Is Doing 20+ Years in the Military Right for You?

Let me start by saying this: I believe every able-bodied young person in American should serve at least 4 years in the US Military. The tangibles and intangibles of serving will provide a solid foundation and will last a lifetime. Some of the tangibles are learning a skill, travel, and getting access to both the VA home loan and G.I. Bill. Some of the intangibles are discipline, leadership, and building lifelong friendships.

First, I want to touch on my military background. I joined the military in 1999 and am currently still on active duty. I am a Master Gunnery Sergeant in the Marine Corps (the rank of E-9). I have been based in Japan, Niger, Turmensitan, Finland, Arizona, Florida, California, and South Carolina. I am an Air Traffic Control Systems Chief. 

Doing 4 years in the military is an easy decision if you have the personality for it. By personality, I mean how you choose to see the world. The military will take away some of your freedom and liberties; this is a fact. It depends on you and how you choose to see these sacrifices. If you envision the greater good that these give you, the military will be right for you. If you hate that someone has removed your freedoms, and dwell on them, then the military isn’t right for you. It comes down to a scarcity versus abundance mindset.

Let’s do a quick example to expound upon this point. I have served in Japan on 3 separate tours of duty. When I come to Japan, I say “Man, it’s amazing that the military moved my family to Japan for free. I also get paid extra to be here. The military arranges trips and excursions for us to explore. Thank you military!” Others say things like this, “I can’t believe I have to come to Japan, I should have gotten orders somewhere else. The military controls my freedom here in Japan. I have a curfew and very specific distances I can travel. I do not like Japanese culture.” 

It is easy to deal with the limits that the military imposes on you for 4 years. When you get past that, only a special breed of people can keep going until 20 years. Many people want to complete 20 years but there are many obstacles that can impede your journey. Some of these are ego, fitness, body, mind, and family. I want to expand on each of these.

Ego. Ego is the number one ender of military careers. The military is filled with ego-maniacs. That is a part of life. What we do is dangerous and it takes a unique mindset to do it. If we go to Afghanistan, we will need to have an “invincible” mindset. The problem is that as people grow in rank, this ego can cause them to do “stupid” things. It causes people to harass others, demand favors, treat others like crap, violate orders and procedures, and generally make a fool of themselves. I call this “thinking they are above the law”. A lot of power is placed in the hands of leaders; power over other peoples’ lives. Many cannot handle this. “With great power comes great responsibility”.

Fitness. For this bullet, I am specifically talking about diet and exercise. The military is mostly easy for people 25 and under. However, as we age, we will need to concentrate on our diet and fitness. We have to look good in uniform and be able to pass physical tests. Getting married, having children, deploying, etc.. all lead to a broken fitness routine. When we have a family and pick up a higher rank, we are mostly removed from the unit physical training program. We are expected to maintain our fitness and diet on our own. This can be very troublesome for many people. If you do not like exercising and maintaining a certain weight standard, doing over 4 years is not for you.

Body. The military will destroy your body. From running, hiking, deploying, traveling, etc.. the wear and tear on your body is ridiculously high. Staying the distance in the military may not be up to you. I have seen many Marines get out due to their body not holding up. The military is particularly hard on shoulders, elbows, backs, necks, legs, ankles, and feet. On top of that, you could also suffer from injuries caused by combat, car accidents, and off-duty incidents. Remember, in order to stay in for the long-haul you will still have to complete a physical test. If you break a leg in a motorcycle accident, you will get some time to heal. However, at some point, you will have to pass a physical test with that leg.

Mind. You are going to see things in the military that you wouldn’t want to see again. Even if you are not in a close combat-related job, you will still be exposed to unnerving sights and sounds. Post Traumatic Stress Disorder (PTSD) is a real thing. I won’t talk about some of the different things that you could be exposed to, but just remember, you will be surrounded by very young, macho people and lots of weapons and machines. Separately, when people are in young relationships and they get orders away, some people can’t handle it. When you are deployed and someone gets a “Dear John” letter, it could be unnerving to see this person with a weapon. The suicide rate is high. In order to go past 20 years, you will need to have an unbreakable mindset. 

Family. If you are lucky enough to survive these four downfalls, then the final one might get you. Each dependent that you add (spouse and children) will also need to pass these downfalls as well. First, you will have to find a spouse that understands that you will be gone a lot and that changing households will be a constant headache. Then, that person also needs to stay mentally and physically strong as well. If your family can’t survive without you, then you are non-deployable. I have seen so many families do very well early in their careers. Once the servicemember gets moved to a station near home or to a non-deployable unit, the servicemember and family get very comfortable. Once it is time to go back to a deployable unit, the family resists. A servicemember cannot last in the military without a strong spouse and resilient children. However, I have seen multiple cases where the spouse is stronger than the servicemember. 

These are the top reasons that people cannot complete a 20-year retirement. Most people who decide to go past 4 years would like to try to make it to 20. However, let’s take a quick detour about mindset. After you decide what mindset you have, I will touch on how to leverage the military over 20 years to make yourself an invaluable member of society.

There are two opposing mindsets that most people do not realize exists. These two mindsets are security and freedom. You can say it in multiple ways: job security versus financial freedom, an employee versus an entrepreneur. I bring these mindsets up because as you continue to stay in, you will realize many people are hiding out in the military. They could not survive in the real world. You will also see people who are fully taking advantage of everything the military provides. Let’s quickly take a look at these two mindsets so that you can understand why it is dangerous to hide in the military and why you should be preparing for your eventual exit.

