Life Will Be the Death of Me with Chelsea Handler - A Late Bloomer with Kaitlin Olson

Episode Date: January 8, 2026

Kaitlin Olson (Hacks, High Potential, It’s Always Sunny in Philadelphia) joins Chelsea to chat about juggling 3 shows at once, forcing her husband Rob Mac to fall in love with her, and why balls are funny… until they’re not.   Then: A postal worker can’t jibe with girls her own age and finds happiness in may-december friendships.  An ex-wife struggles to name a newborn.  And an ex-stripper chases her new dream job - but will her past hold her back? * Check out Redneck Kitty at @redneck.kitty * Need some advice from Chelsea? Email us at [e-mail] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.

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abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse.

Each week, we're connecting the dots between books, the internet, and pop culture. with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Did you hear the new episode of the Hey Jonas podcast? We are at D23, so we'll see who stops by.

The cast of Frozen stopped by. Kristen Bell, Josh Gad, and Idina Menzel. I auditioned for Frozen. What? For Kristoff. They said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get in.

Plus, John Stamos, Hayden Christensen from Star Wars, and more. And I guess I can share that... Listen to the latest episode of Hey Jonas on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I just announced all my tour dates. It's called the High and Mighty Tour. I'm coming to Washington, D.C., Norfolk, Virginia, Madison, Wisconsin, Milwaukee, Wisconsin, Detroit, Michigan,

Cleveland, Columbus, and Cincinnati, Ohio, Denver, Colorado, Portland, Maine, Providence, Rhode Island, Springfield, Massachusetts, Chicago, of course, Indianapolis, Indiana, Louisville, Kentucky, Albuquerque, Mesa, Arizona, Kansas City, Missouri, St. Louis, Missouri, Minneapolis, Minnesota, Nashville, Tennessee, Charlotte, North Carolina, Durham, North Carolina, Saratoga, California, Monterey, California, Modesto, California, and Port Chester, New York, Boston, Massachusetts, Portland, Oregon, Michigan and Seattle, Washington. I will be touring from February through June. So go get your tickets now. If you want to come see me perform, I will be on the high and mighty tour. Hi, Catherine. Hi. Do you hear my voice? I can hear your voice, Miss Critics' Choice Award host. You absolutely crushed it. Oh, thank you. I had such a good time at the Critics' Choice Awards. I can't believe how, I can't believe my dresses and my tux and the way I looked. I was like,

what? I saw pictures of myself. I'm like, oh my God, I can't believe that I'm 50 years old and I look better than I did when I was 35. Every woman that is listening to this, you need to know how much better everything keeps getting. Like, oh my God, my body, my face, everything looks better. I'm so pleased. And I have to tell you, I love the way you look in a tux. You know this already, but I love it. That was my nod to Diane Keaton, but I loved it too. I felt like a real fucking bitch in that tux. That's the best way. Yeah, it was super fun. I'm here in New York City getting ready to do some press. I'm doing Kelly Clarkson, and I'm doing Jimmy Fallon tomorrow night to promote my High and Mighty tour. Tickets are on sale, people. Get your tickets. The tour

jumps off in D.C. in February. So get your tickets. And we have a fun guest today. You know her from It's Always Sunny in Philadelphia, Hacks, and her new show, High Potential. So please welcome Caitlin Olson. Hi. Oh, look who's here. Hi, Caitlin Olson. Oh, my God. I can't believe I've never met you before. This is crazy. I know. I was watching you in High Potential the other night doing your detective work. I'm like, have I met her or not remembered? And I'm like, no, I would remember your energy. Cause I love your energy. I love every time you're in a scene in any of the things that you do, you light up the room. And that is just like, no, I mean it. I mean it. You're just so light filled. And I, I just love that about you. So congrats on being

light. Oh my, thank you very much. I've never been congratulated on that before. And I really appreciate it. There's a lot of things that are going to happen today that have never happened to you before. I can't wait. First of all, I can't believe It's Always Sunny has been on for 20 fucking years or 20 seasons. Is it 20 seasons? 20 years, right? 20 years. It's 20 years, yeah. So you, that's crazy. That's like two lifetimes of television. It's getting weird. Like for a few years ago, it was exciting. We're like, oh, we're breaking records. And now it's like, well, now we're just old and weird. Yeah, it is. It's probably, I mean, I'm not saying it is getting weird, but I can understand what you're saying about it getting weird. I mean, I think the main

reason you have to be always grateful to that show is because you met your husband. So if it weren't for that, then you can't have any mixed feelings about that. I have zero mixed feelings about it. I met my husband. I've got two kids. It's the best thing that ever happened to me. But also, you don't want to overstay your welcome. You know what I mean? So at what point am I like, I should probably Irish exit? Should I just leave the show and not tell anyone? I didn't know if you're talking about your marriage or the show, but copy that. Either way, either way, they both would be very exciting and a fresh start. You guys met the first year and you obviously hooked up right away. Is that right? Or you tell

us what happened? I mean, in the scheme of things, it was right away, but it felt like a lifetime. He loves the story that I definitely was interested in him and took every opportunity to be at a party where there was alcohol to find myself like touching him with some part of my body, just getting really in his space. And he was like, okay, this is, this is unprofessional. And I was like, excuse me, I'm flirting with you. And I didn't understand it. And then I just hammered him with it. You know, I just, and then you hammered him alcohol. Right. And then I hammered him. Well, he, he, in the end, he hammered me. Let's just be very clear. There was a flip that switched. My friend said that to me the other day. And I was staying with my friend

Kat and she's like, did you ever bang that guy? I go, what? Who talks like that? I go, first of all, I go, bang him. And she goes, yeah, you never say bang. I go, no, I don't. I don't ever say that. By the way, you're the one getting banged. I'm not banged. She goes, that depends how you look at it.

