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Work in Progress: Abby Phillip - Work in Progress with Sophia Bush | Wave AI Podcast Notes

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Work in Progress: Abby Phillip

Work in Progress with Sophia Bush

Sat Nov 22 2025

Summary

Work in Progress with Sophia Bush – Abby Phillip
iHeartPodcasts | November 22, 2025
Guest: Abby Phillip

Episode Overview

In this episode, Sophia Bush sits down with acclaimed journalist and CNN NewsNight anchor Abby Phillip. They discuss Abby's journey from childhood in Trinidad and Tobago to becoming a trusted voice in American journalism, her insights on identity and empathy, the significance of her new book (“A Dream: Jesse Jackson and the Fight for Political Power”), and the challenges of telling complex, multidimensional stories—especially in a deeply divided political era. Together, they explore what it means to be both a “masterpiece and a work in progress”.

Key Discussion Points & Insights

Abby’s Early Life and Formation (03:25–09:21)

Immigrant Roots and Identity:
Abby shares memories of moving from Trinidad and Tobago to the U.S. at age eight, the “lore” of the American Dream, and early experiences that shaped her drive and self-understanding.
Balancing Uniqueness and Assimilation:
- “My parents…always kind of instilled in us this sense that we were not…just like everybody else, for good or for bad.” (09:21, Abby)
- Her Christian upbringing taught her to “be in the world but not of the world”, cultivating comfort with difference.

Empathy, Diversity, and Belonging (13:06–15:20)

Growing up among different cultures and races in Trinidad and Tobago taught Abby to easily interact across differences.
“The idea of differences was not something that ever really bothered me…finding what we had in common was always more important than finding what we didn’t.” (13:18, Abby)
Sophia and Abby relate over their family histories of immigration, assimilation, and navigating American identity.

The Power of Storytelling and Journalism (20:12–28:35)

Roots of Curiosity:
Abby reflects on her entry into journalism and how she finds meaning in chronicling both history and the present.
- “History, politics, culture—it’s the story of us. How we came to be, and also where we’re going.” (20:12, Abby)
Explains her attraction to political journalism:
- “I’ve always loved the sort of outsider role…the place that journalism sits, that is somewhere between the two party system.” (23:34, Abby)
Responsibility & Agency:
- Notes that journalists have a special role to “elevate voices” and work for the public.

On Impartiality and Institutional Trust (29:18–35:22)

Abby addresses the difficulty and necessity of maintaining openness and empathy rather than strict “objectivity.”
- “Are you approaching every story with openness and empathy?” (30:43, Abby)
Acknowledges institutional upheaval in both media and politics; emphasizes that democracy requires voices outside the partisan fray and checks and balances.
Sophia and Abby reflect on the importance of traveling, meeting people, and seeking lived experiences to inform their work and perspectives.

The Complexity of Voters & Telling the Full Story (40:52–44:19)

Abby describes the often contradictory and multidimensional beliefs of American voters, and the need to reflect real complexity in public discourse.
- “People are complex…and being open to that is really important because politics…flattens us into two-dimensional R and D.” (40:52, Abby)
She recounts working on stories with diverse communities whose personal and political views don’t always align—insisting these nuanced voters are often the “deciders.”

The Legacy of Jesse Jackson & Lessons for Today (46:55–59:33)

Why Write This Book Now?
- Abby explains that, like today, the 1980s were a time both of “backlash against diversity” and fights over who speaks for the working class.
- Jesse Jackson’s approach—acknowledging difference but emphasizing coalition—offers lessons for politics today.
- “One of the key lessons…is the way that he argued in favor of seeing people with those multiple dimensions.” (47:21, Abby)
The “quilt” metaphor from Jackson’s campaign:
- “All the different parts of this country [are] part of a quilt…that is still something worth aspiring toward.” (50:43, Abby)
The danger of siloing people by identity versus embracing both individuality and shared purpose.
The necessity of not giving up on persuading others, even across lines of antagonism or difference:
- “I think the act of persuasion is the practice of democracy, and you cannot write people off if you say you want to practice democracy.” (58:48, Abby)

Women, Leadership, and Double Standards (68:09–76:22)

