The counselor's role in facilitating career development remains dynamic as lifelong learning, expanding lifestyle options, and the changing workplace present new opportunities. In response, most practitioners follow some common theoretical assumptions as their foundation. As the career development field celebrates its place and embraces the millennium, the work of John Holland, the developmental perspective promoted by JoAnn Harris‐Bowlsbey, and John Krumboltz's social learning theory are captured through this personal view of the career development journey. Unique insights about the context of their work and view of the future workplace are shared.