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.

Show notes

  • 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

Todays guest

Anna Chapman is a session hair stylist with an instinctive understanding of hair. After a decade working in leading salons, she spent over three years as a key member of Guido Palau’s core team and joined Julian Watson Agency in 2018. Anna works with the natural movement of hair, enhancing its inherent tendencies with a perfectionist eye for detail and a refined “undone” finish. In 2014 she founded Session Kit, a curated edit of essentials she’s grown into a globally respected industry business.

Session Stylist Anna Chapman, sat on stool wearing a black suit and trousers

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