I hear people say they are going to transition out of the military in a year. My question is, - Shouldn't we be transitioning all the time?

There's a necessary balance that is dependent upon your personal goals. Would you like to make the military your first career? If so, your first transition is establishing your reputation as an individual worthy of retention. That requires you accept situations that are important in the military, but are Ho Humm to civilians. I have seen people in the military so concentrated on end of tour transition that they limit their value to the service.
If you know "civlant" is your ultimate goal, there is nothing wrong with taking advantage of those opportunities the military offers (schools, etc). You just have to remember you will probably need a few references and the ones a prospective employer are going to look at are those you accrue during your service.
I suppose my core opinion is you've got to plan you long term goals and work toward them, but if you are concentrating so much on the future you are mediocre in the present, you're not doing yourself any favors.

I must be stoopid because I don't understand the question 100%.

Transition is definitely a long-term science project...particularly the resume/LI profile and building a non-military network (give yourself a couple of years for these two, at least). The one-year out mark is when you start focusing on the tactical aspects of the move, but you've gotta build a solid foundation much earlier than that. To your point Tyler, your career moves in the military should always take the long game into consideration (although you'll always be focused on your military service, correctly...part of why it's typically such a difficult transition...we typically put our service in front of our long-term personal goals).