Daily diary writing is widely recognized as an effective method to enhance learners' writing skills, encourage self - reflection, and support personal development. However, maintaining a consistent diary writing habit presents several challenges that hinder learners f-rom fully engaging in the practice. This article explores these difficulties in depth and proposes practical strategies to overcome them. Drawing on both international and Vietnamese research, the study identifies four major obstacles commonly faced by learners: limited time due to academic and personal responsibilities, difficulty generating ideas to write about, a perceived lack of immediate benefit or value f-rom diary writing, and concerns about privacy and confidentiality. These issues often result in decreased motivation and irregular writing habits. To address these challenges, the article offers several actionable solutions, including adopting micro - journaling techniques to make writing less time - consuming, using writing prompts to stimulate creativity, leveraging digital tools such as apps and online platforms for convenience and security, and emphasizing the role of teachers in creating a supportive, judgment - free writing environment. By presenting these strategies in a coherent framework, the article aims to empower educators and learners to overcome barriers to daily writing. Ultimately, it highlights how consistent diary writing can become a powerful tool for long - term academic improvement and personal growth when implemented with thoughtful support and guidance.