I've kept out of this one for a while as I knew there was going to be hundreds upon hundreds of 'art' vs 'disfigurement' arguments.
At the end of the day it's completely down to personal choice. If the OP was truly inspired & encapsulated in Jobs' character then let the poor bloke have a portrait tattooed on his arm. I don't think he'd make such a bold decision without putting A LOT of thought into it (unless he's wrong in the head) & as long as he's happy with it - then who's to tell him otherwise?
To level the playing field I personally think it's absolutely horrific, I think portraits are nye-on impossible draw on a sheet of paper, let alone on someone's skin. It looks like someone smashed his head in with a hammer & the eyes/nose area (arguably he's most distinguishable area) is completely off, but that's totally beside the point.
I'm not against tattoos at all. I'm more into the subtle, 'only noticeable when you're actually looking' kind but again, as I said is completely and utterly down to ME, only only ME. I personally would've gone with something less 'prominent' and going with the Jobs idea, maybe have 'Here's to the crazy ones' or something along those lines.
(A lot smaller than this
)
A side note to the OP - you can't go posting on the most an anonymous place in the world - the internet without expecting some sort of a rebuttal. Enjoy your tattoo, I just hope you'll think you made the right choice in 50 years time.
/2c