Who hosts The Five Year Plan?

The Five Year Plan is hosted by Anna Zhang. They have published 9 episodes. The show covers business, with a careers focus.

What has The Five Year Plan covered recently?

Recent episodes include "Gillian Liu: How She Built a $10M Company While Working a 9, 5", "Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian, Bombing, Starting Over & Betting on Herself", and "Janine Ilya: I Woke Up From a Coma, What Almost Dying Teaches You About Living". The latest went out on 29 Sep 2026 and ran about 60 minutes. Reading two or three of these before pitching is the fastest way to see what the show actually books.

How often does The Five Year Plan publish?

The Five Year Plan publishes weekly, a median of 7 days between episodes. Episodes average about 53 minutes. The back catalogue stands at 9 episodes. A show on this cadence plans ahead, so pitch earlier rather than closer to the date you want.

How hard is it to get booked on The Five Year Plan?

For The Five Year Plan, Booking Probability sits at 18/100, Listen Score at 14/100, and the guest bar is around 80/100. The show has not signalled guest openness recently, which raises the bar on relevance. A verified contact is on file.

Who should pitch The Five Year Plan?

The Five Year Plan covers mental health, personal development, career change, burnout, so guests who can speak to those specifically fit best. The show carries an audience score of 2/100. Lead with a specific result you can describe in numbers rather than a job title, and tie it to something the show has already covered.

business

The Five Year Plan

Hosted by Anna Zhang · business · EN · 9 episodes

Audience: 2

Apple Podcasts Website

About this Podcast:

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.

Pitch Analysis

Required Pod Score for this show. PitchCentric checks your profile against host openness, topical fit, and audience signals before you generate a pitch.

Contact path

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Booking probability

18%

Guest openness

Selective

Verified email on file

80/100

Required Score

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What is The Five Year Plan?

The Five Year Plan is a business podcast hosted by Anna Zhang, with 9 episodes on record and a Required Pod Score of 80.

About the host

Anna Zhang hosts The Five Year Plan, a business show with 9 episodes published.

