There’s an old saying, “How do you eat an elephant? One bite at a time.” In some cases, the task of technology modernization is akin to eating an elephant. Government agencies are filled with legacy applications, many of which have been heavily customized over decades of operation. While moving to modern, cloud-based infrastructure and increasing cybersecurity are necessary, IT leaders often feel overwhelmed by the enormity of the task of modernizing legacy applications. It can be difficult to determine where to start when faced with such an extensive effort. This paper breaks down modernization into manageable initiatives so agencies can begin a modernization journey.