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
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
How To Love Someone Who's Falling Apart
We all know what it feels like to be lost, confused, and uncertain about life. But what it's like watching someone you love go through it in real time?Today, Anna sits down with the two people who have had a front-row seat to every “falling apart” moment she’s had over the last several years: her best friend of 7 years, Megan Davis, and her partner, Abtine Monavvari.From late-night panic spirals t
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
It's Not You, It's Me
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 th
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
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
The Career Advice That Ruined My Life
This piece of advice is one that I guarantee we've all heard before. But when I tried following it, here's what happened: I developed a romanticized view of what my career should be I had unrealistic expectations of what work is supposed to feel like that normal frustrations started to feel like a sign that I was on the wrong path I lost my sense of self-identity Can you guess what this
Why A+ Students Struggle In the Real World
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 Sto