I'm like, well, I'm definitely not banging men when I have sex with them. They're banging me, thank you very much. So your husband's Rob McElhenney, right? But he goes by Rob Mac now. Did he change his name? Yeah, he made a big thing about it. He changed his name and now he's Rob Mac. And I have two kids who are stuck with McElhenney.

So we don't talk about it. Well, he was actually originally Rob McElhenney III. So your kid's, right? Isn't that his real name? There's a whole thing. His name has been a subject of great grief for him, our entire marriage, and I think his entire life. There's a lot of misunderstanding. I think on his birth certificate, it's just Robert McElhenney, but they put a space between the Mac and the Elhenney, I think accidentally.

and so that's been really fun for me trying to figure out what my because i have that technically as my last name i don't use it but it's like on my you know passport and stuff but then his dad and his grandpa were robert but they have middle names and he doesn't so he's not technically a third but i don't care anymore i'm bored i just bored myself for the last 30 seconds who cares rob Mac. That's his name. It's easy. He's great. Again, we're stuck with McElhenney, but that's a subject for another time. So how did you keep it a secret from the other cast members until you decided to go public with your relationship? Well, we were just in our trailers a lot. And I don't know. We thought for sure that they were going to find out because we thought it was

really obvious because we were being very flirty. And we would travel for work back then. This is before we had kids. So we would be staying in hotels in Philadelphia and New York and we'd always end up in each other's hotel rooms and like getting off on the wrong floor

with two cups of coffee and be seen by them and be like, I don't know. I'm not great with floors. I don't know. They had no idea though. We kept it secret

for a whole season. Wow. Well, that's impressive. Which felt like forever. Especially in Hollywood terms. You know what I mean? I mean, those things are pretty obvious.

Staying together for a whole season is impressive. Well, staying together for 20 seasons is even more impressive. I know. I read that you went to a baseball game while you were in labor.

Well, I was planning a home birth. That's, listen, I apologize already. This is going to be irritating. I was planning a home birth. So my midwife was like, you're going to go into labor. You're going to go for a walk. You're going to go grocery shopping. You're going to be in public so that you can't have a meltdown.

You're going to pull your shit together and you're just going to walk around. We're not going to lay down on a bed. And so I started feeling like I was having contractions and we were supposed to go to this game. And I was like, you know what? I'm supposed to go on with my life. Let's go to the game. So we climbed in. I folded myself into his, he had that original Tesla that looked like a little toy car that was like six inches above the ground. I folded my body into that and we went to the game and I think I made it seven innings, something like, I don't even remember, but at a certain point I was like throwing up and having diarrhea in the bathroom. And I was like, probably

time to go. And then what happened? Did you have the home birth? I did eventually. Yeah. At some point the next morning, did you have to do both of your kids are home births? So I got pregnant the second time and I was like, Oh no, I should, I probably have to do that again. So, so that they don't like find out. And that turns into a therapy thing. Like, well, why'd you have me at home and then go straight to that? So I decided to do it again, not because I wanted to. And three days into that when I was like, I fucking hate myself. I hate midwives. I hate babies. I hate everyone. And I did. I had him at home. But three days into what? What do you mean three days into it? I was like two and a half days of labor. It was a lot. It was a long time. My second one I thought

was going to slide right out. Oh, my God. What a nightmare. Two and a half days of labor. You were laboring at home for two and a half days before you had the baby. Yeah. At one point, We drove over the canyon behind garbage trucks because it was garbage day in the backseat of my midwife's Prius to go to the gynecologist to check something out just to make sure. And everything was fine. So then we drove back over the can. It was a lot happened in those two and a half days. Not a baby coming out. Wow.

Wow. Wow. Tell me what playing the character you play on Hacks has taught you about being a parent or what has it taught you not to do about being a parent? Yeah, I don't. I don't, I don't know that I'd take any advice from, from DJ. I love her, but listen, DJ, I think is going to end up being a real good mom. Cause she's just going to look at whatever Debra did and do the opposite, which is always a good pointer. When you have great parents, it's impossible to replicate that exactly. But when you have bad parents, it's almost

a natural instinct to do the opposite of what they've done. Yeah. What a blessing to have a horrific childhood, you know, because then you know exactly what not to do. That's a great way to look at it. I want to know how you managed to be on starring in two shows, also on Hacks. Who's your agent? How are you able to negotiate these kinds of deals?

The good thing about Sunny is that we don't have a set time of year that we shoot it. We kind of shoot it whenever everyone's available, so we can move that around and sort of make it work. it's only been, this is my second year of kind of working literally every day, nonstop. It's, it's starting to get to me. I'll be honest. It's a lot of work. It's a lot of work and it's working through now a second spring break and a second summer break for my kids. So I kind of feel like I should probably be going on vacation with you guys at some point in the next couple of years.

Right. Absolutely. Absolutely. Especially because high potential is essentially a procedural. So that's a lot of hours. It's a lot of hours. Yeah. I want to know about like the most fun memory or the most fun day of shooting that you ever had on. It's always sunny. People ask this. And first of all, I can't even remember all the episodes, but anytime I'm like lit on fire or I'm addicted to drugs or I've been thrown off a building, those are always the really fun ones. You read it. I love when people are like, do you ever read anything and be like, absolutely not. I'll never do this. I was like, no, who's that asshole. They write me like big, funny stuff. I'm so excited. there's a lot of fun like stunt stuff that I didn't get to do on sunny that oh you know there

was the one where we d drowns in a bog that was horrible that was at like two o'clock in the morning um yeah anything like that that's insane yeah well I think that's what comes through in your when I'm talking about your ebullience I'll use that word my favorite word oh I don't know what it means but I just inferred and I think I get it yes that comes through in your willingness to just kind of be silly and outrageous, you know? Like, it's when people take themselves too seriously, you don't see that kind of shine through. That's an effervescence.

