Episode 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar

January 5th, 2026  |  31 mins 12 secs

capital gains tax, estate planning, financial independence, inflation planning, inheritance planning, longevity planning, multigenerational travel planning, primary residence sale, real estate investing, retirement planning, social security timing, tax planning

In this episode, we answer two listener questions that highlight common retirement planning tradeoffs. We discuss Social Security timing for high earners, capital gains considerations when selling a long-held primary residence, and how families think about prioritizing meaningful experiences through educational travel with Road Scholar.