The 5 Questions You Would Not Stop Asking Me in 2026

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And on to the show notes!!
Most of the biggest money questions aren’t really about what to buy. They’re about how to think when the answer isn’t obvious.
In this episode, Tyler answers the five questions listeners have asked most in 2026 — from pensions and politics to healthcare, market concentration, and long-term care — with an emphasis on what you can actually control.
You’ll learn:
How a pension and Social Security can change the way you think about portfolio risk
Why being right about markets or politics still doesn’t mean you can time them
How the return of the ACA subsidy cliff changes early-retirement planning
What today’s S&P 500 concentration does — and doesn’t — tell you
The four main ways to prepare for long-term care, including the risks of each
The recurring lesson is that good planning rarely comes from predicting the future. It comes from understanding the whole picture, knowing what you own, and preparing for the decisions you can control.
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