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Sophia
This is an iHeart podcast guaranteed human.
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Sophia
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Jerry O'Connell
What do you have to lose?
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Sophia
Hi, everyone, it's Sophia. Welcome to Work in Progress. Welcome back to part two of Work in Progress with the lovely Jerry o'. Connell. Now we're sitting at work at Basecamp in my trailer.
Jerry O'Connell
We ran out of time. Sophia's driver was coming and asking for her to come, and I came into our hair and makeup trailer and I said to Sophia, oh, God. So that chat we had, it's got to be top.
Xolair Advertisement Voice
Top two.
Sophia
You said two.
Jerry O'Connell
Top two of Work in Progress. And Sophia didn't even look away from doing her eyeliner. And Sophia said, no, no way. And I went, top three. Sophia went, dude, we've had Michelle Obama on the show.
Sophia
I said. I said, that's very hard for me. I don't really have top persons because there are so many different categories of people who come on the show. I said, I put you in the incredible comedian category along the likes of Chelsea Handler, Whitney Cummings.
Jerry O'Connell
Oh, my gosh, yes.
Sophia
The iconic Jerry o'. Connell. And he was like, I really can't believe you don't just think I'm one of the best. Like, who is? And I said, okay, Michelle Obama, comic guests. Yeah, top.
Jerry O'Connell
My top.
Sophia
Absolutely. You're in. You're. Yes. You can have it. You can have it. You're wonderful. Okay. We were. We were mid interview, laughing and amused in such a fashion that, as you explained, I absolutely missed my pickup time, which I do not do. But luckily I wasn't. I was actually ready early. I was ready before camera was ready, so we were fine. But I don't like to be late to the van. Currently, we have time to finish this because if you can see from the open door of my trailer, the daylight coming in, the scene we're shooting, it is a night scene, and it is an exterior. So we're literally waiting for dark.
Jerry O'Connell
Do you want to know the thing I'm most embarrassed about this film about?
Sophia
Okay.
Jerry O'Connell
These shoes that I have to wear, I'm showing. If you're listening to Work in Progress, my character wears these sandals.
Sophia
I can't believe you're giving people free feet. On the Internet. I would never.
Jerry O'Connell
Oh, yeah. I need that following.
Sophia
Oh, my God.
Jerry O'Connell
But they're super gross. I hate them. And it really is. Honestly, this is the hardest acting I've done is wearing these around. Like I'm a person who wears these shoes.
Sophia
They're your principal shoes. They are very sturdy, responsible, Birkenstock adjacent.
Jerry O'Connell
Yeah.
Sophia
But not as cute as a Birkenstock, I'll give you that.
Jerry O'Connell
Don't like men in sandals. Not my thing. Don't believe Mendels. Sorry. To assign gender and to assign footwear to gender. I don't believe men should wear.
Sophia
Wow.
Jerry O'Connell
Sandals.
Sophia
Okay. That kind of fascinates me.
Jerry O'Connell
Yeah. I'm sorry. I'm so sorry to assign gender.
Sophia
It's okay.
Jerry O'Connell
I think women wearing open toed shoes, I think that's a lot of fun.
Sophia
Wow.
Jerry O'Connell
I think I'm just not a man who wears open toed shoes. You never know if you have to run, kick.
Sophia
Interesting. Well, then how do you feel about being barefoot? Like you're a barefoot at the beach guy.
Jerry O'Connell
Well, if you're at the beach, barefoot is fine.
Sophia
I'm just checking because we're shooting at a beach, so I. I don't. I realize. I don't know.
Jerry O'Connell
Yeah. I'm not weird. I'm not weird about feet. Yeah.
Sophia
I. I do have a question for you because, you know, this is breaking news, friends. You've heard it here. Jerry's foot presence preference, rather, it's a. It's not a typical thing a person would think about something that is not a typical thing, I think, for people in our industry to do, but something I've always kind of wanted to do is a thing you did. You went to law school.
Jerry O'Connell
Oh, yeah.
Sophia
This is crazy.
Mint Mobile Advertisement Voice
Yeah.
Sophia
When. When did you make that decision? Why did you decide to then, you know, go to law school but also come back to acting?
Mint Mobile Advertisement Voice
Yeah.
Sophia
And were you ever caught in a pair of sandals whilst at law school?
