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Ariana R. Cherry has a diverse work experience. Ariana R. began working as a Web Content Writer for Demand Studios in 2007 and continued in this role until 2013. From 2008 to 2014, they worked as a Content Writer for Yahoo! Associated Content, covering various topics such as technology, travel, and small businesses. In 2011, they also worked as a Content Writer for Need An Article, producing web content on different subjects.

In 2003, Cherry joined Cefs Economic Opportunity as a Data Technician/Receptionist, where they handled various responsibilities including data entry, client intake, and counseling clients on referrals and assistance programs. Ariana R. worked there until 2015. During this time, they also started working as a Content Writer for Textbroker International in 2008.

Cherry's work experience also includes roles at Arthur United Methodist Church as an Administrative Assistant starting in 2015, and at Arcola Presbyterian Church as a Secretary from 2014 to 2016. Ariana R. worked as a Staff Writer for Arthur Graphic Clarion from 2019 onwards. Additionally, they worked as a Reporter for Sullivan News Progress from 2012 onwards, covering local stories and events.

Outside of their employment, Cherry has pursued their passion as an Artist/Illustrator/Amateur Photographer since 2012. Ariana R. has illustrated a book titled "Bullying Ben" by Timothy Pina and sells their drawings and doodles online.

Ariana R. Cherry attended Arcola High School from 1995 to 1999 where they obtained their Diploma. Ariana R. then pursued further education at Lake Land Community College from 2000 to 2002, specializing in Computer Applications. Ariana obtained a degree in Computer Applications Specialist and also studied Business Administration during their time at Lake Land Community College.