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Artwork for The Five Year Plan

The Five Year Plan

Anna Zhang
Burnout
Perfectionism
Obsessive Passion
Podcasting
Mental Health
Caregiving
Career Pivots
Toronto
Founders Who Give a Fuck
Happier
Jules Romano
Environment
Relationships
Human Resources
Independence
Law
Artificial Intelligence
Immigration
Content Creation
Personal Development

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.

PublishesWeeklyEpisodes15Founded4 months ago
Number of ListenersCategories
CareersBusiness

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Artwork for The Five Year Plan

Latest Episodes

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 ... more

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 th... more

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 ... more

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 strate... more

Key Facts

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Recent Guests

Kayam Khalfan
Musician, entrepreneur, dual degree holder pursuing law school
Episode: KAYAM: R&B Artist - 20 Million Streams Later, He's Going to Law School
Shawn Kanungo
Accountant turned Innovation Strategist; author of The Bold Ones
Speaker and author
Episode: Shawn Kanungo: Accountant to Innovation Strategist — How To Stay Ahead In The World of AI
Kath Smith
Caregiver turned HR professional and content creator
Episode: Kath Smith: Thirty, Flirty, and Thriving — Starting Over in Her 30s After Spending Her 20s as a Caregiver
Abtine Monavari
Partner of Anna, speaker in discussion
Episode: How To Love Someone Who's Falling Apart
Megan Davis
Best friend of Anna, speaker in discussion
Episode: How To Love Someone Who's Falling Apart
Henna Choi
Former corporate personal injury lawyer turned content creator
18Hens (social handle)
Episode: Henna Choi: The Life-or-Death Decision to Quit Being a Lawyer
Jules Romano
Lawyer, content creator, and public figure known as Jules The Lawyer
Episode: Jules the Lawyer: Corporate Lawyer Turned Famous Person
Maggie Arai
Entrepreneur and founder of multiple ventures including Happier and Founders Who Give a Fuck
Founder/CEO
Episode: Maggie Arai: Law Student Turned 4x Founder
Nathan Ng
Chef, sous chef at TOCA, Ritz-C Carlton Toronto
TOCA at the Ritz-Carlton Toronto
Episode: Chef Nathan Ng: From Neuroscience to the Kitchen

Host

Anna
Host and primary presenter; central voice guiding conversations about five-year plans, pivots, and personal development.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#180
Canada/Business/Careers
Apple Podcasts
#218
Italy/Business/Careers
Apple Podcasts
#78
Singapore/Business/Careers
Apple Podcasts
#102
Philippines/Business/Careers
Apple Podcasts
#140
Hong Kong/Business/Careers
Apple Podcasts
#194
Indonesia/Business/Careers
Apple Podcasts
#222
Norway/Business/Careers
Apple Podcasts
#229
Taiwan/Business/Careers

Talking Points

Recent interactions between the hosts and their guests.

BTS: I've Been Made Fun of for Starting This Podcast
Q: Is there anything new you've learned about yourself through the podcasting process that you wouldn't have learned otherwise?
I've learned that many of my legal skills are transferable to podcasting, especially in research and question framing, and I've also realized the importance of taking the project seriously and treating every opportunity as a learning moment.
BTS: I've Been Made Fun of for Starting This Podcast
Q: How do you keep getting strong guests as a startup podcaster?
I use highly personalized outreach after careful research on each potential guest, leverage informal introductions when possible, and progressively expand beyond cold outreach as more listeners engage with the show.
BTS: I've Been Made Fun of for Starting This Podcast
Q: How are you balancing your full-time job as a lawyer with the podcast?
I'm transparent about not doing everything at once, structure my days to protect work time, and rely on supportive friends and a partner to keep me grounded as I pursue podcasting as a meaningful project.
BTS: I've Been Made Fun of for Starting This Podcast
Q: What is one thing that has shaped who you are today the most?
The core lesson from my dad to replace I can't with how can I, which shaped my problem-solving mindset, and the belief that there are more solutions when you approach challenges with a proactive, open-ended question.
Chef Nathan Ng: From Neuroscience to the Kitchen
Q: On a scale of one to ten, how annoying is it when people ask you if your job is like The Bear?
He indicates it's a ten, noting the show's popularity drives constant comparison, even though he hasn't watched it extensively.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About The Five Year Plan

What is The Five Year Plan about and what kind of topics does it cover?

The show concentrates on non-linear career paths, personal growth, and the realities of pursuing ambitious plans in your 20s and 30s. Across recent episodes, listeners hear intimate stories of leaving traditional professions, pivoting into entrepreneurship, and navigating burnout, identity, and public-facing branding. The conversations balance practical lessons with candid reflections, offering tangible takeaways on making deliberate career shifts, building communities, and evaluating what success really means. A standout thread is the emphasis on authenticity, vulnerability, and resilience as engines for growth, whether someone is transitioning from law, medicine, or demanding corporate tracks into creative, entrepreneurial, or service-ori... more

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Which podcasts are similar to The Five Year Plan?

These podcasts share a similar audience with The Five Year Plan:

1. Giggly Squad
2. Call Her Daddy
3. Armchair Expert with Dax Shepard
4. More Life with Carl Radke
5. Good Hang with Amy Poehler

How many episodes of The Five Year Plan are there?

The Five Year Plan launched 4 months ago and published 15 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact The Five Year Plan?

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What guests have appeared on The Five Year Plan?

Recent guests on The Five Year Plan include:

1. Kayam Khalfan
2. Shawn Kanungo
3. Kath Smith
4. Abtine Monavari
5. Megan Davis
6. Henna Choi
7. Jules Romano
8. Maggie Arai

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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