Samantha’s Fear of Never Being 'Good Enough'

Samantha (36) and Kevin (41) have been together for seven years, but their financial lives couldn’t look more different. He’s a high earner with $800,000 in investments and a paid-down mortgage. She’s still carrying student loans, car payments, and lingering shame about being “behind.” While Kevin saves methodically for the future, Samantha prefers to spend on experiences—especially travel—leaving him questioning whether their financial priorities will ever align. Beneath the surface, neither of them has truly learned how to talk about money without shutting down. Can Ramit help them move from avoidance and resentment to shared goals and real plans for the future?

A special thanks to Ultraspeaking, who worked with Samantha and Kevin to help them communicate more effectively as a couple. Ultraspeaking is the fastest and most effective way to become a great communicator. Learn more here.

In this episode we uncover:

• Why Samantha believes she’ll never be “financially good enough” for Kevin

• How their shared avoidant tendencies have allowed them to avoid financial planning for years

• How their unspoken expectations around “fairness” create tension

• Samantha’s logic for not paying rent or mortgage

• How Kevin’s quiet resentment built up after Samantha didn’t use the housing savings to pay down debt

• The real cost of their “guilt-free” spending, including $15,000/year on vacations

• Why Samantha still feels broke, despite earning $148,000 a year

• Samantha’s fears about not meeting Kevin’s expectations in retirement

• The stark contrast between their savings: Samantha has one month of expenses, Kevin has six

• How Samantha inherited a “spend it if you have it” mindset from her parents

• Kevin’s fear of loss from divorce and why he avoids fully committing financially

• The role of therapy in helping them rebuild communication and trust

Chapters:

(00:00:00) “I’ll never be financially good enough for Kevin”

(00:13:39) “I feel like I have no say because he owns the house”

(00:27:08) Ramit breaks down their numbers

(00:37:44) “I still feel like I’m only making $50,000”

(00:43:59) “Money burned a hole in my pocket”

(01:03:09) “That’s the bed I made and I will lie in it”

(01:08:25) “Closing doors is hard…but staying stuck is harder”

(01:15:59) “It’s not about catching up — it’s about building together”

(01:37:50) Where are they now? Samantha and Kevin’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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