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

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

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

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

Work hard in school. Get good grades. Land a good job. As long as you do those things, you'll set yourself up to live your happiest life.... Right?

Well, Anna followed that formula to a tee: got good grades, went to the best law school in the country, and landed her dream job. But there she was, sitting in the floor of her bedroom at 6:00 am on a Tuesday morning, sobbing about how debilitatingly inadequate she felt. How the hell did THIS happen?

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