In this deeply reflective episode of Silent Service, Matt DiMauro and Will Diesel explore one of life’s toughest questions: how do you know when it’s time to move on? Whether it’s a career, a relationship, or a season of life, the two dive into the tension between comfort and growth, security and opportunity.They reflect on the tension between chasing what looks “great” and appreciating what’s already “good,” drawing from history, personal experience, and faith. Through stories about career moves, family priorities, and the weight of regret, Matt DiMauro and Will Diesel reveal how questions of timing are never simple, but can be clarified by looking at values, opportunity costs, and the life you want to design for yourself.You will also hear reflections on grief, finding focus in turbulent times, and why cultivating self sustaining happiness, joy that is not tied to outside approval or circumstances, may be the key to knowing when it is time to let go.0:00 - Welcome and episode introduction  3:00 - MEPS check-in and emotional resilience  6:00 - Choosing between good and great  9:00 - Why context shapes every decision  12:00 - Career move dilemma: Tampa vs. Seattle  15:00 - Understanding opportunity cost  18:00 - Minimizing regret and future perspective  21:00 - Breaking free from sunk costs  24:00 - The right way to quit a job  27:00 - Defining goals and life design  30:00 - Company culture and personal fit  33:00 - A, B, and C player framework explained  36:00 - The surprising economics of OnlyFans  39:00 - Ethics, business models, and use of time  42:00 - How goals evolve with experience  45:00 - Distinguishing unhappiness from misalignment  48:00 - Sources of wisdom: mentors and scripture  51:00 - Closing quotes and next episode previewFurther Reading:  [Jeff Bezos' Regret Minimization Framework Explained](https://alyjuma.medium.com/the-regret-minimization-framework-how-jeff-bezos-made-decisions-4d5a86deaf24)Follow us on Apple Podcasts, Spotify, YouTube, iHeartRadio, or wherever you listen to your favorite shows. New EpisodesEvery Wednesday and Friday. Follow UsInstagram & TikTok: @silentsvcpod Hosted byMatt DiMauro & Will Diesel Support the ShowIf you enjoyed this episode, share it with a friend! We donate 100% of proceeds to charity.Got a cause you care about? Send a quick pitch to [email protected] — we’d love to hear your story.

Ver todos los episodios