The Five Year Plan

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

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

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

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

And no, we are NOT referring to the cliche break up line. We're talking about all the ways you reject yourself, before the world ever gets a chance to (or not!) In this episode, Anna dives into the invisible limits we place on our own lives—the stories we tell ourselves about who we are, what we deserve, and how we’re perceived. And how those stories end up shaping everything. Because maybe the person preventing us from achieving what we all want is not "you," but "me" after all. Sources:The Dartmouth Scar ExperimentPsychology Today Article About the Scar ExperimentThe Pike Syndrome The Scar Experiment & Elephant StoryShare Your Story: ⁠⁠The Confessions Vault ⁠⁠⁠Tik Tok⁠ |⁠ Instagram⁠ | ⁠Substack ⁠Email: annashuyizhang@gmail.com

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

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

Join Anna today as she explores why the first few years of any career is so difficult. She talks about the ways that school conditions us to think in ways that are not representative of real life and why the "A+ students" are the ones who sometimes struggle the most in the real world. The Article: When The Gold Stars Stop Working: Why A+ Students Struggle in the Real World Share Your Story: The Confessions Vault TikTok: https://www.tiktok.com/@thefiveyearplanpodcastIG: https://www.instagram.com/thefiveyearplanpodcastSubstack: https://substack.com/@thefiveyearplanpodcastEmail: annashuyizhang@gmail.com