The Danger of Not Knowing What You Don’t Know (Ep. 17)

By Ramp Up to Retirement | September 11, 2025

One of the biggest risks to your retirement may not be the market. It could be overconfidence.

Dan Reese examines the genuine risks of DIY financial planning, particularly in a world inundated with AI tools and financial influencers who oversimplify complex decisions. From emotional investing to overlooked tax landmines and Medicare surprises, Dan breaks down why retirement planning involves more than simply choosing investments.

You’ll learn how behavioral biases, sequence-of-return risk, and misunderstood withdrawal strategies may impact your financial future if overlooked.

What to expect:

Why investment planning is the “easy” part, but is rarely done well
The psychological traps of self-managing your money
Medicare costs, IRMAA, and the illusion of “free” healthcare
How a CFP helps you see what you don’t know and plan for what comes next
And more!