How Can We Leave The Military Without Regret?

My friend Bob walked into one of those Transition Assistance Program (TAP) workshops to learn how to leave the military. After 20+ years in the service, he walked out with one thought on his mind: "Now is not the time to leave."

Bob took new orders. Snap.

Why is it so hard to leave the military? Seems to me that one of the features of military life is that the moment we join, we start making plans to leave. Some people are counting down the days to when they leave the service.

So why is leaving the military less like the orderly transition to a new life the rest of the world thinks we should have, and more like leaping naked from a speeding truck off a bridge?

It isn't from a lack of help. In this time of sequestration, there are lots of programs designed to help us make the transition to our "next career." When I have been talking to people making the transition out of the service for Military.com’s Spouse Summit segment Career Endgame I notice how there are some missing pieces.

Whether folks are leaving after five years or 30 years, the endgame is so much more complicated than it looks.The military career endgame is made up of a thousand questions that all hinge upon each other. And no one starts with any of the answers.

-- Are you going to leave the military.  Are you trying to tell me something about that last board?--  What job do you want to do after leaving the military? What am I suited for?-- Where will you live?  Where will the job be?-- Will you sell your house? Will anyone buy it or will we be stuck here forever?-- Will the goals of your family be met at your new location?  I think so—that is if they agree to move again.  The wife is making more money than I am.-- Do you have the right skills for this market? Let me call my Detailer….

The worry factor for all these questions is huge. Maybe all these folks are a lot like me. Maybe they are worried that whatever they do, it will be the wrong thing and that they will live to regret it.

Which isn’t surprising. In the research about regret, the top two regrets of Americans always center around education (I should have stayed in school, studied harder, got my degree) and career (should have picked a different field, should have taken that job in Kentucky, should have jumped ship sooner).

The researchers note that we tend to collect our regrets in life at the decision points where we think we once had the most opportunity. We don't regret natural disasters. We don't regret buying a car. We regret the moments when we had the biggest array of choices that would make the biggest difference ... and chose the wrong thing.

So of course our regrets and our fears make a big play right at the moment when we look to leave the military.This is a time of huge opportunity. This is a time to get the life we were all longing for during those deployments and separations and moves. Make a mistake here and you will regret it.  SO DON’T MAKE ANY MISTAKES!!!

That's just dumb. We will all have regrets about the process of transition. There are too many decisions to be made to get them all right at the same time.

That's why we are taking a new approach to the Military Career Endgame at the Spouse Summit this year. Instead of the usual questions, we have another layer of the process to add that you may have never considered before. (So definitely plan to attend the Summit!!) We have another way to approach the Endgame that doesn't require you to know every benefit or be able to recite you exact income needs for the next five years.

Leaving the military with a sense of meaning and purpose--and few regrets--is what we want for all of you.  So if you have made the transition, what kind of advice would you give to couples who are considering whether this is a time to leave the service?

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