Jerry O'Connell
No. Never sandals at law school.
Sophia
Just checking.
Jerry O'Connell
I, you know, I was acting, and then it got very slow for me. Acting. And my wife was very busy and we just had two children. We have twin daughters.
Sophia
Yep.
Jerry O'Connell
And they were about one. And I applied to Knight Law School at an accredited law school in Los Angeles called Southwestern Law. It's good law school. It's in that old Bullock's Wilshire building right there.
Sophia
Okay.
Jerry O'Connell
And I had always wanted to go to grad school. And I was like, oh, well, while my wife is working, I'll apply to grad school. And I was like, what do I Apply to, like, what kind of grad school? And I was like, I mean, the only thing that interests me is, like, law school. Like, I didn't want to go to English. I didn't want to study English. I didn't want to study film.
Sophia
Wow.
Jerry O'Connell
I just wanted to. I was like, let me just go to night law school. Let me see if I get in. So I took the LSATs, and I applied to two night law schools in Los Angeles, and I got into one, and I went to night law school for. For. For a year. And then. And then what? I. Ironically, it's funny, I had a. I had a TV show that was canceled abruptly.
Sophia
Okay.
Jerry O'Connell
And I was like, that's it. My. My career's done. Like, it's over. I know, but. But you know how it feels.
Sophia
It's jarring every time.
Jerry O'Connell
And so then about a year passed, and I started to audition for TV shows again, and I got a TV show for cbs, ironically enough, playing a defense attorney.
Sophia
Oh, my God.
Jerry O'Connell
And I think they. I think they hired me. A lot of it had to do with. They were amazed that I was. That I was in law school.
Sophia
They were so funny.
Jerry O'Connell
Yeah, it was. It was funny.
Sophia
Okay, so.
Jerry O'Connell
But I'm a. I'm a law school dropout. I. I dropped out because I realized you can make way more money playing a lawyer on television than actually being a lawyer. But, you know, I might go back.
Xolair Advertisement Voice
Yeah.
Jerry O'Connell
School is really fun for me, too. I want to say what's really fun about school is a. You're around people who want to learn, which is fun, you know? And by the way, the fun thing about night school, I thought for sure I was going to be the oldest person there.
Xolair Advertisement Voice
I wasn't.
Sophia
I was, I would say, in the middle.
Jerry O'Connell
In the middle.
Sophia
Wow. I love that.
Jerry O'Connell
Grad school is something that people do.
Sophia
Yes.
Jerry O'Connell
Late in life.
Sophia
Yes.
Jerry O'Connell
And so don't be afraid to do it if you're like me and an oldie and like, oh, God, I don't want to be the. I don't want to be the oldest.
Sophia
I've been thinking about that a lot lately. I was right before the holidays in December, I went and spoke at Harvard, and I was on campus doing various things for two days, and I just was like, I want to go here.
Jerry O'Connell
Yeah.
Sophia
I want to be back in school. I miss school.
Mint Mobile Advertisement Voice
Yeah.
Jerry O'Connell
You know, if I can make a suggestion, you're residing in New Jersey now. Rutgers is like, an incredible school. It's right there. And you'd be like, anything. You're Smart. And it's like, you're gonna find something and be like, yeah, you know what? I'm gonna study that. And you could.
Sophia
Yeah.
Jerry O'Connell
Call them up and go.
Sophia
You know, it would be very cool when you talk about, you know, pursuing a passion when work was slow. It strikes me as a really proactive thing to do. You know, I. I like to be a proactive person. And also, sometimes things feel really hard. And I'm curious, when you think about the times when success felt easier and the times when success felt harder, how. How do you grapple with that? Like, are you a person who experiences imposter syndrome and says, well, I gotta get over it because I gotta live and move on? Or do you have sort of more specific, like, tactics and tricks to get you through things?
Jerry O'Connell
Being in the entertainment industry is. Is really all I know. So it's all I can speak on.
Sophia
Yeah.
Jerry O'Connell
And it's crazy because when you're younger, you're busy all the time. It's just. It's a young person's medium. Like, they're the ones who are in demand the most. There's the most amount of roles for the ages of 20 to late 20s. You know, it's just. It's what they make. They make young people. Young people are in tv, you know.
Sophia
Right.
