Post Military Retirement: Considerations on Seeking a Second Career

In recent posts, I discussed why we need purpose after retiring from the military and provided some examples of people I have observed that left service without purpose and balance and, in my observation, have done retirement all wrong.   The questions for us are why and how might we avoid this trap?  I contend that the problem begins with expectations set generally by external sources.   A simple Google search of related topics returns a majority employment and job sites.

This popularity is based primarily on what people search for and believe to be important.  However, there is also a certain inertia going on here.  People approaching transition use the Web to search topics, they see a majority of results related to employment and they get a sense that this should be a priority.  The preponderance of sites represented builds a social critical mass that reinforces the popularity of the subject and paints a narrative. That narrative is. “the normal and expected thing to do is to look for a second career”, it then follows that the searcher should also look for a new job in order to be like everyone else.

Is it appropriate to accept a norm that many others follow just because it is popular and it seems expected?   Will this bring each and every one of us happiness and provide sustaining purpose?  Following expectations for the sake of saving face, filling a void and doing what one thinks they should do is not a recipe for happiness.

The following are points I suggest you consider before diving into an all-consuming career search.


We dedicated our lives to a career that demanded we live and work in places mostly not of our own choosing.  Many of us experienced divorce and marriage difficulties as a result.  All of us with children lost time and opportunities that can never be replaced.   Only you can know what you need (financially, emotionally, intellectually) at this point in your life.  Sometimes one or more of those need factors dictate for us a requirement to either look for work or to look for a particular type of work in specific a location.   My point here, as you consider the points below, separate wants and needs in your considerations and to place your family as a need.


We live in a consumer society, many people go their entire lives spending at, just below or, sadly, sometimes just above their income.  Oftentimes, our wants expand to a level equal to our means, if this persists our debt creates an actual need.  Each of our situations is unique.  Taking the long view, it is wise to separate real wants from needs and ensure that current and future spending does not create a debt related need.   Nothing can rob you of your new-found freedom quicker that expanding your post-retirement bill.  One of the first steps is to get clear about your financial situation, what you really need to live a fulfilled life; separate wants and needs.


Terms like “cultural fit” are common in the employment space.  Ideally, companies have a firm grasp of their real culture and there is a true alignment between their stated principles and real actions.   This is not always the case.   Likewise, job-seekers should have a firm grasp of the sort of culture they want to be involved with.  During the interview and pre-employment phase full disclosure and vetting by both parties should occur.  This is not always the case.   Job seekers often dismiss warning signs of a cultural mismatch.  As military veterans we pride ourselves on our adaptability, we assume standards are standards, we know we can adapt and we have faith that despite any warning signs, we can work it out.

Culture is, in my observation, more important to veterans than most.  It is critical to place this element high on your needs list before deciding to seek employment.  High pay, a title or a nice office cannot overcome our inherent need to fit ethically and culturally with the organizations and people we associate with.


In our profession, there were many opportunities to utilize the fullest our capacity of thought, intelligence and innovation.  Certainly, the military has a system, constraints and a bureaucracy, and certainly not each and every assignment was intellectually challenging, but the profession was what you made of it and it allowed you to use, within the system, all of your faculties and abilities.  It is important to ask yourself how important this is to you before deciding to (or not) begin a career search.   Not every job or role will challenge you.  Perhaps you believe you would be happy with a position that left energy available for other pursuits.  The thing with full-time work is, it consumes most of your energy and time.   Just because the work appears doable and the pay is acceptable does not mean it may not prove menial, boring and perhaps soul-sucking. Remember, full-time work takes up a full week, be careful what you ask for.

After honestly and fully pondering all the above to identify your real needs and wants and a priority of those you will have a better idea of what right look like for you in terms of if you should seek a post-retirement career, a job (full or part-time) or to make your own way via some other means.   Just because so much of the noise and traffic related to transition talks about employment does not mean that must be your first and only option.

Last point

If after a complete inventory of your needs, wants and values you conclude that you want to seek a second career I suggest you forego any thoughts of a long (think 12 months or longer) “sabbatical” or break after retirement.   A vacation, a trip, a month to reorganize and settle is fine, but a long break diminishes your value.   Hiring managers, HR people and, well, people in general in the civilian world just do not understand fully the financial freedom you enjoy and are unlikely to understand a break.  It is not part of the general cultural norm.  In the civilian world, a break equals less value and diminishing skills.

There is great power in interviewing while you are still on active duty.  In the minds of civilian employers, there is greater value in a person that has a position.  Right or wrong, that is a general perception.  When you are still on active duty and interviewing, you appear as a free agent, someone to be recruited.  Afterward, you appear like a job applicant.   It is a subtle reality of the world of civilian employment.   This fact should not be taken to mean you rush your decision as to whether you seek a career or follow another path.   It is just a data point to add to your evaluation of the operational environment.

I would love to hear from others that have entered the workforce or chose a different path, what were your considerations, mistakes and lesson-learned?  Comment below.

Read about my mission here.