Olivia: Alright, Jackson. Stacey Abrams' Lead from the Outside. Review it in exactly five words. Jackson: Outsiders, your secret playbook arrived. Olivia: Ooh, good. Mine is: "Stop asking. Start taking. Strategically." Jackson: I like that. "Strategically" is the key word, isn't it? Olivia: It absolutely is. We're diving into Lead from the Outside by Stacey Abrams. And what's fascinating is that this isn't just theory. She wrote this while being a political powerhouse in Georgia, famous for her work fighting voter suppression. This book is forged in real-world political battles. Jackson: So it’s less of a philosophical guide and more of a field manual from the front lines. It’s not about wishing for power, it’s about the mechanics of seizing it when you’re starting with nothing. Olivia: Exactly. She argues that for anyone who feels like an outsider—whether because of race, gender, class, or just personality—the traditional rules of success were not written for you. So you have to learn how to hack the system.

Jackson: "Hacking the system." That sounds a little rebellious. Where does someone even start with that? It feels huge. Olivia: It starts with something surprisingly personal and, as you'll see, a little bit heartbreaking. It starts with giving yourself permission to be ambitious. Abrams tells this incredible story from when she was eighteen, in college. She’d just had her heart broken by her boyfriend, Chad. Jackson: Ah, a classic villain. Chad. Of course. Olivia: Of course. And in that moment of feeling like her personal life was a mess, she went to the computer lab late at night and, instead of wallowing, she created a spreadsheet. Jackson: A spreadsheet? That is the most INTJ breakup response I have ever heard. I love it. Olivia: It was a spreadsheet of her entire life, mapped out for the next forty years. Columns for year, age, job, and tasks. And the goals on it were not small. By age twenty-four, write a best-selling spy novel. By thirty, become a millionaire. By thirty-five, be the mayor of Atlanta. Jackson: Wow. Okay, that's not just ambition, that's audacity. I think most of us have those wild dreams but we'd never write them down. It feels too… arrogant or something. Olivia: That's her entire point! She says we, especially minorities, are taught to edit our desires until they fit what society expects. We’re told to be realistic. But she argues that "logic is a seductive excuse for setting low expectations." The spreadsheet wasn't a rigid plan; it was an act of rebellion against that internal editor. It was her daring to want more. Jackson: Okay, a spreadsheet is one thing, but ambition without a path is just a wish. How does she make this practical? How do you get from a spreadsheet to becoming mayor? Olivia: This is where the "hacking" comes in. She introduces a simple but powerful framework she learned from a professor, Anne Alstott. It’s just three questions: What do I want? Why do I want it? And how do I get there? Jackson: Simple enough. Olivia: But the "why" is the engine. She tells another story about visiting a woman named Valerie while campaigning. Valerie was so proud her kids were going to college, but when Abrams asked, "What do you want for yourself?" Valerie was stumped. She'd spent her life providing for others. After some gentle probing, Valerie admitted she'd always dreamed of opening a day care for unwed mothers. But she immediately dismissed it. She lacked the faith to even consider her own ambition. Jackson: That’s heartbreaking. Because you know there are millions of Valeries out there who have just forgotten how to want things for themselves. Olivia: Exactly. The "why" helps you rediscover that. For Abrams, wanting to be mayor wasn't about the title. Her "why" was tackling poverty. A mentor later challenged her, asking if being mayor was a big enough platform for that vision. The "why" allows you to see that the goal isn't the job title; it's the mission. And there might be multiple paths, multiple "hows," to get there. That's the hack. You're not tied to one door if you know what you're truly trying to achieve.

Jackson: Alright, so you have your 'what' and 'why.' But the 'how' is where most outsiders get stuck. Fear, money... the big ones. It’s easy to say "be audacious," but it's terrifying in practice. Olivia: She dives right into that. She says fear is the primary tool used to keep outsiders in their place. And she's brutally honest about her own experience. During her first run for governor, she was calling friends, mentors, potential donors for support. And the response she kept getting, even from allies, was, "Stacey, we love you, but Georgia’s not ready for a black woman." Jackson: Oof. Hearing that over and over again... I can't imagine how corrosive that would be. Olivia: She said her certainty began to crumble. She started dreading making the calls. She was afraid of hearing that same dismissal again. It got so bad that after one particularly painful rejection from a mentor, she almost quit the race entirely. Jackson: Wait, she almost quit? That's not the invincible image we see. Olivia: And that's why she shares it. To show that fear is real and potent. But her solution isn't to ignore it. It's to name it, own it, and use it. She talks about the "authenticity conundrum," this tightrope walk where you have to be yourself, but a version of yourself that's palatable to the mainstream. You have to be "black" but not "too black." "Ambitious" but not "threatening." Jackson: It sounds exhausting. Like you’re constantly performing a role. Olivia: It is. And it's why she says the traditional idea of finding a single, all-knowing mentor is a myth for most outsiders. They're too busy, and they often don't understand your specific tightrope. So she proposes a different model. Jackson: Let me guess, another hack? Olivia: The ultimate hack. Forget a mentor, build a "Board of Advisors." An à la carte support system. She tells this fantastic story from when she was a young deputy city attorney in Atlanta. She was managing a team that resented her and she was failing badly. Jackson: Been there. The team that hates the new boss. Olivia: Her savior wasn't a high-powered lawyer. It was Laurette Woods, the law department's financial manager. Laurette had no legal training, but she understood people. She sat Stacey down and gave her brutally honest feedback. She told her, "The head of the table is wherever you sit." She role-played with her how to fire someone. Laurette was a "situational mentor." Jackson: I love that. A situational mentor. Someone you go to for a specific problem, not for your whole life's plan. Olivia: Exactly. You might have a sponsor who advocates for you in meetings, an advisor for tough negotiations, and a peer mentor—like her business partner Lara—who you can be brutally honest with. This 'Board of Advisors' idea feels so much more achievable. It's like building a personal brain trust instead of searching for a unicorn mentor. Jackson: And it puts the power back in your hands. You're curating your own support. What about the other big fear-inducer? Money. She's famously candid about her own financial struggles. Olivia: Yes, she dedicates a whole chapter to it. She talks openly about the credit card debt she racked up in college and law school, not just for herself but to help her parents. She argues that financial fluency is a non-negotiable tool for power. You can't lead if you're constantly terrified about making rent. And you can't change an organization if you don't understand its budget. For her, financial transparency isn't a weakness; it's another way of owning your story and showing others how to navigate a system that's often rigged against them from the start.