Jerry O'Connell
So that's when you're in the most demand. It's funny, when you get a little older, you feel. And. And there's not as much opportunity. I'm not saying, you know, I'm happy with the opportunities that I've had, but there's not as much, you know.
Xolair Advertisement Voice
You do.
Jerry O'Connell
Like, I did start to panic a little bit. I don't know if it was having kids. Definitely insecurity, I think mostly feeling like I had no control of something. And now that I'm older, I've come to terms with. I have no control over anything. I have no control. I. As cheesy as this sounds, I. Now, if I realize I have no control over something, I really.
Xolair Advertisement Voice
Don'T worry.
Jerry O'Connell
About it and really just try to, because I do. Have we talked earlier about, like, having. I'm not diagnosed with obsessive compulsive disorder, so someone told me I'm not allowed to call myself that. But if I have obsessive thoughts, I try to. I try to navigate them towards solutions like that.
Sophia
It's how I feel about my sprout.
Jerry O'Connell
I try to obsess.
Sophia
I can't control it.
Jerry O'Connell
I try to obsess over solutions.
Sophia
Yeah.
Jerry O'Connell
I think that's allowed me, you're allowed to obsess about this?
Sophia
No, I'm not. We'll be back in just a minute, but here's a word from our sponsors.
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Sophia
Tell me if I'm alone here. Whip Smarties but shopping used to feel more fun before all the algorithm fed blah and the endless sea of dupes. But I have a confession. I have found that fun feeling again on ebay. Because on ebay it's not just shopping, it's a full on fashion pursuit. And when you find the thing that adrenaline hit is real. Like when you score that rare Adidas collab that's lived on your mood board, the Dior saddlebag you ripped out of a magazine in 2007 and never got over. Or something like The Cecile Bonson XGT2160s that sold out in five seconds? Yeah, those. It's about the thrill of finding pieces that feel like me. And I want you to find pieces that feel like you. There's always more to discover. Ebay has millions of pre loved finds from hundreds of brands backed by ebay. Authenticity Guarantee Ebay Things people Love I don't know about all of you, but when things feel overwhelming or hectic, the easiest thing in the world is to put self care on the back burner. And yet one of the things that makes me feel the absolute best is when I put five to 10 minutes into my morning routine. So I go out in the world and feel like I'm a little put together. It actually shifts my mood. It makes me feel more ready to tackle the day. And there's science to back that up. Why am I not doing this all the time? Like, seriously, A glossy lip or a smoky eye seems sometimes the smallest things have the biggest impact. Which is why I'm a fan of our friends at Thrive Cosmetics. Every product is 100% vegan, cruelty free and made with clean ingredients that work with your skin, not against it. And when we use Thrive Cosmetics, we're helping others shine too. With over $150 million in product and cash donations to over 600 giving partners, every purchase fuels real impact. And that's beauty with purpose. In the wintertime especially, I love a bold lip. So I use the Empower Matte Precision Lipstick Crayon. This one comes in 18 buildable long lasting matte shades designed to be worn as either a liner or layered, leaving lips looking luscious and fuller. Also, I tried the brilliant eye brightener. It is a waterproof eyeshadow highlighter stick made to brighten and open your eyes. It definitely comes in handy during long days on set. So amplify your everyday. Go to thrive cosmetics.com progress for an exclusive offer of 20% off your first order. That's thrivecosmetics. C A U S E M E t I c s.com progress well, the.
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Jerry O'Connell
What do you have to lose?
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Sophia
You are a very dedicated person I've come to observe. Like I watch the way you talk to your kids. I watch. I watch the way you are a family man. They're clearly so comfortable coming to you, telling you anything. You are. You are at once like their safe person. And also you manage to make light of things. You keep things funny. You, you have this really interesting blend of humor and real vulnerable honesty in Your life. And you do it in public. You know, you. You do it on social media. You definitely did it on the talk show. That's exactly what we have to do as actors, even though we're not playing ourselves. Do you think you're actually both self deprecating and really confident?
Grainger Advertisement Voice
I think.
Jerry O'Connell
I really. I try and live my life with humility. For sure.
Sophia
Yeah.
Jerry O'Connell
I try not to think I'm. Yeah. We gotta call him in. Get in here. Come on.
Sophia
Hi, guys.
