl...

Jules The Lawyer: Who Are You Without Your Job Title? (Re-Release)

Oct 27, 2026 55 min

Thank you to ⁠⁠Strawberry.me⁠⁠ for sponsoring this episode. Visit ⁠⁠strawberry.me/thefiveyearplan⁠⁠ to get 50% off your first coaching session. It’s officially been six months since I sat down with Jules the Lawyer —the first real interview I ever did for The Five Year Plan. This week, I’m bringing back our conversation from Season 1 about career, identity, and figuring out who you are beyond your job title: Jules Romano, better known as Jules the Lawyer, is a lawyer turned full-time content creator who built an online following by sharing the realities of working in law, her signature humour, and her journey to becoming a “famous person.” In this episode, Jules shares how she balanced practising law with creating content, why burnout eventually forced her to choose, and the identity crisis that followed. She opens up about finding herself outside work and being told she wasn’t living up to her potential. Plus, Jules shares her MasterChef audition story, thrifting tips, and disaster stories from her wedding. --- Follow Jules here: ⁠https://www.instagram.com/julesthelawyer/⁠ ⁠https://www.tiktok.com/@julesthelawyer⁠ ⁠https://www.youtube.com/@julesthelawyer --- 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 IG: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: anna@thefiveyearplanpodcast.com --- Timestamps: 00:49 "Fame" as a Brand Strategy 05:45 Joking About Big Ambitions 07:26 Growing Up and Choosing Law 10:12 Law School Why and Structure 15:01 Robbed by Legal Reality 17:30 Starting TikTok 23:28 Leaving Big Law for Nonprofit 26:41 Two Full Time Jobs 30:25 Persona Protection and Haters 31:54 Strawberry.Me 33:15 Quitting Law for Content 34:47 Living Without a Plan 37:11 Handling O...

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All episodes

How To Be Ambitious Without Burning Out

Nov 10, 2026 43 min

Dr. Noam Raiter: The Price Women Pay in Traditional Professions

Nov 3, 2026 57 min

Jules The Lawyer: Who Are You Without Your Job Title? (Re-Release)

Oct 27, 2026 55 min

The Executive Coach to CEOs: Why Getting What You Want Can Leave You Unhappy | Rachel Barbaro

Oct 20, 2026 57 min

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...

The Nurse Who Built Graze Anatomy: How to Re-Start Your Life And Pursue Your Passion | Sophia Cong

Oct 13, 2026 55 min

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: Instagram: https://www.instagram.com/thegrazeanatomy/ Website: https://thegrazeanatomy.com/ ---- 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/@thefiveyearplanpodcast Newsletter: https://substack.com/@thefiveyearplan Email: anna@thefiveyearplanpodcast.com ---- 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 27:0...

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

Oct 6, 2026 39 min

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/W4xNQhL3...

$10M Founder: How She Built a $10 Million Company While Working a 9-5 | Gillian Liu

Sep 29, 2026 59 min

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...

Policy Analyst to Viral Comedian: She Turned Down a 6-Figure Job to Pursue Stand-Up Comedy | Hilary Henderson

Sep 22, 2026 58 min

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...

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

Jul 6, 2026 1 hr 12 min

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?

Jun 30, 2026 35 min

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

Jun 23, 2026 56 min

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)

Jun 21, 2026 55 min

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

Jun 16, 2026 57 min

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

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

Jun 14, 2026 50 min

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

Jun 2, 2026 1 hr 12 min

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

I Love My Job. So Why Am I Struggling?

May 19, 2026 42 min

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

May 12, 2026 1 hr 0 min

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/@18hens https://www.youtube.com/@18hens

Jules the Lawyer: Corporate Lawyer Turned Famous Person

May 5, 2026 57 min

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/@julesthelawyer https://www.youtube.com/@julesthelawyer

The Perfection Paralysis Problem

Apr 14, 2026 35 min

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 Study 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

Apr 7, 2026 1 hr 5 min

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/@thefiveyearplanpodcast IG: https://www.instagram.com/thefiveyearplanpodcast Substack: https://substack.com/@thefiveyearplanpodcast Email: annashuyizhang@gmail.com

The Shame of Burnout

Mar 31, 2026 31 min

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/@thefiveyearplanpodcast IG: https://www.instagram.com/thefiveyearplanpodcast Substack: https://substack.com/@thefiveyearplanpodcast Email: annashuyizhang@gmail.com

Chef Nathan Ng: From Neuroscience to the Kitchen

Mar 24, 2026 59 min

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/@thefiveyearplanpodcast IG: https://www.instagram.com/thefiveyearplanpodcast Substack: https://substack.com/@thefiveyearplanpodcast Email: annashuyizhang@gmail.com

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How To Be Ambitious Without Burning Out

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Podcast details

Created by: Anna Zhang
Status: Active
Latest episode: Nov 10, 2026
Episodes: 22
Release period: Weekly
Avg. episode length: 53 min
Explicit: No
Language: English

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