Get rid of the small town mindedness that seems to infect this city. It seems that we think that we are simultaniously the next New York or London on the Financial/Economic/etc stage and some small town rural speck where there should be no noise except for the cows and the crickets.
To become a world class city we are going to lose some of our small town roots.
I wouldn't quite call it small town roots, but Toronto does seem to have an affinity to calling themselves not worthy to the global spotlight. And if we continue that, it's certainly going to drag us down. One just needs to look at Transit City to see how much we believe we can't have nice things like other cities our size.
These are valid, those sentiments really do live here in Toronto. However, when the present decade is over, I believe we're going to look back and realize that this has been our decade, and we will probably see Toronto gain a much more confident mindset. Achievement breeds confidence, and confidence feeds on itself.
And even when we get there, there is something that you may be assured of: London, Paris, New York, Tokyo, they have their beefs too, people will always complain collectively about some things (with New York, the issue for decades has been increasing noise levels, and some good people are starting to win the fight).
Closer to home, however, I believe that Toronto's biggest hurdle to "bigness" is our attitude to public spaces. All of the giants, (London, Paris, New York, Tokyo, etc.) are very mindful of their appearances. Toronto has yet to show that it gives a hoot about that. Heavens, Paris is totally a/r about its appearance -- you won't see one overhead wire anywhere at all in central Paris.
Jack Diamond expressed his disappointment that the street furniture program here didn't see the value of going for a "signature look" and he is correct. We opted, instead, to keep the helter skelter newspaper boxes, and we obtained those totally gross new garbage bins. When you see Toronto getting a bit more touchy about how the public areas look (including the squares, of course) then you'll know we're actually starting to arrive. Some politicians argue that we don't have the money for such “attention to details”, while I argue that we can’t afford to have that sort of politician around any more (but those North Etobicoke types will vote them in, watch and see).