Technological innovations and digital transformation initiatives are difficult to adopt. Some of the leading hurdles are culture, archaic IT systems, lack of skills, and lack of a clear leadership vision. During my last years in the Army, I had the opportunity to develop various strategic visions and organizational mission statements that were focused on delivering disruptive technologies and digitally transforming enterprises. Now that I am transitioning from the Army, I had time to reflect on the outcomes of these visions and learned some lessons along the way. The purpose of this article is to share these lessons and describe how I used systems thinking as a foundation to my leadership style, the culture I fostered, and the management of my efforts to achieve strategic outcomes. First, I will introduce systems thinking, then provide references to the various mission and vision documents I created and conclude with the lessons I learned.