When should a 'transition' program begin?

SGM, having just recently passed into the 'Undiscovered Country' of retirement, I can say that there is never enough time to be prepared for this. My latest advice to friends still serving is to do SOMETHING for their transition every week; make a connection, read an article, work on a resume bullet, research a career field. Whatever it is, the process is more important than the actual act. Anything that gets your mind prepared for the inevitable day where you hang up the uniform for the last time is valuable.

That said, from an institutional standpoint, I don't think it's practical for the service to actively provide pre-transition services more than 24 months out.

I highly suggest your wife attend transition briefings with you. The briefers will throw a lot at you, and 4 ears are better than 2. It will also make her feel like and integral member of the transitioning process. Good luck!

Transition (on an individual level) should begin as far out as it needs to. By that I mean that if a service member knows he or she wants to be an accountant after the military, for example, but doesn't have an accounting degree, then transition for them should begin 4-5 years out so they can complete their degree prior to leaving the military. I've shared my recent experience (retiring) with many of my former Soldiers and told them it is never too early to start thinking about life after the military.

As far as what the Army (or any other service) does, the programs in place are probably adequate. The real kicker is whether the unit will allow the service member to prepare; a week long transition course provides good information, but is no substitute for training, education, financial preparation and networking necessary to have a good transition. Those activities take time and energy and if a unit keeps an individual in key positions until their last day, well, they probably won't have a good transition.