The Five Year Plan
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.
Episodes
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.Specia
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 fal
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 h
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 worryi
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 today
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 surger
I Love My Job. So Why Am I Struggling?
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.
Henna Choi: The Life-or-Death Decision to Quit Being a Lawyer
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
Jules the Lawyer: Corporate Lawyer Turned Famous Person
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 lif
The Perfection Paralysis Problem
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 podc
Maggie Arai: Law Student Turned 4x Founder
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 som
The Shame of Burnout
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)Th
Chef Nathan Ng: From Neuroscience to the Kitchen
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 succe
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