The Pathless Path with Paul Millerd #146 Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood
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May 22, 2023 
A childhood shaped by four parents and unspoken career scripts leads to poetry, journalism, and a spontaneous trip around the world. Simone Stolzoff and Paul Millerd explore the myth of the dream job, the tangled relationship between work and identity, and the challenges of writing and promoting a book without letting work take over.
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Impulsive Trip Changed Career
- Simone bought a last-minute $200 multi-city flight ticket after a friend tipped him off to a glitch.
- This impulsive trip became an 11-month world journey that changed his life direction.
Travel Builds Ambiguity Tolerance
- Simone's world travel cultivated comfort with ambiguity and the unknown rather than concrete career answers.
- This period emphasized living fully rather than following a strict vocational plan.
Choosing Between Two Selves
- Simone faced an existential choice between continuing writing or joining a design consultancy.
- This conflict inspired him to explore separating identity from work in his eventual book.