Is Doing 20 Years in The Military Worth It?

One of the most fascinating and difficult questions I’ve ever tried to answer goes something like this, “So, is staying 20 years to retirement worth it?” I’ve given various answers, but as I’m nearing the end of my time in the Army, I’ve personally been thinking about military retirement more.

A big part of why I started Enlisted Money was to help people like me get their finances in order so they can choose to stay (or leave) and feel empowered to live life on their terms. I made the choice to stay in because of money for my first reenlistment, less so the second, and a bit more the third (and final) reenlistment.

So, let’s get into it. Is it really worth doing 20 years in the military?

Understanding the 20-Year Military Retirement

First off, let’s talk about why you’d want to stay in the military for 20 years in the first place. It’s actually one of the most famous and notable benefits of military service. In general, if you serve 20 years of service, you’ll earn a pension (retired pay) for the rest of your life.

The most unique part of the active-duty pension is that you start receiving retirement benefits immediately after you exit service. Reserves and National Guard work a little differently, and typically start to receive their retired pay at age 60 (but there are always exceptions). For me, I’ll start receiving retirement benefits at age 39.

Legacy Retirement System

Many retiring servicemembers today are part of the “legacy” or “high-3” retirement system. The short of it is you get 2.5% times the number of years served, times your average highest 36 months of base pay. So, at 20 years, you’d get 50% of the highest 3 years of base pay.

For me, I’ll have an estimated pension of $3,200 per month. My life expectancy is another 38 years, and I’m 38 years old today (based on Social Security life expectancy tables). That means I’ll receive an estimated $1,459,200 in retired pay alone. However, the lump sum, net present value of that today is much more.

The Blended Retirement System (BRS)

There’s a misconception that the Modernized Retirement System, often referred to as the Blended Retirement System (BRS), isn’t as good a deal as the Legacy system. I disagree. It’s more complex but offers some very unique benefits for service members.

The biggest basic differences are a lower service multiplier (2% per year for the pension), Thrift Savings Plan (TSP) matching, and Continuation Pay (a unique mid-career bonus). This means a 20-year career would earn you 40% of your highest 36 months of base pay instead of the old 50%.

However, if you start investing in your TSP early, take advantage of matching contributions, and take Continuation Pay (and invest it), you will likely be ahead over time. If I could go back in time and choose, I’d choose the BRS.

Other Benefits Add Up Too

On top of the retirement pay, I’ll also have access to cheap healthcare for life for me and my family. I transferred my GI Bill to my son before he could say the word college. If the average price of in-state tuition stays the same, that’s worth around $46,440 to $123,120 or more on average. That’s not even including the housing stipend.

There are also numerous benefits and discounts available to veterans and their families. Many articles have been written about all the different benefits. These little things can really add up.

Non-Financial Benefits of 20 Years in the Military

It’s hard to really understand the true impact of military service until you’ve done it. Disclaimer: experiences may vary – a lot. Even if two people are in the exact same unit at the exact same time, their experience will be different.

Hard-Boiled Eggs and Mashed Potatoes

If you’ve ever heard the saying that an egg hardens when you boil it and a potato softens, the military can be the same way. In my experience, a lot of your qualities you already have will be amplified by military service.

Actually, money does something similar. In a way, they’re both catalysts for whatever your natural predisposition is. However, the unique experience and pressures of the military can shape and change these to an extent.

So, in other words, you are a key variable in whether you become a hard-boiled egg or soften into mashed potatoes when exposed to heat (the stress of military service).

Personal Fulfillment and Sense of Accomplishment

One thing I look back on and count as a blessing is the amount of responsibility I was given early on. I was put in charge of millions of dollars of equipment, many Soldiers to care for, and highly sensitive missions and information. I felt the weight of it, did my best, and grew a lot. People used to accuse me of having an “old soul” because of the seriousness I displayed.

I’ll never forget being a 22-year-old Sergeant put in charge of 52 Soldiers headed to Afghanistan. I can still remember staying awake for what felt like days, trying (and eventually succeeding in restoring communications in rough conditions.

You Create Your Own Reward System

In most cases, I felt my achievements weren’t valued the same as my peers, but that just happens sometimes. I decided early on that the one thing nobody could take away from me was the fact that I gave 100%. I still carry that same attitude as I enter my final stretch.

Lifelong Camaraderie, Network, and Community

The number one thing I’ll miss about being in service is the people. Where I grew up, there was no diversity at all. We all looked alike, talked alike, and thought the same thoughts. Whatever the most boring flavor of vanilla is, that’s what we were.

When I joined the Army, I was instantly exposed to so many new fascinating people and cultures. I traveled all over the world (mostly against my will) and gained experiences which have permanently given me a new perspective on life. Our tours in Germany and Korea were fantastic experiences.

However, these experiences only deepened my love for America. I’ve always found it fascinating that overseas, there are many countries where you can easily spot who doesn’t belong. But in the military, everyone looks different, yet we’re the same family. America doesn’t have a look, but I know what it’s supposed to feel like. We have a special kind of freedom that you’ve got to feel to understand.

