​Most career advice assumes the problem is a lack of information.

​But I’ve found the real struggle is that the rules we’ve been following no longer fit the life we’re building — or the next level we’re reaching for.

​Career Positioning Room is a live strategy session for ambitious professionals navigating career pivots, leadership transitions, portfolio careers, burnout, and growth, especially now as AI reshapes what expertise and value even mean.

​Over my career, I’ve pivoted across six industries and six functions — from investment banking to consulting, product management, and marketing leadership — while taking two career breaks of more than a year each without derailing my long-term growth. Those instincts got me to the VP seat. But the further I went, the clearer it became that the biggest challenge isn’t information. It’s learning to trust yourself, manage your energy, articulate your value, and move before you have certainty.

​I treat a career the way I’d treat a product: to grow, it needs a clear position, not just more effort. Through live case studies, audience Q&A, and practical frameworks, we’ll work your real questions, so you leave with more than advice. You leave with a clearer read on how to position yourself for the AI-era and your next move.

​Whether you’re considering a new role, stepping into leadership, building a portfolio career, returning from a break, or just trying to figure out what’s next, this session is designed to help you move from overthinking to clear action.

​Because the most important career decisions are rarely about your resume. They’re about the stories you believe, and the ones you’re ready to stop telling.

​Meet Your Host

​Jameelah Calhoun

​is a marketing executive, strategist, speaker, and founder of Unpopular Decisions, a media platform exploring the high-stakes decisions that shape our careers, identities, and lives. Having navigated career pivots across six industries and six functions, she is passionate about helping high-achieving professionals build influence, navigate uncertainty, and make aligned decisions with greater clarity and self-trust. Jameelah currently serves as VP of Market Strategy at Forter, an AI commerce intelligence platform, where she leads product marketing, brand marketing, and communications. She holds an M.B.A. from Harvard Business School and a B.A. from Yale University and lives in New York City.