In today's rapidly evolving technological landscape, organizations must be agile and adaptable to stay competitive. However, many organizations find themselves trapped in terrifyingly difficult IT habits that hinder progress, innovation, and growth. These habits, such as resistance to change, outdated technologies, and siloed thinking, create roadblocks that impede success. In this article, we explore these terrifyingly difficult IT habits and provide insights on how organizations can break free from them, embrace change, and foster a culture of continuous improvement.