In November 2006, Middleton commenced part-time work for twelve months as an accessory buyer with the clothing chain Jigsaw. Later that year, she curated a photography exhibition to mark the book launch of "Time to Reflect", by Alistair Morrison, to raise funds for UNICEF. In 2007 and 2008, Middleton made several trips to Naomi's House Hospice, where she brought gifts and read to children. In 2008, she organised an 80's-themed roller disco fundraiser which raised money for Place2Be, an organisation which improves mental health in schools. Middleton also worked until January 2011 at the family business in catalogue design and production, marketing, and photography. While working for the company, she launched the firm's junior brand for toddlers, and began working with the Starlight Children's Foundation, which helps terminally ill youth, providing party essentials for sick children. Middleton also helped coordinate the Boodles Boxing Ball, which raised money for the charity.