What is the first question you would want answered when you start planning your military to civilian career transition?

Jennifer, hope all is well. Merry Christmas to you! The first question that I wanted answered during my transition was how do my military skills and experience relate to the civilian employment world, and also what occupations would I be a good fit for? As a senior military officer (0-6), it was too easy for me to believe that my final rank and all of the leadership experience it holds would be a sought after commodity for just about any business or organization , when in fact it was not. My age and rank both worked against me in many respects. I have all the education in the world (2 Masters Degrees - one is an MBA) and based on experience of others who retired before me, I did not think finding a good opportunity would necessarily be an issue. However, it took me almost four years to land a position where my experience and not necessarily leadership has finally paid off. Part of that I can probably attribute to my location and the job market, which took a severe dip when I retired in 2010. You are exactly right when you say that 'creating a plan starts with knowing what you are hoping to achieve and asking questions.' You also have to be prepared for some lean days/weeks/months if things don't work out for you immediately. It can be extremely frustrating to see other people you know pick up great opportunities while you sit idle, asking yourself what is wrong with you. So have a plan for what you want to do, but also have a backup plan for what happens if things do not progress. Start preparing now for your transition. I should have started two years out from when I retired, but I did not make the decision to retire until I was 10 months out. Best wishes you all of you who will be transitioning in the near future.