There have been a lot of points in my life where I've felt like a real failure - a lot revolving around my professional and educational career (much like Jobs's speech here). But my experience with these failures has been similar to his (aside from the stupendous amounts of money, of course) - they've provided a way forward that I never would have anticipated before. The big failure for me was being rejected from PhD program after PhD program when I graduated from William and Mary, which eventually directed me toward the Urban Institute and GWU's public policy master's program. It felt like a miserable failure at the time - but as regular readers know it has shaped how I've moved forward, and given me incredible opportunities thanks to the senior researchers there who took me under their wing. I also simply could not have had a better exemplar than the Urban Institute of objective research on policy issues that is still able to make a positive difference in the world. My more recent failure has been another round of rejections to the programs I really felt I belonged in, namely Georgetown and Maryland. I don't feel as downtrodden as I did in 2006 when this happened, because I'm starting to see how failures happen for a reason (did I really belong there?) and open new doors. I may not get an academic position after I graduate from American - I'm certainly not likely to get a high-powered academic position. But I wonder if I could do more good not just for the world - but for the science of economics - outside of academia. Just as Jobs points out in this speech, I am more open to how we grow from failure than I was when I was younger.
One more thing I have to mention: I've been very disturbed by how politicized some of the blogosphere reactions to Jobs's death have been. Why is this where so many people's minds go after a tragedy? Why do people have to assume that because they support the good things that Jobs stood for, their political opponents somehow don't? I don't know - I'm not going to link to any of them, but I encourage people to try to stay edifying.