Discuss the contrasting standards for men and women in politics—men are often allowed to be “fabulous and flawed”, women are held to perfection.
- “We hold ourselves, women, to a higher standard…But also, I think [women’s] allies sometimes create a cocoon…and I don’t know that the cocoon is helpful.” (73:25, Abby)
The road ahead:
- “At some point a woman candidate is gonna sort of blow through some of that, and that’s what’s gonna be necessary to get women into that final tier of American politics.” (75:45, Abby)

Abby on Anchoring, Leadership, and Evolving Media (80:18–86:44)

She describes consciously facilitating conversations across divides on “NewsNight.”
- “I don’t want to be the center of that conversation. I want to be the facilitator of it.” (83:08, Abby)
Normalizes resilience in the face of identity-based attacks and rapid media change.
Abby sees her work as “seasons,” constantly balancing professional and personal life, and is looking forward to new chapters of both rest and creativity.

Notable Quotes & Moments

On the eternal balancing act:
- “You are allowed to be both a masterpiece and a work in progress, simultaneously.” (Show theme, Sophia)
On building bridges:
- “Can candidates figure out how to…bring people together not by ignoring who they are, but by saying, I see who you are, and I acknowledge it—but also, let me show you what we all have in common.” (49:32, Abby)
On the role of journalists:
- “The First Amendment is the First Amendment for a reason…you cannot have a democracy without a free press.” (26:30, Abby)
On women in politics:
- “We can be whole people. We don’t have to be perfect people.” (75:45, Abby)

Important Segment Timestamps

Abby’s childhood, moving to the U.S., and identity: 06:01–13:18
Entering journalism & why she chose it: 20:12–26:30
Objectivity/impartiality discussion: 29:18–35:22
On voters’ complexity and misconceptions: 40:52–44:19
Jesse Jackson’s candidacies—lessons for the present: 46:55–59:33
Portraying complex leaders & double standards for women: 68:09–76:22
Anchoring, leadership style, and balancing life: 80:18–88:23

Tone & Language

The tone is intimate, thoughtful, and candid—marked by warmth between Sophia and Abby, frequent laughter, and mutual admiration. Both lean into complexity, reject easy answers, and embrace the messiness of progress, both personal and political.

For Listeners New & Old

Even if you haven’t listened to the episode, this conversation will leave you with:

A deeper appreciation of the importance of multidimensional storytelling in democracy.
Insights on how empathy, curiosity, and open-mindedness improve journalism and civic life.
A renewed sense of how history—specifically Black political organizing—shapes the present.
Reflection on the persistent double standards women face in leadership, and the ongoing work to change them.

If you enjoy intelligent and nuanced conversations about identity, politics, and change—this episode is for you.

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Transcript

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B (3:25)

Hi everyone, it's Sophia. Welcome to Work in Progress. Hello friends, and welcome back to this week's Work in Progress. Today we are talking to a journalist that I deeply admire, and she also happens to be a woman I really like to hang out with. Abby Phillips is our guest today, and she has become one of the most trusted and incisive voices in American journalism. She is known for her unflappable energy, her sharp political analysis, and her incredibly steady presence as the anchor of CNN's Newsnight. And Abby is here with us today because she's just released a new book which feels incredibly relevant for these times, even though it's a study of the 1980s. It is called A Dream Jesse Jackson and the Fight for Political Power. It looks at his 1984 and 1988 runs for President and really the way he was shaking up a system that clearly needs some shaking. Abby's here today to talk about the research that went into this book, the lessons that it holds that are relevant for all of us in this moment, her thoughts about what it will be like in the future when we look back at this current political time. And she's also going to share some of her personal stories. From growing up in Trinidad and Tobago to moving back to the United States, to studying government at Harvard, she has really led a life that has allowed her to approach the world with a drive to understand people and to make sure their stories are being told well and fairly and in ways that might unite rather than divide us. So let's jump in with Abby, Philippines. I like to go backwards with people before we dig into the present because everyone I get to sit with has some amazing story, some amazing career. You have an audience that knows your life, but I like to know how people were made. So if we could have like a very cool animated movie, Day of our Own and like bend space time and step out onto a playground and see our eight year old selves. If you got to hang out with that little girl who I know you still carry with you.

