Hilary Henderson: From Policy Analyst to Viral Stand-Up Comedian — Bombing, Starting Over & Betting on Herself
Sep 22, 2026 · 58 min · 14 segments
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…
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
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…
