Is it more difficult to obtain employment in the civilian sector if you obtained your degree too far in advanced before retiring?

I worked in both the private and public sector as a hiring manager. Often experience and accomplishment will trump education. Recent education may be great for a highly technical field, such as cyber security, but otherwise a track record of accomplishments in jobs of increasing responsibility is better. Companies or Government agencies may look for "recent graduates" for some jobs. They often are entry level jobs with fairly low pay. The organization is probably looking to hire low and then grow an employee with the needed knowledge, skills, and abilities within their own training programs; or they are just cheap and will exploit your knowledge and abilities until you burn out. For management jobs, a degree is often a "requirement" but more of a square filler. The company or organization may want all of their project managers to have at least a bachelors degree and be a certified Project Management Professional. They will advertise for that and usually hire against that standard. Sometimes Government contractors will be hiring against a contract specific requirement. For example, they may have promised the Government that all of their "Senior Analyst" labor category personnel will "have a Masters Degree or 10 years relevant specialized experience." The Government may never check the qualifications of the people on the project, but I always did. Read the job requirements carefully and shape your resume to match. If the employer puts education up front in the job requirements, put the education block near the top of your resume. That way the HR person can see it, check off the requirement, and possibly put your resume in the "look at" pile for the hiring manager. If education isn't mentioned, then put the education block after the experience block on your resume. My bottom line: it's best to have both education and experience. Often experience with great accomplishments is better than a degree.

Get your degree when you can -- it will assist in your military career progression also. As you approach transitioning from the Army, obtaining a degree should not and need not be one of your concerns. I've seen too many wait until the last minute to get their degree; retirement is a significant emotional event and you don't need the additional stress.

Finding employment is conducting your own research into what profession you want to be in, network with folks in that profession and at the company where you want to work.