How To Stop an Anxiety Spiral, The Best Protections Against Financial Ruin, and a Workaholic's Guide to Productivity (and Self-Care) | Andrew Ross Sorkin

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• The enduring lesson from financial history, exemplified by the 1929 crash, is that human nature's tendency toward collective fever and overconfidence requires humility as the true antidote to irrational exuberance.  Copied to clipboard!
• The mantra "Would It Help?" derived from the movie *Bridge of Spies*, serves as a practical tool to stop mental spiraling by forcing a pause to evaluate if continued rumination will change the outcome.  Copied to clipboard!
• For personal finance, the most economically and emotionally successful approach, endorsed by figures like Warren Buffett, is consistent saving into low-cost index mutual funds rather than actively tracking or trading individual stocks.  Copied to clipboard!

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Origin of 1929 Book

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(00:05:32)

• Key Takeaway: Andrew Ross Sorkin wrote 1929 to provide a character-driven narrative of the crash, filling a gap left by existing historical accounts.
• Summary: The book 1929: Inside the Greatest Crash in Wall Street History–and How It Shattered a Nation was motivated by the need to understand the 1929 crash through personal stories, similar to narrative non-fiction styles like Den of Thieves. Sorkin spent eight years uncovering memos, diaries, and letters to convey the emotional experience of the people involved during that euphoric, FOMO-driven period. The core insight is that the crash was driven by human nature, not just rates or regulation.

Human Nature and Humility

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(00:07:37)

• Key Takeaway: The ultimate lesson of financial history is that the antidote to irrational exuberance is humility, recognizing that no system is foolproof and generations easily forget past lessons.
• Summary: Financial booms and busts are fundamentally about human behavior, specifically the FOMO that drives excessive confidence. Humility is essential to protect against this, as excessive certainty inevitably leads to a harder fall. The crash of 1929 was not preordained by the crash itself, but by subsequent policy choices that exacerbated the situation.

Generating Financial Humility

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(00:11:11)

• Key Takeaway: Detachment from the ’thing of the moment,’ exemplified by Warren Buffett’s adherence to understandable principles and simple index investing, fosters financial humility.
• Summary: Warren Buffett maintains detachment by living simply and sticking to what he understands, avoiding investments like technology stocks or Bitcoin when outside his expertise. His emotional approach is to get excited when stocks fall because they are ‘on sale’ for long-term holdings. For most people, the safest approach is consistent saving into index funds rather than active trading, which is an emotionally taxing business.

Debt and Financial Survival

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(00:20:12)

• Key Takeaway: The primary danger in financial downturns is taking on debt, especially borrowed money used for investing, while serviceable debt for living expenses requires careful budgeting.
• Summary: The danger in market downdrafts comes from those who take on remarkable risk, often through leverage. People should assess if they can survive six to twelve months of unemployment without needing their invested cash. While debt like mortgages is sometimes necessary, the key is ensuring monthly payments are serviceable and that one is not relying on selling investments monthly to cover basic living costs.

Budgeting and Frugality

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(00:25:25)

• Key Takeaway: Detailed budgeting provides a soothing sense of control by replacing the ‘miasmatic fog of unknowing and dread’ with reality-based financial decisions.
• Summary: Both Sorkin and Harris find detailed budgeting for personal and business finances oddly soothing because it grounds decisions in reality. This contrasts with friends who prefer not to know their financial details, living with ‘blinders on.’ Frugality, valued by Sorkin’s family, means prioritizing spending on experiences like vacations over material items like fancy cars.

Stopping Mental Spirals: Would It Help?

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(00:30:25)

• Key Takeaway: The ‘Would It Help?’ mantra, inspired by the movie Bridge of Spies, is a clarifying mindfulness tool to halt unproductive anticipatory anxiety and spiraling thought patterns.
• Summary: When anxiety causes mental permutations to overtake a situation, asking ‘Would It Help?’ forces a step back to assess if continued mental processing changes the outcome. This functions as a cousin to meditation, waking one up from habitual thought patterns. Sorkin even keeps a sign with this phrase on his desk.

TM Practice and Benefits

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(00:34:43)

• Key Takeaway: Transcendental Meditation (TM) provides a familiar, calm internal state that Sorkin can access quickly even when not formally meditating, aiding performance anxiety.
• Summary: Sorkin practiced TM consistently for many years, describing the experience as transcending the egoic mind into a state of stillness, sometimes accompanied by visual phenomena like blackness or orange light. The long-term benefit is an acquired ability to self-calm in high-pressure situations, like backstage before speaking, without needing the full meditation session.

Productivity: Calendar Blocking Over Lists

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(00:42:32)

• Key Takeaway: Sorkin relies on time blocking—putting every task onto the calendar—rather than to-do lists to accurately estimate and execute his demanding schedule.
• Summary: Because everything takes time, Sorkin schedules specific time slots for tasks, which prevents overestimating daily capacity and combats procrastination, often using timers for focused work blocks. A major drawback of this hyper-scheduled system is the complete loss of serendipity and spontaneous interaction, which Sorkin acknowledges can negatively impact relationships.

Productivity: The Polite No

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(00:54:09)

• Key Takeaway: Issuing a quick, polite ’no’—a concept borrowed from Vince Gilligan—is crucial for productivity, as delaying the answer hurts both the requester and the person needing to commit.
• Summary: When an opportunity does not align with core priorities, a swift refusal prevents the internal ‘snowballing’ of indecision and anxiety. Sorkin advocates for quickly returning emails or calls to state inability to commit, without always needing lengthy explanations, as letting the decision drag out is the worst outcome for everyone involved.

Disclosure and Public Sharing

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(00:56:32)

• Key Takeaway: Disclosure from public figures is useful when the personal information reveals something valuable or normalizes experiences that others feel shame about, such as Sorkin’s past cocaine use leading to meditation.
• Summary: The traditional journalistic ethos of detachment is becoming outdated in an era of greater openness. The line for sharing is drawn by usefulness to the audience; personal details that lead to actionable insights (like Sorkin’s path to meditation) are valuable. Sharing normalizes experiences that listeners might otherwise feel shame over.