Ramit's initial assessment of their dynamic

Jamie (45) and Ryan (36) have been married for nearly a decade and share three kids, but their financial foundation was shaken when Ryan quit his high-paying finance job and cashed out his 401(k) without telling Jamie. Now earning far less, they’re still spending like nothing changed, running up credit card debt and ending each month wondering where the money went. Jamie, the higher earner, is anxious about retirement and trust after years of financial surprises, while Ryan avoids money conversations and struggles with insecurity. Layered on top are a 10-year age gap, deep past trauma, and very different visions of a Rich Life. Can Ramit help them rebuild trust, create a real plan, and finally start acting like partners instead of adversaries?

In this episode we uncover:

• The moment Jamie learned Ryan quit his high-paying job and cashed out his 401(k)

• How Ryan’s breaking point at work led to a “nuclear option” decision that shifted stress from the office straight into their marriage

Why earning nearly $300K still leaves them feeling broke

• The trust fallout from repeated unilateral decisions, including quitting jobs, cashing out retirement accounts, and impulsive purchases

• How Ryan’s spending on shoes, clothes, and even a classic car mirrors patterns he watched growing up

• Jamie’s role as the default financial manager

• The vacation-vs-things blame cycle that keeps them stuck spending instead of saving

• Why hiding money in a separate savings account felt like the only way Jamie could protect their future

• The uncomfortable truth behind their $13K emergency fund

• How calling their own spending “stupid” and “dumb” keeps them trapped in shame instead of change

• The emotional toll of living in constant financial vigilance while still spending freely on convenience and comfort

• How a failed $500 spending rule exposed their lack of shared systems

• The powerful influence of Midwestern money guilt, family secrecy, and conflicting childhood money messages

• Jamie’s past divorce and financial trauma

• The shift from adversaries to collaborators

Chapters:

(00:00:00) “We’ll just go our separate ways”

(00:18:56) Ramit breaks down their numbers

(00:40:49) “Smart people can make stupid choices”

(00:52:26) “Can we become a team again?”

(01:02:09) “Is this a Rich Life—or just a really long to-do list?”

(01:14:36) “You’ve turned dysfunction into permission”

(01:28:57) “I’m bitter that I have to pay it off”

(01:39:21) Where are they now? Jamie and Ryan’s follow-ups

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Links mentioned in this episode

• If you want help with your finances, join my Money Coaching program at https://iwt.com/moneycoaching

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If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here.