Originally Posted by
FBinNY
What I suggest, is that you try to find some routes with hills and do more hill climbing, though less ambitious, to build up to where this one can be taken in stride.
BTW - an easy way to gauge overall fitness is to climb stairs, or a hill of known height against the clock. This isn't a scientific or precise measure, but it will give you a sense of what you can do.
^This. Eliminate all of the weight that you don't need for your commute. Carrying a lock? Leave/lock it at work. Carrying extra gear "just in case"? Minimize it. Extra body weight? Revise your diet with simple changes.
Are there any stairs that you can walk daily? A stairwell at work? A nearby tall building? Start walking stairs at lunch.
In a month, you'll be blasting up that hill...