3 Questions to Ask Before Continuing or Separating from the Military

Photo by Luemen Carlson on Unsplash

Serving in the military is a time-honored tradition for some Americans and their families. Such so, that our culture and politics continues to highlight the esteem of military service and the reverence placed on service members. The topics of national defense and the military have always served as talking points for political candidates, the inspiration for Hollywood action movies, and as a nontraditional career path for entering the workforce.

We can further see the importance and priorities the military receives by looking at how Congress handles it’s yearly budget appropriations. On multiple occasions when the federal government has had to shut its doors, congressional bipartisanship has passed bills to continue funding the military. These bills pass because Senators, Representatives, and Presidents can’t afford to lose political capital for alienating the military. “Support the troops” has become America’s unofficial slogan.

Regardless of how you view the military as a whole, most individuals come into the military, hoping to take advantage of the benefits and pay. I can’t even count how many people I’ve talked to that said they joined in paying for college, travel, or as a way to support their families.

What do I know about the military?

Before spending my Saturdays writing tech-related articles, I committed seven years of my life to the United States Air Force. I enlisted back in 2009 and started my career as Cyber Transport Systems (3D1X2). To those unfamiliar with the career field, it’s not driving around a Tesla Cybertruck, though I might reenlist if that became a possibility. The following is how the Air Force describes the Cyber Transport Systems role.

A vast, global communications network is one of the many things that makes us the most powerful air force on the planet. Making sure the underlying infrastructure of this network is operating properly is the responsibility of Cyber Transport Systems specialists. Whether it’s repairing a network hub at a stateside base or installing fiber-optic cable at a forward installation overseas, these experts keep our communications systems up and running and play an integral role in our continuing success.

Around my seven-year mark, I decided to separate and take my chances in the real world, like billions of people across the earth.

Like a good portion of vets, I ended up becoming a defense contractor. This employment choice provided me the perspective of being involved in the day-to-day operations without being beholden to the rigor and stress of military expectations. Still being surrounded by Active Duty members, it’s no surprise I get asked often, “Should I get out or stay in?” So let’s dive into the three things I tell people to consider when faced with that dilemma.

1. Are Your Skills Transferable to the Civilian Sector?

This question makes people assess the skills and talents they have been cultivating since entering the military. The main factor is taking stock of both the hard skills (career-field specific) and soft skills (managerial/interpersonal skills). If you were an infantryman in the Army, it would be quite a challenge to find employment outside of security contracting or law enforcement, that values being able to perform 12-mile road marches or proficiency in firearms. In contrast, I’ve also seen tons of forums where prior infantrymen claim to have become successful Wall Street traders because the Army taught them how to handle themselves under pressure and developed higher levels of discipline compared to other members of society.

Photo by Specna Arms on Unsplash

Of course, there are also highly technical career fields like my former profession or aircraft mechanics. At the end of my enlistment, I was applying for Senior Network Engineer positions because the Air Force was able to train me in both hard and soft skills that were in demand.

2. What is the Market Outlook for your Profession?

Let’s say you want to stay in a related profession like the one you have been enjoying (or hating) so far. Would you be better financially in the private sector?

The Army has an occupation called Culinary Specialist (92G). Their primary duty is mostly cooking for the other members. An E-5 with minor supervisory responsibilities in the Army, living in Alaska, makes about $66K a year. This figure doesn’t include free healthcare, free education, and highly competitive retirement benefits. A comparable position, in the same location, averages around $31K annually. This comparison might be a good enough reason to decide to stay in the military.

One of the downsides of military pay is that it doesn’t reflect competitive rates for all positions. If we took that same rank and location but made the person working in the Cybersecurity field, they would still receive the same $66K a year. Again, in that same location, someone working in Cybersecurity outside of the military could earn upwards of a six-figure salary. Perhaps those six figures are incentive enough to get out.

Photo by Markus Spiske on Unsplash

Lastly, we have to factor in section 1 to this consideration. Are you basing your decision entirely on the training provided by the military, or did you pursue applicable education, licenses, or certifications in your spare time? The armed services have tons to offer, but its still a gigantic, bureaucratic behemoth, slow to incorporate new processes, technologies, and methodologies into daily operations.

I had a commander that used to say, “We are using yesterday’s tools tomorrow.”

3. Do you enjoy the military?

Writer’s Note: Some argue this question be the first thing you ask yourself. I disagree on the basis that the answer is entirely subjective. If you enjoy your time in the military, you are less likely to look into the world of possibilities outside the DoD. I know an Air Force member that thought the military was the best thing in the world. That was until I showed them the perks and benefits afforded to people in their career field by both large companies and startups. Anecdotes aside, we’ll dive in.

Few organizations can provide challenges and fulfillment afforded by the military. Even fewer can provide the same level of camaraderie and personal support. And even fewer than that can provide you with a mission and purpose on such a large scale. Also, if the DoD mission is to mobilize military forces needed to deter war and to protect the security of the United States, the DoD engages in many peacetime operations that positively change the lives of people across the world. These operations delivered critical supplies to an earthquake-stricken Japan, relief efforts after Typhoon Haiyan hit the Philippines, and medical support after the Ebola outbreak in West Africa. What other organization or company can accomplish so much?

Regardless of how you answered the previous two questions, if you love what you do, then keep doing it. Personal satisfaction from such rewarding opportunities can easily be more fulfilling than a high salary on the outside.

If you aren’t happy or are just looking for new experiences, circle back to Sections 1 and 2. You’ll be able to evaluate better what you need to do to prepare for life outside of the military.

Final Thoughts

Even nearing the end of my enlistment, I was sure I would be continuing my service. It wasn’t until a 6–8 months before the end of my contract that I decided to separate. Even though I planned to stay in the military, I spent parts of my time self-educating and preparing for civilian life on the off chance that I would be making the jump. If I did not exhibit my due diligence, the transition might very likely have been a disaster. As the adage goes:

Expect the best, prepare for the worst.




Cybersecurity Professional, AI Engineer, Data Scientist

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Kyle Topasna

Kyle Topasna

Cybersecurity Professional, AI Engineer, Data Scientist

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