Security mindset. No matter how you look at it, the military pension is amazing. So amazing that for many people their only goal is to get their paycheck. I have heard multiple people say “I just retired after 20 years, now it is time for my spouse to carry the burden.” “I did my 20 years, I am good. I’ll go work at Walmart”. The scary part is that they mean it. Do not let this be you. The military pension is a great start to your life. However, do not let it limit your dreams. Dream big and let the military be a stepping stone to a higher purpose.

Financial Freedom. I have seen this play out two different ways. I have seen people set themselves up to become super employees when they get out and others become full-on entrepreneurs. Either way, the military can help you achieve your dreams. I was setting myself up to become a super employee until I stumbled across the path of entrepreneurism. The military provides infinite ways to improve yourself, however, it is not going to hold your hand. In the end, the military wants you to pick up a gun and go to war. Anything you do beyond that is on you. 

Now let’s look at some of the benefits of staying in 20 years. I will break them down between the super employee and the stout entrepreneur. Each person can do well in the military and use the military as a springboard to obtaining great wealth. 

Employee Education. The military has tuition assistance which covers the cost of a civilian college degree. This is separate from the G.I.Bill. Over 20 years, you should be able to get a bachelor’s degree and a master’s degree. I have known many people do this. And if you are an officer, it is expected. The military has a program called troops to teachers that helps you get your teaching certificate before you retire. Also, as a 20 years veteran, you are in a prime position to get a teaching position as a Reserve Officer’s Training Corps (R.O.T.C.) instructor. 

Entrepreneur Education. I did not take one day of college during my 22 years of service. However, I am now taking advantage of entrepreneur programs inside the military. The military has a program called boots-to-business that helps create military small business owners. They offer free business courses at large colleges. The Small Business Association also backs veteran business loans, as does the VA. The number of business opportunities in the military is staggering, and spouses can get it on the fun as well.

Employee Training & Certifications. There is a never-ending amount of certifications and training that you can attend and obtain while in the military. The training can be even remotely based on your military specialty. Programs such as lean six sigma, program management professional (PMP), Security+ and Network+, teaching certificates, Department of Labor apprenticeships, etc. If you use your time wisely, you can obtain a new certification each year, on top of your college degrees. You can easily become the top qualified applicant for any job, and you have 20 years of experience to back it up.

Entrepreneur Training and Certifications. You can use the above qualifications in your own business. You can also use your military background to set yourself up to obtain business loans across a wide range of lenders. People love military veterans. The military will teach how to leverage this to start a small business.

Employee Travel. Once you get past 20 years, traveling in the military takes on a whole new meaning. Since you have set yourself up to be the super-employee, you can leave the military when the right job opportunity shows up. You will be able to network yourself and get the job you want. I have seen many people leave in uniform on a Friday and arrive to work in civilian attire on Monday, as a civilian employee. They played the game correctly. 

Entrepreneur Travel. Making connections is a must for entrepreneurs. While having a homestead in one location is preferred, you can still be very successful while in the military. Moving your business to online-only will make it leaner, more agile, and 100% portable. This lean mentality will make you a lethal entrepreneur. Embrace the online world. And when you retire, you can build out a physical location based on your online business. All too often, veterans wait until they retire and set up a business near the base. They create a job and not a business. 

Super-Employee final thoughts. The military will train and equip you to become great in your military occupational specialty. Then they will pay for multiple college degrees. On top of that, they will pay for important certifications and apprenticeships. Going further, they will give you a network of employers and give you veteran preference for government jobs. However, you have to decide to take advantage of all these programs. The best thing about the military is the mentorship. If you mention any of these programs, someone knows someone who took advantage of them. You can navigate these programs very easily. In the civilian world, you may not have anyone that will help you to this extent. Everyone who leaves the military after 20 years should be walking into a six-figure job, to put it bluntly.

Stout Entrepreneur final thoughts. Most of us military types will have to learn to become an entrepreneur. A lot of us joined for job security. Becoming an entrepreneur is the exact opposite of job security. I found that I have a passion for this challenge. I am now using my remaining years in the military to build up my business mindset and business network. The military is a great place for entrepreneurs to learn their new trade. And when we get out, we have a safety net. Also, the military allows us to get involved in real estate markets that we may not have had access to before. It really is a great opportunity. Every entrepreneur should walk out of the military prepared for the exciting world of business.

So, is doing 20 years in the military right for you? It is a tough question for sure. I always see the glass as half full and focus on all the benefits the military provides. If you have that mindset, then there are an unlimited amount of programs and assistance available for you to become a great employee or entrepreneur. I have no regrets about doing 22 years and counting. I am prepared for the next step when the time comes. I have built an amazing life because of the military and have seen the world. It is also important to point out that you can also do between 4-20 years as well. The retirement plan inside the military has become more portable due to 401K style plans. Only you can decide what is best for you. If you would like for me to expand on any of these topics, please leave me a comment. I have only touched the surface of the benefits of the military. I think the benefits of the military far outweigh the negatives. What are your goals and how do you plan to achieve them? Let me know in the comments below. 

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Disclosure: I am not a financial advisor or money manager, and any knowledge is given as guidance and not direct actionable investment advice. I am an Amazon Affiliate. Please research any investment vehicles that are being considered. I wrote this article myself, and it expresses my own opinions. I am not receiving compensation for it.  I have no business relationship with any company whose stock is mentioned in this article.


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