I would argue that a conviction on record in the "security field" is arguably more a PR boost and a boost to his cause than something that hinders your ability to either get a job or support yourself financially post jail time.
I reckon that if Aaron would have gone to trial, he would have most probably not done 35 years, more probably from one to four years - that is taking into account most high profile hacker convictions in the past ten years, with one exception of five years and change plus a screwed up supervised release which I can't remember the timespan of. Six years would have been even better than that.
Look at Kevin Mitnick (the exception to the rule mentioned above), Adrian Lamo, Mark Abene, Kevin Poulsen, etc, etc... They've all had successful careers either as Security Consultants, Technologists/Speakers, Journalists, et al. And you could easily argue that having served time has made them all notable figures in the technology and security scenes. Aaron Swartz could have pleaded guilty (he did steal the documents and trespass) and do his 6 months or go to trial and end up doing a couple of years - and come out a hero with a strengthened cause and higher profile. A Reddit cofounder and high profile activist doing some jail time for his cause is something that would not have been forgotten.
Don't get me wrong, I'm on Aaron's side. The charges where preposterous and the way he was treated was barbaric. I can definitely sympathize. That been said I would have taken the charges and 6 months of jail time as a badge of honor. I mean he did break the law and caused monetary damages to JSTOR. At the end of the day this man would probably have entered that elite group of "convicted computer criminals" who have been able to turn their convictions around to become successful entrepreneurs, public figures, and hell maybe even a Movie/TV personality. Hell Mark Abene even had his debut as an actor in some movie I can't remember.