The Trouble with Optionality - Deepstash
The Trouble with Optionality

The Trouble with Optionality

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The allure of optionality

“Maximizing optionality” - the state of enjoying possibilities without being on the hook to do anything - is a key reason young people give when going for big school or employer.

  • working at a consulting firm creates optionality because of the broad exposures & skills
  • going to graduate school creates optionality by enabling more opportunities than a narrow professional trajectory can provide.
  • working at prestigious firms and developing social networks are similarly viewed as enabling more choices and more optionality


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Optionality is like playing the lottery

Optionality is like playing the lottery

Like lottery ticket buyers, the people pursuing optionality postpone their dreams and undertake choices that they think will enable their dreams. 

The shortest distance between two points is reliably a straight line. If your dreams are apparent to you, pursue them. Creating optionality and buying lottery tickets are not way stations on the road to pursuing your dreamy outcomes.


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Life-long learner. Passionate about leadership, entrepreneurship, philosophy, Buddhism & SF. Founder @deepstash.

Vladimir Oane's ideas are part of this journey:

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