The Military Guide


5 Reasons Why Military Retirees Keep Working


A reader posted a forum comment about his co-workers:

I’m always intrigued when I hear about recently retired military personnel with pretty good pensions who take new jobs after retiring in their mid to late 40’s. If they want to work that’s fine of course, but it’s pretty sad that many of them probably feel they need to work, because of society, pressure from their spouse etc. My personal favorites are the upper middle class level military retirees, like junior officers up to majors whose pensions are somewhere in the ballpark of my annual earnings (or maybe more) and are working at new jobs. A clear case of financial independence and not knowing it, or at least not embracing it.

It’s far more nuanced than that, and everyone faces similar issues when they reach financial independence. I’d pay attention to these examples (positive or negative) and learn from them.

Commitment to service

Some retirees feel a commitment to service because they’ve spent over two decades taking care of people. It feels perfectly natural to move to customer service, education, police/security, EMT/medical, or some other field that lets you continue to take care of people. One of my college classmates earns a large income and donates it to charity. He’s just happy to show up to work every day and help other veterans. I joke that he’ll never learn how to retire, and he jokes that he’s given up on finding me a job.

Image of money in a pile of 20 dollar bills |
It’s not just about the money.

I personally fit into the “take care of people” category. But I want autonomy to go with my complexity and fulfillment, and I don’t want to take on the commitment of supporting a team. Writing on my own gives me the best compromise.

“You Can’t Handle The Truth!”

A few vets have acquired the “military inferiority complex”. We’ve been told our entire time in uniform that we’re worthless and weak, we’re barely able to perform at our current rank (let alone promote), and we can’t hack it in the civilian world (“Now drop and give me 20!”). Then we leave active duty for the Reserves/Guard (or leave the military entirely) and we discover that we have skills. Those core skills that we bring from the military (augmented by training in the new job) can translate to fulfilling careers with ample incomes. I’m sure a few vets belatedly realize that they let themselves be tricked into staying in uniform as long as they did.

I’m a nuclear-trained submariner and I still feel like that myself occasionally. I’m perpetually surprised at the revenue opportunities all around me with low barriers to entry. I personally regret staying on active duty for 20 years when I could’ve gone to the Reserves at 12 (but was too busy and too ignorant to recognize the opportunity).

Some retirees just want to see whether they can hack it in the tough civilian job market. If you got paid six figures to supervise a financial educational foundation with a few employees, you’d be tempted. If you knew that some of your routine would be talking story with clients in their 20s, traveling around the nation, attending events, and doing interviews for national media… why would you ever retire from that career?

Some vets want to see what they can do with their abilities. I personally know at least two dozen military veterans who worked hard to become entrepreneurs (Blake Hall of comes to mind, as does Jacob Wood of Team Rubicon). When you can apply your military skills to a project where you have complexity, fulfillment, and autonomy (plus a lot more control than you had in the military) then you have no reason to quit.


Some of us are adrenaline junkies. We thrive on danger & crisis, even if it’s “just” a short-term administrative deadline. That motivation certainly correlates to careers in police, fire, security, medical, disaster response, sports, and just about anything competitive. And yes, it’s generally a testosterone-poisoned issue, which in my case is mostly handled by surfing & full-contact taekwondo. Yet even my spouse, with her background in emergency planning and disaster response, can hardly bear to watch our state civil defense staff scramble to keep up as the hurricane approaches.

Some vets start a bridge career for the camaraderie, especially in the defense or utility industries. It’s a whole new audience for your sea stories, and it’s much of the routine that you were accustomed to on active duty. Nuclear reactor operator at the electric company? Maybe. Test pilot or aircraft designer? Sure! It also involves elements of service, adrenaline, and climbing the career ladder. But it’s good to hang out with people you enjoy being around.


A few vets have their identity tightly tied to their military career. They didn’t really develop many outside interests, let alone hobbies. They miss having a staff whose sole duty seemed to be to entertain them and make them feel needed help them get things done. Now they’re adapting to a new identity and trying to figure out how to do things for themselves. Eventually they’ll have to figure out what they want to do with the rest of their lives (or have it figured out for them by a major life event)… but not today.

