What does it mean to think in both pictures and spreadsheets — to blend instinct with insight? In this episode, Rob Pepper is joined by Jenna Littler, whose career has spanned luxury fashion, public policy, and global communications, including a decade at Burberry.

Jenna reflects on the growing value of “50/50 thinking” — where creativity and strategy are no longer siloed, but interwoven. She shares her journey from government to the fashion industry, and offers advice for young people trying to build confidence, find their voice, and navigate careers that don’t follow a linear path.

This conversation explores the skills that matter most in today’s world of work — from adaptability and storytelling to the ability to translate between teams and mindsets. Whether you’re just starting out or rethinking your direction, Jenna offers a grounded, generous perspective on how to lead with clarity, curiosity, and care