March 5, 2019

Can You Be Ambitious and Happy?

by The Cut on Tuesdays

Background show artwork for The Cut on Tuesdays

This week, we take a look at ambition: the internal force that wakes you up at 2:30 am full of ideas, that makes you want to do more than you thought you could, or than anyone else said you can.

We talk with writer, director, and actor Pamela Adlon; The Cut's Stella Bugbee, and outgoing New York Magazine editor Adam Moss about how they've each embraced (or rejected) their ambition. 

Where to Listen


Molly: Hello! This is Molly Fischer from The Cut.

Adlon: You almost sounded like one of those sexy machine bots just now.

Molly: Oh God. Like an Alexa calling you up? Or a Siri?

Adlon: Yes! Exactly!


From the Cut and Gimlet Media, this is the Cut on Tuesdays. I’m your host, Molly Fischer.


Adlon:  I have to full disclosure. So I'm at my office and my hair guy is gonna come quietly flat iron because today I'm meeting Barack Obama!

Molly: Oh my God!

The person I’m talking to right now is Pamela Adlon, the actor, writer, and director. Her show Better Things just returned for its third season on FX. It’s a semi-autobiographical portrait of a single mom in LA with three daughters.

Pamela’s character makes her living in Hollywood’s unglamorous day-to-day grind: She’s working steadily as an actor and supporting her family, but she’s not out there on any red carpets.

Here’s a scene with Pamela’s character and her teenage daughter.

 Sam: You had a party

 Max: It wasn’t a party, and anyway you left

 Sam: I had to work

 Max: You don’t HAVE to work

 Sam: What? How do you think we have anything?

 Max: You work because you want to be famous. 

Sam: That is so unfair that I think I’m going to pass out. 


I’m talking to Pamela today because her career is a case study in the subject of this week’s show: Ambition. That internal force that wakes you up at 2:30 am full of ideas, that makes you want to do more than you thought you could, or than anyone else said you can.

We’re going to be talking to two women who have embraced their ambition, and one man who’s trying to let go of his.

And we’re going to start with Pamela Adlon. 


Her story is about power of ambition. It’s also about the limits of what ambition alone accomplish. She’s wanted to do the same thing for decades, but it’s only in the last few years that she’s reached the meeting-Barack-Obama stage of her career. And she got started when she was young.

 <<MUX OUT - throw a verb on it!!!!!>>

Adlon: I was a kid and we moved to L.A. and I met this one girl who was like, "I have an agent." And I was like, "What's an agent?" "I want an agent!"

So I opened the phone book and I looked up the name of an agency, 

And I sat my parents down on the couch in our living room of the house that we later had to move out of because my parents went bankrupt. I sat them down on that couch and I said, "I just want to tell you guys, I want to act and I want to get an agent." And "Also, I made an appointment and it's on this day and it's with this lady."

And my mother was like, "Well, it's gonna be a lot of you know, cattle calls, 

and a lot of rejection." I was like, "I don't care. I want in. I want in."

Pamela was 12 when she cold-called the agent. Before long, she was in the agent’s office. 

Pamela: She was just like the, the original like OG, you know, cool, um, you know, one of those, uh, New York-y--"The kid's terrific."


Pamela:"I- I love the kid. I'm gonna sign her."  

Her agent started sending her out on auditions. Pamela’s mom had warned her there’d be lots of rejection-but pretty quickly she booked a dream job. 

Adlon: When I booked a Barbie commercial I was out of my mind because I was such a Barbie fanatic growing up, and I was so fucking excited! I couldn't believe that I got this Barbie commercial!

On the day of the shoot, Pamela showed up on set, and the director told her what she was supposed to do--strut, turn, toss her hair. So Pamela does it--she nails it--and the director tells her she’s nailed it. Then he turns to a blond girl who’s also on set. He tells her to do it just like Pamela.

ADLON: I realized, "Oh I'm here to teach the blond girl how to strut like me.” So I guess they liked my strut, but they didn't like my look. I never was in the commercial. And that was my first commercial experience.

This is the point at which the pure and total superficiality of the entertainment industry might be enough to stomp out a person’s ambition. She’s twelve! Imagine being a seventh grader and basically having a grownup in charge tell you that nobody wants to see you. 