A (9:21)

Yeah, I mean, I think there was totally a sense of lore. I mean, any immigrant experience when you come to America, like the movie Coming to America, it's. It is an experience, right. And it is something that most people that I grew up with in Trinidad never experience. But I always. We always knew, me and my sisters, that we were. We were born in America. And so we always had that kind of part of us that was, what if we used to watch, like, Sweet Valley High? Oh, my God, the Throwback, and, like, all these shows, you know, I mean, we would. We would watch American TV and just kind of dream about what it would be like. And when we did come to the United States, I mean, first of all, our parents had come up a little bit before us to kind of get everything ready. And so a lot of it was just being reunited with them. And the other part of it was just experiencing America snow and, you know, the leaves changing and Christmas and bar real Barbie dolls, not the fake ones that we had growing up. And all of those things were part of the lore. And. And. And. But also, I mean, I have to add that growing up, my parents, regardless of where we were born or the America of it all, I mean, I think they always kind of instilled in us this sense that we were not. We were not just like everybody else, for good or for bad. I don't know where that came from for them. I mean, some of it was that we were raised pretty religiously in a Christian household, so it was always like, you know, you're in the world, but not of the world. So we were always kind of expected to be different from other people. And I think that actually, in a weird way, helped me acclimate and. And adjust to being in a completely different place, because I was very different. I used to have an accent, a Trinidadian accent when I was 8, and I, I lost that accent. But I also just, I was okay with being different from other people, even though I observed our differences. And I think it helped that my parents were always like, you're, you're not like these other kids. You're gonna get A's, you're smart, you're. You know, they would always sort of reinforce in us this sense that we weren't gonna just go with the crowd. We had to have our sense of individuality and our sense of purpose outside of what was happening around us. Yeah.

A (20:12)

Yeah, I think that it's about stories, you know, I mean, I think that fundamentally history, politics, culture, it's the story of us, how we came to be, and also where we're going. And I think I've always been drawn to that. I've been drawn to the way in which history sort of paints a picture that leads us to the present. And I also have been drawn to the way in which our present day actions are doing the same thing for the people in the future. And so, yeah, I mean, I just think we as human beings, we have so much power and agency and the ability to kind of shift space and time around our actions. And that's always been fascinating to me because I think of my whole life as a bit of an anthropological moment. Right. You know, when a family leaves one place and goes to another, they create a whole new timeline for their descendants. And I'm literally living in that timeline that was created for me in part because of my parents actions and who I am as a person is because of their decisions. It's because of my experiences growing up as a child, living in one place and coming to another and knowing what that feels like to have to adapt and, and, and change and, and adjust. And I, I think that is, that's my story. But everybody has a story like that. And I find that fundamentally interesting because that tells us a lot about what people are really like, what they're going to do, what motivates them, what's important to them. And the truth is that we have all of those things, we have those things in common more than I think we know. And in a way, I mean, the politics of it all, like, I mean I, I've, I love politics because I do think that is sort of history in the present day. But I do think that if there's one thing that's wrong with politics, it's the way that it flattens us all into just kind of two dimensional R and D or whatever it is. And I think the promise of journalism is that we kind of expand the dimensions of who people really are beyond just what labels they put next to their names and really start to Learn more about what really motivates them, how they came to be. And I think that is what I have always been drawn to in doing this.

A (30:43)

