The Retirement Trap Nobody Talks About #softretirement #retirementplanning #retirepreneur

Added: 2026-05-24

[00:00:00]One more year syndrome. You probably felt it even if you never heard of me.

[00:00:04]It goes like this. Your numbers look fine. Your plan shows sustainability, but you tell yourself one more year just to be safe. Then it's another, then another, then the transition simply never stops. Here's how you know if you have it. You check your portfolio obsessively even though the math already works. You haven't defined what enough equity looks like. Your identity is so tied to your title that you can't picture who you are without it. And on Sunday nights you feel the dread with the thought of withdrawing from your nest egg feels worse than staying in a job that's draining you.

[00:00:36]I could have stayed employed longer. I had the option to take on a significant consulting engagement with my former company, but I passed. The COVID years, the PPP chaos, the internal fighting. I was stressed and I was done and I needed a break. But that break led to my master's degree at the University of Florida, which led to building retirepreneur. None of that happens if I talked myself into just one more year.

[00:00:59]So here's the CFA self-fix. Pick a specific fully retired date, not a range, not sometime next year, a day.

[00:01:06]Then work backwards with a milestone checklist. Let's say five years out, three years out, or one year out, wherever you are at this time.

[00:01:14]Every year you trade for more money is a year of health and autonomy you cannot buy back. At this stage of life we have earned the right to build something better.

[00:01:22]The full transition checklist is in my self-retirement series. Links in the description.