How to Know When to Quit (And When to Keep Going)

About this episode

Anna Kai reflects on the challenges of knowing when to quit and when to keep going, using her experience from the New York City Marathon as a metaphor for life's struggles.

This week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line. Learn more about your ad choices. Visit podcastchoices.com/adchoices

People in this episode

Host: Anna Kai

Topics covered

• quitting
• perseverance
• career challenges
• personal growth
• marathon analogy

Keywords

• quitting
• marathon
• personal growth
• career
• mental health
• spirituality
• disappointment

More episodes of Brutally Anna

• The Myth of the Soulmate · November 7, 2025 · 25 min
• Laziness as a Love Language · October 31, 2025 · 22 min
• Fertility Math Will Make You Crazy · October 24, 2025 · 25 min
• Stop Needing A Witness For Your LIfe · October 17, 2025 · 24 min
• Everybody Wants A Piece of You · October 10, 2025 · 25 min
• The Art of Dining Alone (and Redefining Community) · October 3, 2025 · 23 min