I have special bonds with the people I’ve served with. We’ve been in “the suck” and we’re all a (very strange and rowdy) family.

Potential Downsides and Trade-Offs of Military Retirement

Don’t get me wrong, there’s a reason why most service members leave after one term and very few stay to retirement. It ain’t easy.

Physical and Mental Toll of 20 Years

The physical and mental toll of military service is real. I actually feel like the mental aspects are the most difficult. In many cases, you just have to “suck it up” and drive on. This is very glamorized, but it can take a toll.

Even non-combat specialties have a lot of physical aspects to the job. Carrying heavy loads, working long hours, ridiculous exercises five days a week, poor sleep cycles (night shift, staff duty, etc.), and more can really wear down your body. I don’t know how many miles I’ve run in my career, but it’s enough to give me arthritis in my foot and back, and I’m not even 40.

Challenges to Getting Help

Going to the doctor is often a pain in itself. Depending on where you’re at, specialty care may require a referral off-post, long travel times to another installation, or may take months to schedule. There’s a saying that you can have two out of these three: cheap, fast, or good. Well, I’d say you really only get the first, never the second, and the last only if you’re lucky.

For many of us, we just take our daily “vitamins” (you know, Motrin), and keep pushing on because we don’t have time to deal with doctors or career-impeding profiles.

Mental Health Is Important

I’ve recently started going to therapy (which the Army provides), but it’s still time-consuming and inconvenient. There are many reasons why people don’t use behavioral health services, but none are more important than getting yourself in a good place.

I’ve also gotten counseling over the years from Chaplains and Military Family and Life Counselors (MFLCs), but I was always guarded in those conversations because of all the disclaimers they say up front. I’ve been pleasantly surprised that my therapist didn’t freak out or overreact when I opened up about my thoughts and feelings. I wish I’d gone sooner.

Bottom line, you have mental health resources available and should use them. Full stop.

Family Challenges

Between frequent moves, separations, and missed family events, it can be tough on the family. Luckily, I’ve been able to be a big part of my son’s life so far. Many parents in the military aren’t as fortunate.

I’ve known many spouses and children who have a hard time adjusting. They often didn’t sign up for any of this lifestyle. However, others do exceedingly well.

Regardless, I can totally understand why divorce and other issues happen in the military. My wife and I have had our fair share of struggles throughout the years. Big shoutout to Military OneSource for free counseling and other resources!

Career Opportunity Costs

In many cases, your annual income could be higher in a civilian career. In our case, having the ability for my wife to go back to work would be very helpful. My wife hasn’t been able to work full-time because of childcare costs for many years. The military lifestyle creates even more issues by cutting off support from trusted friends and family members.

Gaining Education and Credentials

When you first start life in the military, you have a baseline set of skills and qualifications. The military has a culture of an ever-growing list of “must-have” degrees and certifications to stay “competitive” for promotions and top assignments. In my opinion, most of these have more utility outside the military than inside it.

The side-effect is that your earning power outside the military will outpace your earning potential inside the military. In the military, your earning potential is permanently capped, but the opportunities are endless outside. However, the job security in the military is very good compared to “on the civilian side” of the job market.

My Personal Story of Wrestling with Staying to 20 Years in Service

If you’re reading this and trying to decide if you should stay past your first enlistment, you’re not alone. I think it might be helpful to just summarize my enlistment periods and the thought process that led to me staying. In short, I “step-sold” myself into staying longer and longer.

The resulting regrets are a big reason this blog exists in the first place. I want people who are brave enough, patriotic enough, and qualified enough to serve to have the ability to serve on their own terms, not because they feel they have to. Getting your personal finances in order is a big part of that.

My First Enlistment – 2005

When I joined the Army, I was looking to solve two main problems:

1. I wanted to do something more than what I saw around me.
2. I didn’t want to go to college.

There Must Be More “Out There”

I grew up in a place where nobody went anywhere. The people in my hometown are the nicest people you’ll ever meet, but I knew there was more in the world than a canvas of corn fields and truck beds. I guess you would say I was curious.

Why Would I Go to College?

I hated high school, and college seemed like harder high school that you had to pay for. I didn’t have money for college anyway. Everyone also said I should get into tech and computers. The Army offered me the opportunity to at least have access to free college and to give me a tech job. I chose satellite communications. In short, the Army allowed me to make everyone happy(ish).

Deploying to Iraq During the Surge

My first enlistment was mostly consumed by my first deployment. My wife and I started dating the summer before my senior year. We got married just two months before I deployed. We didn’t really plan it that way; it just was. The time apart was hard on us both.

I was a 19-year-old PFC (E-3) when my unit deployed in 2006. I learned a lot, got extended for a total of 15 months, and learned a ton about the world. We lost one of the guys in my company in a helicopter crash. My perspective on life was permanently altered.

