Yeah buddy, it is kind of tough for us to advise you, especially at work. We don't know what the work atmosphere is like...But, it sounds like you have a good plan in place...
I bought a pair of 4" boots at a thrift store the other day, covered them up with my levis and headed out...Went to the gas station, took a tour through Walmart and the food store...It really felt great to be in my boots publicly, the four inch heels were easy to walk in too...
Let us know how you make out at work...Does your wife like how you look in your boots?