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

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 careers
• How your childhood quietly set you up for this
• The difference between being overwhelmed and being fundamentally misaligned
• And how to start letting go of the shame of burnout without blowing up your entire life

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

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 kitchens
• The "open secret" of substance abuse in the hospitality industry

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

This piece of advice is one that I guarantee we've all heard before. But when I tried following it, here's what happened: 

1. I developed a romanticized view of what my career should be 
2. 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 
3. I lost my sense of self-identity 

Can you guess what this piece of advice is? 

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

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/@thefiveyearplanpodcast

IG: https://www.instagram.com/thefiveyearplanpodcast

Substack: https://substack.com/@thefiveyearplanpodcast

Email: annashuyizhang@gmail.com

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

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 Experiment

Psychology Today Article About the Scar Experiment

The Pike Syndrome

The Scar Experiment & Elephant Story

Share Your Story: ⁠⁠The Confessions Vault ⁠⁠

⁠Tik Tok⁠ |⁠ Instagram⁠ | ⁠Substack ⁠

Email: annashuyizhang@gmail.com

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

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

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

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 to weekly conversations about the same thing, they talk about what it means to love someone struggling through uncertainty, career confusion, identity crises, and the messy in-between.

They also explore the ways to support someone experiencing these challenges: when to give advice versus when to simply listen, how to set boundaries without abandoning someone, and the challenge of supporting someone when there’s no clear solution to the problem.

Megan and Abtine: Thank you both for being a light in all my darkest tunnels. This podcast exists because of your friendship, patience, and unwavering support.

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