Summary6 min read

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.

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[00:00]
A
AI had the time of my life. A. I never felt this way before. From building timelines to assigning the right people, and even spotting risks across dozens of projects, Monday Sidekick knows your business, thinks ahead, and takes action. One click on the star and consider it done. And I owe it all to you. Try Monday Sidekick AI you'll love to use on Monday.com. so the new York City Marathon was a week ago, and it's been a long time since I've run that marathon. I ran it in 2017, and even though I couldn't run a mile in high school, I ended up running the marathon when I was 27. So it's pretty incredible what life can do if you just keep living. And I was thinking about this the other day, because in a marathon, you know you have to run 26.2 miles. So when you're at mile 14, you're like, damn, this sucks, but I gotta keep going. Then you're at mile 20, and you're like, oh, my God, I can't go on any longer. And I don't know if any of you have run a marathon, but for me, I was actually doing pretty okay until mile 20. I know that sounds insane, but I think, like, the first 10 miles, first of all, piece of cake. You're just running on adrenaline. Like, I don't care who you are. The vibes are so high. The New York City Marathon is such an amazing energy. Then you get to mile 15, you're like, I'm tired, but, like, I can still go mile 18. You're like, damn, this is not fun, and I have a lot longer to go. Then you hit mile 20, and you're like, I have 6.2 miles left. Are you kidding me? And the thing is, though, when you hit mile 20, you know you have 6.2 miles left. So it's like, I'm not stopping now. And I feel like life would be a lot easier if we knew we were at mile 20 of 26.2 and then mile 24, which sucks even worse than mile 20 and mile 25. Okay, I don't know where these photos are, but they take photos of you all throughout the race. And my girlfriends came, and they were all watching, and then I looked at the photos after, and one of them was like, oh, my gosh. I, you know, followed you to the finish line. And I think I saw you at mile 23, and you looked really beat up. Like, I could no longer hide it. Like, all the photos from the first, like, 18 miles, like, every time I see the Camera or the mile marker. I, like, throw my hands up. I'm like, woo. I do the woo hands. By mile 23, my face is just in a grimace that I didn't really know I made that face. But apparently when you're running a marathon and you're towards the end, you make that face. And I ended up finishing it. Yay. Which was my goal. I had no time goals. I was just like, I just want to finish. Okay? I want to finish, and I don't want to injure myself. And I accomplish both things. But I think about how often we quit at mile 22, 23, 24, 25. Okay, 09, or 26.1. How many times we quit before we get to the end, because we don't realize that at 26.2 miles, we get the prize, we get the medal. The tides turn, luck turns in our favor. But we quit before we get to that point, thinking, this is just going to go on forever. This marathon is never going to end. I'm never going to see the end of my struggle, so I might as well just quit right now. And everything good in my life has always come from pushing past the point of failure. I think that's the only way you get better. I feel like I sound like a weird version of David Goggins right now. I've been listening to a lot of David Goggins. I do find him oddly inspirational in a really, like, I'm a you up kind of way. Because sometimes I just, like, don't want to be coddled when I'm looking for advice. I'm looking for somebody to, like, amp me up. And I think what he's always preaching and what I have really just tried to tell myself over and over again, especially this year. This year was easily the hard year of my career so far. And not even, like, the whole year. I would say, really the last, like, six to eight months have been very challenging, mentally, spiritually, everything. I've had a lot of changes in my career, and it's just tough because you get used to doing things a certain way for the first two and a half years of this. And it's such an amazing job that I get to do. And I can't believe that this is my life. But 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 on top of the fact that we're trying to have a kid, and I am not pregnant yet, so that's how that's going. And I'VE forgotten what it felt like to like really struggle for a little while there because for the first two and a half years of my career, it was just this rocket ship. Like it came out of nowhere. It was from zero to a million in an instant. I was just holding on for dear life, hoping it wouldn't stop. And then all of a sudden things started to feel a little bit different. You know, the outcome didn't always match the effort and that's always disappointing, you know, but we're in a very fluid business and the business I'm in is really up and down and nothing is ever guaranteed. And I was reminded on a week like this how poetic life can be. And maybe it's just me, and I love to draw conclusions and parallels and full circle moments from everything. But this week started off a little bit rough. There was an opportunity that was on the table and then it wasn't. And I found out on Monday and it was a little disappointing. Was it a life changing opportunity? Absolutely not. But in any case, it was an opportunity. And it's always tough having something presented to you like, oh, you have the option to take this and then have it taken away. And I'm actually pretty proud of myself for how I handled it. I got off the call with my agent and I didn't spiral. I didn't draw sweeping conclusions from it. I just thought, okay, it's one opportunity, one deal that didn't happen. We're going to move on. Because every time something has been taken away from me over the last couple years, so something better has come along and that better opportunity came today. And I'm being so vague about everything, but I can't talk about it yet. And I don't want to jinx it either, but I really actually just can't talk about it. It's like way too soon. However, today was just one of those moments that made me realize that if you don't quit at mile 20 or 23, there is something so much better waiting for you at the end of it other than the relief you feel when quit. I don't know who these people are that are always like, I've never thought about quitting anything in my life. Girl, I think about quitting all the time. I thought about quitting acting in my 20s. I thought about quitting social media. A year and a half in when I had 2500 followers and I wasn't growing my accounts, I thought about quitting influencing. 