Sep 29, 2026 · 37 min
Retirees struggle to spend the money they saved
09.29.26 Ask An Advisor With Wes Moss
The episode examines how retirees can turn accumulated assets into usable income while navigating taxes, market risk, and incapacity planning.
- 1Retirees often underspend because investment assets feel less spendable than dependable income streams.
- 2A paid-off mortgage can redirect monthly cash flow toward Roth contributions and stronger retirement savings.
- 3Lump-sum investing generally beats dollar-cost averaging historically, though spreading purchases can ease anxiety about market declines.
Don't miss
Wes Moss describes the retirement paradox of someone dying with more money than she started with, illustrating how fear of spending can defeat financial security.
The brief
Krista Divias and Wes Moss open with a retirement paradox: people who spent decades building assets may still hesitate to use them, especially when income arrives from investments rather than a paycheck.
Moss argues that dependable income can create psychological permission to spend, while annuities are only one option; investors must weigh fees, control, growth, and the desire for a steady paycheck.
The practical questions range from redirecting a paid-off mortgage into Roth 401(k) contributions to balancing 529 savings with newer Trump accounts and choosing between Roth and pre-tax withdrawals.
The episode also weighs lump-sum investing against dollar-cost averaging, explains how money creation can contribute to inflation, and considers professional fiduciaries for people aging without trusted family.
Its sharpest tension is between preservation and purpose: a retiree can protect principal so successfully that the money outlives the life it was meant to support.
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