Jerry O'Connell
Violet, get in here.
Sophia
We're finishing our podcast.
Jerry O'Connell
Come here. This is the star of our movie.
Sophia
Say hi on our. On our little video feed.
Jerry O'Connell
This is the star of our movie. Have a seat right, right here. Mom too. Get in here. Mom's important.
Sophia
Say hi to the people. Hello, everyone.
Jerry O'Connell
This is your microphone. This is very.
Sophia
Oh, my God, I love this. Wait, now you're. Scoot this over, Jerry, so you're still in frame. I meant the iPad, not your body. But you can do that too.
Jerry O'Connell
Yeah. Wait, this is the star of our film. This is Violet. What have you learned from watching from. What wisdom have you gotten from myself and from Sophia.
Sophia
I don't know. I mean, she's like, you guys aren't wise.
Jerry O'Connell
How have we blown your mind?
Sophia
You guys are really good at improv.
Xolair Advertisement Voice
Oh, okay.
Sophia
Like really good at improv. I've learned a lot from both you guys. From improv. It's so fun, you know?
Jerry O'Connell
I'm gonna take this moment to say what I've learned from Violet.
Sophia
Okay. You share your microphone.
Jerry O'Connell
I've learned. I've learned that if another actor throws a drink in your face in a scene to, you know, to be. To not like, be visibly upset about it and be okay and realize that that's great. I had to throw a drink in Violet's face yesterday. And I. I want to say it is the hardest thing I've done as an actor. I just had so much trouble. I don't know if it's cuz I have daughters. I had so much trouble throwing a drink in a 14 year old's face.
Sophia
Okay.
Jerry O'Connell
I love that.
Sophia
And I was like, no, it's great. It was a team effort.
Xolair Advertisement Voice
We both did it.
Sophia
You guys, actually, you made the accidental spill look very, very naturally accidental.
Xolair Advertisement Voice
Great.
Sophia
You did great. Proud of you both.
Jerry O'Connell
You're such a great actress. Thank you. It's so fun working with you. It really is. Sophia and I have worked with young people for years and you have a real talent.
Sophia
Thank you, guys. Thank you. You're a special one, kid. Thank you, guys. Thank You. I just want to clarify. She is my child. In the movie. You are soon to be stepchild. She's.
Xolair Advertisement Voice
We are.
Sophia
We are. We're special babies.
Xolair Advertisement Voice
We are.
Sophia
Yeah. It's okay.
Jerry O'Connell
All right. Get out of here.
Sophia
Thank you.
Jerry O'Connell
Let me finish my interview.
Sophia
Have you guys seen what's up?
Jerry O'Connell
What was I saying? I was saying. Oh, yeah. That I'm. That I. Yeah. That I. That I try to.
Sophia
Humility.
Jerry O'Connell
Lead with humility. Mostly because it's funny. Acting has really taught it to me.
Sophia
Yeah.
Jerry O'Connell
And in the sense that you're.
Grainger Advertisement Voice
The.
Jerry O'Connell
You are one job away from never working. You know, I mean, I hate to say that, but, like, you know, when you've had, like, professional failures. Okay. It is hard to get a job immediately after that. And so you have to sort of believe in yourself. And so I try not to think I'm really that important. Really?
Sophia
Yeah.
Jerry O'Connell
It is funny. I have daughters, specifically one daughter who's getting into the entertainment industry.
Sophia
Yeah.
Jerry O'Connell
So it is fun to see someone. She gets a lot of auditions just because there's a lot of roles for teenage girls.
Sophia
Really.
Jerry O'Connell
And I really hope it's. It's fun to sort of give her the tricks of the trade, you know?
Sophia
Yeah, it's really sweet. It's really sweet. Do you think. You know, I think about this a lot. You're, you know, your kids are teenagers.
Jerry O'Connell
17, and they got wasted last night. They went to. They have fake id. They went to a bar.
Sophia
Steve, I can't tell you everything.
Jerry O'Connell
They told it to me. They got. I. I haven't talked to them, but I think they got drunk because they wouldn't answer my Snapchat. I Snapchat with them. If you want to talk to a teenager girl, download Snapchat.
Sophia
They have fun filters if they're your teenage.
Jerry O'Connell
Oh, yeah, yeah.
