The Hardest Thing About Early Retirement | 9 to FI 049 episode artwork

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

Episode metadata supplied by the publisher feed · Published Jun 29, 2026

Embed this episode

NOW PLAYING

The Hardest Thing About Early Retirement | 9 to FI 049

0:00 57:51

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of 9 to FI - Financial Independence Conversations?

This episode is 57 minutes long.

When was this 9 to FI - Financial Independence Conversations episode published?

This episode was published on June 29, 2026.

Can I download this 9 to FI - Financial Independence Conversations episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!