Adjusting to change can be difficult for anyone. A commitment to continuous learning can help in coping with change. This chapter presents a picture of real lifelong learning in a field that has undergone dramatic changes. The author, Philip Doesschate, has had wide-ranging experience in the information technology field over almost five decades. As he recalls his career accomplishments and challenges, he identifies a set of personal life lessons from his work in this rapidly changing field. During his career, Doesschate has worked in numerous roles, industries, and specialties, on projects of small to significant size, using many different computer languages, operating systems, application frameworks, architectures, application packages, and analytical tools. The lessons illustrate issues not only of staying current but also of mastering new approaches as they evolve to meet customer needs and expectations.