The Pensioner's Paradox
Essays on retirement tax planning and income strategy, written by Phil Gaudiano, CPA.
About the newsletter
The Pensioner's Paradox is for pre-retirees and retirees who want to understand what their money is actually going to cost them — in taxes and in decisions — over the next thirty years.
Most retirement writing focuses on the accumulation phase: how to save, how to invest, how to think about compound returns. Comparatively little serious work has been done on what happens after the paychecks stop. The decisions get harder, not easier — Roth conversions, the Gap Years between 65 and 72, IRMAA tax traps, RMDs, and the behavioral reality of spending down a portfolio you spent decades building.
This newsletter sits in that gap. New essays arrive every other Tuesday. Free, no spam, written by a working CPA who does this planning for clients every week.
Start here
If you're new to my work, three pieces worth reading first:
- The Pensioner's Paradox — a four-part series on the framework
- I Wish I'd Known this at 65
- 70% Safe, 100% Anxious
Browse by topic
- Roth Conversions & Gap Years — On strategic timing, the math, and the Gap Years window that almost no one uses well
- IRMAA and RMDs — On the embedded tax liability most retirees don't see coming
- The Behavioral Side — On the psychology of spending down a portfolio you spent decades building
All essays
Looking for something specific? Browse the full archive →