Coping Mechanism For Disabilities

A distressingly large number of vets are severely disabled and dealing with tremendous pain or depression. Working might not be a fun barrel of monkeys, but it gets them out of the house and distracts them from problems that will accompany them for the rest of their lives. For a few, it gives them a reason to live… or at least to not think about killing themselves today.

For a few, it gives them a reason to live… or at least to not think about killing themselves today. The vets in this category are generally glad to be employable, especially considering that they’re paying huge sums for long-term care insurance or concerned about having enough assets to cover their care if they’re crippled. This issue doesn’t always manifest as a wheelchair or other visible signs, either— I personally know a few dozen veterans who struggle with huge issues on the inside that can’t be seen from the outside.

A Changing Family Dynamic

Some vets have disabled family members who will need lifetime care. The vet is contributing their income to a special-needs trust or paying for caregivers.

A very few vets start a bridge career because they’re uncomfortable with their families– or their families can’t stand having them around the house.

These vets have been absent for much of the family’s last 2-3 decades, and they don’t understand who’s really running the household. Instead of hanging around the home trying to take charge, or optimizing domestic routines, or setting new disciplinary standards, or offering helpful suggestions… they come to the workplace where they can be paid to do those things. Or their spouse told them to find a job and get the heck out of the house for at least eight hours a day.

All too many vets have gone through financially devastating divorces. It’s possible that those “upper middle class level military retirees” with “pretty good pensions” have given at least half of that income stream to their ex-spouses. On top of that they may also be paying child support, college expenses, or even mortgage payments. This is a controversial and highly-charged issue among both vets and ex-spouses.

A handful are trying to make up for perceived failures in their military careers. One of my old commanding officers claims that there are dozens of retired generals, admirals, and senior enlisted who are crying themselves to sleep every night because they only made the top 10 of their rank instead of being #1. That CO, however, cheerfully retired to start his consultant firm to advise other companies on corporate crisis management.



But yes, the original comment at the top of this post speaks some truth. A fraction of the military’s retirees never saved any money on active duty, and they have the possessions to prove it. They have no idea how to manage their finances, and frankly they don’t see the point.

They just keep converting paychecks into new consumerism lifestyle responsibilities as quickly as they can. They’re usually assisted by one or more spouses and perhaps adult children. Because life is too short to drink cheap beer, even if they’re working 40+ hours/week to pay for it.

I personally knew a retired admiral who never saved or invested. He was well into his 70s and still working to pay for his family’s lifestyle… because his pension wasn’t enough to cover the expenses.

“Wait, what?”

It’s possible that some military-retiree workers are blissfully ignorant about financial independence. Please send them my way so that we can help them work through the lifestyle questions.

Call to action:

Rather than feeling sad for your co-workers, you could ask them what motivates them to go to work. The answers might surprise you and could offer new opportunities for self-reflection on your career goals.

Another poster chimed in:

I’m financially independent, retired from the military with 22 years. I’m 44 years old, single, and can easily live off my pension and savings. I have a paid off residence and a paid off car. I just always wanted to teach. When I retired I started in JROTC (high school) and then moved to a contractor position as a college ROTC instructor in a location I preferred.
I don’t know for how long I’ll do it, and I have a ton of things I want to do when I stop working. It was just something I wanted to check out. It was a chance to figure out my actual expenses after living overseas for many years. I also liked the idea of having a “soft landing” and some structure in transitioning from military service to civilian life and eventually to full retirement.

If you’re a military retiree who’s financially independent and still working for a paycheck, please tell us why! Your story will help other servicemembers understand, and it may even motivate them.

Related articles:
Outliers: The Story Of Success by Malcolm Gladwell
Finding Your Military Work-Life Balance
Reader story: Stay For 30 Or Retire At 27?
“Just One More Year” Syndrome
“I’m Setting A Good Example By Working At A Job”
Ernie Zelinski’s Get-A-Life Tree