Thinking of jobs, careers, and pay is–by some–being replaced with the idea of work, relationships, and meaning. Technology and the resulting connectivity are a part of this. In the 21st century, we all have personal “brands”–digital footprints that precede and proceed us, leaving a record of our interactions and ideas for anyone to see. The concept of career-readiness is changing because how we live and work is changing. Traditionally, this conversation is reduced to a “characteristics of” dialogue, where we promote ideas like collaboration, creativity, and critical thinking. The more precise we can be as educators in our views of what work is actually becoming, the better we can prepare students for that always-changing reality.