I Hate It Here S10 E7: Proof Your Job Is Rewriting Your Personality in Real Time with Jessie Stettin
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Dec 8, 2025 Jessie Stettin, VP of Customer Success at Encompass Labs, discusses the profound impact of workplace culture on identity and behavior. With a unique background that includes being an end-of-life doula, he reveals how childhood experiences can unconsciously shape professional dynamics. Jessie highlights the importance of emotional granularity at work and the need to redesign social interactions around feelings. He also shares insights on rethinking success and the responsibility of leadership in influencing organizational culture.
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Culture As An Invisible Operating System
- Jessie Stettin argues workplace culture acts as an invisible operating system shaping how we communicate, lead, and find meaning.
- Hebba Youssef agrees culture rewires identity, confidence, and behavior often without our awareness.
Youngest Sibling Shaped Workplace Observation
- Jessie describes being the youngest sibling and learning to observe and fit into dynamics before acting.
- He brought that observational style into early workplace roles to learn norms and where he fit.
"Delusional Relationship" With Authority
- Hebba recounts a travel security moment and a friend calling her "delusional relationship with authority."
- She connects that to childhood dynamics and how her first job cemented skepticism toward authority.