Episode Summary: "How to Know When to Quit (And When to Keep Going)"

Brutally Anna | Host: Anna Kai | Date: November 14, 2025

Episode Overview

In this raw, honest, and self-reflective episode, Anna Kai delves into the messy complexity of knowing when to quit and when to push through—in careers, creative projects, and life. Framed by her own experiences with burnout, disappointment, and growth, Anna shares stories from running the NYC Marathon to navigating career plateaus, and ultimately announces the (for now) end of her Brutally Anna podcast. Rejecting toxic positivity and empty encouragements, Anna offers hard-earned wisdom about resilience, failure, self-honesty, and listening to your gut about when it's time to call it.

Key Discussion Points & Insights

The Marathon Metaphor: Endurance and Uncertainty ([01:00]-[05:55])

• Anna recounts running the 2017 NYC Marathon, describing the phases of excitement, exhaustion, and the psychological challenge of not knowing how close you are to relief in life, unlike in a clearly measured race.
  • “Life would be a lot easier if we knew we were at mile 20 of 26.2...” ([02:15])
  • By mile 23, Anna recalls feeling so spent the effort was undeniable even in race photos: “I could no longer hide it. By mile 23, my face is just in a grimace that I didn’t even know I made.” ([03:10])
• She draws a parallel: in life, we often quit just before the finish, not realizing we’re close to a breakthrough.

Struggling Through Burnout and Career Transitions ([06:00]-[13:00])

• Anna reflects on the hardest year of her career, after an initial “rocket ship” launch.
  • “With much privilege comes much responsibility and the pressure to keep up everything and to keep growing. And I was feeling really burnt out this year..." ([07:30])
• She touches on the emotional toll of fertility struggles, shifting industry tides, and how unpredictable opportunities can be a test of resilience.
• A story about losing a minor opportunity and then gaining something better:
  • “Every time something has been taken away from me over the last couple years, something better has come along. And that better opportunity came today.” ([11:40])

The Perpetual Urge to Quit—and Why We Don’t ([13:05]-[17:10])

• Anna is candid about frequent thoughts of quitting throughout her career: “I think about quitting all the time. I thought about quitting acting in my 20s. I thought about quitting social media...this year, I thought about quitting everything. I was like, what would it be like to just be a hermit? Part of that was probably the depression talking, but a huge part of it is like, quitting just feels like relief, right?” ([13:20])
• She references David Goggins: “The body doesn’t give up before the mind does. The mind gives up before the body.” ([14:30])
• Anna reflects that most pain this year was mental, and she’s working on retraining her brain to resist the urge to catastrophize setbacks.

Mental Health, Therapy, and Cognitive Reframing ([17:15]-[22:40])

• Anna discusses her ongoing therapy journey, how she outgrew her previous therapist, and now finds connection with her psychiatrist (though not a talk therapist).
  • “I’ve gone through three [therapists] already. And I was just like, you know what? I’m going to take a break. I love my psychiatrist.” ([18:35])
• Advice from her psychiatrist: focus on basic cognitive behavioral swaps—don’t jump to negative conclusions, reframe disappointments as opportunities.
  • “You’re not going to believe it at first, but over time...I’ve noticed I’m a much more positive person.” ([21:40])
• She shares the mantra: “I ask God not for a lighter burden, but broader shoulders. Like, I’m really asking for massive shoulders here.” ([22:20])

The Hard Decision: Knowing When to Quit ([22:45]-[30:50])

• Anna officially announces the pause (or end) of Brutally Anna: “This is my final episode of Brutally Anna for now. And I want to thank all of you who have tuned in over the last year and change to this podcast. It really was a labor of love.” ([22:45])
• She’s honest about the decision: podcasting wasn’t as fulfilling as her writing, nor was it hitting her hoped-for growth.
  • “I don’t enjoy it as much as I do communicating with you all via my Substack and my writing…and as always, my short form content.” ([23:40])
• Anna reframes quitting: “If I didn’t [try this], I would have always been wondering, well, what if I tried podcasting? What if that was the next step for me, and I didn’t do it because I was afraid? Like, I have no regrets.” ([25:10])
• She shares wisdom about pivoting: “You have to know when to quit, when something’s not a fit. That goes for everything. Relationships, jobs...There’s just people that do it better than me. There’s people that make better content in that arena than me...if you cannot put out a product that you are reasonably certain is more or less better than the competition, you shouldn’t be putting it out there, because there is just so much content, so much to consume…” ([28:00])

Emphasizing What Works: Writing, Substack, and Community ([30:55]-[33:30])

• Anna encourages listeners to follow her Substack, offering a free month for those interested:
  • “If you’re listening to this and you are not a paid subscriber yet, email me. Okay. askannakaimail.com. I will send you a free subscription for a trial month.” ([31:40])
• She describes greater satisfaction and resonance with her writing.
• Shares new directions—running an advice column, building community.

Open Endings and Lasting Lessons ([33:30]-[end])

• Anna remains open to future podcasting but is content with moving on for now:
  • “Am I saying goodbye to podcasting forever? Absolutely not. I may be back in this format in some other way. I have no idea where life is going to take me...” ([33:55])
• She closes with hopefulness and gratitude, noting how unpredictably good life can become if you persevere:
  • “If you stick it to the end, you’ll find that even if you didn’t get where you wanted to be, you end up somewhere pretty cool...And I just want the lesson of this final episode of this season of my life and this podcast to be that it’s okay to quit. Not everything, but you do have to know when to quit, when something isn’t working.” ([34:20])

Notable Quotes & Memorable Moments

“Life would be a lot easier if we knew we were at mile 20 of 26.2…” — Anna [02:15]

“Every time something has been taken away from me over the last couple years, something better has come along. And that better opportunity came today.” — Anna [11:40]

“Quitting just feels like relief, right?” — Anna [13:30]

“The mind gives up before the body.” — Anna quoting David Goggins [14:30]

“I ask God not for a lighter burden, but broader shoulders.” — Anna [22:20]

“This is my final episode of Brutally Anna for now.” — Anna [22:45]

“You have to know when to quit, when something’s not a fit. That goes for everything. Relationships, jobs...” — Anna [28:00]

Timestamps for Key Segments

• Running the Marathon & Life Metaphors: [01:00]-[05:55]
• Career Struggles & Burnout: [06:00]-[13:00]
• On Wanting to Quit: [13:05]-[17:10]
• Therapy & Cognitive Shifts: [17:15]-[22:40]
• Quitting the Podcast: [22:45]-[30:50]
• Writing & Substack Community: [30:55]-[33:30]
• Final Reflections: [33:30]-[end]

Tone & Takeaways

Anna’s trademark brutal honesty is front-and-center: self-deprecating, warm, a little raw, and full of hard-won insight. She rejects empty motivationalism, instead offering nuanced encouragement for listeners to both grit their teeth through the hard parts—and to recognize when it’s time to pivot or let go.

Core message: The line between grit and self-delusion is thin. Know when you’re at mile 24 and just need to hang on—and know when your energy belongs somewhere else. Both count as growth.