Oct 29, 2026 · 31 min
Retirement planning meets the risks of staying invested
10.29.26 Ask An Advisor With Wes Moss
The discussion connects everyday retirement decisions—from fees and insurance to market losses—to the larger question of how dependable income should shape investment risk.
- 1Advisory fees, HSAs, direct indexing, and the Rule of 55 can materially affect retirement planning decisions.
- 2A substantial pension may function like the bond allocation, potentially allowing a retiree to hold more stocks.
- 3Staying invested during downturns requires confronting fear, while future technology could make retirement readiness easier to assess.
Don't miss
Wes Moss explains why he did not sell during market downturns, recalling the fear surrounding the COVID-era crash and earlier investment losses.
The brief
Clark Howard and Wes Moss open with practical questions about negotiating advisory fees and using HSAs to cover future medical costs while preserving assets for heirs.
The conversation moves through long-term Treasury bonds, direct-indexing taxes, and a timing nuance in the Rule of 55—small details with large retirement consequences.
A substantial pension changes the usual allocation debate: dependable income may serve some of the role traditionally assigned to bonds, leaving more room for stocks.
The hosts weigh whether keeping life insurance can protect a surviving spouse from lost Social Security income, especially when replacing coverage later becomes expensive.
Wes Moss revisits the fear of market crashes and explains why he has stayed invested, framing panic selling as a risk that can outlast the downturn.
The closing idea is technological: health data, wearables such as the Oura Ring, sleep tracking, and gamification could produce a retirement-readiness score.
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