"I Should Have" Is Keeping You Stuck: This One's For the Women Living in the Aftermath

"I Should Have" Is Keeping You Stuck: This One's For the Women Living in the Aftermath

July 13, 2026 · 27 min · Episode 142

About this episode

Michelle discusses the damaging effects of the phrases 'I should have' and 'I can't' on women's confidence and mindset.

Michelle records outside her office unpacking two phrases that are quietly doing damage—one she never says, one she says a million times a day without realizing it. She doesn't say "I can't." She figures it out, she does the thing, she makes it work. But then she gets stuck in the aftermath, replaying everything she should have done differently, should have bought, should have said. Josh finally called it out: every "I should have" is just self-blame in disguise, keeping her mentally stuck in the past instead of planning for the future. The reframe? Replace "I should have gotten hot dogs" with "next time I'll get hot dogs." Simple, but it changes everything. If you're an "I can't" person or an "I should have" person—or somehow both—this one's the mirror you didn't know you needed. Timestamps: 00:00 Two Phrases, Two Problems 03:14 I Don't Say "I Can't"—Here's Why 06:28 But I Say "I Should Have" Constantly 09:42 What "I Should Have" Actually Does to You 13:17 Josh Called It Out 16:44 The Reframe: "Next Time I'll..." 20:33 What Happens When You're Both 23:18 Take It Out of Your Vocabulary If you know someone stuck in "I should have" or "I can't," share this—sometimes you just need…

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Host: Michelle Stokes

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