Why You Second-Guess Yourself—even When You Know What You Want

Masks Off: Inner Freedom For People-Pleasers and Perfectionists · Oct 8, 2026 · 26m

Have you ever known exactly what you wanted—only to talk yourself out of it five minutes later?

Maybe you weren’t actually confused. Maybe you became afraid.

In this episode of Masks Off: Inner Freedom for People Pleasers and Perfectionists, Kim Gross explores why clarity can so quickly turn into self-doubt, especially when you’ve spent years people-pleasing, striving for perfection, or looking outside yourself for reassurance.

Kim shares a personal story from Free to Be about wanting to write, podcast, and put her work into the world—and the self-doubt that surfaced when being truly seen…