Reflective writing is one of writing assignment that is implemented in higher education. This type of writing has been claimed as the difficult activity for most of students when they are asked to write at the end of the semester. That way, the students might have different perception in conducting reflective writing. So, this research aims to discuss the obstacles revealed by students in conducting reflective writing assignment and to explore the strategies of the students in solving the problem of reflective writing assignment at English Language Education Department of a private university. This research used qualitative research approach and descriptive qualitative as the research design. The data were gathered by interviewing three students of ELED batch 2014 at a private university in Yogyakarta. The findings of this research revealed that the students faced the obstacle namely; content problem, vocabulary problem, grammatical problem, sentence structure problem, paragraph writing problem, and topic problem. The findings also showed that content problem and paragraph writing were the most difficult things in doing reflective writing assignment. Moreover, the content problem was caused by the lack of seeking the proper ideas, lack of uncomfortable atmosphere in doing assignment and the lack of adequate tool to do assignment. Then, the vocabulary problem was caused by the lack of vocabulary knowledge and the grammatical problem was caused by the lack of reading English book. The paragraph writing problem and sentence structure problem were caused by the lack of English writing practice. In addition, the findings also showed the strategies in solving the content problem that could be solved by reading some references, making some highlights and asking the lecturer about the assignment. Then, grammatical problem could be handled by learning about grammar. The paragraph writing problem could be solved by reading some references and practice writing. Moreover, the topic problem could be overcome by asking the lecturer about the assignment. Furthermore, sentence structure problem could be overcome by reading some references and practice writing.