Day 5 · Friday, October 30 · The Polite One
Why You Say "I'm Fine" When You're Not (and Why "Just Speak Up" Hasn't Helped)
with Jenn Fast
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Why You Say "I'm Fine" When You're Not (and Why "Just Speak Up" Hasn't Helped)
You said it this week. Maybe to your doctor, maybe to your partner, maybe to whoever asked how you were holding up. You said "I'm fine," you heard yourself do it, and some part of you knew it was not true. This session is about where that reflex came from, why all the advice telling you to advocate for yourself has never quite touched it, and what changes when you stop treating your own silence as a personal failing.
What you'll walk away with
- Why "just advocate for yourself" has never worked for you, and why that is conditioning rather than a confidence gap or a skill you somehow missed.
- How to catch the moment you are about to minimize, from the tells in your body to the phrases that give you away like "it's probably nothing," so you notice it in the room instead of in the car afterward.
- What to do when you finally say the true thing and it lands badly, because being called aggressive or too much is not proof you did it wrong.
Jenn Fast
MBA
Midlife Reinvention Strategist, Reinvention with Jenn Fast
Jenn Fast is a reinvention strategist and the founder of Reinvention with Jenn Fast. She works with women in midlife through the transitions that arrive all at once: perimenopause, career shifts, divorce, empty nests. Most midlife advice stops at insight, which is why women leave feeling seen and still stuck. Jenn pairs the identity work with the systems that carry it, drawn from a 30-year corporate career.
She also knows this terrain from the inside. Raised in a family and a culture whose message was to be seen and not heard and take up less space, she spent decades being useful and quiet before she understood what it was costing her. She now teaches women to take up more room. She also hosts The Comeback Show podcast and is a published author and audiobook narrator.
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