Yes, an effervescence. Thank you. You're so welcome. Who's more vain, you or Rob? Me. He's not that vain. No? There are other men on my television show

that are a little bit more vain. Do you want to name names? Glenn. What about your kids? Do you let your kids watch any of your shows? Are they too little? No, they're not. My older one just turned 15 and he has been sneaking Sonny scripts since he was about seven or eight. We'd find him in bed reading Sonny scripts and we were like, well, this is bad. And then a few years ago, we would show them different chunks of episodes and he's just obsessed with it. And now it's off the rails. He's seen every episode. He thinks it's amazing. And I love that because it is a really funny show.

But when you're 15, you got to kind of fine tune that. I mean, I'll I'll pause things all the time. He'll say stuff all the time where I'm like, whoa, that's not funny. And then we have to have those conversations in time. He's going to be a very, very funny young man. Yeah. Who's funnier, you or Rob in the family dynamic? I'm funnier.

You're funny. And he'll tell you that. Yeah, he's smarter. He's he identifies himself as more of a writer, producer. He loves acting, but he would say that I'm funnier. Okay, well, that's good. That's smart. And which one of your children is more like you?

Is there one that's more like you and one that's more like him? Yes, the older one who's sneaking sunny episodes is more like him. And the younger one is more like me. And he legitimately cracks me up. I think Rob talked about finding out he was neurodivergent. Like when you found that out,

I always find this to be fascinating. Did any of the aspects of his relationship or I mean, aspects of his personality, within your relationship click yes like what what kind of stuff I remember going oh that's why like we would be in the car just the two of us like talking about something and then he would just go silent like even while we were dating and I was like does he know I'm still in the car with him like he could just be completely in his own world and I'm like I'm not good with silence I'm a person who has to like fill it or let's have a car turn the music on or something but what are we doing

sitting here, like not talking. And I was like, oh, there's so much going on in his brain at all at all times. Like he can easily be in a conversation with me and then just absolutely shut me out. And I'm like trying to pick up the pieces of what just happened. That was one thing. There's a there's a million of them, though. But he's also like very prolific. He's super, super smart. And he's constantly coming up with ideas or business ideas or show ideas or doing things the way they've never been done before. It's it's pretty fascinating. It's very impressive. yeah he probably misses you doesn't he want more time with you with all of your responsibilities he does they all miss me it's very sweet but it's one of those things too where it's like

he loves me a lot these days because i'm not around i'm like this totally works i'm off doing my thing our relationship is great you're missing me yeah but yeah it's exciting when we get to see each other but i'm home to be fair like i only work they have me for 11 hours here so plus drive to like i'm i'm home for evening so we spend time together at night well then maybe it is the perfect schedule yeah you know yeah it's great I just need a vacation every once in a while and we're fine yeah and then you get to get all your kinks out on on set like get all of your energy out and that way you can be like you know a full complete mother when you get home you're not there all day dealing with them I like that schedule I love it yeah anybody can be a really excellent parent for

three hours at a time Rob's really doing the heavy lifting right now I come home and I'm just a dream like the best mom ever. Yeah. That's the spirit. Um, I always think about like mothers and how people handle stuff, especially in this business, because there's so much to deal with, you know, and I could barely take care of my dog. I don't even really take care of my dog, to be honest today, he had a limp and I just was like, who do I text about this? You know, I'm like, and then they're like, did he, did anything happen yesterday? I was like, well, I was wrestling with him. So I'm probably the culprit, but I'm always just, I love your dog by the way. Oh, thank you, Doug he's so beautiful he's so beautiful and he's got these big beautiful brown eyes it really makes

me appreciate brown eyes because as a blue-eyed person everyone in my family has blue eyes so I always think of it's this weird childhood thing where I always look at blue my parents both had blue eyes and all my siblings have blue eyes and so I always looked at everyone with blue eyes like that's home and now that I have a dog that has these beautiful brown eyes I'm like that's home yeah you're like there's some soul there what's this yeah he's definitely soulful I feel like his voice, if he could talk, would be like Luther Vandross. Absolutely. Absolutely. And that big thick tongue. Yeah. Yeah. Yeah. And they have purple tongues, chow chows. You know that? They have those purple tongues. So everyone always wants to see that. And you know what's so sweet

about Doug, actually? He's so sweet with children, which is something that like, you know, it's such a nice feature for a dog. He knows when to be gentle with small children, not with small animals, unfortunately. That's okay. Do you guys have pets? Yeah, we have two dogs and a cat and they're all really good friends, obsessed with animals. Yeah. I always wonder how cats get along with dogs, but I guess it's happened. I guess I grew up and they, we always had our cats and dogs completely separate. Other people seem to be able to integrate, but. Well, I think it depends on the cat. Rob didn't think he was a cat person for this reason. He's like, cats are all like finicky. This cat, I rescued him and brought him home, got him neutered and deflead and all that. And he,

we had like him in a room and he came out of the room and saw the dogs came running towards him. and he was like, hey, and flopped on his back. It was like, smell me. So I don't know. He just decided he was fine with it. Now they all play together. It's the best. And is it a fluffy cat or is it a skinny cat?

