Digging a Hole / Work Will - Convention 1999

Synopsis

The talk revolves around the speaker's personal journey and philosophy regarding work, willpower, and entrepreneurship. It presents a metaphorical method for deep self-commitment, using work as both a challenge and an opportunity for transformation. The speaker rejects conventional employment and stresses personal initiative, sharing experiences from different fields such as retail, corporate environments, performing arts, and online marketplaces. Key themes include resilience, creativity, leveraging technology, acts of kindness, and navigating modern challenges.

Summary

The speaker articulates their long-held views on self-driven work and the importance of cultivating a special kind of willpower, referred to as "work will." They reject the notion of personal exceptionalism, asserting that everyone has the potential to dig themselves into a situation requiring resourcefulness and dedication to succeed. Using vivid metaphors, such as digging a hole one cannot easily escape and the use of ‘alarm clocks as shovels,’ the speaker illustrates the necessity of intense commitment.

A major focal point is the rejection of corporate employment, which they argue stifles personal growth due to imposed quotas and rigid hierarchies. They share personal experiences, including working in large corporations and observing systemic inefficiencies. Instead, they advocate for self-employment and leveraging modern platforms such as eBay, Amazon, and emerging digital economies to generate income and independence.

The talk includes anecdotes about unconventional pathways to success, marketing strategies that defy conventional wisdom, and the principles of self-sufficiency. Additionally, it touches on the importance of philanthropy, suggesting that one’s ultimate goal should be the ability to give freely to worthy causes without financial constraint. The speaker integrates economic observations, humor, and a broad perspective on societal dynamics, challenging attendees to rethink their approach to work, money, and personal agency.

The latter part of the talk dives into modern opportunities, technological trends, and future-proofing one’s livelihood. The speaker anticipates shifts in publishing, commerce, and digital interactions, emphasizing how adaptability will be key in an evolving world. There is a heavy focus on marketing and human interaction as critical components of success, beyond simple financial gain. The speech is laced with stories of past risks, successes, and failures, framing them as learning tools. Ultimately, the talk serves as both motivational guidance and a critique of societal conventions, urging individuals to take strategic control of their work and financial futures.

Keywords & Key Phrases

• Work will
• Digging a hole
• Self-driven work
• Alarm clocks as shovels
• Corporate stagnation
• Productivity limits
• Retail mindset
• Creative entrepreneurship
• Digital economies
• eBay marketplace strategy
• Amazon selling dynamics
• FatBrain publishing
• Internet as public space
• Stock market sector rotation
• Online auction psychology
• Emerging business models
• Marketing self-exposure
• Acts of kindness as currency
• Future of publishing
• Technological adaptation
• Guerrilla marketing
• Economic pitfalls
• Y2K societal fears
• Philanthropy mindset
• Handmade craftsmanship
• Artistic self-sufficiency
• Alternative commerce
• New wealth resistance
• High-end antiquities market
• Internet retail dominance

Graphic Prompt

A surreal digital painting of a solitary figure standing inside a deep, self-dug pit, arms raised toward the sky. Above, a silver shovel lies just out of reach on the edge of the surface, illuminated by golden dawn light. Faint images of alarm clocks are embedded in the earthen walls of the pit. Overhead, the vast sky is filled with floating digital market icons (eBay, Amazon, stock tickers) merging into abstract patterns of data streams and interconnected commerce. The mood is dramatic, evoking both struggle and revelation, symbolizing entrepreneurial self-transformation.