Grainger Advertisement Voice
Not.
Jerry O'Connell
Not strange teenage girls, 100%. But, you know, what can I say? Like. And, you know, some of the parents are gonna read this and be like, you should punish them. You should come down on them. Just like, no drinking and driving girls, you know, like, please, like, if it becomes a problem and we're starting to do it too much, you gotta let me know, you know, Obviously, no drugs. No drugs. Hell no, you know, no nicotine, please.
Sophia
It's so addictive.
Jerry O'Connell
So addictive. You know, I struggled. I struggled with nicotine for decades. Struggled with it. Had to get hypnotized to quit. Yeah. Haven't had a ciggy in, like, 14 years.
Sophia
Good for you.
Jerry O'Connell
Also, my wife said she would not touch me if I smoked and that lasted about two months. Had. And by the way, no contact. My wife said, I'm not touching you anymore until you quit smoking.
Sophia
Wow.
Jerry O'Connell
And I thought it was a joke. And then after, like, two weeks, there was no physical contact.
Sophia
Wow.
Jerry O'Connell
After about three and a half weeks, I.
Sophia
You realized it was serious. Game on.
Jerry O'Connell
And I was like, I gotta do something. And I tried to quit and I couldn't quit.
Mint Mobile Advertisement Voice
Wow.
Sophia
And then you got hypnotized.
Jerry O'Connell
You know, I knew a girl who had quit smoking, and I called her up and I said, how did you do it? And she said, I'm going to give you the number of this lady. And I went to see her and I had to bring a photo of my children and my wife. And I sat down on her like. Like, wow. What do you call those beds? Those chairs?
Sophia
Recliner.
Jerry O'Connell
A recliner. And she put headphones on me and there was like, spa music. And she was like, I'm going to count to 10. 10, 9, 8. And I fell asleep.
Sophia
And when you woke up?
Jerry O'Connell
When I woke up, I was like, I had to pay her cash. When I woke up, I was like, it was cash.
Sophia
Like, how much, though?
Jerry O'Connell
You want to know?
Sophia
Yeah. Like hundreds of dollars or thousands of dollars.
Jerry O'Connell
This was 13 coming up on 14 years ago. I had to pay her $800 cash.
Sophia
$800 for each hour?
Jerry O'Connell
Yeah. No, I don't know how long. I don't know how long it was. I don't know how long it was.
Sophia
But it's a good gig if you can do it.
Jerry O'Connell
I woke up and I was like, that was baloney. What a joke. I can't believe I just gave some old lady 800. What a waste of money.
Sophia
And you've never had a cigarette since.
Jerry O'Connell
I walked in my car. I got in it, I had a pack of. Sorry to give them a plug. I don't want them to be a sponsor of the show. Marlboro Mediums.
Sophia
What a random cigarette.
Jerry O'Connell
Well, I didn't want to. Lights were too light and reds were too heavy. I'm not, like, not an addict. Mediums were just right. Got to my car, put the ciggy in my mouth, brought the lighter up.
Sophia
And you just didn't want it.
Jerry O'Connell
And I know I wanted it so bad. No, I couldn't light it. No, I. I swear to you. I swear to you. I am a real. I've never been hypnotized for anything else. I know. They do, like, everything. Sugar.
Sophia
Wow. I kind of want to do it.
Jerry O'Connell
Sales.
Sophia
Sales.
Jerry O'Connell
If you're in sales and you need to be motivated. Because I sent you another buddy of mine who was a. Who was a. Who was like a chain smoker. I told him what I did, and he went to go get hypnotized.
Sophia
Wow.
Jerry O'Connell
He said he works. He works in corporate sales, he said.
Sophia
Made him better at sales.
Jerry O'Connell
The hypnotist said to me, if you ever want to come in for sales, let me know. Now he goes in for sales.
Sophia
Stop. Wow. That's insane. Okay, we've been called to set. I had two more questions for you, but I'm just going to ask you my last and favorite question to ask everyone, which shouldn't be a surprise, because it is also the title of the podcast. I want to know at this stage, whether it's work or parenting or coming up on 20 years of marriage or some other goal, going back to law school. What. What feels like it's your work in progress right now in your life.
Jerry O'Connell
This is going to be the best answer to this question.
Sophia
I can't wait.