He's a white fluffy cat with a big fat fluffy tail. Oh, yeah. He can pull on it. He likes it. Does he have a fat face, a fat fluffy face? Yeah, he's like, he's all fluff. He's like a big giant. And if you hold him like this,

he just like flops on either side. He's fine with whatever, which I like. I need that. I need you to be fine with me manhandling. Yeah, yeah, yeah, yeah, yeah. I like to put animals on their back and then just kind of molest them. You know, I want the bodies.

I like the fur and I like the meat. The bigger, the better, the puffier. Yeah. All of it. Yes. All of it. Don't give me a skinny. I don't want to have to be fragile.

I got to throw you over my shoulder and you're coming with me. That's how I feel about babies too. I prefer them to be oversized. You know, like I want a big nugget. If you want, if you have a baby on a plane or like, you know, then like the chunkier, the better. If you see a skinny baby, it's like, I'm not drawn to that.

And I mean, we already know how I feel about children, but babies obviously get a pass because they can be so luscious and just scrumptious, you know? But when they're thin, I don't like that. It's like a twig. Like it's, it's too fragile. I'm not, I don't want to be responsible for it. Did you have big babies? Yeah. Big fat babies. I feel like thin people. I know you're very thin. Cause even on camera, you look thin. I feel like thin people have the fattest babies. It doesn't make any sense. I don't know how it happened, but yeah, They were both almost nine pounds. Oh, God.

Those are big babies. Yeah. That is a big baby with your home birth, with your two and a half day home delivery system. Yeah, yeah. Let me be very clear. It was terrible. Bad idea.

We're going to take a break, and we're going to be right back with Caitlin Olson to take some callers. The new Red Bull Dragonberry and Tropic Berry Energizers, now at McDonald's. Made with freeze-dried fruit and an electric burst of flavor. The all-new Red Bull Energizers, now at McDonald's. This product may not be right for you.

High in caffeine. Details at mcdonalds.ca and participating Canadian restaurants, excluding Quebec. When I was 14 years old, I was kidnapped and held captive for nine months. I survived, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files. I just remember this low, taunting voice next to my ear saying, shut up, don't say anything. Every week, I'm with survivors who live through the unthinkable. I knew if he woke up, without a doubt, he was going to hurt me.

I started feeling that there was someone at the end of my bed, and I just started screaming. They are abducted, stalked, controlled, and nearly silenced. but these aren't stories about what's taken from them. They're stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page

are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsessives, and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo, and every week we're connecting the dots between books,

the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From best-selling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table. It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse. Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

See you between the pages. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Every time I tried to be alone, I kept meeting people, and they were like, you smiled at us. Not a lot of people smile around here.

It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it. It can be a time where you push your limits, change your mind, or wake up to a new version of yourself. So whether you're a solo travel veteran or you're too nervous to book your first trip, I hope you listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And we're back with Caitlin Alston. who is the, she's on Hacks. She's the star of High Potential and she's on It's Always Sunny in Philadelphia. So you really can't miss her. Caitlin, what was the best, before we take a caller, can you think of the best career advice that you've ever been given? You know what? The

best audition advice, which is basically career advice for me, was to make it your own and stop reading all of the character descriptions so perfectly and trying to be exactly what you think they want because they don't even know what they want. Just read the material, make the material as good as you can in your own voice and switch it up. Just make it your own and then go in and have fun. And that was honestly, that was very freeing. Once you stop caring about like, oh, I wonder if they're going to want this. They don't know what they want. They just want you to come in and be good. That was the best audition advice I got. And I still do it. Yeah. Yeah. You have to own what you're doing, right? You have to make it your own and you have to make it personal

to you. And that's kind of the only way to set yourself apart in any sort of creative, I feel like any sort of creative medium. I think it absolutely, it, it, it, you can use that across the board. Just, just do what you want to do. Be the best version. People like it. Great. If they don't, great. It wasn't for you anyway. You can't cram yourself into a box. Okay, great. All right. Well, are you ready to give some advice? Yes. Excellent. Excellent. Always. Always. Me too. Me too, sister. So our first question, this one's just an email, but this comes from Nicole. She says, Dear Chelsea, I'm writing in with a bit of a unique circumstance and would love

some guidance on this. I'm recently divorced, and it's as amicable as it could have been. We share tween twins and co-parent great. I kept my married last name because I hated my maiden name. I'm a veterinarian, and everyone in town knows me as Dr. Ex-Husband's Last Name. That name is my kid's last name, too. My ex was totally fine with me keeping the name and using it how I wanted,

even in our separation agreement. Now comes the tricky part. My ex never wanted more kids, but I do. I'm in the process of freezing eggs and hope to use a sperm donor before I'm all dried up and my clock is ticking. I just turned 41. My ex is supportive of this.

But do I give the potential new baby from donor sperm the last name of me and my kids? I feel weird, not that my ex will mind too much, but I'm also thinking of his very traditional family who may find it offensive that I'm giving their name to a child that's not biologically theirs. That said, I want this child to share my current last name and the name my kids all have.

Any advice, Nicole? I mean, that is your last name. When people divorce, does the husband have to give permission to give your name, to keep your name? It's not an engagement ring. That's your last name. And also, who cares about the ex-in-laws? Keep the name.

