Henna Choi: The Life-or-Death Decision to Quit Being a Lawyer

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 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.

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. 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 [https://www.psychologytoday.com/ca/blog/building-the-habit-hero/202008/two-types-passion-harmonious-vs-obsessive] Passion Study [https://selfdeterminationtheory.org/SDT/documents/2003_VallerancBlanchardMageauKoesnterRatelleLeonardGagneMacolais_JPSP.pdf]

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 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.instagram.com/18hens/] https://www.tiktok.com/@18hens [https://www.tiktok.com/@18hens] https://www.youtube.com/@18hens [https://www.youtube.com/@18hens]

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 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.instagram.com/julesthelawyer/] https://www.tiktok.com/@julesthelawyer [https://www.tiktok.com/@julesthelawyer] https://www.youtube.com/@julesthelawyer [https://www.youtube.com/@julesthelawyer]

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 the person preventing us from achieving what we all want is not "you," but "me" after all. Sources: The Dartmouth Scar Experiment [https://www.researchgate.net/profile/Robert-Kleck/publication/232481827_Perceptions_of_the_impact_of_negatively_valued_physical_characteristics_on_social_interaction/links/56a4f54d08aeef24c58bae73/Perceptions-of-the-impact-of-negatively-valued-physical-characteristics-on-social-interaction.pdf] Psychology Today Article About the Scar Experiment [https://www.psychologytoday.com/ca/blog/beyond-school-walls/202410/invisible-scars] The Pike Syndrome [https://tash-willcocks.medium.com/breaking-the-glass-what-pike-syndrome-teaches-us-about-work-bf736f095c21] The Scar Experiment & Elephant Story [https://medium.com/health-science/dartmouth-scar-experiment-changed-everything-i-knew-about-mindset-19962385ced3] Share Your Story: ⁠⁠The Confessions Vault ⁠⁠ [https://forms.gle/XzW8Vo6pc4Y3ZhLG8] ⁠Tik Tok⁠ [https://www.tiktok.com/@thefiveyearplanpodcast⁠⁠] |⁠ Instagram⁠ [https://www.instagram.com/thefiveyearplanpodcast⁠⁠] | ⁠Substack ⁠ [https://substack.com/@thefiveyearplanpodcast⁠⁠] Email: annashuyizhang@gmail.com