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Recent episodes

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

The Five Year Plan
Gillian Liu: How She Built a $10M Company While Working a 9–5
Sep 29, 20261 hour
Most entrepreneurship stories start with someone quitting their job and going all in. Gillian Liu did the opposite. Gillian is the co-founder of Kiyoko Beauty, one of the largest Asian beauty retailers in North America. She and her co-founder started Kiyoko as a side project in 2021 and grew it into a $10 million business — all while keeping their corporate jobs. In this episode, Gillian shares why she waited nearly five years to leave her 9–5, how keeping her job actually helped Kiyoko grow, and why she thinks we’ve romanticized the idea that becoming an entrepreneur means risking everything. We talk about immigrant parents and traditional definitions of success, fear and financial security, building a business on nights and weekends, knowing when to delegate, and why you don’t necessarily have to blow up your life to build something big. Follow Gillian Here: https://www.instagram.com/hi.itsgillian/?hl=en https://www.tiktok.com/@hi.itsgillian https://www.youtube.com/@hi.itsgillian --- Follow Kiyoko Beauty Here: https://www.instagram.com/kiyoko.beauty https://www.tiktok.com/@kiyokobeauty --- -------- Sponsors: Thank you to ⁠Strawberry.Me⁠ for sponsoring this episode. Visit Strawberry.me/fiveyearplan for 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com ---- The Five Year Plan Instagram: ⁠https://www.instagram.com/thefiveyearplanpodcast/⁠ Tik Tok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠ Newsletter: ⁠https://substack.com/@thefiveyearplan⁠ Email: anna@thefiveyearplanpodcast.com ---- Timestamps: 00:00 Meet Gillian Liu00:47 Childhood Goals01:57 Immigrant Success Mindset03:38 No Entrepreneurs Around05:43 Excellence And Pressure09:07 Resentment To Respect11:10 Biochem To Business Pivot16:16 Kiyoko Origin Story19:56 Bored In Consulting25:33 Choosing A Co Founder27:03 When It Got Real27:54 Mom Becomes COO28:33 Making It Feel Real30:03 Balancing Two Jobs31:54 Toxic Startup Wakeup35:20 Delegation Over Perfection40:57 Why Not Quit Yet46:51 Fear And Monkey Bars49:13 Owning Entrepreneur Identity53:33 Kiyoko North Star Vision54:22 Off Plan Segment 56:51 TFYP Concluding Question
Show Notes
The Five Year Plan
Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself
Sep 22, 202658 min
Most of us spend years working toward a career before we ever find out what that career actually looks like day-to-day. In 2021, Hilary Henderson, a stand up comedian, was working a desk-job as a policy analyst when she had that realization. Hilary studied international development and economics, earned her master’s in public administration, and built a career in policy — only to realize the life she had worked so hard for wasn’t one she actually wanted. In this episode, Hilary shares how she went from policy analyst to stand-up comedian, what it was like becoming a beginner again, and how she eventually knew it was time to leave her 9–5. We talk about bombing, perfectionism, sexism in comedy, and why sometimes the only way to figure out what you want is to be willing to try something you might fail at.------ Follow Hilary here: ⁠https://www.instagram.com/hilaryhendersonn ⁠https://www.tiktok.com/@hilaryhenderson https://www.youtube.com/@hilaryhenderson -------- Sponsors: Thank you to Strawberry.Me for sponsoring this episode. Want to partner with us? anna@thefiveyearplanpodcast.com ---- The Five Year Plan Instagram: https://www.instagram.com/thefiveyearplanpodcast/ Tik Tok: https://www.tiktok.com/@thefiveyearplanpodcast Newsletter: https://substack.com/@thefiveyearplan Email: anna@thefiveyearplanpodcast.com ---- Timestamps: 00:00 Meet Hillary Henderson01:36 Ten Years Ago Dreams03:51 Policy Passion Reality Check07:25 Comedy Roots Early Life09:48 Post Grad Cliff Content11:49 Learning Stand Up Basics14:05 Turning Down Ottawa Job17:19 First Open Mic Story21:09 Grinding Mics Content Sales22:57 Burnout Tipping Point26:24 Sexism In Comedy Industry30:55 Handling Being Undervalued31:58 Control What You Can33:03 Bombing Defined33:45 First Bomb Lessons35:27 Lawyer Court Bomb37:03 Shame Versus Mistakes39:13 Perfectionism And Drafts40:23 Starting The Podcast43:26 Becoming A Beginner Again48:38 Reps Stress And Burnout50:16 Comparisons And New Careers52:34 Smash Or Pass Game55:46 Five Year Vision
Show Notes
The Five Year Plan
Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living
Jul 6, 20261h 12m
In January 2025, Janine Ilya fell into a week-long coma. Against all odds, she woke up. But she couldn't walk, couldn't speak properly, and had lost much of her memory. She had to relearn everything—from taking her first steps to rediscovering who she was. This isn't just a story about surviving. It's a story about what happens when you're given a second chance at life—and how coming face-to-face with death changes the way you think about time, ambition, relationships, and what really matters. If you've been waiting for the "right time" to start living, this conversation is your reminder that tomorrow is a promise none of us are guaranteed. ---- Special note from Anna: Guys.... this is the final episode of Season 1. Thank you for being part of an incredible first season. Whether you've listened to one episode or all of them, I can't thank you enough. Stay tuned for Season 2 this fall!!! --- Follow Janine here: IG: @janineilya TikTok: ⁠@janine.ilya Youtube: ⁠@ janineilya ---- Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠ ⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ | ⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠ Email: annashuyizhang@gmail.com
Show Notes
The Five Year Plan
Am I Falling Behind?
Jun 30, 202636 min
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
Show Notes
The Five Year Plan
KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School
Jun 23, 202657 min
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 ---- Share Your Story: ⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠ ⁠⁠⁠Tik Tok⁠⁠⁠ | ⁠⁠⁠ Instagram⁠⁠⁠ | ⁠⁠⁠Substack ⁠⁠⁠ Email: annashuyizhang@gmail.com
Show Notes

Guest Appearances

Recent guests on The Five Year Plan. Study who booked and why before you pitch.

Nathan Ng

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Best industries to pitch The Five Year Plan for

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

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Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.