Exactly. Who cares about the ex-in-laws? I was going to say you could ask them, but then I thought, no, wait, why even bother asking them? Who cares a shit? we're never talking to them again. Yeah. And you also want your kids to all have the same last name. Yeah. Yes. They're siblings. That's your argument for that. If anyone comes to you or comes for you, I should say about passing that name along. Yeah. Especially if the ex-husband is okay with it. Yeah. Yeah. That's easy. All good. Problem solved. That's an easy one. Problem

solved, guys. That was easy. You're welcome. All right, Nicole. Good luck, baby dust. Our next question comes from redneck kitty she says dear chelsea my name is rachel but my dj producer entertainer name is redneck kitty i'm 31 and i started djing when i was living in australia at the start of covid i was a covid dj it's a thing i'm single with no kids nine years ago i lost my brother and partner and that cracked me open in a very yolo way of living i traveled the world stripped to fund my dive trips and went on skiing and climbing adventures went from mansions to dumpster diving, and had all sorts of wild adventures in between. Wow. Therapy eventually reminded me that I might live longer than tomorrow, so maybe I should plan a future.

After being at my soul's end with stripping last year, I was messaging chat GPT about switching careers, but decided first to consult Mother Aya, and she was very clear. Music is my path. So I gave up stripping after nine years to pursue music. Luckily, I've saved smartly, and along the way, I met a couple sugar daddies who believed in me enough to give me some cushion to focus on my art. Now I've moved across the country to study under a legend in the electronic music industry. I'm in school and I love what I'm learning. But here's the problem. There's still this gremlin in my head screaming, who are you at 31 to suddenly decide you want to be a DJ? You're too old. It's a stupid choice. You'll never make it. You'll be a broke, struggling artist

forever. I should have started 10 years ago. Pursuing art feels scarier than free climbing a cliff without ropes. And I'm terrified. So here's my question. How do you draw from that deep well of self-belief and confidence. How do you drown out the gremlins when your heart knows what it wants, but your head just wants certainty? Is this a stupid idea? How do you trust yourself when your path isn't normal? Any advice on pushing past the fear and owning my space would mean the world. Redneck Kitty. Hi, Redneck Kitty. How are you? Hi, I'm good. I'm actually just like so excited right now. This is our special guest today. Caitlin Olson is here. Hi. Hi, Caitlin. Nice to meet you. You too. Oh, I love your story. What a nice adventurous life

you've lived and you're only 30. You have a whole, you have two thirds of your life left to go. And by the way, maybe more than that, because they say if we make it through the next 10 to 15 years, you can extend your life until you're 150. I don't know who the fuck wants to do that, but. I think I'll cop out before then. Yeah, I know. I mean, who could afford to do that? I think, listen, we all have those voices in our head, right, Caitlin? I mean, we all kind of don't know what we're doing or not certain of what we're doing. The proof that you have is that you're here

and you got the choice to do what you wanted to do and you got yourself all this way so far. You're 31 years old. You're not too old for anything. This is the beginning of a new adventure. You've got yourself in a situation where you can actually choose what you want to do. That is so powerful.

I think it's just like I don't know I kind of get in like the comparison space which I know is like comparison is a thief of joy but like I compare myself to all these like musical prodigies who like started when they're 18 and I'm or even you like you know you kind of like knew since you came out of the womb that you were like destined for greatness like you were like I'm above all of you guys you know and I was like I kind of like a late bloomer in this of like I don't know realizing my path. And so I kind of like get in my head about it because I didn't know sooner that it's not right. And I don't know, that's just kind of like what I get in my head about. And like you talk a lot about wanting women to know they have like this deep well of resilience and strength and

confidence that they can call on. And I'm just like curious, maybe like more practical tips on how you actually do that. But don't you, when you look back on your life, go, oh my God, look at everything that I have accomplished and lived through and here I am. And everything took you one step closer to where you are right now. And I think that you, I get that feeling at 31 felt really old to me too. I started doing Sunny when I was 29. And like, and then I always say my 30s were way better than my 20s, which I thought was going to be impossible. And then my 40s were way better than my 30s. You're just getting started. And I think practically when you look back and you go look at everything I've survived. I'm sure you've been through a lot more than what you

have written out in your email. So you rely on that stuff and you go look at me now. And you also, you're so charismatic and beautiful and what do you have to lose, you know? Yeah. Thank you. That's really nice. Yeah. And also, you know, off of what Caitlin just said, a great exercise, and this is in that book David Hawkins wrote that I always talk about letting go, is writing down all of the things that you have accomplished, writing down where you came from, what you went through, how you, you know, all of the things you listed in that letter alone. I'm sure there's a zillion other things, but writing down as a reminder. And every once in a while, like when I read that book,

I'm reminded to do that. Like all of the milestones I've reached, all of the accomplishments that I've had, even if you just go back a year and think about the biggest moments that you've had in the last year, as a reminder of your tenacity and as a reminder to yourself of how powerful you are, you're choosing to make a decision. You're not letting life happen to you. You're happening. You know what I mean? You're making your life happen for you. And there's a lot of power in that. And there's so many people who call into this podcast who don't have half of the confidence that you have and who haven't made those choices or haven't had the strength of mind to make determinations about what they want to do in their future. And you're already doing that.

