Episode 599: 3 Big Early Retirement Mistakes We Made (So You Don’t Have To)

Everyone makes early retirement look like beaches and banana hammocks—especially the gays. But behind the glam is the grit.

In this week’s episode, we’re getting brutally honest about the three biggest mistakes we made on our path to early retirement. From missing Roth conversions to underfunding HSAs and after-tax accounts, we’re sharing what we wish we had done differently—so you don’t make the same missteps.

We also open up about the hard truths: losing 70–80% of our income, getting ghosted by potential employers, and why we're being pushed into early retirement (spoiler: America kind of gave up on us first).

If you're thinking about retiring early—whether by choice or circumstance—this is your roadmap to avoid regret and build a fabulous future on your own terms.

🎯 Grab the Happy Gay Retirement Calculator to start planning your exit strategy today.

Chapters:

• 0:00 - Intro
• 0:30 - Why are we retiring early?
• 2:20 - How we're able to retire early
• 4:08 - Why we didn't "just get jobs"
• 6:07 - Tradeoffs for early retirement
• 7:31 - Mistake #1 - Roth Conversions
• 9:03 - Mistake #2 - HSAs
• 10:35 - Mistake #3 - After-tax investing
• 11:34 - Wrap up