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

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Sponsors:

Thank you to Strawberry.Me for sponsoring this episode.

Want to partner with us?

anna@thefiveyearplanpodcast.com

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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

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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

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.

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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!!!

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Follow Janine here:

IG: @janineilya

TikTok: ⁠@janine.ilya

Youtube: ⁠@janineilya

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Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠

⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠

Email: annashuyizhang@gmail.com

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