Stay In, Get Out?

I greatly appreciate all of the advice and suggestions, and I'm thinking I'll stay in and see how it goes. I have options on the outside however, I think the stability in the military will help overall.

I was in your shoes.  I had E-6 orders, but the bar was too high.  I got out.  I wish I could go back and do a retake.  I would have retired 15 years ago had I stayed.  But I still look at my time in the military as the most honorable and challenging job I've had.  It was a bunch of sh** at the time, but that all changes.  There is always sh** wherever you go.

Find yourself a ROTC college campus; Attend that college, work as a Sgt and get ur degree; Go OBC and teach on campus as an instructor. Stay there until the active Army expands its personnel. Right now...big draw down which means the war will be within the ranks, and I would not wish my worst enemy on the inside of that mess. 

I picked up 5 when I was just shy of 5 years. Since I reenlisted, I have no choice but to stay in right now. But I feel that if I can continue to get competitive and challenging assignments instead of stagnating somewhere, then staying in provides the greater benefit for me and my family.

If you truly love what you do, then there should really be no doubt. If you don't like what you do, or are "burned out" then getting out might be a nice change of pace. Some people find it easy to make the transition from military to civilian life, but there are some that have an extremely hard time with the pace of civilian life. Either way it is a difficult choice, and maybe a Pro/Con type list might help. I wish you well with your decision!

You need to consider a few things since you are an E-5 with 6 years in.

Do you enjoy your job/work and what you do in the Army?
What are your prospects for promotion in your field?
What, if any, bonus will you get if you reenlist? Orders?
If you get out, I see that you have looked into the Guard, what does that look like for you?
How does employment look where you want to settle? Are you ready to get out and what do you still need to do to prepare for civilian life?

Once you have answered these questions - look at the advice others have given and follow through. Make sure your Resume is ready for Civilian Employers if you go that way, they will not understand military and Army terms so get rid of them and translate them.

Shop jobs wisely and start NOW if you are getting out in December. You are closer than you think. Do not burn any bridges, you may change your mind between now and Dec. My best job offer at the 10 year point came a week AFTER my reenlistment (LOL).

Good luck with your decision. You may choose to follow SPC (Join to see)'s advice, but others have offered more insightful mentoring for sure.

In the end you are the one that need to decide, it is a huge decision. Don’t always think that the civilian life is way better, it could very well be but you never know. I love the military and I have a great pride in what I do it is the best “job” (I know it’s not a job it’s a profession) I have ever had. The army has given me a lot and I bet it has given you a lot also. If I was you talk to you Battalion Career Counselor and check what he can offer you if you do stay in. Then make a pro and cons list and decide on what you want to do. I hoped this helped you, I know I am going to stay Army.

Stay in whether it is active,reserve or national guard.
I found out after I left active duty USMC that I missed the structure of the military, joined the guard and ended up retiring after 26 years.

Just FYI pinning E-5 requires two years of retainability. If you choose not to re-enlist and your ETS is less than two years away, they will have to take the rank. Just giving you a heads up because I had a similar issue just recently with a Soldier.