There is no better time than now to take action IMO. Congratulations on your successful name change and being out full time. Those are things to celebrate and acknowledge at home and at work. Oregon has been very responsive and I will, barring an unlikely challenge, be officially Tessa James as the new year of 2014 begins.
Then, like you, I can begin the name change process in a zillion places from DMV to Social Security.
This change is good!