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 preview

Further Reading:
[Jeff Bezos' Regret Minimization Framework Explained](https://alyjuma.medium.com/the-regret-minimization-framework-how-jeff-bezos-made-decisions-4d5a86deaf24)

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