Olivia: The most common career advice for women is to ‘lean in,’ be tougher, and act more like the men in the room. What if that's not just wrong, but the very thing holding them back? What if the real power move is to cry more? Jackson: Cry more? That sounds like career suicide. Where is this coming from? My performance review has never had a section for 'demonstrates vulnerability through tears.' Olivia: It comes from a fascinating book, Jennifer Palmieri's Dear Madam President. And what makes her perspective so compelling is that she's not an academic or a theorist. This is a woman who was the White House Communications Director for President Obama and then the Communications Director for Hillary Clinton’s 2016 presidential campaign. She has lived in the absolute eye of the political storm. Jackson: Okay, that’s some serious front-line experience. She’s seen it all. The book is framed as a letter to a future female president, right? I know it got a lot of attention and was highly rated, but also stirred some debate for being very pro-Clinton. Olivia: Exactly. It's part memoir, part manifesto, and part advice column for any woman who wants to lead. And she argues that before you can even think about changing your own internal rules—like allowing yourself to be emotional—you have to understand the brutal external rules of the game she witnessed firsthand. Jackson: And I’m guessing those rules aren’t written down in any employee handbook. Olivia: Not even close. In fact, the best summary of the first rule came from a dark joke told by the people tasked with protecting Hillary Clinton’s life.

Jackson: A joke from the Secret Service? This sounds good. Olivia: Palmieri tells this incredible story from the campaign trail. Whenever the Secret Service agents on Hillary's detail hit some bureaucratic roadblock or internal disagreement, they had this gallows-humor catchphrase they'd say to each other: "Well, guess we only have one option left. Move forward, draw fire." Jackson: Whoa. That’s… bleak. And revealing. The very act of advancing means you're going to get shot at. Olivia: Precisely. And Palmieri realized that phrase perfectly described Hillary Clinton's entire public life, and by extension, the experience of many ambitious women. The central idea of this first part of the book is that for a woman, ambition itself is seen as a provocation. Simply by moving forward into spaces traditionally occupied by men, you will inevitably draw fire. Jackson: It’s the motion itself that’s the problem for some people. Not the destination, but the fact that a woman is moving toward it. Olivia: Exactly. And that fire isn't always obvious. It often comes disguised as something else. Palmieri uses the email controversy as a prime case study. Jackson: Okay, let's get into this, because this is where the book gets controversial for some readers. They argue it was a legitimate issue of national security and judgment, not just a gendered attack. Olivia: And Palmieri doesn't necessarily say the issue was illegitimate. What she focuses on is the nature and scale of the fire it drew. She tells a story from the summer of 2015 when the campaign was just drowning in this story. They were constantly being told by the press what Hillary needed to do to 'put it to bed.' First, she needed to be more transparent. She was. Then, she needed to express remorse. She did. Then, during one interview, a reporter blindsided them with a new demand: "Does she think she owes the American people an apology?" Jackson: The goalposts just keep moving. It's never enough. Olivia: That was the realization. Palmieri writes that the press wasn't looking for an apology; they were looking for a confession to a crime she didn't commit. The fire wasn't about finding a resolution. It was about feeding a pre-existing narrative of distrust. Palmieri's argument is that this deep, vague feeling of "there's something about her I just don't trust" is often a stand-in for a more uncomfortable, unconscious bias against a woman unapologetically seeking the highest office in the world. Jackson: So the email story became the vessel for a feeling that was already there. If it hadn't been the emails, it would have been something else. Olivia: That's her core argument. She quotes the common refrain they heard: "I am fine with a woman being president, just not this woman." Palmieri sees that as a classic manifestation of unconscious bias. It’s a way to support the idea of female leadership in theory, while rejecting the actual, real-life, ambitious woman standing right in front of you. Jackson: It's a way to sound progressive while maintaining the status quo. That's a tough, almost impossible, dynamic to fight. So if you're constantly drawing fire just for showing up and doing your job, how on earth do you survive that without completely burning out or becoming a robot? Olivia: Ah, and that is the perfect pivot. Because that's exactly where Palmieri's most radical and, I think, most important advice comes in. She argues you can't just grit your teeth and bear it. You have to start an internal revolution. You have to learn to nod less… and cry more.

