Technology has received much praise and blame for its uses and influence in higher education over the past twenty-five years. It has been widely praised for its contributions to management efficiencies, information access and analysis, improved communications, and innovative educational applications in colleges and universities. But it has also been blamed for inflated expectations, enormous added costs, depersonalized human contacts and community on campus, and fostering trivial pursuits among college students. There is overstatement no doubt in many of these compliments and complaints, but few today would doubt Bill Gates's claim (Gates, Myhrvold, and Rinearson, 1995) that technology is the one revolution about which we have no real choice. Few other applications of technology in the higher education setting offer so many possibilities for the reconceptualization and enhancement of career development, student learning, and educational assessment as do e-portfolios. The author offers some observations about the implications of e-portfolios for student affairs leadership and practice and some recommendations for future directions.