In this episode of What-If Syndrome, Jake Carson and Lily Morgan dive into a growing trend within the FIRE community: people “what-iffing” themselves into delaying retirement indefinitely. We explore common concerns like changes to health insurance, doubts about Social Security, potential tax increases, and the fear of not having enough for every contingency. While financial prudence is essential, we discuss the risk of over-preparing and working too long to achieve perfect security. If you’re struggling with when to stop working and enjoy the freedom you’ve been saving for, join us as we share insights on balancing preparation with the courage to embrace the RE (Retire Early) in FIRE.