That's why this play presents an excellent opportunity for you to start talking with your students about the meaning of success. How do they define it? How does Willy define it? How does popular culture define it? And whose definition is correct?
Many of your students, especially if you have 11th or 12th graders, are starting to think about their futures—what they want out of life and how they intend to achieve it—so they'll have plenty to say on this subject, and they're likely to have opinions on Willy's approach to reality as well.