You know, I think it might be just that. That we are in the middle of. We're in the middle of a moment, and it's a very significant moment. And I don't know really how it's going to end. I don't think the story is over. You know, I don't think the game is done. I think we're just. We're right in the middle of it. And, you know, if there's anything I learned from my studies of government is that the structure of these institutions really matters. And we live in a society where we have all these layers of. These layers of structures that are intended to protect democracy. And sometimes we find gaps where there are. They're just blind spots where there are things that the framers didn't even envision that are happening, that we're dealing with, and where sometimes many layers of those structures are being captured all at once. And we don't know what that means because it's never happened before. So that's how I kind of look at it, is that we are still seeing how our institutions and our democratic structures hold up in this moment under probably the most concerted effort to control and restructure them than I think our democracy has ever seen. And I don't know how it's gonna end. That's the truth. But I do think what I've seen is a bit of a mixed bag. And that's good, actually. I think that it's meant to be that way, that the system is actually meant to produce a lot of different outcomes, and it averages out to something in the end. But I think it is a good sign that. That you can see that sometimes they win, sometimes they lose. That's what it's supposed to be like. If it were that one team was winning 100% of the time, that would be a different story. And I know that sometimes it feels that way to people, but I think it is not that way. Based on the fact that I follow a lot of this stuff very closely, I think it is still a mixed bag. And I think what that tells me is that we still have this really kind of brilliant system in which there are so many different checks and balances on power that no one's ever really able to run all the way to the end zone without encountering resistance. I hope so. And that is the way that this place is supposed to operate. And as long as that continues to happen, I. I have a lot of confidence still in the way that this country is set up. And on the impartiality question, I mean, I think that this has been one of the most hotly debated things right, in journalism. Is it possible even to be objective? Is it possible to even be impartial? And sometimes I think that's the wrong question to ask. I think the right question is, are you approaching every story with openness and empathy? And I think that if you can do that, you. What that requires is an acknowledgement of who you are and some of the things that you bring to the table because of who you are and where you come from and what you know and also what's in front of you. Recognizing that what's in front of you might be different from what you know and being open to what you're hearing and you're seeing. And I think that is really. That's the real challenge of journalism, because I think for too long, people have thought that they were burying their biases, and they weren't. They were just trying to present their biases as impartiality when it was not. And I think that just being upfront about how you come to a story and also being open to what is actually in front of you, that is the real test of journalism. That's why it's so important to go places and actually talk to people. Because when you talk to people, you receive what they are telling you. That is sometimes different from what you.

A (40:52)

Yeah. And I think that when you talk to people, you see how multi dimensional they are. And I think that is the, that's the thing. I think a lot of people don't understand about just voters out there, that, yeah, they have a lot of contradictory views on things. And that's because people are complex and they see different parts of their lives in different ways. And being open to that is really important because again, politics, sometimes you. In politics, it's the job of a political party to have all these things that they believe in. And most people who align themselves with that political party probably believe in a lot of those things. But there are many, many people who take a little bit from over here, from the left and a little bit from the right, and they're somewhere in the kind of weird, bizarre middle. And it doesn't really make a lot of sense to me, to you, but that's okay. And giving voice to those people is super important because guess what? Those are the people who actually determine how elections go in this country. They're the ones with the kind of strange, weird, like, points of view on all these different issues and you don't know exactly where they're going to come down. Well, guess what? They're the deciders. And so those types of people I encounter all the time, and I think they probably could be better represented in our public discourse. I mean, I also think that, you know, when we talk about characteristics of different people, and I remember a couple years ago I was in Kansas doing a story after the Dobbs decision and I went into this working class Latino neighborhood and was talking to people about it because there are actually a lot of Latino voters in Kansas that were actually very significant in those elections. And you know, the thing that I think a lot of people don't see is the way that Latino voters are, many of them deeply religious people and they're hardworking and, and they have personal views that are actually very strong about things like abortion. But their political decision making is different.

B (44:19)

Well, and it's also so refreshing to hear you speak about people that way, because it's a great reminder that no person is a stereotype. No person is just a data point. You know, that. That kind of dynamic and I would say very human reality of saying, I believe this, but I don't think my beliefs should legislate everyone else's lives. That's. That's a powerful example, you know, and I. And I think when we. When we consider, as you were saying earlier, that right now we are making marks that people who come after us will look back at. Those are the kinds of marks I hope we get to make, that we figure out how to show up and allow people to be fuller humans and listen before we judge and perhaps advocate for the best outcomes for the total of us. You know, you hear a lot lately about how people are focusing on the wrong 1%. And I'm like, you think. And really does. When I, when I think about. Feels like we've gotten people really hyped up about some of the wrong things, and we're missing. We're missing our legacy and. And we've clearly forgotten some of our history. And that's why I'm so excited about your book, because I feel like a broken record at this point being like, is anybody paying attention to the correlation between what's happening now in Germany in the 1920s and 1930s? And it's like the. The history nerd in me is just flipping out all the time. And you gave me another gorgeous piece of history to dive into, you know, elements of which I've studied. And. And there's things in your book that I learned for the first time. And for our friends who are going to watch our little clips. Yes, I have it here. And yes, I also brought a Sharpie so I can ask you to sign it for me later. And I did the thing because I'm so excited about this, where I prepped for the podcast, reading the PDF, making notes on my iPad because I didn't want to absolutely destroy the paper copy of the book because I can never read a book and then give it to anyone. They're just like, what is. What is this? What is going on? Like, what is this Gray Gardens thing you've handed to me? In tatters, But I love it.

