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Sydney Bern-Story's work experience began in 2009 as an Education Intern at the United Nations Association San Diego. From 2009 to 2011, Sydney worked as a Resident Assistant at the University of San Diego. In 2011, they became a Reproductive Health Assistant at Planned Parenthood of the Pacific Southwest and held the position until 2012. Sydney then worked as an Office Manager at Global Majority from September 2012 to December 2013. In 2014, they interned as a Monitoring and Evaluation Intern at Heartland Alliance for Human Needs & Human Rights from January to June. Finally, Sydney joined Ingenuity Prep in August 2014 as a Lead Teacher, where they are currently employed.

Sydney Bern-Story completed a Bachelor of Arts (B.A.) degree in International Relations at the University of San Diego from 2008 to 2011. From 2012 to 2014, Sydney pursued a Master of Arts (M.A.) degree in International Policy Studies at the Middlebury Institute of International Studies at Monterey. Finally, from 2014 to 2016, Sydney attended Lesley University to obtain a Master of Arts (MA) degree in Elementary Education and Special Education.