How to figure out what you want with Simone Stolzoff
Episode
53 min
Read time
2 min
Topics
Career Growth, Productivity, Health & Wellness
AI-Generated Summary
Key Takeaways
- ✓End of History Illusion: Psychologists identify a consistent bias where people easily recognize how much they've changed over the past decade but assume their current preferences will remain fixed forever. Recognizing that your values will shift significantly in five to ten years reframes job decisions as "who to date" rather than "who to marry," reducing decision paralysis.
- ✓Three-Question Values Audit: Ethicist Ira Bredzow uses three sequential questions to cut through career decision noise: What do you want (gut-level, not intellectual)? Do you want to want that (examining second-order desires)? What does this choice say about who you are? This sequence surfaces hidden motivations and social scripts driving decisions.
- ✓Odyssey Planning Framework: Stanford d.school's three-path exercise maps distinct futures simultaneously — continuing your current trajectory, pursuing an adjacent path if your current role disappeared, and a third path with no financial or social constraints. Laying out all three reveals unavoidable trade-offs and clarifies which compromises feel most acceptable at your current life stage.
- ✓Desirability-Feasibility-Viability Career Test: Borrowed from IDEO's product development methodology, this three-part filter applied to career decisions asks: Do I actually want this work? Do I have the skills to do it? Can it sustain me financially over time? Running any job opportunity through all three criteria simultaneously prevents optimizing for only one dimension while neglecting the others.
- ✓Suck Tolerance as a Decision Filter: Rather than romanticizing the best-case version of a career path, Stolzoff recommends explicitly identifying what is unpleasant about a role and asking whether you can tolerate it. Philosopher Alain de Botton's framework for romantic partners applies directly — evaluating the undesirable qualities of any option produces more accurate predictions of long-term satisfaction than focusing on upsides.
What It Covers
Author and consultant Simone Stolzoff joins host Molly Graham on WorkLife to examine why identifying what you want from work is harder than it appears, offering concrete frameworks including values clarification, odyssey planning, and the "only option test" to help listeners move from career drift to deliberate decision-making.
Key Questions Answered
- •End of History Illusion: Psychologists identify a consistent bias where people easily recognize how much they've changed over the past decade but assume their current preferences will remain fixed forever. Recognizing that your values will shift significantly in five to ten years reframes job decisions as "who to date" rather than "who to marry," reducing decision paralysis.
- •Three-Question Values Audit: Ethicist Ira Bredzow uses three sequential questions to cut through career decision noise: What do you want (gut-level, not intellectual)? Do you want to want that (examining second-order desires)? What does this choice say about who you are? This sequence surfaces hidden motivations and social scripts driving decisions.
- •Odyssey Planning Framework: Stanford d.school's three-path exercise maps distinct futures simultaneously — continuing your current trajectory, pursuing an adjacent path if your current role disappeared, and a third path with no financial or social constraints. Laying out all three reveals unavoidable trade-offs and clarifies which compromises feel most acceptable at your current life stage.
- •Desirability-Feasibility-Viability Career Test: Borrowed from IDEO's product development methodology, this three-part filter applied to career decisions asks: Do I actually want this work? Do I have the skills to do it? Can it sustain me financially over time? Running any job opportunity through all three criteria simultaneously prevents optimizing for only one dimension while neglecting the others.
- •Suck Tolerance as a Decision Filter: Rather than romanticizing the best-case version of a career path, Stolzoff recommends explicitly identifying what is unpleasant about a role and asking whether you can tolerate it. Philosopher Alain de Botton's framework for romantic partners applies directly — evaluating the undesirable qualities of any option produces more accurate predictions of long-term satisfaction than focusing on upsides.
Notable Moment
Stolzoff describes a computer scientist who built an algorithm to make every life decision for him — where to travel, which events to attend, where to live globally — and spent two years following it completely. A psychologist reframed this not as mastery of uncertainty but as a classic avoidance behavior.
Episode Transcript
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Books, tools, and gear mentioned in this episode
SignalCast may earn commission on purchases via these links.
Tools
by IDEO
“Desirability-Feasibility-Viability Career Test: Borrowed from IDEO's product development methodology, this three-part filter applied to career decisions asks: Do I actually want this work? Do I have the skills to do it? Can it sustain me financially over time?”
course
- Odyssey PlanningRecommended
by Stanford d.school
“Odyssey Planning Framework: Stanford d.school's three-path exercise maps distinct futures simultaneously — continuing your current trajectory, pursuing an adjacent path if your current role disappeared, and a third path with no financial or social constraints.”
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