What preparation is essential to successfully transition to the civilian world?

I'll add to Vikki Nicometo solid advise that you do a baggage check of your attitudes and be prepared to take a humble pill if necessary. How you orient yourself to job seeking, being responsive to good counsel, and learning from the bumps like you had to learn as a MIL are good attributes. You see a lot of deep six the jargon, acronyms, and other things that are in your comfort zone. Transition by its nature isn't comfortable and needs to be managed. It also means in some or more ways, you need to change, but a better word is grow. Good luck on your journey.

Ranger Decker, looks like your at the top if your educational goals and possibly interested in security and defense matters. If you're considering getting out, start working on your IPBA, Intelligence Prep of the Business Area, for potential employers that you're interested in. Then start drilling down into potential neighborhoods or areas where you might consider establishing your base of operations.
Remember too, that the civilian world is different than the Army. Civilian supervisors and administrators are not necessarily leaders. They may or may not have large egos that get bruised easily. You may have to temper a direct and truthful military response so that it does not cause injury to someone with thin skin. That's been the hardest part of my transition. Best of luck to you in your transition.

Brilliant question! I’m going to answer this with a focus on just the parts I know – that is, finding civilian employment. I’m certain there are other parts related to family, military separation, etc. that others can give better advise on.
For finding civilian employment, these are the steps that I think are CRITICAL:
1) Get clear on what type of civilian career/job you WANT – not what you think you can GET, but what do you actually want to do? (There are resources to help you with this. A good coach is one. Feel free to message me for more info.)
2) Target VETERAN FRIENDLY employers who have those types of jobs. The reason I stress the veteran friendly part is that I understand that many employers don’t know enough about military experience to understand what you did. But veteran friendly employers usually have a dedicated team of recruiters to guide you and the hiring managers through the process. Many of those recruiters and hiring managers are also veterans.
3) Then start the tactical pieces – next up: the resume. Translate your military experience into civilian language. There are TONS of free resources out there to help you with this.
4) Network like your entire career depends on it – because it does!! Blindly sending resumes to online job postings is the WORST way to find a job.
5) Get some interview prep! From a pro! Not your friend, but someone who is an expert at interviewing.
I could go into salary negotiations, etc. but this is a good start.
If you want to ask questions, you can do so here or you can message me, or you can ask them live at the free transition teleconference I’m offering. If you’re interested in that, shoot me a message and I’ll send you the link to register.

SGT,
You need to be looking for a position you want to step into a year out from your ETS. Research what skills are required for the position you want. See what skills you already have. Anything you're lacking on, go seek either civilian education, find a training program through the Army, or find a technical school to enroll in so you can get develop those skills. Bank up your money as much as possible and try to save three months worth. Don't go buck wild making purchases until you have your new job. Don't be afraid to take an initial entry position if it means it could lead into an intermediate or advanced position a year or two down the road. You have to develop experience. Most importantly, sell your military experience. There is more to you than your MOS duties. Good luck to you.
-MSG Reeve

DO NOT transition, continue to adapt and overcome. You will always stand out, BE A SOLDIER.

Be prepared for an unenthusiastic reception in many civilian workplaces. Have a thick skin. Let your performance do your talking. Many guys that haven't served may feel threatened by you and try and make patronizing remarks. It's tricky. Be thoroughly prepared when you interview, make sure you know all you can about the company before you meet them.

If you're planning on using Veterans benefits, understand that sometimes these can take MONTHS to actually pay you. Uber and Lyft can be good ways to bring in short term cash in an emergency. I went into the Guard (eventually) and ended up retiring from it. Looking back on it, it went by really fast and will be a very nice addition to my retirement earnings, it's also giving you access to tricare, which is significantly cheaper than most employer plans.

For active guys going onto the Guard, the big thing to understand is that in the Guard, it's easy to move - even to get a different MOS. The Guard is not like the Dept of the Army in that each Adjutant General answers to the Governor, not DA, not NGB. Schools that were impossible to get on active duty can be relatively easy to get . There are also MANY different duty statuses that you can volunteer for. This can come in handy if youre ever in between jobs. I'd encourage you to use a program - regardless of whether or not you join the Guard - called Work For Warriors. It was started here in CA by some very bright Guard officers and is very successful in matching up Soldiers, Sailors, Airmen, Marines, and prior service veterans with very good jobs. They're on facebook.

The Guard can keep the Army close, and although she can be a pain in the ass, she's also very comforting to have nearby.

I'll try to answer this as a civilian employer. What you do in civilian life is irrelevant; unlike the military, your success will depend only on your attitude, your work ethic, and your output, and also your tollerance for risk. The market is a true meritocracy. Some large corporations may be more like the military in that they are bureaucracies run by petty people that play identity politics. Be prepared to pay for your mistakes. Excellence is rewarded in every field. Don't waste your time/money with education unless it is absolutely mandatory for what you want to pursue. Be the best at whatever it is you're doing and you will succeed, period. Beyond that, I encourage you to network, network, network. It's what enlisted people call "being political," or what officers do apparently. But in real life, there are infinite doors, and the relationships you foster will either open them or keep them hidden. Best of luck Sgt.

The first step in my honest opinion, LET GO! The civillian workforce does not care or acknowledge your rank or stature. For purposes of frusturation be wise to military talk and jargon. People ask too many intrusive questions. If possible, don't even let it become a part of the discussion. Also, civillians are known to feel intimidated by prior military members.

Take part in any workshops that may be available. The Army has ACAP. You can always ask them questions. Local Veteran Service Organizations can provide a plethora of knowledge

There are the healthy habits that we must hold on to. Arrival, personal accountability, values, leadership skills and problem solving.

If possible, take some time for yourself to decompress and shed your military skin.

Networking is paramount.

Lastly, acknowledge that you will never fully transition to civillian life.

I'm impressed that you have a PhD. That alone may open some doors. Here's a few ideas from my own transition and from others I've watched:
-Set your priorities before you leave the service. Decide what's important to you in terms of family life, work life, spiritual life. Use these priorities to guide your post-service decisions. In my case my highest priority was supporting my family leading me to follow the employment opportunity in selecting where we lived and for whom I worked.
-Build a network of people who may be able to help you fulfill your priorities. Join professional associations that support your preferred field(s) of future employment. Your previous work at Rand may provide a great opportunity to network into a good job. I didn't do this enough and it was a down falling in my career path.
-Civilianize everything. Translate your military experience to civilian speak in your resume--no military jargon or acronyms. Make sure your resume shows accomplishments as well as responsibilities. Work on freeing your everyday communication of military terms, jargon and acronyms. Buy a couple of good suits, shirts, ties, shoes and get comfortable with wearing them (I always found Men's Warehouse to be very helpful). Expect to come in on the ground floor and work your way up.

I see some areas you might consider as possible relatively easy hits Academia. Your PhD may allow you to get a teaching position at a college or university. Government employment. Your veteran status plus the PhD may open opportunities for you in federal government service. Government contractors. Military experience, foreign language skills, and PhD may fit with some contractor jobs.

Jeff,

The best thing I can tell you is to start to prepare for corporate interviews. Rehearse, rehearse, rehearse. First impressions are lasting.

Take a look at this post I published on LinkedIn.

https://www.linkedin.com/pulse/principles-patrolling-post-military-job-search-john-tolentino?trk=mp-author-card