This book is a compilation of my personal journey in higher education and of what I have seen and learned from 30 years working in that field. To say there has been a sea change in how students perceive and navigate college and in the level of parental involvement since I began working with college students in the early 1990s is an understatement. The changes have been epic. There are four parts to this book. The first part (Chapter 1) is my story where I share my experiences growing up, getting to college, and then getting to graduate school. Chapters 2, 3, and 4 (the second part) include the history of higher education, what it has become and what I think it should be, and the value of the liberal arts. In Chapters 5, 6, and 7 (part three), I share some of the situations I dealt with as a dean and advisor, offer reflections on the pandemic and higher education, and then offer some advice for students. These sections come together at different points and in different ways for the fourth and concluding part of the book—the epilogue.