EPISODE · Jun 29, 2026 · 57 MIN
The Hardest Thing About Early Retirement | 9 to FI 049
from 9 to FI - Financial Independence Conversations · host Elliot and Josh
The Hardest Part of Early Retirement: Mental Health, Rumination, and Finding HappinessJosh and Elliot discuss common challenges of early retirement—shifting from saving to spending, boredom, healthcare uncertainty (ACA subsidies and planning), loss of identity and guilt when saying you’re retired, social isolation, and fear of running out of money (Monte Carlo simulations, one-more-year syndrome, expense lumpiness, and flexibility). Fourteen months into early retirement, Josh says most of these weren’t major issues for him, but his biggest struggle has been mental health and happiness: after an initial honeymoon, stress from helping with a newborn granddaughter in the ICU, sleep disruption, recurring funks, irritability, and rumination over trivial and family/tenant issues. He describes using reframing, reducing complaining, reading self-help and mental-health books, drafting an “It’s a Wonderful Life” personal policy statement, and focusing on controlling what he can; Elliot shares returning to therapy and the idea that money only solves money problems.00:00 Early Retirement Struggles01:10 Saver To Spender Shift02:58 Boredom And Purpose06:05 Planning The Tuesday Life10:18 Healthcare And ACA Fears13:16 Identity And Guilt21:31 Isolation And Community24:48 Running Out Of Money34:15 Mental Health Reality Check42:01 Tools To Stop Rumination45:10 Therapy And Taking Control57:33 Closing ThoughtsDo you have feedback or suggestions? We want to hear from you!Contact Elliot: [email protected] Josh: [email protected]’s other podcast: Stuck In BetaJosh’s YouTube channel: How To Fix It WorkshopAny of these products help the show. Thanks for your support!Buy Us a Coffee - One time donation or monthly, it’s up to youWe both use Mint Mobile and save a ton on our phone plan: Empower is Josh’s choice for Net Worth and BudgetingWanna create a podcast? We use DescriptLooking for a new credit card? We’re big fans of ChaseWant to save money on gas, groceries and dining out? Try Upside!Books mentioned in this episode:Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
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The Hardest Thing About Early Retirement | 9 to FI 049
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