A few years ago I had a student named Gene. Gene had an encyclopedic knowledge of every movie he had ever watched, and he expressed a strong interest in working in a movie store. My school’s administration was eager to match him with his preferred job. As the schoolbased case manager, I made arrangements with a local video rental store owner for Gene to test out different jobs. Gene adapted quickly to the steps necessary for restocking videos. He rewound the video tape, entered the video into the computer system, located the genre, and re-shelved the video. Gene worked during school hours, and after graduation the manager of the store hired him, and he worked for a number of years-until the store closed and the era of video rental stores was gone. Gene was unprepared for a new job search. Instead of preparing Gene for a variety of different jobs, we customized his high school experience to maximize his chances for getting his then dream job. Now, I wish we had developed a broader range of skills to prepare Gene for a variety of employment and education options. I wish we had helped him learn how to use transportation, how to enjoy community services, how to explore a multitude of employment and postsecondary education options, and hot to locate support systems outside the school. And I wish we had been able to find a way to do this without considering academic preparation as expendable. Like every other high school student, Gene needed that academic preparation to have the broadest range of postschool options available.