Pamela, however, did not quit. Pamela came back. 

ADLON: I got hired again for another Barbie commercial. I'm like, "Oh yes! Reparations. Here we go! ." So then they said, "Okay, go to makeup." I'm like, "Oh shit, it's real this time.-"

MOLLY: Oh my God.

ADLON:  ... I go to makeup and they put makeup on my hands and I take Barbie out of the shower and I turn her towards the sink and the mirror and then you cut away, and it's the same blond girl.

MOLLY: Your enemy.

ADLON: I was her hands in the second commercial!

ADLON: Oh, Molly can you hold on for one sec?

MOLLY: Sure.

ADLON: My hair guy's here.


Pamela wound up finding a very un-Barbie niche in the industry. She worked steadily through her teens, playing tough-girl tomboy parts--like the the skateboarding kid sister of a Pink Lady in Grease 2

 <<CLIP: Dolores>>

She actually went to one audition dressed as a boy, and gave her name as Paul instead of Pamela. She got the part. 

She did well for herself--when she was 17, she was able to buy her own apartment with money she’d made. But then, just at the age when most actresses’ careers would be taking off--the peak ingenue years of your early twenties--she stopped getting parts. 

ADLON:  I was in a bad place where the jobs were drying up. Like the on camera 

jobs and stuff like that. 

I really couldn't pay my rent and then all of a sudden I started booking voice 

overs and it completely turned my life around.

<< MUX ENDS >>

ADLON: My first job in VO was a commercial campaign for 7/11. I played young Kevin in these 7/11 spots. I was young Kevin, always on the go. "Hey dad! I've got a big thirst for a Big Gulp 'cause I'm always on the go! Can I borrow the car?"

 MOLLY: laughs

ADLON: And I did that for years and years. And then I started kind of getting parts, like guest star parts, on animated shows. It was a thing that you looked around, you're like, "This is a real job? You can come and do voices for cartoons?" And so I desperately desperately wanted to do that. And then in my late 20's I booked King of the Hill. That’s like the holy grail of voiceover.  

King of the Hill was an animated series that ran for 13 seasons and developed a quiet, steady following. Pamela once again found herself playing a boy--Bobby Hill, the family’s pre-teen son, whom Wikipedia describes as “husky.”

CLIP: I haven’t even hit my growth spurt yet and I’m already a stud. 

In 2002, she won a voiceover Emmy for her work as Bobby. This wasn’t the fantasy version of showbiz success, but still---she’d found a way to make a living in the industry.

Molly: How did you feel about not doing on camera stuff as much?

Adlon: It is a very unique ability to be able to use your voice in that way, and so I never felt that I was missing out on anything, I felt like I was part of an elite, brilliant club. But there was a point where after I had my third daughter, I started thinking about my life and I started thinking, hmm I wonder how much longer king of the hill is going to be going on. 

because I watched my dad's jobs dry up. 

When Pamela was growing up, her dad had worked in TV as a writer and producer… and her mom held down a series of jobs that supported the family when his work was patchy. But after her dad turned 50, things got tough; he wasn’t getting hired at all. Her parents eventually filed for bankruptcy, and had to move out of their house.

Watching this all happen had shaped Pamela’s choices. It had taught her that you never knew when things could fall apart--ambition was risk, and it required a kind of scrappy resourcefulness.  

Adlon: You can't rest on your laurels because there are no laurels. You have to anticipate things. So I started auditioning again.

She got a call about a TV part. A writer she’d worked with on a pilot years before remembered her--he remembered that she’d been funny, but that she’d gotten fired because the executives didn’t think she was hot enough. He recommended Pamela to a comedian who was creating a new sitcom for HBO. That comedian was Louis CK. And in 2006, he hired her to play his wife on Lucky Louie.

She co-starred in the series, but she also got a producer credit, and started contributing story ideas. For the first time, all the experiences she’d had offscreen, struggling and being a mom, became professional assets.

Barbie clip: you know how I feel about barbies and that they completely misrepresent 


Oh phoey girls love barbies look how happy she is 

Well I don’t want my daughter to grow up and worship a tiny stripper! 

