“I sold my practice in 2025 and thought I'd planned every dollar and detail. What blindsided me was grief, on a random Tuesday, for the woman the work made me. Nobody warned me I would grieve her.”

“I spent decades telling clients to save enough for retirement, and I did, but I was caught off guard by how much I missed the daily identity of the work. The money was fine; the quiet was harder.”

“I retired from neurosurgery after twenty-one years, and the surprise was how little I missed the title once the pager stopped. What I actually lost was the daily friction of hard decisions, and I have had to build that back deliberately with hiking, reading, and courses like visual metaphors.”

“I retired in 2021 after forty years of counseling, and what surprised me was not a missed career move but the regret of not starting my Civic Center photography sooner. The light I chased across Wright's arches taught me that some work waits too long for permission.”

“I regret not realizing sooner that the only time I felt normal was right after a workout, and that the right exercise, not just any exercise, was the thing that could have changed everything.”

“I regret not starting my own creative work decades earlier. I spent 36 years at NSA doing serious, valuable work, but I told myself the stories could wait; now I see how much living I poured into other people's missions while my own sat quiet.”

“I regret how much of my identity I let get tied up in my jobs, because when the work stopped I found myself sitting with all this free time, still trying to figure out who I am outside of what I did for a living.”

“I retired after 22 years at CU Denver thinking I’d miss the classroom most, but the surprise regret was losing the daily collision of student questions that kept my own thinking sharp. Now I build study guides and AI tools partly to keep that edge alive.”