So like I would say when you get off of this call to literally just write down everything you've accomplished in the past year and then you're going to see it in writing and you're going to understand how far you've come. And if you do that every few months and as a reminder and like set it in your calendar and your phone as a reminder to really reflect, because this is the problem that I I find is that we go so fast sometimes. And Caitlin's life is just as busy as anybody's like you forget, you know, you forget to sit there and actually take a moment and be like, wow, you just got through all of this stuff and you just did this and you did this. and you did, you know, I made this decision and I made this decision. I got out of that relationship. I'm into this, like all of the things that make you a person are really important to constantly think about instead of just zipping through life with no time to enjoy the, what you've done. No, you're so right. Like even just hearing you talk about it, like when I moved to Australia, I had like $500 in my pocket and now here I am even just saying that I'm like, yeah,

damn yeah i have done done it yeah that's cool so hang up from here and do that will you i will i'm gonna make my list okay great great and then put it on your refrigerator and kiss it every morning yes i'm here different color lipsticks yeah exactly that's right that's the morning that's the spirit and then also if you have like a soundcloud or something send me the link and we'll put it in the description so people can check you out oh nice yes i have a new ep coming out bootylicious bootlegs um it's basically a bunch of remixes to like the crunk dirty south hip-hop i was raised on made into like tech house so if you're into that kind of stuff yeah i'm excited it's my first songs i've made i've made a song i'm so excited there you go you

made a song that's number one on your list song i can't believe it i know this podcast is amazing i feel like i'm having a moment like my best friend she saw you in vegas and she had like a moment where she like touched your hand and had a full anxiety spiral for three days that I had to talk her out of. Cause she was like, I felt like I met God. Oh my God. Oh, poor thing. Well, tell her I said hello. And she has not met God and none of us ever will, as far as I'm concerned. No, she's the one who put me on this podcast and I haven't even told her that I was going on it. And hear it. And so shout out, you know who you are. I'm not going to say your name cause she'll get pissed but yeah she loves you so much all right thanks so much we'll talk to you soon

okay you guys have a great day bye bye look at how healing you are caitlin with this is two two home runs back to back i mean that's that good light energy that's that ebullience we're really doing it we're really saving everyone i love this way to hop on the train and get the party started so our next question comes from jen she says dear chelsea i have a seven-year-old daughter who's a spitfire. She's wonderful and loving and kind, but also she's exhausting. She challenges every single thing when she doesn't get her way. With her negotiation skills, she'll be an amazing lawyer or hostage negotiator someday. I don't spoil her and she's very upset about that. She feels that each day after school, if it was a good day, we should go to Starbucks

or Target or somewhere and get a treat. I tell her no and that we're going home. She throws a fit and whines and cries that she had a good day and she just wants a treat. I get it girl, but we can't support a Starbucks habit for the both of us. How do I help guide her to be a respectful person who listens to me and trusts me, especially as she gets into her teenage years, yet not extinguish her fire that I know will someday change the world. Jen. Well, I read, somebody said to me the other day, I always love to ask people about their kids. Like if they have favorites, I love to ask this question to men because men always have a favorite and it changes And it moves around. But somebody said, you know, the kid that gives you the most trouble is going to be the most successful.

So so that's something to hang on to a way for your to teach your child about responsibilities and money like is to actually break. Go to Starbucks one day. Go get those treats and then break down the receipt with her when you get home and show her exactly how much everything costs. I mean, I got something at Starbucks the other day that was seventeen dollars and it was one thing. I don't remember what it was, but it's absolutely ridiculous. So I think just kind of getting in there early and teaching them the value of money and maybe she can do little things around the house. You have to kind of reprogram her, it sounds like, just because she had a good day. That's a reward in and of itself.

You don't get a reward for a reward. You know, her having a great day is great, but that's not something to be. But also, I'm not a parent. Caitlin, do you want to chime in here with any parental advice you might have? Well, you should be, because that was perfect. And this just happened the other day. Rob took one of our kids to a doctor appointment. And so he was like, if you get up early enough, we'll go to McDonald's.

I'm like, why? Why? It's a doctor appointment. You're a teenager. You go to a goddamn doctor. And then you go to the dentist sometimes. And then you go to the, like, that's just, that's part of life. You don't get McDonald's every time you have to do something out of the ordinary.

but because I think it's like there's no like reward for having to just deal with like life stuff but I love what you said about come up with not basic cleanup after yourself because I don't think you should pay children for cleaning up after themselves we all live here we're all cleaning up after ourselves but come up with little jobs for her where she can save money and then when she saves up enough money she can go to um Starbucks and spend it on something I think that's great but I totally agree with like it was a good day so everybody fawn all over me for not, you're what, in second grade? Like, it should be a good day.

Yeah, and also there's other ways to reward that, you know, like, oh, like non-monetary ways to go home and play. Okay, well, you know, on special days, on special occasions, we'll go home and we'll play a board game together for an hour. I'm gonna give you my sole attention and we'll do something like that together.

Or we'll plan something this weekend, just you and me, and we'll do something like, there's other ways to make it special other than, you know, going to Starbucks or go to any of those places after school. And also, I just think like, I remember my parents financially struggling growing up and I understood about money very early

that if I wanted it, I was going to have to go get it. Like I, you know, and I was resourceful enough. And this girl sounds like she's going to get to that point. I know she's only seven, right? Is that what she said? She's seven. But you really just want to impress upon her how much things cost to the world we live in.

and the reality. Like that's something you do once a week on a Friday, you know, to celebrate the weekend. Okay. We'll go to Starbucks, you know, you know, and there's no reason to do that all the time. So that's my parenting advice for today's episode. All right. Our next question comes from Kristen. She says, dear Chelsea, my name is Kristen and I'm 23 years old. I'm currently a mail carrier for USPS and I'm fully independent. I live by myself and fully support myself and my animals. I'm finding it hard to relate to people my age and connect with them. I live in a college town at the moment so most of my friends are in college or fresh out and i'm having a hard time keeping friends i feel like i don't really relate to people my age and they're all immature and i