A (47:21)

Yeah. You know, I think that this story actually has a lot of lessons for where we are right now in this country, because I do think we're in a moment of kind of backlash against the growing diversity of the country. I think that there's also an active fight going on about who can speak to and appeal to the working class. And both of those themes are kind of at the heart of what was happening with Jesse Jackson's campaigns in the 1980s as well. One of the key lessons that can be taken away from his campaigns is the way that he argued in favor of seeing people with those multiple dimensions that we were just talking about, the way in which people have all these different desires and all these different motivations, and that even though we might all look different, we might be black or white or women or men or farmers or, you know, city workers or whatever it is, factory workers, we share a common desire to have a better life, to have a government that works for us, to have a society that feels like it is invested in its citizens and not in other pursuits. And that was a lot of what he campaigned on in the 80s. And I think that one of the unfinished pieces of this is actually what do we do in this moment of division, where it's actually very effective to divide us along all of these different, you know, identities? And can candidates figure out how to do the opposite, how to actually bring people together not by ignoring who they are, but by saying, I see who you are, and I acknowledge it. But also, let me show you what we all have in common. I think that that is. That. I call that unfinished business, because I do think that is still yet to be done. And I think there is a lot in Jesse Jackson's vision for politics, his dream, so to speak, that I think is still worth contemplating. Today, can it be done? And in a way, both parties are kind of engaged in that conversation to some extent, or at least it seemed to be in the last election where, you know, in 2024, despite all the rhetoric, I think the Trump campaign actually they were carrying out like a get out the vote strategy that was geared toward all these different groups and had some success in chipping away at the Democrats diverse coalition. And so I do think that that reality, plus the fact that the Democratic Party does right now have as its base a very diverse coalition, means that there just needs to be a sort of refocusing on what does it really mean to craft a message that can actually speak to all Americans, that doesn't slice and dice them along their different identities, but finds the unifying ties. And, you know, Jesse Jackson used to talk about the country as a quilt. He used to talk about his grandmother using scraps of clothing because they grew up very poor in South Carolina to make a quilt that would keep them warm in the winters. And he would talk about all the different parts of this country as being a part of a quilt. And I think that is still, for so many of us who really do believe in the beauty of this very diverse country, that is still something that is worth aspiring toward, regardless of your political persuasion. And I. I still think that there is a lot of work that needs to be done to bring our politics to a place where that really, we can say that that really is true.

A (53:49)

Yeah, it's both of those things. And it's such a. It is. It is a nuance. Right. Because I. I think that sometimes when people talk about identities, they want them to disappear as if they don't exist. But I think that is. That's. That's one version of doing it. The other version of doing it is to say, I recognize who you are and your individuality, what. That. What you bring to the table, what matters to you. But I'm saying that you can take your individuality and hold hands with someone else who has a different experience, and you can have a shared sense of purpose. And in a way, you know, I do think that that actually comes out of Jesse Jackson's experience in the civil rights movement, because when you really think about what that movement did, it actually helped spur change, not just for black people, but for all kinds of other people, for women, for LGBTQ people, for Asian Americans, for Arab Americans, you name it, Latino Americans. I think that that movement gave all these other movements sort of language and power in the political system. And the civil rights movement has not ever just been liberation and justice for black people. It's been for making the country actually live up to its promise to everyone. And so, because of that tradition, when he comes into the 1980s and says that black voters are going to lead the way, we're going to use our political power to force the Democratic Party to recognize all of us. I think that was just a continuation of the story that began in the 50s and the 60s, in the height of that civil rights movement that everybody now understands and knows. And it is. The black struggle has always been inseparable from the struggles of all these other people. And in some cases, he would go to the south and campaign there and had a lot of support from black voters, but he would also be speaking to white voters, and he would say to them, you know, it's really only the cynics and the people who are full of hate who want you to believe that you have more in common with the uber wealthy white man than you do with the working class black man.