How to Take Risks in the Free Agent Economy?

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O'Sharmosy Ventures is a venture capital firm based in New York. Founder and CEO of the company, Jim O'Sharmo says he's been thinking about how to get people to take more risks at work. He believes that by taking fewer risks when opportunities present themselves, they'll unlock more opportunities. The first step for him was leaping from the paycheck economy to the gig economy.

Venkatesh Rao is a writer, consultant, and author. He has been writing about indie consulting for years and has recently published The Art of Gig, Volumes 1 & 2, which together take an in-depth look at the gig economy. Venkatesh joins the show to discuss tragic luck, becoming slightly nonsensical, the advantages of mediocrity, and a whole lot more! Important Links:

Show Notes:

Origins of The Art of Gig
Paycheck People
Learning how to take risks
Is there a risk-taking gene?
The case for fixed-point futurism
Finding meaning
Personality types, narrative, and becoming a courageous thinker
Don’t get tragically lucky
Generational agency
Sparring, pressure and meaning-making
Be slightly nonsensical
Teaching others to appreciate randomness
Towards infinite games; be mediocre
Understanding divergentism
MUCH more!

Books Mentioned:

The Art of Gig: Volumes 1 & 2; by Venkatesh Rao
The 4-Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich; by Tim Feriss
Free Agent Nation: The Future of Working for Yourself; by Daniel H. Pink
The Pathless Path: Imagining a New Story For Work and Life; by Paul Millerd
Tempo: timing, tactics and strategy in narrative-driven decision-making; by Venkatesh Rao
The Redemptive Self: Stories Americans Live By; by Dan P. McAdams
Finite and Infinite Games: A Vision of Life As Play and Possibility; by James Carse
Getting Things Done: The Art of Stress-free Productivity; by David Allen