EP389: The Brutally Honest Reality of Becoming a Session Stylist with Anna Chapman

EP389: The Brutally Honest Reality of Becoming a Session Stylist with Anna Chapman

April 28, 2026 · 1h 1m

About this episode

Anna Chapman discusses the practical steps to becoming a session stylist and the realities of the industry.

Want to become a session stylist? This episode with Anna Chapman is the practical route in — not the fantasy. I’m back in the HTCI PodShed with Anna Chapman, a leading session hair stylist with an instinctive understanding of hair and over a decade in top salons before moving into the session world. Todaywe’re to have real catch-up since we last spoke in 2020 podcast episode. Anna breaks down the actual steps to get into session work today: how to position yourself if you’re coming from salon, why session styling is a different job entirely, and what you need to do first to get on set. We get into the assisting ladder (what assistants really do, how to reach out, how to follow up, and how to get yourself rebooked), plus the skills that matter when the pressure’s on for major brands. Anna also shares what to post on Instagram if you want work—how to show range, not just “glam”—and why persistence, visibility and standards are the long game. If you’re serious about building a career in session hair, start here. CHAPTERS 1:25: Breaking into Session Styling 6:47: The Reality of Assisting 12:21: Getting Paid as an Assistant 15:04: Defining Session Stylists 19:35: The Importance of…

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Host: How To Cut It Media

Guest: Anna Chapman

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Organizations: How To Cut It Media

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