Robert L. Glass (Bob) has meandered the halls of computing for over 45 years now, starting with a three-year gig in the aerospace industry (at North American Aviation) in 1954-1957, which makes him one of the true pioneers of the software field.
That stay at North American extended into several other aerospace appearances (at Aerojet-General Corp., 1957-1965) and the Boeing Company, 1965-1970 and 1972-1982). His role was largely that of building software tools used by applications specialists. It was an exciting time to be part of the aerospace business - those were the heady days of Space Exploration, after all - but it was an even headier time to be part of the Computing Field. Progress in both fields was rapid, and the vistas were extraterrestrial!
The primary lesson he learned during those aerospace years was that he loved the technology of software, but hated being a manager. He carefully cultivated the role of technical specialist, which had two major impacts on his career - (a) his technical knowledge remained fresh and useful, but (b) his knowledge of management - and his earning power (!) - were diminished commensurately.
When his upwards mobility had reached the inevitable technological Glass ceiling (tee-hee!), Glass took a lateral transition into academe. He taught in the Software Engineering graduate program at Seattle University (1982-1987) and spent a year at the (all-too-academic!) Software Engineering Institute (1987-1988). (He had earlier spent a couple of years (1970-1972) working on a tools-focused research grant at the University of Washington).
The primary lesson he learned during those academic years was that he loved having his Head in the academic side of software engineering, but his Heart remained in its practice. You can take the man out of industry, apparently, but you can't take the industry out of the man. With that new-found wisdom, he began to search for ways to bridge what he had long felt was the "Communication Chasm" between academic computing and its practice.
He found several ways of doing that. Many of his books (over 20) and professional papers (over 90) focus on trying to evaluate academic computing findings and on transitioning those with practical value to industry. (This is decidedly a non-trivial task, and is largely responsible for the contrarian nature of his beliefs and his writings). His lectures and seminars on software engineering focus on both theoretical and best-of-practice findings that are useful to practitioners. His newsletter, The Software Practitioner, treads those same paths. So does the (more academic) Journal of Systems and Software, which he edited for many years for Elsevier (he is now its Editor Emeritus). And so do the columns he writes regularly for such publications as Communications of the ACM and IEEE Software. Although most of his work is serious and contrarian, a fair portion of it also contains (or even consists of!) computing humor.
With all of that in mind, what is his proudest moments in the computing field? The award, by Linkoping University of Sweden, of his honorary Ph.D. degree in 1995. And his being named a Fellow of the ACM professional society in 1999.
On the personal level, he is the father of two biological and two adopted interracial children, and is married to Iris Vessey, an Information Systems academic.