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.

Special shoutout to the listener who submitted their story to the Confessions Vault and inspired this entire episode. Your fellow planners are rooting for you!!

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

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 fall in love with music. He also shares how navigated being mocked for pursuing music in high school, and why he believes the most successful people are often "delusionally optimistic."

Follow Kayam here:

IG: @KAYAM403

TikTok: @KAYAM403

Youtube: @KAYAM403

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Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠

⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠

Email: annashuyizhang@gmail.com

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 him.

He packed his bags, left behind his family and friends, and moved across the world to Canada—alone. He didn't speak the language. He didn't understand the culture. He had no job, no connections, no family, and no clear plan for what came next.

In this special episode, I sit down with my dad to talk about the risks he took, the sacrifices he made, and the unexpected twists that brought our family to Canada. We discuss ambition, reinvention, immigration, regret, resilience, and the moment he realized that success meant something different than he once thought.

This is the story behind my story.

Thank you, Dad.

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Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠

⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠

Email: annashuyizhang@gmail.com

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 worrying about what other people think, and why the most successful people aren't necessarily the smartest—but the most curious.

Shawn, who started his career as an accountant, shares how the death of his father changed the trajectory of his life, the concept of building your identity "room by room," and why he believes we're living through the most exciting time in history.

We also dive into AI: why so many people fear it, why most of that fear comes from misunderstanding, and how anyone can start using these tools today and become the most dangerous person in the room.

If you've ever felt pressure to follow a certain path or wondered how to stay relevant in a rapidly changing world, this episode is for you.

Topics discussed:

• Growing up in a traditional South Asian household
• Why there is no longer a "golden ticket" career
• Portfolio careers vs. staying the course
• Why the most successful people explore before they exploit
• AI, innovation, and the future of work
• Knowing when to persist and when to quit
• Building an identity "room by room"

Follow Shawn:

https://www.tiktok.com/@shawn.kanungo

https://www.instagram.com/shawnkanungo/

https://www.youtube.com/@shawn.kanungo

https://shawnkanungo.com/

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Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠

⁠⁠⁠Tik Tok⁠⁠⁠ |⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠

Email: annashuyizhang@gmail.com

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
• 2) How I balance law and podcasting
• 3) Whether I've faced negativity from the legal community
• 4) How I've booked guests as a brand-new podcaster
• 5) Public speaking, confidence, and self-criticism
• 6) The biggest lessons I've learned about myself through this process

This episode is about more than podcasting. It's about believing in something before anyone else does—and having the courage to keep going even when people don't understand what you're building.

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Share Your Story: ⁠⁠⁠The Confessions Vault ⁠⁠⁠

⁠⁠Tik Tok⁠⁠ |⁠⁠ Instagram⁠⁠ | ⁠⁠Substack ⁠⁠

Email: annashuyizhang@gmail.com

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

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

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