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Oliver Buchannon
Jameelah Calhoun

Jameelah Calhoun is a storyteller, strategist, and senior tech executive with 15+ years of experience building and scaling global products at companies like Eventbrite, Audible, and American Express. She writes about the messy, high-stakes decisions we make in our careers, relationships, and lives—especially when choosing authenticity over approval. Jameelah is the host of Unpopular Decisions, a podcast exploring the courage and consequences of choosing differently. Her mission — and the driving force behind Unpopular Decisions — is to make authenticity contagious.

Comfort is Poison

Feb 13, 2026

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8 min read

Comfort is Poison

Fear is a reaction. Courage is a decision.

Jameelah Calhoun
Jameelah Calhoun

Decision Diaries

Don’t Identity Shift. Remember Who You’ve Always Been

Feb 8, 2026

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6 min read

Don’t Identity Shift. Remember Who You’ve Always Been

What if changing your life isn’t a transformation — but a return?

Jameelah Calhoun
Jameelah Calhoun

Decision Diaries

Living With Regrets or Consequences

Feb 8, 2026

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5 min read

Living With Regrets or Consequences

The decision to quit my job that started with Abbott Elementary— and why it matters now

Jameelah Calhoun
Jameelah Calhoun

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Unpopular Decisions

Unpopular Decisions is a biweekly note for people navigating life’s toughest crossroads — the moments when internal alignment conflicts with external approval. Each issue weaves together personal reflection, behind-the-scenes insight from the Unpopular Decisions podcast, and stories from a growing community of people choosing differently. Written and curated by Jameelah Calhoun, this newsletter isn’t about self-optimization or easy answers.📬 Delivered biweekly. Free to subscribe.

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