Approaching Military Retirement

Nathan Goodall

When I was commissioned into the Army in 1999, I had absolutely no idea that I would continue in service for nearly 22 years until retirement.  My original idea was that I would serve for four years.  In those days, I viewed the military as a byzantine organization with a strangely delightful culture and unique dialect of English.  Fast forward a few years, and it was my comfortable home amongst my fellow brothers and sisters in service.  Moving further on to the twenty year mark, I viewed the return to civilian life with a mixture of excitement, mystery, and fear.  I’ll talk about those emotions and thoughts below, and then discuss how I prepared for retirement.


Like many retiring Soldiers, I had some pretty grandiose visions of retirement.  I envisioned a nice retirement ceremony, followed by a long family trip to an exotic location to celebrate.  I ran some optimistic calculations and I thought that I might be able to “retire early!”  I considered all the ways my life might change and how I could pursue some long set-aside goals, such as spending more time woodworking, going to my kids’ school events, and finding that “amazing job” that perfectly matched my desires.


I went to college on an ROTC scholarship right out of high school at the age of 18.  My whole adult life was, in some form or fashion, shaped by the military.  I didn’t know what to expect from the civilian sector.  I heard all sorts of advice from senior leaders about the security of the military and how civilian jobs worked.  In retrospect, it’s pretty funny, because very few had spent a considerable amount of time outside the military as an adult.  It really was the “blind leading the blind” in this area.

I knew that civilians often had less stable jobs, that some civilians made more (or less) money than I did, and that our benefits were pretty good.  I had little information about how employable I was outside the military and I wasn’t sure what life would be like.

As I approached retirement, I knew that I was entering a new phase in which I would need to learn new skills and grow in new ways.


Military retirement was scary because I thought about all the good things the Army had provided to me and my family.  When I left my parent home to start ROTC in College, I was an 18 year old child who had only lived at home.   Throughout my adult life, I had received an Army paycheck, benefits, and extremely secure employment.  I knew who my friends were, how to dress for work, how to behave, and what to expect.  Leaving that behind was disconcerting.

I doubted that I would be truly employable.  I felt that much of my knowledge was hyper-specialized to the military.  Further, I thought that employers might question my ability to learn new things.

Preparing for retirement

Like many Army officers, I received some pretty clear signals that retirement was approaching.  I was an alternate for battalion command, but was not selected.  After my CSL looks, I took a deep breath and realized that the Army had given me a fantastic signal.  It was now time to start thinking about the future outside the Army, while still doing some good work inside it.  I think some of my best staff work occurred at this point, because I was a “dangerous Lieutenant Colonel” with lots of experience and a desire to see the right things happen for the Army and for Soldiers.

I started thinking about retirement in early 2018, after that CSL look.  I started going to the doctor, ensuring my medical records were up to date.  I started to make a plan to eliminate any debt and build up a cash reserve.  I also started to research the SBP program.  Once I knew more, I looked into commercial term life insurance to give myself a potential alternative to SBP.

“Caterpillars talk to caterpillars, butterflies talk to butterflies”

As I started thinking about retirement, I realized I was mostly talking to active duty folks about it.  I was once again blind, talking to other sightless people.  I found it much more helpful to reach out to my retired friends to get their perspective.  Almost all of them had great transitions and consistently told me: “retirement is great.”  My favorite quote from this was my friend Pat Major, who told me the quote above.  I was still an active duty caterpillar, but I needed to talk to the butterflies.

Additionally, a great bit of feedback was “focus on taking care of your medical and administrative requirements, those have a clock and they are really important.”  Looking back, I can’t agree more.  Most of the actual work of leaving the military falls upon you, no-one else helps you with that.  That includes writing your retirement award, taking care of your clothing record, clearing the installation, and making sure your financial records are properly closed out.

Employment nuggets and my story

Like most active duty people, the number one question I had was: “how will I survive and pay the bills?”  My friends assured me there were a lot of good opportunities, and that networking, polishing my resume, and continuing to look would yield good results.

Many of us on active duty described how we would find the “perfect job” after retirement, maybe being a “harbor master”, “dive coach”, “finance executive”, “VP of Operations”, etc.  Some will be able to achieve the dream, by investing significant time during their final year in service.

Keep in mind, though, that the military gets a vote on all of this until you are retired.  Being on the Army staff, I worked pretty hard up until my permissive TDY started.  I didn’t have a bunch of time to attend job fairs (which were all virtual due to CoVID-19) or do much research on what I wanted to do.

Faced with those challenges, my number one effort was to enter civilian life, find something that allowed me to employ skills honed over my career, and develop new ones.

Another thing that I, and a lot of other retiring/separating service members I know, had trouble with was knowing when to advertise our availability.  Don’t do this until you are seriously ready to entertain offers.  I started getting calls within a few days of posting “open to work” on my LinkedIn.  You need to know that companies are generally looking for people to fill an opening as soon as possible. They have a problem they are trying to solve.  When you post availability, they will see you as a potential solution to the problem they are trying to solve.  In some rare cases, they know you and they will try to sign you early, but that is much more unique.

Networking really helped me.  I worked on my LinkedIn profile, and I announced my last day in the office on Facebook.  Within five days, some of my old colleagues and friends were reaching out to me about positions. I decided that my number one priority was to work in a field where I had some competencies (IT) and, most importantly, work with people I liked, in a comfortable environment.  Immediately after starting transition leave, I joined Phase II.   It was a great fit, I knew almost all of the management team and I had many friends who had performed consultant work.  It’s allowed me to grow into this next phase of my life, to learn to work as a civilian, to gain new skills, and to help other veterans.