At what period in life, does one accept their relative stage in their employment and stop looking? At what point should I start planning my final retirement?
NEVER ... not until you are satisfied with your work! Don't settle.
And if you are already thinking about retirement while in a dead end job or a job that doesn't fuel your passion, then perhaps think about how to take it early?
"Any form of complacency is the kiss of death for any professional." ~ Joan Rivers
Best to you!
As Gerald says, tough question.
Scanned your profile and you are bringing solid skills and experience to the table. You are a veteran "Veteran Logistics Specialist". As a Staff Sergeant, you have management experience. You added educational certifications to further strengthen your value.
On the other hand, the wording of your question suggests looking at how you are transitioning all that into the civilian culture.
You were told "You're a Veteran. Everyone will want to hire you!" Civilians may pay lip service to Vets -- "Thank you for your service." -- but the civilian sector is a cold world where "What have you done for me lately" rules.
Your career goal, "I've tried to remain in the career field I was in while serving", requires that the civilian sector provide you with the same structure as the military sector and it precludes you finding motivation that might better match the culture of the civilian sector company you join. Only large companies in the civilian sector can match the Military's ability to let you be a single-function cog in a system. Most civilian employees have to be useful in a variety of ways. Smaller companies create the most jobs and they need people to move things (Logistics) but they also want you to be interested in what's being moved.
You say that Management says "I can't make work for you to do". Are you too low in the hierarchy?
You also say "after two college degrees and certifications, here I am; sitting around waiting for something to do."
What I remember most from my father's transition was the stark difference between the security offered by the Military and the insecurity that par for the course in the Civilian sector.
I suggest that you not expect anything for having served, shift into a sector that interests you profoundly, keep Logistics as your core offer but also offer everything else you know, shift to a smaller company where you can manage people (remembering that civilians don't take orders), and don't every be "sitting around waiting for something to do."
When you stop expecting security from your employer life gets a lot scarier but in that cold reality you are also free...so soar!
Speaking to you from the heart,
I've tried to remain in the career field I was in while serving. Can't say life has been good. I'm in a job that has no visible upward mobility.
Was told "You're a Veteran. Everyone will want to hire you!" Well, after two college degrees and certifications, here I am; sitting around waiting for something to do.
Management says "I can't make work for you to do. "
I guess that depends on what your goals are. I just saw a feature on the news about a barber that's 90+ years old, he started when he was in his teens and has no plans to stop.
So, I believe it depends on your goals and what you want to do moving forward. These days, it's much easier to make a career change in later years than ever before. Consider your goals and all your options as you consider acceptance of your current situation as well as retirement.
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