Jerry O'Connell
It's going to be better than Michelle Obama.
Sophia
Wow. It's going to make you the number one.
Jerry O'Connell
It's going to be better than Hillary Rodham Clinton. It is going to be better than Kamala Harris. Vice President Kamala Harris, all podcast guests.
Sophia
This is why he's saying this. If you've been living under a rock.
Jerry O'Connell
My work in progress.
Sophia
Yeah.
Jerry O'Connell
Is everything. Everything is a work in progress.
Sophia
Fair.
Jerry O'Connell
Everything fair. My marriage, my career, my health.
Sophia
Yeah.
Jerry O'Connell
My relationships with coworkers.
Sophia
Yeah.
Jerry O'Connell
Everything is a work in progress. It never ends. It never ends.
Sophia
It's true.
Jerry O'Connell
It's so funny. I'll say professionally, as an actor. A big thing they say to actors is you must not have to audition anymore. Of course. It never ends. No, it never ends.
Sophia
You just go up against better people. That's how you know you're moving up. You just go up against better people.
Jerry O'Connell
It never ends, man. Don't expect there to be an ending. Don't expect you to be cured. Don't expect. Okay, I did the work. There's progress.
Sophia
That's it.
Jerry O'Connell
The end. There is no the end. It's continual.
Sophia
Well, that's the goal, right? I mean, if. If it's the end, you're dead. So I would. I would much rather continue working on evolving everything, practicing more patience. Sure. By the way, look how nonchalant I was about sprout, but I'll sprout.
Jerry O'Connell
I mean, I talked to my wife while we're traveling and doing this film.
Sophia
Yeah.
Jerry O'Connell
And my wife was like, I think I said this earlier. You are like a stressful presence in our home. I'm not kidding. I actually thought about me, like, saying that out loud to you. I need to go home and be less of a stressful presence. It's something I have to, like, really, like, think about. I'm gonna say to my wife, like, tell me what I'm being. Tell me when I'm stressing you out. Tell me when I'm stressing out.
Sophia
You know what? You just need like a code word. Like you need a phrase.
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Sprout.
Sophia
Or she. I was gonna say, like, hey, six. Like, take it to a six. Okay, you're at a ten. Take it to a six.
Jerry O'Connell
I thought you said six. I was like, what? Okay, four.
Xolair Advertisement Voice
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Jerry O'Connell
Sophia told me. Sophia said this.
Sophia
That is definitely not my advice. Jesus H. Guys. This is why he's fun to improv with. And we have to go back to work.
Jerry O'Connell
Yeah, let's go make a movie. It's called Summer's Last Resort.
Sophia
It's going to be on Tubi this summer.
Jerry O'Connell
Really enjoy Tubi.
Sophia
It's so fun.
Jerry O'Connell
You're blessed.
Sophia
Well done.
Jerry O'Connell
I hope we do it again.
Sophia
We're going to first of many.
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Sophia
This is an iHeart podcast. Guaranteed Human.
Release Date: February 13, 2026
Host: Sophia Bush
Guest: Jerry O’Connell
In this lively and candid continuation, Sophia Bush welcomes back actor Jerry O’Connell for part two of their conversation, recorded on set in Sophia’s trailer as they wait out daylight for a night shoot. The episode explores the idea of embracing one's status as a "work in progress," diving into Jerry’s unexpected detour into law school, his philosophy on humility, family, parenting teens, personal struggles and successes, and how he finds humor and gratitude in his life and career. Alongside playful banter, Sophia and Jerry are briefly joined by Violet, the young star of their current film, highlighting the collaborative and often improvisational culture on set.
On podcast guest ranking:
On sandals and masculinity:
On leaving law school:
On acting and insecurity:
On quitting smoking:
On being a work in progress:
The tone is warm, playful, candid, and lightly irreverent — full of mutual respect and quick wit between Sophia and Jerry. The episode gives listeners a look behind the curtain on life as an actor, with honest talk about career uncertainties, personal evolution, parenting, and the value of humility. Jerry’s refrain that “everything is a work in progress” echoes Sophia’s core message and offers listeners permission to embrace their own ongoing journeys—no matter their stage of life or career.
For fans of conversations that blend humor, authenticity, and a healthy dose of self-deprecation, this episode delivers wisdom and laughs in equal measure.