Courtney (40) and Ray (41) have spent their entire adult lives in the structure of military life—but with retirement on the horizon, they’re about to face a future filled with choices for the first time.

For Ray, that means walking away from the rank, routine, and pension he’s built for over 20 years and entering a civilian job market he knows little about. For Courtney, it means finishing grad school, becoming a therapist, and finally stepping into her own career after 12 years as a stay-at-home mom.

With three kids, a cross-country move coming soon, and dreams of settling down for good, can they stop optimizing for retirement and start asking better questions on building their Rich Life?

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