I'm not sure exactly what you mean by 'where we are at', but here's my read:
Where are we at in 2014? I think Calgary has successfully reversed the trend of urban decay that was worst in the 70's and 80's (though probably extended from the 1950s to the 2000s). Early-century houses, shops, and apartments have made way for mid-century parking lot after parking lot after parking lot. FINALLY, I think the tide has turned and people are investing in even our most dilapidated hoods.
Calgary is not unique in that regard (Toronto, Ottawa, Vancouver, and Montreal all had the same issue and all reversed it; Edmonton, some areas of Toronto, Hamilton, Saskatoon, Winnipeg, and two dozen American cities are lagging a bit IMO but are
just on the verge of reversing urban decay), but Calgary, I think, is perhaps unique in that it may have jumped a weight-class in the renewal. To compare us to Toronto, Calgary used to feel like the harbourfront (rundown parking lots with a few scattered, sterile office developments), and now certain areas of Calgary feel like Queen Street or Midtown, albeit smaller. In fact, perhaps other cities are becoming less useful as comparators as Calgary's own character develops - one that has increasing focus on our greenspaces, street life, and urban culture.
What's the next step? One of the biggest and most visible changes I've seen lately in North American cities is BIKES. Bike lanes and bikesharing has popped up even towns and small cities I did not expect. Last week I visited Madison WI and was blown away by their bike infrastructure. Wisconsin is one of the coldest states with the most snow! Given the relatively minuscule cost of improving bike infrastructure, it's a no brainer. Another thing that Calgary is doing great at and should continue to do is improving green spaces. The Bow and Elbow are assets that other cities ought to envy. Toronto and Montreal have nothing like it. Let's embrace our parks and improve green streetscape. The last thing that Calgary will have to do in the future, in my opinion, is to be openminded/flexible with zoning and land use. If we can enable privately-developed inner-city lofts for 200k by reducing parking requirements, let's do that, and let's make sure those people have access to other options like cycling and Car2Go. If relaxing a bylaw gets us Festival Hall, "temporary" (actually permanent) curbside bikeracks, and block parties like the one at Lukes Drug Mart, let's relax. Let's plan development that can adapt to include new uses as new industries and technologies arise. Let's give people as much choice as we can - about how they get around, where they live, what they do for entertainment, and where they work. From 2014, the future of Calgary looks very, very bright.