Jackson: Okay, I’m still stuck on this 'cry more' thing. In any professional setting I've ever been in, crying is seen as the ultimate sign of losing control. It feels like the opposite of what a leader, male or female, is supposed to do. Olivia: And that’s the exact assumption Palmieri wants to shatter. She starts by describing what she calls "the stoic nod." On election night in 2016, as the disastrous results were coming in, she had to tell Huma Abedin, Hillary's close aide, that they were going to lose. And Huma just responded with a quiet, firm nod. Jackson: The "we can take it" nod. Olivia: Yes. Palmieri instantly recognized it. It was the same nod Hillary gave when she was told the FBI was reopening the email investigation days before the election. It was the same nod Palmieri herself had given countless times when hearing bad news. It's a conditioned response for high-achieving women: absorb the blow, show no weakness, and signal to everyone, "I can handle this." Jackson: It’s a survival mechanism. You do it to prove you belong in the room, that you’re not too ‘emotional’ for the job. Olivia: But Palmieri argues that this constant suppression is incredibly damaging. It disconnects you from your own feelings and from the people around you. The antidote she proposes is radical authenticity. She tells another story, this one from after the election, at a postmortem event at Harvard. The Trump campaign team was there, gloating and smug. Jackson: That sounds excruciating. Olivia: It was. And for most of it, the Clinton team just sat there, doing the stoic nod, being the "gracious losers." But then a reporter asked about the Trump campaign's hiring of Steve Bannon and their use of what many saw as race-baiting tactics. And Palmieri just… broke. She stood up, and through a shaking voice and tears, she told them that she would rather lose than win the way they did. Jackson: Wow. So she finally let the fire out, instead of just absorbing it. What happened? Olivia: The media, of course, reported that she had an "emotional outburst" and wasn't "gracious." But Palmieri says she has zero regrets. Because in that moment, she wasn't performing strength; she was demonstrating it. She argues that crying isn't a sign of weakness; it's a powerful demonstration of emotion. It can be anger, frustration, passion, or grief. It's human. She even mentions that in the Clinton White House, her office unofficially became known as "the crying room," a place where staffers—men and women—could go to release the pressure without judgment. Jackson: A crying room in the White House. That’s an image. So it’s not about being weak, it’s about being whole. It’s about not having to amputate a part of your emotional self to be taken seriously. Olivia: Exactly. And this ties directly into her next point: embracing your battle scars. She talks about the pressure on women, especially in public life, to look perfect and ageless. But she encourages the future Madam President to let the lines on her face show. To let the gray hair come in. Jackson: Like the 'elevens' between her eyebrows she talks about. Olivia: Yes! She noticed them when she was working in the White House and was initially proud of them, thinking they were a sign of a life lived, of wisdom gained. Then she saw a spa brochure advertising how to get rid of them and realized society saw them as a flaw to be erased. She made a conscious choice to let them show. Because those scars, physical and emotional, tell a story. They tell us what you've endured, and in turn, they tell us what we can survive. Jackson: That’s a powerful reframe. Your vulnerability becomes a source of strength and connection for others. Okay, I can see how navigating the external fire and cultivating this internal resilience are connected. But what’s the final piece? How do you tie it all together? Olivia: It all builds to Palmieri's ultimate point. Navigating the fire and embracing your scars is all in service of one thing: gaining the power to write your own story.

Jackson: Write your own story. That sounds a bit like a self-help mantra, but coming from her, I imagine it has a much sharper political edge. Olivia: It absolutely does. And the most poignant story she tells to illustrate this is about Hillary Clinton herself. In early 2015, the campaign was planning the official announcement speech. The staff was scouting locations, and Palmieri was pushing for a site in New York City with a beautiful glass atrium—a perfect metaphor for breaking the glass ceiling. Jackson: Makes sense. It’s visually and thematically on point. Olivia: But Hillary was hesitant. She felt she needed a location with more historical weight, something that connected her to a lineage of past presidents. When Palmieri pushed back, Hillary revealed something stunning. She confessed that she didn't think her own life story was particularly interesting or compelling to the American public. Jackson: Wait, what? Hillary Clinton? Former First Lady, Senator from New York, Secretary of State… she thought her story wasn't interesting enough? That’s unbelievable. Olivia: It’s shocking, isn't it? Palmieri was floored. Here was one of the most accomplished women in modern history, and she had internalized this idea that her story—a woman's story of navigating power—wasn't as valid or resonant as the traditional male stories of struggle and triumph. It perfectly captures the core problem: women's stories have been so systematically undervalued that even women themselves can fail to see their power. Jackson: Wow. So it's not just about other people not listening to your story. It's about you, yourself, not even believing you have a story worth telling in the first place. That feels like the real, hidden battle. Olivia: It is. And Palmieri faced it herself. After the campaign, she was told that a book from her would only sell if she had "juicy" gossip about the Clintons. The message was clear: her perspective was only valuable in relation to a more famous person's story. She almost gave up on the idea. Jackson: But obviously, she didn't. This book exists. Olivia: She didn't. She realized that if she didn't tell her story, someone else would—and they would get it wrong. She decided she wasn't powerless. She had to write her own narrative. And this individual act of empowerment is a microcosm of what she sees as a massive cultural shift, exemplified by movements like #MeToo. Jackson: Where the entire point was women collectively taking back the narrative, refusing to be silenced and telling their own stories, on their own terms. Olivia: Precisely. The power of #MeToo wasn't just in one story, but in the tidal wave of millions of women realizing their "uninteresting" personal stories were actually part of a massive, shared, and world-changing narrative. Palmieri's message to the future Madam President, and to all women, is to stop searching for your role in his story. Write your own.

Jackson: So when you put it all together, the book is really a three-part playbook. First, understand that if you're an ambitious woman, the world will throw fire at you just for moving forward. It’s the cost of entry. Olivia: Right. That's the external reality. Jackson: Second, the way to survive that fire isn't to become harder or more stoic. It's to become more authentically yourself. To embrace your emotions and your scars as sources of strength. That's the internal revolution. Olivia: The internal mindset shift, exactly. Jackson: And finally, the ultimate victory, the thing that all of this leads to, is seizing control of your own narrative. To define yourself before others can define you. It’s a roadmap for women to stop trying to play by the old, broken rules and start creating new ones, for themselves and for everyone else. Olivia: That’s a perfect summary. It’s a call to move from being a character in someone else's history to being the author of your own. And while the book is addressed to a future president, its message feels incredibly relevant to anyone who's ever felt underestimated or has been told to be quiet. Jackson: It really does. It makes you think about all the subtle ways we police our own behavior to fit into boxes that were never designed for us. Olivia: Which leads to a great question for everyone listening. Palmieri’s journey was about recognizing and breaking the unwritten rules she’d been following. So, what's one 'unwritten rule' you've followed in your own life or career that you're now ready to question? Jackson: That’s a powerful question. We’d love to hear your thoughts. Join the conversation and let us know what you think. Olivia: This is Aibrary, signing off.