Why do servicemembers leave without a solid plan?

tl/dr: Culture shock, no systems, no such thing as a board. Sorry for the length - this is an area I am kind of passionate about. I would edit, but I do have to get to my day job at some point. 

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It appears to me that most military personnel don't realize just how throughly planned/structured/organized/etc. the military is, or appreciate that there is always someone in charge making decisions based on semi-transparent criteria - carefully weighing the mission, the needs of the organization, and its people.   

In can hear keyboards starting to click right now about all the flaws that exist in the military, all the seemingly senseless decisions made, and horror stories about terrible leaders.... Post if you want. All I can say is you are comparing apples to carburetors.  As bad as you think any of the systems are in the military, the dirty secret is that they don't EXIST in any meaningful sense in the civilian world. 

Or, perhaps better stated: There are untold THOUSANDS of discrete, empirical, non-synchonized, contradictory, and non- or poorly documented systems. And generally what is published is a polite fiction, aimed at avoiding lawsuits.  

I'll give just a few examples from my day job:

1. Hiring. I have about a dozen people who work directly for me. What is the board process to get selected for this? There isn't one. You submit a resume and cover letter. If it appeals to me, You get an interview. If you get an interview, and I like your answers, You are competitive. I compare the competitive people. If I think you're the best fit, I'll offer  you the job. What makes your resume appeal to me?  There are certain things I look for. I look for self-directed people who have been able to get results in an unstructured  environment and present a professional image. However, there exist NO  objective criteria which will ensure your resume stands out to me.  [in another post, I would be happy to talk about tips & hints for resumes]  Moreover, the things that will make your resume pop for me may get it round-filed by John, the manager in the next office over.  And that's in one section of one division of one employer... And I haven't mentioned that I chose to NOT have HR screen resumes - I get them all. HR prefers to screen them so as to not waste my time with resumes that they don't think make the cut. I stopped letting them after they failed to forward me a resume from someone I had directly recruited. 

2. Evaluation. How are you evaluated? Depends on the employer. We have a structured evaluation process that is comprehensible compared to the OER/NCOER, with initial and mid-year counselings. However, it generally doesn't matter, unless you suck and I'm putting together a packet to fire you. It is very largely a Skillcraft drill where I work. That said, I tend to take it somewhat seriously (mostly because of my military background), and try to work in good counseling. At other employers I have worked for, it was a matter of life or death, where poor evals would lead to termination (not as support for a termination event, but as the event itself) or determination of a raise.

3. Raises. My employer has a rigidly established "step" chart. Comprehensible to the military. You get set raises basically every year until you hit 15 years. There are no performance raises or bonuses. I have worked for employers that did performance raises and bonuses. As well as employers that just pay straight commission. I have also worked for employers that hire you for a set wage, and that's your wage until you leave.

4. Promotions. Some employers have some idea of merit-based semi-automatic promotions, I'm told. I've never worked for one. In every employer I've ever worked with, you get promoted one of three ways: A) You apply for a new job - either with the current or different employer,  B) You are by-name recruited into a new position, either with the current or different employer, or C) You get a position created for you.  At my current employer of 15 years, I was initially hired as an "in training" computer programmer (so, technically, there were a few semi-automatic "promotions" until I hit the full-performance level of the position hired for), I applied for a higher-level programming job and got it. I was by-name recruited to replace a project manager that left unexpectedly. Finally, I lobbied to create my current position - then lobbied that I should be the person to do it. If I wish to be promoted again (and I do), my options are to A) create a new position, B) get selected for the CIO position when my boss leaves, C) get my resume out there...

5. Workplace Norms. Some employers are suit and tie, button-down and terribly proper. Some are jeans and t-shirt and nerd fights in the office. In my case, as a programmer, I was in jeans and a t-shirt, and was seen as professional. As a project manager I work khakis and polo shirts and was good to go. In my current position, it's dress shoes, slacks, shirt and tie. Other managers at my level are suits every day, while others are still at jeans and t-shirt.  And I've only hit on dress codes at ONE employer. I had a meeting with the well-respected head of another agency yesterday - He was in a hawaiian shirt. This is why I often bite my tongue in posts about the military presenting a "professional" appearance. I have very little idea what that's supposed to mean.

So, I just picked 5 big items to highlight. Think of it this way. When someone enters the military, they go through a structured and intentional program to explain the new rules of the new organization they joined. Then those norms and success patterns are reinforced for every day of their service. It is IMPOSSIBLE to do the same transitioning to the civilian world. Not difficult. IMPOSSIBLE. Because there is no one organization, set of norms, or success patterns. Not taking away from ACAP. It's better than nothing, but the cultural shift is just huge.