Olivia: And managing that brain trust, your finances, your ambition... it all comes down to her most brilliant metaphor: forget work-life balance, it's Work-Life Jenga. Jackson: Okay, I love the image, but what does that actually mean in practice? How is it different from just being overwhelmed? Olivia: Work-life balance suggests a perfect, static equilibrium is possible. It’s a myth that just makes us feel guilty. Jenga, on the other hand, is a game of strategy and constant adjustment. You know the tower is inherently unstable. The goal isn't to keep it perfectly still; it's to make a strategic move—pulling a block from one area to place it on top—without the whole thing crashing down. Jackson: So some weeks, the "career" block is on top and the "family" blocks are holding the base, and other weeks you have to shift it. Olivia: Precisely. It’s about prioritizing what matters most in that moment, and knowing that it will change. It’s a dynamic, sometimes precarious, process. And a key part of playing Jenga is accepting that sometimes, the tower will fall. And that's where her ideas on failure come in. Jackson: You mentioned she learned from failure. Give me the best example. What's a failure that actually led to a win? Olivia: The story of Nourish is perfect. Early in her career, she and her business partner Lara started a company called Nourish, which made bottled water specifically for babies and toddlers. They had a great product, they were getting into stores. They even landed a huge order from Whole Foods. Jackson: Sounds like a success story. Olivia: It was, until it wasn't. The Whole Foods order was so large they couldn't fulfill it without automating their production line, which was basically them hand-assembling everything. They needed capital to buy the machinery. They went to banks, to lenders, to everyone. And no one would give them the money. The business failed. They had to wind it down. Jackson: That's devastating. All that work for nothing. Olivia: But here’s the Jenga move. One of the lenders who rejected them, a man named John Hayes, was impressed by their pitch even though he couldn't fund them. After Nourish failed, he called them. He had another problem he thought they could solve. That consulting gig led to a deeper partnership, and together, the three of them co-founded NOW Corp.—a thriving financial technology company that helps small businesses get paid faster. Jackson: Wow. So the failure wasn't just a lesson, it was literally the map to the next, bigger success. The relationship they built while failing was the asset. Olivia: That’s it exactly. She says failure is a map. It shows you where the dead ends are, but it also reveals new paths you never would have seen otherwise. The tower fell, but they used the scattered blocks to build something stronger.

Jackson: So when you boil it all down, what's the one thing Abrams wants an outsider to do after reading this book? It feels like it's about more than just getting ahead. Olivia: It is. I think the core message is that power isn't something you're given, especially if you're an outsider. It's something you take. But "taking" doesn't mean being a bulldozer. It means being a strategist. It's about understanding the rules of the game so you can bend them, or just create your own game entirely. Jackson: It’s not about just getting a seat at the table... Olivia: It's about building your own table, or maybe just kicking a leg out from the old one to make it wobble. She uses this wonderful quote: "If you see a turtle sitting on a fence post, you know he didn’t get there alone." For outsiders, it means we have to be the ones lifting each other up onto the fence post, because the system won't do it for us. It’s about using your otherness, your unique perspective, as your primary weapon. Jackson: That’s a powerful way to end. It feels like the first step is just giving yourself permission to even think about what you want. Maybe the first step is just making that spreadsheet. No judgment, just write down the wildest things you want. Olivia: I love that. A "Spreadsheet of Dreams." It’s a fantastic, concrete action. And for everyone listening, we’d love to build on that. What’s one audacious goal you’d put on your own spreadsheet? Share it with the Aibrary community on our social channels. Let's see the ambition out there. Jackson: Let your haters be your motivators, as she says. Olivia: And let your dreams be your guide.