It only lasted one season, but Louie brought her with him when he started his next show--Louie--on FX. She had a recurring role, and the two also became writing partners. And, when FX decided they wanted a Louie-esque show centered on a woman, Louie recommended Pamela. The two of them created Better Things together.  

Louie had been the accelerant to her ambition--working alongside him, her career ignited in a new way. After years in Hollywood, as a middle aged mom, she’d come into her own as a TV auteur.

And then, of course, in the fall of 2017, the New York Times published their report on the longstanding rumors--that Louie had a habit of masturbating in front of unconsenting women. FX cut ties with him. Pamela did, too. But without him, she wasn’t sure what would happen to Better Things

Adlon: I had to take some time to really figure out if I wanted to, and how to, rebuild and get back to a place where I could make my show.

Louie is a subject she’s reluctant to talk about, She’s finally reached a point in her career where she can do exactly what she wants, and he’s the first thing anyone wants to ask her about. “I just need to focus,” she told the New Yorker. “I don’t want to have to weigh in on his sets.”

This has been one of the lingering questions of the last couple years--what to make of all the women whose lives were intertwined with guys like Louie. Whether you think they’re complicit enablers or collateral damage, they’re within the bad-man blast radius. And when a man helps enable a woman’s rise, what happens to her in his fall?

Ultimately, Pamela decided to make a third season of Better Things. She’s starring, directing, and--for the first time--running a writers room by herself. The season premiere aired last week, and she’s coming to terms with being on her own in the spotlight.

Chasing your ambition for decades means overcoming obstacle after obstacle after obstacle. Then finally you get there, you’ve got the thing you’ve always wanted, you’re in charge, and the only thing left is…  you.

ADLON: it's an enormous amount of responsibility, because if it works, I get all the glory, 

and if it doesn't work, I'm totally to blame. 

 Adlon: I never imagined that I would be in a position like this because coming from so

 many moments that you're almost there, you're almost there and it's taken away, it's 

taken away, it's taken away, you know what I mean? I just didn't think that that was in the

 cards for me.


Adlon:  A women who turns 50 all of a sudden finally, I've arrived! You know? I'm like

 Tootsie! It's crazy. You know? It's unbelievable. 

Pamela’s path has been unlike that of pretty much any other woman in Hollywood… and it all starts with that 12 year old girl, picking up the phone and deciding to get herself an agent.

She’s dealt with setbacks, but she’s never really felt ambivalent about her ambition itself. That’s not the case for the two people we’re about to hear from.  

Coming up after the break: Two terrifyingly ambitious people... on trying to make themselves live without ambition.

<<< MIDROLL >>>

Welcome back. We’re leaving Hollywood ... for my office, but stay with me; I swear it will be fun.

This week, we’re talking about ambition--it’s a subject we think about a lot at the Cut. And recently, New York magazine’s insanely ambitious editor in chief, Adam Moss, announced he was stepping down. That made my boss, Stella Bugbee, think more closely about her own ambition 

Stella: Like I close my eyes and I think ... how does this feel? How does this actually feel? And it's so corny, but I was like, it feels like I have mercury or something in my body and it rises and it falls and it kind of chases me around. It's in there and I don't know where it came from.

And half the time, when I'm driving myself super crazy with something, I think, "Why am I like this? Where does this come from? Who made me like this? I can't be of me, this is some alien feeling." I feel like it's both poisonous and electrifying.

She wrote about all this last month in an editor’s letter she called “the Half Life of Ambition,” where she talked about her career and her mercury blood. But after it was published, looking back at the letter, she saw all the other things she wished she’d written. 

Stella:  I realized I had been holding back on several things in the letter.

Molly: Why do you think that was?

Stella: I think talking about ambition is unappealing to a lot of people. And admitting that

 you have it is tricky. But probably on some level I was embarrassed? 

I’d argue that there’s something kind of vulnerable about ambition. Owning up to ambition means acknowledging there’s something you want and you don’t have--something you might not get. Which is not always easy to do. 

So we sat down to talk about what she’d left out.

She’d always been ambitious, she said--it went back to when she was a kid. She’d settled on a career--graphic design--when she was still teenager, and all through college, she was doing internships that would set her on that path. Right out of college she got a job doing the exact thing she wanted to do. Or, the thing she thought she wanted to do. She’d been ambitious enough that she managed to give herself a midlife crisis at 22. 

