I agree with City Flyer!
Everyone in the industry had these same dreams and aspirations, and funnily enough pilots aren't born in a 777!
Wherever you are now in your career its natural to look up, whether that be on a Cessna wanting to move onto the Boeing, Or a captain wanting to go into training. Some may not want to move forwards in their career and that's because they have reached their goal or they are currently happy with the situation.
If you don't want qualifications to hinder your chances then don't let it! Plus i think once you have your first job under your belt it wont really matter.
Not all about what you know, sometimes its about WHO you know.
( oh and FL390 and capt.Dave is brilliant! deffo worth having a look or 'Cockpit Chronicles')