Do you have feedback or suggestions? We want to hear from you!
Contact Elliot: [email protected]
Contact Josh: [email protected]
The Great Transition: How to Move from Full-Time Work to Early Retirement Without One-More-Year SyndromeElliot and Josh discuss the under-covered topic of transitioning from full-time employment into early retirement. Josh recounts how he ended up at a company he hadn’t heard of, worked there for 25 years, and viewed work primarily as a means to provide benefits and income rather than an identity. They share tactics for excelling while protecting time—prioritizing what a boss says matters most, pushing back on low-value meetings, managing deadlines, and avoiding burnout by not immediately turning in work early—which Josh says helped him become highly efficient and even led to two back-to-back promotions. The conversation then shifts to retirement logistics and psychology: Josh gave 14 months’ notice to a new manager, explains why he wasn’t worried about being let go, and contrasts Elliot’s experience of being quickly escorted out of a sensitive cybersecurity role (though paid out for his notice). They address “one more year syndrome,” with Josh describing how he delayed retirement for milestones like paying off the house and getting their youngest through high school, and how setting a firm retirement date tied to his 25-year anniversary helped commit him to leaving. Josh emphasizes preparing for retirement by testing hobbies and routines before quitting, asking what a perfect day looks like, and ensuring activities are scalable and fulfilling; he admits to pre-retirement anxiety about running out of things to do despite having many interests. They also discuss the social friction of being retired—how people ask “what do you do?”—and how the FI community provides more authentic conversations than broader work-centered culture. Josh shares a recent doctor visit where the doctor was surprised by his retirement and Josh framed his activities as managing rental properties. They close by encouraging listeners to flip the “I’ll be bored” script, use current interests (including social media algorithms) as clues for passions, and start experimenting with how to spend time if money were not a constraint.
00:00 Kicking Off: From ‘Being Vertical’ to Early Retirement Talk
00:29 Why the ‘Retirement Transition’ Is the Missing FIRE Conversation
02:43 Josh’s Career Origin Story: Falling Into a 25-Year Job
04:33 Work as a Means to an End: Not Living to Work
07:43 Cracking the Corporate Code: Priorities, Saying No, and Time Defense
15:54 Cruise Control & Side Hustles During the Workday (Rentals + Woodworking)
20:01 Giving Notice: Why Josh Told His Boss 14 Months Early
21:36 Risk of Getting Shown the Door + Beating ‘One More Year’ Syndrome
28:30 Coordinating Retirement Timing & Hitting Key Milestones
29:10 The ‘One More Year’ Trap: Layering Conservatism in FIRE Plans
32:23 Two Sides of the Decision: Money Confidence vs. Time Purpose
36:44 Designing Your Perfect Day: Test-Driving Retirement Before the Ripcord
39:37 ‘What Do You Do?’: Identity, Productivity, and Being Authentic After FIRE
45:51 Why Community Matters (and When FIRE Media Becomes Consumption)
51:33 Closing Advice: Flip the Script on Boredom & Reverse-Engineer Your Day
Any of these products help the show. Thanks for your support!
Mint Mobile - We both use Mint Mobile and save a ton on our phone plan: https://fbuy.me/vgAmz
Empower is Josh’s choice for Net Worth and Budgeting
Wanna create a podcast? We use Descript
Looking for a new credit card? We’re big fans of Chase
Buy Us a Coffee - One time donation or monthly, it’s up to you
Want to save money on gas? Try Upside!
Books mentioned in this episode:
Come find us and subscribe on YouTube: http://www.youtube.com/@9toFI
