Chloe Messer didn’t finish sixth form. She didn’t go to university and left virtually every job she ever had after just a year. But this year, she found herself on Dragon’s Den, showcasing her upcycling hat business Hat & Spicy, which sells colourful hats that Penelope Cruz and Julia Fox have since worn.
While from the outside Chloe, 33, may look like she’s got it all figured out, her career trajectory has been anything but linear. Throughout her career, Chloe has done what career advisors usually advise against: moving around with no clear plan.
Career coach Kat Koh, who writes the substack Exquisite Work, describes Chloe’s strategy (or lack thereof) as “popcorning around”, referring to a pattern of quickly switching between different roles, industries, or projects (similar to how popcorn jumps around unpredictably).
At school, Chloe describes herself as “academic, in a way”, but “really naughty, so I wasn’t good at sticking to anything.”
In her 20s, Chloe worked for MTV, Asos and Lush









