This case examines the design and practicalities of a survey conducted among young Germans (aged 18–35) and their parents. The survey presented is part of the CUPESSE (Cultural Pathways to Economic Self-Sufficiency and Entrepreneurship: Family Values and Youth Unemployment in Europe) project (2014–2018)—a large-scale research project examining young Europeans’ cultural pathways to economic self-sufficiency. The survey was designed to not only capture the economic and educational situations of young people but also how their family background and upbringing influence their relevant life choices. We provide insights into the planning and development of the survey instrument, paying particular attention to both the successes and setbacks encountered. The reader will gain an in-depth look into the practicalities of designing and executing survey research, as well as the trade-offs involved.