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In 2005, the publisher Hubert Burda and the investor Yossi Vardi initiated the Digital Lifestyle Day to connect key players of media-related enterprises with founders of new and hot companies, bringing together technology with arts and design. The first event was a success and Burda and Vardi have helped evolve the conference into one of the hottest and most prestigious new media events of the year in Europe, with a visibility that now reaches other continents. In a familiar atmosphere, business suits meet t-shirts and sneakers to discuss the challenges and opportunities of tomorrow's digital lifestyle. In 2007, DLD became Digital, Life, Design (see http://www.dld-conference.com/) but maintained its goal to provide a small but very nice event for connecting with others and having intense discussions, all in an inspiring atmosphere. This year, the experts met under the slogan "Uploading the 21st Century." The participants discussed the challenges, consequences, and opportunities of the increasing digitization in our daily life. This article presents insights formed from DLD 2008. A separate article—see this issue's Visions and Views, "Digital Lifestyle 2020"—provides a snapshot of views and opinions from other presenters and participants.