Stella: about six months into that job I realized I did not want to do that job. And I called my mom and I said, "I picked the wrong profession and it's too late! And now I'm stuck for the rest of my life." And she was like, "You're insane! You're 22, what are you talking about? Just change." And I said, "Oh no mom, you don't understand. I've invested so much in this career."

Molly: I love trying to convince your parents that ... I love that conversation where it's like, "No, no, no. I actually am fucked."

Stella: I really, truly felt like, now what? I'm the victim of my own ambition.

This was a moment when she had to confront her ambition and ask what she actually wanted. Her job wasn’t making her happy. And there were other things in her life she wanted to change, too.

Stella: Right before I met my husband I had a different boyfriend. He was great. He was like the sweetest person on earth and at a certain point in that relationship I realized he had no ambition. And that was the moment where I thought, "Well, I can never stay with this man. I have to go find another man." And I wrote a list of things I wanted in my next boyfriend after we broke up and ambition was the top of the list.

Molly: Did you then subsequently end up finding them?

Stella: I did. Right away, yeah. I did.

Molly: How long did it take?

Stella: Found a very ambitious man. And I have to say, that's still one ... I mean, we're still together and it's been 22 years. And it's one of the things that I think keeps me interested in him as a person, is that quality .

Molly: Yeah.

Stella: And I really feel that way about most of my lasting relationships have that quality to them. Where we may not be ambitious about the same things, but it's this drive for excellence 

By 27, she’d married an ambitious man; she’d gotten a big new job. She was going after the things she wanted to be when she found out she was pregnant...with twins.

This is the classic challenge for ambitious women—if you want kids, they’re probably going to have to happen during the exact same years when you’re working hardest at everything else. And Stella wanted kids. So she decided to step back, focus on being a mom, and set aside her other ambitions, at least for the moment.

Stella: I quit that job and I was a stay at home mom for 18 months... And I went insane 

I went to an event ... I left the kids and went out to a thing and someone introduced me to someone else as, "Oh this is Stella and she used to be a designer." And I had this horrible panic, rage filled ... Of course it was a man who said it; wanting to punch him in the face. Like, "Ahhh! I'm still ... I'm still a designer!" You know at the time I was like ‘oh I should probably do something.’

It wasn’t going to go away, she realized--ambition would just go into hibernation, waiting for a chance to reemerge.

despite my intentions of taking on less, I was probably never going to actually take on less.


Molly: Is it possible to be ambitious and happy?

Stella: No. I don't think so. I think you have moments of happiness.

Molly: Yeah.

Stella: You have fleeting moments of happiness-

Molly: Yeah.

Stella:  ... and then you're right back to wishing for more or being self critical.

Stella: Part of why I wrote the letter, but also just the last several years have been coming to terms with the idea that this ambitions not gonna get fun and easy and relaxed and resolved. And just kind of learning to appreciate the discomfort of it.

Stella: My anxiety now is not  whether or not I'm going to be ambitious, but just whether or not there will be an outlet for all of this stuff, for all this energy. 

Stella: I would hate to feel this way at 80.

Adam:  I have been in a tortured relationship with ambition my whole life. 

That’s Adam Moss. In her letter, Stella wrote about Adam: “Never before coming to work here had someone enabled me to push past what I thought I was capable of. That was thrilling. I wish that experience for all ambitious people.”

Adam’s been editing New York Magazine for fifteen years, and his ambition is almost a running joke for the people who work for him. One time, I remember, he casually suggested that we ought to try to make the Cut the center of national conversation... at least once a week. Stella and I were like, OK! Sounds good; we’ll get right on that.

When Adam announced he was leaving, he said that his plan for the future was to try living with less ambition. But based on everything we’d ever seen of Adam, “living with less ambition” seemed unlikely. 

Adam: From the beginning I was really ambitious and thought ambition was a 

terrible thing. 

Molly: Why?

Adam: Because when I grew up which was just at the very end of the 60s

hippiedom which I so romanced in my head was exactly the opposite of ambition

ambition was considered like the man slick and corporate and ugly. You know it was for


Molly: God forbid 

Hippies be damned, Adam had ambition: it was in him and it was going to get out.