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? It's like that moment in the gym where you're like, I just, like, really can't do one more rep. Like, I just. I can't do one more sit up or push up. I'm just going to quit. But the body, as David Goggins says, doesn't give up before the mind does. The mind gives up before the body. And I think most of what I felt this year, most of the pain and suffering that I have felt has been mental. And I think I am slowly, very slowly but surely starting to retrain my brain. I go to see a psychiatrist still, even though I'm no longer on medication, because honestly, even though she's not a psychologist, she's not a talk therapist. She's like, the only mental health professional right now that I really click with. I kind of outgrew my old therapist from my 20s, even though she was great during that period of my life. And I've really just been at a loss trying to find a different talk therapist that I click with. And it's not easy. It's not easy to find that. I've gone through three already. And I was just like, you know what? I'm going to take a break. I love my psychiatrist. And she was like, look, even though I'm not a talk therapist or a psychologist, I'm still trained in therapy, so I can still help you to the extent that I can, even though you don't want to be on medication. And so what she said to me after I, you know, trauma dumped all of my anxieties about my career and my life onto her the other week was she's like, I know this sounds simple, and I know this sounds stupid, but you really need to work on cognitive behavioral therapy, changing the way your brain works to stop jumping to negative conclusions all the time. And she's like, in the way you do that, it's. It's simple, you know, but it's really stupid. It's. Something bad happens, and you're not like, oh, my God, this is the end of the world. You say, no, no, it's not. This could come of it. Maybe this will happen. This is how I'm gonna use this opportunity that didn't come through to fuel me for the next one. And you're not gonna believe it at first, but over time, even in the last, like, week or two that I've been doing this, I've noticed I'm a much more positive person. I don't take every failure so personally anymore. And over time, it's like that phrase. It's like I ask God not for a lighter burden, but broader shoulders. Like I'm. I'm really asking for massive shoulders here. Because if life keeps going in the direction I want it to, I want to keep growing, both personally and professionally. And with growth comes a lot of pain. But if I can get massive traps to handle that pain and the burden, then there's really nothing that can stop me. And that brings me to the point of today's episode, is that 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. I put everything I had into it and would I have liked to see it top the charts, perform better? Of course I would have. There's a huge part of the reason why I'm stepping back is just because it's not performing the way I want to. But more so than that, 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. I don't know what it is about podcasting. Everyone said it should have been a natural fit given the nature of my content, but I think what it is is that I am first and foremost a writer and I have always scripted out all of my reels and my tiktoks and I record them line by line so it doesn't feel like I'm reading. But that's how I think. I need time to think and process and just marinate on an idea that I want to communicate with you guys. And podcasting is a little bit more spontaneous than that. In any case, though, I am really glad I tried this because if I didn't, 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. I had an amazing ad partner, my agent just hustled for me to get this thing going. I interviewed so many amazing guests. I had the opportunity to speak to so many different people and it's been really Fun the last 8 weeks checking in with you guys. But I know when something is not working, there are always signs and I know when something is working. And right now podcasting is just that thing that is not working. But my substack, if you guys haven't signed up for it yet. Is. And 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 so you can see how it goes. I've been posting two times a week right now, and I'm running a little advice column over there, and it's just been a really wonderful community with all of you writing in your questions and me having the time to really marinate over every word I want to tell you guys. So if you're listening to this and you want to sign up and you just want to test the waters, email me. I'd love to bring you all into the next phase of my life and career, which is hopefully writing. Um, and also, if you want to listen to each of my posts, there is an audio feature. It is read by an AI woman, but she doesn't sound horribly robotic, and you kind of get the gist. So I know a lot of people will just listen to substacks during the workday if they have to do something mundane. And that's something you can totally do, too, if you prefer an audio format. 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. I had no idea I'd be here three years ago. Hell, five years ago. I mean, five years ago when I was just hoping for 10,000 followers on Instagram and to make a little bit of money off of affiliate linking. No, I did not think I was going to be here. But life is pretty crazy. And I think 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'm not where I want to be yet, wherever that is the arrival point. But I am 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. I think about this with my content creation career, my influencing career. You know, I started off as a home decor blogger, and then I switched into fashion, and I was making these fashion reels that were taking me like seven or eight hours end to end to, you know, prepare outfits for shoot, edit. It was so time consuming and for like 200 views on TikTok. And I was like, what am I doing? And I feel like the common piece of advice everybody always gets is, oh, don't stop. Like, you just keep going. But, like, you have to know where in which direction to keep going. If I'd continue making fashion reels, I'd still probably be a failure, or I wouldn't be anywhere where I want to be today. And the thing is, you have to know when to quit, when something's not a fit. That goes for everything. Relationships, jobs. Fashion was not my avenue. I like fashion. I like clothing. There's just people that do it better than me. There's people that make better content in that arena than me. And to that end, I think there are better podcasts than this one. And so I just realized, too, it's like, 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, to buy. Like, if you don't think you have a unique worldview or a unique offering to the world, like, don't put it out there. I never really felt quite grounded in what I had to offer in this podcast. I felt like I did all the right things, and I tried my best, and I put in the time and the effort, but, like, the heart was missing. And I think that translated to you guys. But what I couldn't do with my podcast is what I feel like I am doing with my writing right now. And that's why it's resonating. And so I'm grateful for this experience. I look forward to the day when maybe life brings me back to podcasting, or maybe it doesn't. But in the meantime, I will still be around via Instagram, TikTok, and, of course, my newsletter. So thank you to you all and to all a good night.