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The Five Year Plan

Gillian Liu: How She Built a $10M Company While Working a 9–5

Sep 29, 20261 hour

Most entrepreneurship stories start with someone quitting their job and going all in. Gillian Liu did the opposite. Gillian is the co-founder of Kiyoko Beauty, one of the largest Asian beauty retailers in North America. She and her co-founder started Kiyoko as a side project in 2021 and grew it into a $10 million business — all while keeping their corporate jobs. In this episode, Gillian shares why she waited nearly five years to leave her 9–5, how keeping her job actually helped Kiyoko grow, and why she thinks we’ve romanticized the idea that becoming an entrepreneur means risking everything. We talk about immigrant parents and traditional definitions of success, fear and financial security, building a business on nights and weekends, knowing when to delegate, and why you don’t necessarily have to blow up your life to build something big. Follow Gillian Here: https://www.instagram.com/hi.itsgillian/?hl=en https://www.tiktok.com/@hi.itsgillian https://www.youtube.com/@hi.itsgillian --- Follow Kiyoko Beauty Here: https://www.instagram.com/kiyoko.beauty https://www.tiktok.com/@kiyokobeauty --- -------- Sponsors: Thank you to ⁠Strawberry.Me⁠ for sponsoring this episode. Visit Strawberry.me/fiveyearplan for 50% off your first coaching session. Want to partner with us? anna@thefiveyearplanpodcast.com ---- The Five Year Plan Instagram: ⁠https://www.instagram.com/thefiveyearplanpodcast/⁠ Tik Tok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠ Newsletter: ⁠https://substack.com/@thefiveyearplan⁠ Email: anna@thefiveyearplanpodcast.com ---- Timestamps: 00:00 Meet Gillian Liu00:47 Childhood Goals01:57 Immigrant Success Mindset03:38 No Entrepreneurs Around05:43 Excellence And Pressure09:07 Resentment To Respect11:10 Biochem To Business Pivot16:16 Kiyoko Origin Story19:56 Bored In Consulting25:33 Choosing A Co Founder27:03 When It Got Real27:54 Mom Becomes COO28:33 Making It Feel Real30:03 Balancing Two Jobs31:54 Toxic Startup Wakeup35:20 Delegation Over Perfection40:57 Why Not Quit Yet46:51 Fear And Monkey Bars49:13 Owning Entrepreneur Identity53:33 Kiyoko North Star Vision54:22 Off Plan Segment 56:51 TFYP Concluding Question

Show Notes

Every question we get asked before
someone starts their trial.

If you have a concern about deliverability, AI quality, data privacy, or whether this will actually work for your specific situation, it's probably answered below.

What is the difference between Founder Solo and Founder Pro?

How do agency tiers work?

What is a talent profile?

Can I switch plans later?

Yes, at any time. Upgrades take effect immediately; downgrades apply at the end of the current billing period. Contact support if you need help migrating between plan families.

Do you offer a free trial?

Every paid plan includes a 15-day free trial. Your card is saved at signup but you will not be charged until day 16. Cancel any time from your dashboard.

What happens if I cancel?

You keep access until the end of your current billing period. No charges after that. Your data is retained for 30 days in case you reactivate.

Is the 20% annual discount automatic?

Yes. Select Annual on the pricing toggle and the discounted price is applied automatically at checkout. The annual price shown is the full year cost.

What if I have more than 50 profiles or 20 clients?

That is our Enterprise tier. Contact our sales team and we will build a custom plan with volume pricing, a dedicated account manager, and SLA guarantees.

The Five Year Plan

About this Podcast:

Pitch Analysis

What is The Five Year Plan?

About the host

Recent episodes

Gillian Liu: How She Built a $10M Company While Working a 9–5

Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself

Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living

Am I Falling Behind?

KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School

Guest Appearances

Nathan Ng

Advertisers on this show

Best industries to pitch The Five Year Plan for

Podcasts like The Five Year Plan

Every question we get asked beforesomeone starts their trial.

The Five Year Plan

About this Podcast:

Pitch Analysis

What is The Five Year Plan?

About the host

Recent episodes

Gillian Liu: How She Built a $10M Company While Working a 9–5

Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself

Janine Ilya: I Woke Up From a Coma — What Almost Dying Teaches You About Living

Am I Falling Behind?

KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School

Guest Appearances

Nathan Ng

Advertisers on this show

Best industries to pitch The Five Year Plan for

Podcasts like The Five Year Plan

Every question we get asked beforesomeone starts their trial.

Every question we get asked before
someone starts their trial.

Every question we get asked before
someone starts their trial.