Is it worth it to ask out a woman who's way higher than you, career-wise?

There's a lady I connected with through a social networking site, who attended my alma mater. Currently I'm in lousy shape, in terms of what I have to offer, financially, and achievement-wise, at my ripe age of almost 40.. I am unemployed, am living temporarily at my father's place, don't own a car (I did..but had to donate it..long story..and now don't have the funds to buy a used one..) and have never held any real managerial position; there has been no true signs of mobility through all my years of employment, after graduation..on the other hand, the lady I'm speaking of - she has a terrific employment record and has an executive title in her corporate office, and I imagine is doing well financially as she likes to travel often and to pricey destinations. I'm a little hesitant of (well, once I land work) asking her out due to this stark reality.. she's really attractive on top of that (and I'm kind of shocked she's single ; I'm guessing she's ultra-picky) so I don't know.. I'm not too good handling rejection from the ladies when it comes to dating.. basically I'm the type of guy who, after getting turned down, will head to the pub for more than one pint, and shake my head. So, I don't know if I want to go through that. At the same time, isn't this part of dating? Rejection? Even guys who I guess look almost like Derek Jeter or Brad Pitt or whoever women these days fawn over, will get rejected. Let me know what you think. I think my chances are slim due to our polar opposite realities.