Military Retirements Gone Wrong

It is hard, impossible actually, to look at the life choices another person makes and truly evaluate the merits or estimate all the factors that went into their decision. On clear-cut situations of morals or ethics, we can often be sure, but other matters are more complicated.   I say upfront to establish that I can never know why the characters in the stories I am about to relate made the choices they did.  My perception was and is based on the facts that I could see. 

Having provided that disclaimer, herein I have listed the stories of a few individuals that, in my opinion, did things all wrong once they retired from the military.  I have changed the names, and in some cases minor specifics about geography, just to make sure not to personally insult or identify anyone.


Jerry does not fit squarely into the demographic I focus on here.  He was a civilian GS employee, a lawyer, and had never served.   Jerry was in his 60’s when I meet him.  I include Jerry because frankly, he is almost a caricature of so many military retiree government employees I have seen over the years.  Jerry represents all that is depressing about civilian government service – many military retirees become some version of Jerry.

I meet Jerry in a relatively calm middle eastern country, we had several civilian lawyers on staff.  My organization had a budget with almost unlimited overtime funds for the civilians, and Jerry was on that like a fat kid on a donut.

My evaluation of Jerry is that he turned virtue into vice.

He worked, many long hours, hard work is a virtue.  He was in the office all day, middle of the night and all weekend with breaks to shower, eat and sleep.  He accumulated the regulatory maximum allowed overtime hours each week.  (for those that do not know, in civilian government work all hours above 40 per week are compensated in either overtime pay or compensatory time that carries over like vacation)

Jerry had was divorced, owned a home in the Washington, DC area and had an adult daughter that was going to law school.  Jerry’s entire life revolved around “taking care of his daughter”.   In this Jerry turned another virtue into a vice.  His daughter went to prestigious schools for her undergraduate and graduate degrees, paid for by Jerry, and he was paying all expenses for her law degree.  In one regard, Jerry should be commended for being a wonderful provider.

Here is the problem with Jerry, and so many folks I have seen in civilian government service over the years that make his mistake, he worked hard because he kept adding to his bill. Jerry was an angry, bitter, nasty little man.  Jerry had no joy in his life.  I suspect his relationship with his daughter was really one of he gives, and she takes and in the end, he will have taught her how to live poorly.


Terry was also a man in his 60’s and a fellow that I meet in yet another middle eastern country.  Terry was a military retiree, a retired Chief Warrant Officer 4, and a GS-14 government employee.

Terry’s problem was twofold. First never transitioned and second, he never thought he had achieved the level of authority he deserved.   Terry was married to an awfully patient lady, he was a grandfather to a bunch of little kids, but he had spent most of the years since retiring in the middle-east searching for a way to achieve the level of authority he thought he deserved.   Our office was in a converted villa and Terry had a desk in the next “bedroom” over from mine.  I could occasionally hear him on the phone with his wife, she begging him to hang it all up and come to sit on the porch with her.  Terry always refused, until the day his heart gave out and we shipped him home.

In that job, our civilians would occasionally wear uniforms when dealing with our foreign military counterparts.  The standard for such is that they wear a symbol that represents their GS status with their name.  Not Terry, he took to wearing Lieutenant Colonel rank, he was one of those that firmly believed his GS paygrade had a direct correlation to a military rank (it does not).   Our counterparts respected age and since Terry was old and in charge of completing the paperwork that authorized funds they thought he must be very important, this is after all, what Terry sought.

I recall on many occasions one of them asking me, where is “Colonel Terry”, “there is no Colonel Terry” I would retort in frustration, Terry was basically an overpaid administrator that should have been filling out forms, not running around the desert living a fantasy.

Terry was another grumpy, angry little man.  He essentially abandoned his wife and family in search of something that would make him feel whole, something he never really found.  In the end, it cost him his health and he returned home, just as his wife asked, but not in the state she wanted.


Ted was one of those field grades that retired in the late 1990’s and he epitomized the characteristics of the cohort he belonged to.    In the early 1990’s the military conducted a reduction in force (RIF).   Many smart folks have written about the impact that RIF had on the culture of the officer corps for the next decade.   Ted and folks like him were young officers when the RIF occurred.  They saw good people shown the door and this taught them a terrible lesson.   Basically, this group grew up to become career focused in a very negative way.  By the end of the 1990’s, when this group was in charge, the military was infected with a toxic culture of leadership, this group generally did everything in their power to ensure that no mistakes attached to them.  They feared the RIF they saw when they were young.

Their negative impact was so great that by the early 2000’s the Army was losing Captains at an astonishing rate.  Young officers were leaving as soon as their commitment was up.  Exit surveys indicated that this group placed the blame squarely on the field-grade officers that were Ted’s contemporaries.  The young folks felt the senior guys could not be trusted, they had their self-interest as a priority and that they treated people wrong.

Ted retired about that time and entered civilian government service.   Sixteen years later when I meet him he was a stereotypical representative of everything bad about his cohort.  He ran a directorate that to his superiors seemed to get things done.  Inside, morale was low, people were unhappy, and I actually met one man that was physically and mentally affected by his daily dealings with Ted.

Ted was terrible for the Army while he served, that is obvious just looking at his character.  He has been terrible for the Army since retiring, that too is obvious.  What is more, Ted does not even seem happy for all the misery he creates around him as he seeks to maintain a role and title.  Ted is a fat, sweaty man, has had a couple heart attacks and seems stressed all the time.

It seems to me, Ted has made poor life choices for a long time, and very likely when his end comes nobody will really miss him or think highly of the work or position he coveted.   Ted has done life and retirement all wrong.


Bob and I worked together on several assignments and deployments. He was just a few years older than me, thus I watched his transition to retirement closely.  Bob was on his second wife when he retired, she was younger and seemed excited by the prospect of moving into a new phase of his life with him.

Bob was an adrenaline junkie.   He loved deployments, he loved doing “stuff and things” and he never seemed happy at home.   Overall, he was a very decent guy, the sort you could count on to do the right thing when it counted.  He was also something of a smart-ass and this did not always go over well with less capable leaders.  Bob retired because he had too, passed over twice because of his mouth.   I suspect he would have stayed until he had to use a walker if given the choice.

He did not look for work long, really, he did not even look for real work.   Bob went straight into the employ of a security contractor and went right back to the middle east.  I received messages from him for two years related to his latest exploits.  In 2012 I got a message that his young wife was divorcing him and taking his newest child.   In 2013, I learned that he was fired from a major security contractor for being drunk on duty in Afghanistan.   Later that year I learned that Bob had shot himself in a small apartment in North Carolina.


Is there a theme to these four examples?   I believe the theme is that none of these fellows found balance.   Some tuned virtue into vice, all placed their needs above others – even when they perhaps thought they were being selfless.  None of them found happiness in retirement.  All of them sacrificed their health or life in their struggle.

Lesson’s learned is an important concept in the military.  We can learn from the mistakes of these four men as we plot our own course and find a pathway to purpose and happiness.

Read about my mission here.

Author: Barry

Southerner, father, husband, Christian and a retired Army field grade officer. Author of five books and of several papers and articles on ethics, culture, history, geopolitics and military affairs. He is the Executive Director of The Calhoun Institute and a partner at B&B Clark Consulting.

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