Getting started painting

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I've been fortunate in having been given the chance to paint portraits of past alumni within the athletic division of Yale University. It's been quite an opportunity for me to paint these portraits but for some reason I can't surmise, it's been very difficult for me to get started painting a new painting. I have about 10 paintings to start and have finished 12 paintings so far. I think I am getting a bit strung out with the work load. Anyone have ideas how I can get through this without loosing my sanity?