“I’m 40, burned out, and don’t know what’s next in my life”

Ramit Sethi of I Will Teach You To Be Rich talks to Courtney (40) and Ray (41) who 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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⏩ CHAPTERS
(00:00:41) Why they applied to be on the show
(00:07:48) “I don’t know what I want to do when I grow up”
(00:16:01) Ramit goes over their numbers
(00:18:56) Stashing money in a separate account
(00:34:07) Using the no-numbers Rich Life journal
(00:44:11) Ramit points out “Can we retire?” is the wrong question
(00:57:43) “What will our kids remember about money?”
(01:16:42) Where are they now? Courtney and Ray’s follow-up

Produced by Crate Media.