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

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 Communication 23:11: Challenges for Women in the Industry 27:20: The Competitive Landscape 34:33: The Path to Success 37:49: The Importance of Apprenticeships 43:09: The Role of Social Media 50:26: How to Become an Assistant RESOURCES FROM TODAYS EPISODE FOLLOW ANNA CHAPMAN ON INSTAGRAM @ANNACHAPMANHAIR FOR EVERYTHING SESSION KIT CLICK HERE CONNECT WITH SESSION KIT ON INSTAGRAM @SESSIONKIT GET TICKETS FOR HAIRCON VISIT HERE : (USE CODE HTCI10 FOR 10% DISCOUNT) CONNECT WITH HAIRCON ON INSTAGRAM @HAIRCONSHOW FOLLOW HOW TO CUT IT ACROSS SOCIALS @HOWTOCUTIT

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EP389: The Brutally Honest Reality of Becoming a Session Stylist with Anna Chapman is an episode from How To Cut It in the Hairdressing Industry by How To Cut It Media.

This episode is 1:00:55 long.

This episode was published on Apr 28, 2026.

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