Lucas and Luna explore an unconventional boundary tool: a career swear jar where every complaint, over-commitment, and boundary breach costs a dollar. Lucas shares how $47 in one week revealed his biggest boundary blind spots, and why the friction of a tangible penalty works better than digital reminders. They discuss the psychology of self-penalty, how $4.50 for saying 'yes, I can squeeze that in' rewired his decision-making, and whether a swear jar could work for different personality types. The conversation includes a specific breakdown of categories—over-commitment complaints, after-hours work complaints, scope-creep complaints—and how tracking them changed his behavior. Luna challenges whether cash penalties actually change habits or just create shame, and Lucas draws a distinction between guilt and friction. They wrap with a practical takeaway: start with $1, use a physical jar, and review weekly. This episode offers a concrete, low-tech alternative to apps and spreadsheets for anyone struggling with work boundaries.