quite frankly can't stand them they're very self-centered and weirdly mean i'm not sure if it's me or why i'm struggling to keep female friendships please help kristin and she'll be joining us here in a moment oh how old is she 23 23 hanging out with college kids that are what 18 to 21 or like just out of college sort of thing did you go to college caitlin i went to the university of oregon oh that's fun i love oregon it's so pretty yeah i wanted to be i wanted to be close to my my parents i really um i didn't want to leave them i was a very late bloomer i went home on the weekends caitlin were you a late bloomer in other ways or in every way in every i was a late bloomer in every way i never snuck out of my house i was like why would you do that

my mom would be upset if she, like, if I was missing, I, all I wanted was boobs. I still kind of do, but not as much as before. Didn't have a boyfriend all through high school. Very, very late bloomer. I was like a little kid for a very long time. Got it. Hi, how are you cutie pie? How are you? You're so cute. Look at you on your job sitting on your, oh, that's okay, honey. We're all sweaty. I'm going through menopause, so I'm sweating too. Um, so you're hanging out with younger people or people your age yeah i hang out with a lot of older people i just turned 24 okay and i can't seem to keep friends my age what happens i don't know they ghost me i just had a friend recently she just unadded me on everything and i don't know why and i don't want to reach

out because she clearly doesn't want to be talking to me so i'm just not sure why i connect with older women a lot better like 50s 60s i just get along with them better and it's easier to maintain in relationships, but I want friends my age to like hang out because I'm the same age as their kids. And that's just not what I'm looking for. Well, okay. It's not what you're looking for, but go where the light is. Like if you're having relationships that are respectful and like, and you're getting like something out of it, it doesn't matter how old those women are. I have tons of older, I just went to dinner last night with like three 70 year old women. They're way older than me, but like I have friends that are 20 years younger than me. I have friends that are

20 years older than me, wherever the light is, wherever those friendships, you're going to make other friends in your life. This woman, obviously, or this young woman that ghosted you, don't worry about her. I understand that hurts your feelings. It hurts all of our feelings when we get ghosted, but just move on with the intention of being open to friendships, whatever shape or age or size they come in. You know what I mean? Because when you have that attitude, I feel like that has more of like a magnetic attraction and it brings people who are more like-minded into your kind of sphere and in the meantime hang out with these older women that's fine that's not going to be the rest of your life you're going to make other friends you're so young you're 24 years old like

you're going to meet other people and you're going to figure out how to maintain friendships for longer periods of time it might not have anything to do with you quite honestly is there anything you can think of that you would have done to end any of these friendships or well the last one she asked for money and I said I can't give you money so I was like she unadded me on everything and I thought it was because of money but I'm like there's no way she wouldn't add me just because of money well I mean who cares listen bye bye girl Chelsea's so right also I think you need to just focus on what it is that you want in a friendship and then you're gonna find that in in good friends it doesn't matter how old they are and like she said that it's that this is all

temporary. Who knows? Listen, girls can be really awful to each other. And I like to think it's typically around like sixth, seventh, eighth grade, but it's truthfully, sadly can be much longer than that. And that's just not something you need to be around. The second you get a weird energy or you get ghosted, then happily let that go. Just figure out what does friendship mean to you and what is it that you're looking for? And if you're finding that in older women for this small period of time, then enjoy it. I'm worried that it is something I'm doing because I continuously have these like friends that I'll be with for like one to two years. And then randomly they just like ghost me. So I'm worried I am doing something and I've been trying to note that,

but I'm not sure how to like keep track of it. I hear what you're saying, but also like a friend isn't just going to ghost you after one to two years for, I hate when, you know, when I was growing up and I had problems with like socially or whatever, those things don't go away. There's always people in your life that are going to not be there permanently. But like, sometimes it really doesn't have anything to do with you. I'm not saying you're completely absolved of anything, you know, maybe you maybe you are doing something. But also, people, when as you get older and more mature, people know that you're not going to get 100% of everything you want out of every friendship, you kind of have to be willing to make mistakes or, or have people see all of you

and still want to be friends with you. Like that's the sign of a strong friendship. So if somebody is fickle enough to kind of ditch you after something, like, you know, it is important to have self-awareness and be aware of the kind of friend you are and not maybe, you know, not be too needy. I don't know if these are any of the qualities

that you might recognize in yourself, not be too needy, not be too demanding, you know, not be putting so much weight on every friendship and just kind of go at it with a more ease. like just think of it as more of like it's an audition it's not permanent you know what I mean and just to kind of think of it in that way like building blocks it takes a long time to build a really solid friendship it doesn't happen over six months you know that's kind of like a almost like love bombing but with friendships so just give yourself a little grace and the women that

you are friends with ask them if there's anything odd about you or weird about you that they might recognize because they sound like real friends. Maybe they have some feedback because they know you better, but I wouldn't focus on your shortcomings. I would really focus on just your attitude towards friendship. Yeah. And even like this friend who asked for money, like it's likely not that she's mad at you for not giving her the money. She might be, let's say, embarrassed that she asked and you know, those sorts of things that she doesn't want the reminder. And I also just think this like 22 to 27 friendships are going to be changing. You It's not an easy thing to go through, but some of my best friends I didn't meet until

I was in my late 20s, and they're some of my closest people, but sometimes the people you meet in your 20s, they're kind of in and out for a couple of years. It's just sort of a transient time, friendship-wise. Okay. Yeah. Yeah, that's just good. I get told I'm weird and off-putting a lot. I am very blunt, and I say what I mean, and I don't know.