Adam: In junior high school A student got to direct the school play and that was like a 

little theater geek you can actually get you know a lot of theater experience and I felt that I was like obviously the person who should be the director of the school play. And I thought I would get this job. I thought it was obvious there was no one else. 

Molly: There was no one else! Even now! 

Adam: As a 14 year old to do this and I didn't get it. And I was like weeping 

And my mother who did not ordinarily stand up for me and went and stormed the 

principal's office asking why I didn't get it. And the reason he gave was you know he's just not a leader. He's just not strong enough. And that was like I think maybe that was the beginning of my real ambition because I said fuck that. Yes I am strong enough I can do this. 

Leaving college, he knew he wanted to make magazines, and that’s exactly what he did. His career has been pretty much a straight line going up for 40 years. So what did that feel like at its height, to be able to give ambition free rein?

Adam: I would just like jump out of bed it's as if I had a defibrillator like a trigger and 

I just jumped out of bed and then I would maniacally make lists. 

Adam: I was a crazy list maker. And And I’d jump on my bicycle and race to

 work and then couldn't wait to go you know tell everyone my brilliant ideas that I had 

that morning. And by the way the night the middle of the night before because I would 

like this did not start in the morning it started when I would wake up with a jolt to 30 in 
 the morning every night with like a million ideas that I had to like the list actually started 

in the middle of the night. I was just racing my mind was electrified. 

Things have changed, though. After following the straight line of his ambition for decades, he realized it had taken him away from the work he actually wanted to do—he spent more time being a boss than making magazines. Even the mornings felt different.

ADAM: I just woke up every day slightly less neurotically consumed with the excellence of the thing that were making my job had evolved in ways that I didn't necessarily it wasn't the things that I actually loved like I really I love working on stories. I was like working on stories so infrequently. 

Hearing Adam talk about his career after Stella and Pamela, something occurred to me.... when you’re never forced to pause or change course… when you just get validation and rewards and success… you never have to re-examine what you really want. You never have to reconsider or recommit to your ambition. Adam’s never been told he wasn’t pretty enough for a Barbie commercial; He’s never gotten stir crazy on maternity leave. In all those years since he didn’t get to direct the school play, it’s been pretty much up and up. 

Stella: You've had this nonstop success basically for the last 30 years. Right. 

Adam: Something like something like that. Well I would call it successes. But 

definitely. OK. 

Molly: Are you going to let yourself take the victory lap 

Stella: but just that it made me realize like there have been times where I've had to take time off let's say for pregnancy or whatnot and that's when I learned how ambitious I was like oh I really hate this I hate this I hate not having anything to do. 

Adam: I don't know that it will be a better life for me but I've never tried it. 

So the question is can you change. 

Adam’s trying. He’s said that once he leaves New York, he wants to spend some time painting. It’s something he just picked up recently.

ADAM: I like did some things quickly that were pretty good. And I got ambitious for my painting and I thought hmm maybe I can be a  painter and then like just as quickly I realized no I hit the ceiling- I really I got like OK. And then I was like no like I suck. And so then it was like I was really bummed and then I thought to myself Well no I really love it.  So if I can accept not having ambition for my painting then just being 

mediocre or just being mediocre, God then I could have a good time and I could continue to do this thing that was giving me joy.

Stella said she didn’t think it was possible for an ambitious person to just let go and be happy. But Adam’s going to give it a shot. 

We wish him all the best in what might be his greatest challenge yet: the quest for contented mediocrity. 

That’s it for this week’s show… We’ll see you next Tuesday.


The Cut on Tuesdays is produced by Sarah McVeigh and Olivia Natt.

Our senior producer is Kimmie Regler.

We’re edited by Stella Bugbee, Nazanin Rafsanjani, Lynn Levy, and Alex Blumberg, who told me that he likes me both as a person, AND on this podcast. 

Mixing by Emma Munger and Andi Kristins, our music is by Haley Shaw and Emma Munger. Our theme song is PLAY IT RIGHT by Amelia Meath, Nick Sanborn, Molly Sarle, and Alexandra Sauser Monig.

Special thanks to: Sasha Levine and Phoebe Unterman,  ‘Better Things Footage Courtesy of FX Networks’

The Cut on Tuesdays is a production of Gimlet Media and the Cut.