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Katharine Graham: The Woman Who Took Down a President [Outliers]

Jul 29, 2025 57m 36s 22 insights
When Katharine Graham took over the Washington Post in 1963, she was a shy socialite who'd never run anything. By retirement, she'd taken down a president, ended the most violent strike in a generation, and built one of the best-performing companies in American history. Graham had no training, no experience, not even confidence. Just a newspaper bleeding money and a government that expected her to fall in line. When her editors brought her stolen classified documents, her lawyers begged her not to publish. They said it would destroy the company. She published them anyway. Nixon came after her, attacking her with the full force of the executive. Then Watergate. For nearly a year she was ridiculed and isolated while pursuing the story that would eventually bring down the president.  Graham proved that you can grow into a job that initially seems impossible and no amount of training can substitute for having the right values and the courage to act on them. ------ 10 Lessons from Katharine Graham: ⁠⁠⁠https://fs.blog/knowledge-project-podcast/outliers-katharine-graham/ ------ Approximate timestamps:
Actionable Insights

1. Step Off the Edge

When facing significant challenges or new roles, don’t wait to feel qualified; instead, put one foot in front of the other, shut your eyes, and take the next step, as confidence is earned through action. This approach allows you to move forward even when terrified, leading to growth and eventual mastery.

2. Lead with Principles

When everything is on the line, make decisions based on your core principles and character, rather than solely on strategy or tactics. This approach reveals what you truly stand for and is crucial when stakes are highest, even if it feels terrifying.

3. Keep the Main Thing

Consistently prioritize your core mission or principles, even when facing immense pressure to compromise for profits, safety, or short-term gains. By keeping the main thing the main thing, everything else, including success and profitability, will follow, as principles serve as your compass.

4. Uphold Your Word

Maintain your integrity and keep your promises, especially under extreme pressure, because your word is your most valuable asset. Breaking it renders it worthless forever, while upholding it builds unwavering trust and resilience.

5. Cultivate Quiet Power

Develop a leadership style that is soft-spoken yet firm, demonstrating that competence whispers rather than shouts. This “velvet hammer” approach allows you to be as hard as steel when necessary without resorting to aggression, proving highly effective against adversaries.

6. Believe in Others

Offer the gift of belief to others, especially when they lack confidence in themselves, as this can be transformative. Your conviction can empower them to recognize and achieve their potential, even if they’ve been “pushed down so far” they don’t see it.

7. Embrace the Grind

Understand that confidence is not inherited but earned through consistent effort, hard work, and overcoming challenges, especially during difficult and unseen “dark hours.” Keep putting your head down and grinding away, as this persistent effort will lead to growth and competence.

8. Seek a Teacher/Mentor

Be humble enough to acknowledge what you don’t know and smart enough to seek out brilliant teachers or mentors. Actively engage with their guidance, taking notes and learning line by line, to demystify complex subjects and transform your understanding.

9. Prioritize Talent Over Politics

When building a team, choose talent and an outsider’s fresh perspective over internal politics or insider loyalty, even if it makes others uncomfortable. The person who challenges your thinking is often more valuable than one who simply confirms it.

10. Ask Simple, Crucial Questions

Regularly step back and ask fundamental questions about excellence, rather than just focusing on survival or maintaining the status quo. This helps identify stagnation and drives improvement, even if the questions seem obvious.

11. Choose Curiosity Over Fear

When faced with potential threats or problems, choose curiosity by investigating the situation and engaging with the source, rather than succumbing to fear or external panic. This approach can transform perceived problems into valuable opportunities.

12. Prepare for Crisis

Anticipate potential challenges and secretly prepare for them by training backup personnel, arranging alternative resources, and creating contingency plans. This foresight allows you to withstand unexpected attacks and emerge victorious.

13. Project Outward Strength

During times of intense pressure and internal doubt, project an outward image of strength and resolve, even if you feel desperate or unsure. This steadfast demeanor can inspire confidence in others and help you navigate overwhelming difficulties.

14. Work Alongside Your Team

During crises or challenging times, actively work alongside your employees, rolling up your sleeves and offering assistance, regardless of your position. This hands-on approach builds deep loyalty and strengthens team cohesion.

15. Operate for Decades

Manage your company with a long-term vision, prioritizing generational sustainability over short-term quarterly earnings or exciting acquisitions. This involves strategic actions like buying back undervalued stock and making selective, often “boring,” acquisitions that generate long-term growth.

16. Embrace Accountability

When mistakes or scandals occur, do not cover up or deflect; instead, ensure swift and transparent accountability. This involves publicly acknowledging errors, investigating circumstances, and taking corrective action to preserve credibility.

17. Foster Freedom with Transparency

Grant maximum freedom to your team members, especially in creative or critical roles, but balance it with a “no surprise rule” requiring full transparency. This approach encourages bold action and innovation while maintaining accountability and alignment.

18. Embed Core Principles

Actively embed fundamental principles such as editorial independence, financial discipline, long-term thinking, and public service into the very DNA of your organization. This creates a lasting culture where purpose is the foundation of profit and ensures the company’s endurance beyond individual leadership.

19. Excellence & Profitability Complement

Understand that journalistic excellence and profitability are not opposing forces but complementary ones. Strive for both, as a commitment to quality and mission can drive financial success, and vice-versa.

20. Diversify Strategically

When expanding your business, diversify into related fields rather than making random acquisitions. This focused approach helps weather storms and builds a balanced portfolio that leverages existing strengths and expertise.

21. Maintain Conservative Balance Sheet

Ensure your company maintains a conservative balance sheet with minimal to no debt. This financial discipline provides stability and resilience, allowing the company to navigate economic downturns and crises more effectively.

22. Use Subtractive Tools

To enhance focus and deep work, utilize “subtractive tools” that eliminate distractions like notifications, inboxes, and apps. This creates a dedicated space for your ideas, allowing you to concentrate without interruption.