I'm not always unkind in the way I say things, so I'm worried that could be it, too. I just I feel like that's why older women get me because it's like they say what they want They say what they mean. They don't take anyone's bullshit. And that's how I am that's how my mom raised me to be and so I feel like those friendships don't last because I can be too like This is what I want. This is what I don't want. Right? Well, do you like that about yourself? I do I think i'm way older than I am because of how I am Listen that there's nothing wrong with being upfront about what you want and and blunt about what you think you would recognize if you were being unkind i think don't you yeah i i don't i would i think

i'm sorry so too and listen don't be sorry i think it's a dangerous game to start micromanaging and really putting such a microscope on every single thing that you're doing and trying to figure out what you're doing wrong i think you need to just know what kind of person you want to be and seems like you're a pretty kind person who knows that you want friendships and knows that you're going to be honest about how you feel about things there's nothing wrong with that so i i don't know I don't think you should be scouring every move to be like, did I do something wrong? Did I do something wrong?

Because that's not a way to live. Just be, figure out what your intentions are and focus on what it is that you do want and then enjoy the friendships that you have. And then they'll just kind of keep coming. Okay. Yeah. Don't edit your personality.

Being blunt and being direct. You're going to find your people. I promise you. Yeah. You will. And we like your energy. Yeah. I'm into it.

Maybe we'd be friends. Yeah. You're Chelsea Handler approved. Exactly. All right, Kristen. Thanks, Kristen. Check in with us. All right.

Okay. Thank you. Bye. We're going to take a break and we'll be right back to wrap up with Caitlin Olson. The new Red Bull Dragonberry and Tropic Berry Energizers now at McDonald's made with freeze dried fruit and an electric burst of flavor. The all new Red Bull Energizers now at McDonald's. This product may not be right for you.

high in caffeine details at mcdonalds.ca and participating canadian restaurants excluding quebec when i was 14 years old i was kidnapped and held captive for nine months i survived and i've spent my life exploring how other people survive what should have destroyed them i'm elizabeth smart and these are the survivor files i just remember this low taunting voice next to my ear saying shut up don't say anything every week i'm with survivors who live through the unthinkable i knew if he woke up without a doubt he was going to hurt me i started feeling that there was someone at the end of my bed and i just started screaming they are abducted stalked controlled and nearly silenced but these aren't stories about what's taken from them they're stories

about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsessives, and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo, and every week we're connecting the dots between books, the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From bestselling authors and your favorite

book talk creators to the latest pop culture moments, nothing is off the table. It's like, if you can hide some real messages inside compelling characters, then that is a Trojan horse. Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. See you between the pages.

Hey, this is Hayes Davenport. And Sean Clements. We host the podcast Hollywood Handbook on the Big Money Players Network. Our show is extremely accessible to first-time listeners. Each week, we talk to someone in show business, a.k.a. the biz, and try to help them with their careers and see what they have to offer us. Everyone has a good time and no one gets mad at their publicist for letting them do our show. We've had a lot of great guests like Sarah Sherman, not that great.

Actually, can you help me shape this? How about we flip it on its head? How about we flip this around? What if the surprise woman, who actually you think is the straight man, is actually the one who's acting weird? Adam Scott. this entire time you've been expecting adam sandler to come to visit the show i i would never let go of that i have i would never set expectations for something like that it seems like if the universe allows for something like that to happen i'm open to it i'm always going

to accept you know danny mcbride fine yeah it's all this fragile masculinity exuding i could smell it walking down the hallway to be honest with you i was like is that weed nope it's fragile masculinity yeah ben stiller no because a lot of times in out of context people don't get it or even know what a circle is you know what i mean like they're like oh what's this everyone's so dumb and fake right fake and and also not interested or just like oh i've got my life i don't care about your life and a lot of other big shots that wouldn't be where they are without us oh and by the way will ferrell told us personally he loves the show and he wants to be a guest on every episode but he's just so busy listen to hollywood handbook on the iheart radio app

apple podcasts or wherever you get your podcasts and we're back with the magical caitlin olsen who is so good at dishing out confidence to young girls today i love it i love these young ladies Come on. We have to build them up. I needed this. I know. I needed it too. I know.

I needed this when I was that age. Yeah. Thank you so much for coming on. Congrats on all of your success. I wish you the best. I can't wait to meet you in person one day. I can't believe we haven't met. I love you so much.

I can't wait to meet you too. Thank you for everything you do. Very inspirational. Thank you. Take care. Thank you. Bye bye guys. I just announced all my tour dates.

It's called the High and Mighty Tour. I will be touring from February through June So go get your tickets now If you want good seats And you want to come see me perform I will be on the high and mighty tour Do you want advice from Chelsea? Write into DearChelseaPodcast at gmail.com

Find full video episodes of Dear Chelsea on YouTube By searching at Dear Chelsea Pod Dear Chelsea is edited and engineered by Brad Dickert Executive producer, Catherine Law And be sure to check out our merch at ChelseaHandler.com i survived nine months in captivity and i've spent my life exploring how other people survive what should have destroyed them i'm elizabeth smart and these are the survivor files every week i'm with survivors who live through the unthinkable abducted stalked controlled and

nearly silenced. These are stories about what it takes to make it out alive. Listen to the Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. each week we're connecting the dots between books the internet and pop culture with your favorite writers book talk creators and plenty of overthought opinions yeah i'm obsessed i'm obsessed listen to pro society on the iheart radio app apple podcasts or wherever you get your podcasts

did you hear the new episode of the hey jonas podcast we are at d23 so we'll see who stops by the cast of frozen stopped by kristin bell josh gad and adina menzel i auditioned for frozen what For Kristoff, they said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get it. Well, you probably won. Plus, John Stamos, Hayden Christensen from Star Wars, and more. And I guess I can share that, uh, no way.

Listen to the latest episode of Hey Jonas on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus, or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro, and I travel by myself

because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.