Aberdeen Proving Ground

You probably couldn’t tell it now, but I used to struggle with being overweight (by the Army’s standards, at least). My biggest issue was that I have a small neck, and I carry all my weight in my love handles and “innertube” on my gut. For the “old” tape test, this is a terrible combination.

This made it so that I was on and off “the program,” and didn’t really feel like I belonged in the Army. I did get promoted to Sergeant (E-5) before I PCSed to Aberdeen Proving Ground (APG). I was dead set on doing my time and getting out.

You’re Going to Germany

My decision to reenlist was forced on me by a combination of things. I was put on orders to Germany, and we weren’t prepared financially. I originally asked how I could get out of the orders and was told I’d have to sign a “dec” statement (declination of continued service). They also gave me bad information about what a dec statement means. It’s not as life-altering as career counselors and early 2000s era First Sergeants and Sergeants Major make it sound.

I Had No Plan

On a TDY trip to Korea, an NCO of mine, SFC Del Rosario, pressed me on my plans after the Army. In short, I really didn’t have a plan. I said I was going to get out and go to school. For what, I didn’t know. I didn’t have any money saved up to speak of. As a matter of fact, I’m pretty certain our net worth was in the negatives. We had two vehicle payments, credit cards, and I may have still been paying off our wedding ring set.

In short, I had no plan, just ideas. After talking it over with my wife, we decided I should reenlist. Her job at The Home Depot wasn’t great, and it wouldn’t be enough to pay our bills. So, I kept the orders.

We didn’t know it then, but this experience became the catalyst for getting our finances straight. We made one more major financial decision to buy a brand-new truck to ship to Germany as a compromise between my wife’s SUV and my truck. Off to Germany we went!

Germany and Afghanistan

I’ll never forget the conversation my new Platoon Sergeant had with me the first night in Germany as he drove my wife and me from the bus stop to lodging. He asked, “When did you get back from deployment last?”

I said, “November 2007.”

He replied, “Good, you won’t have any dwell time issues then. We leave for Afghanistan in March.”

My wife held it together until we got to the hotel room, but she spent the first night in Germany worried and bawling her eyes out. Welcome to Germany!

The Next Reenlistment

Fast forward past a 9-month deployment to Afghanistan and a mid-tour PCS to another duty station, and we were once again trying to figure out what to do. We didn’t want to get out of the Army from Germany, so we decided to look into our options. I decided when I reenlisted the first time that I would “play it like I was in it to win it” regardless of how long I actually planned to stay in the Army. That was a wise move given what we know about my career now.

Voluntold for Recruiting

Because of that, I was looking at what a young Staff Sergeant (E-6) should do to be competitive for my “first look” for Sergeant First Class (E-7). I emailed my branch manager and asked for Drill Sergeant. I didn’t get any reply from her, just an automated email notification saying I was DA Select for recruiting. HRC has always had interesting customer service.

Through some back and forth with USAREC, I completed my packet and received assignment instructions for the Kansas City Recruiting Battalion.

I did sign a short reenlistment (and narrowly missed getting a big bonus). Somewhere in the middle of all this, we started our journey to become debt-free. We only had the truck left to pay off once we returned to the States.

The Final Reenlistment and Going “Indef”

I’ll spare you the boring details of how I started as the worst recruiter in my brigade, maybe all the Army, but ended as a Sergeant First Class (E-7) and top recruiter in my company. I worked really hard, built great relationships, and helped a lot of young men and women get a start to their Army career.

Over the Hump

At that point, I was just over the ten-year mark in my career. I was, as they say, “over the hump” for a 20-year retirement. We really loved Kansas City. We had bought a nice house there, and my son had just been born. Making the choice to reenlist this time was the single hardest career decision I’ve ever made.

I knew that if I signed up to be “indefinite” (technically called the career status program), I would probably be a lifer. However, one thing that helped me rationalize staying was the ability to use the Temporary Early Retirement Authority (TERA) and retire at 15 years. The joke was on me because they took TERA away about a year before I could have requested retirement.

The Last Half of My Career

I’ll summarize the last half of my career – it goes quick.

I was given the choice between Kuwait or Korea, so we all went to Korea together. I highly suggest it if you get a chance to go. Then we were assigned to Fort Meade, where I’ve been stuck since. Don’t get me wrong, there are worse places to be, but it’s not the sexiest duty station either.

I earned my final promotion to Master Sergeant (E-8) in January of 2023, which started my final three-year clock (3-year service obligation). With the Army’s ability to request retirement 24-months prior, I did just that. The choice to retire and not stay past 20 years was the easiest career decision ever.

What Made the Decision to Leave at 20 Easy

One key thing I want to mention is that my self-confidence has grown tremendously. The first ten years, we went from living paycheck to paycheck and thinking small to knowing there’s no limit to the possibilities in life. Getting out of debt and investing in my education and earning ability really gave me confidence.

The Shifting Dynamic Between Dependence and Confidence

I’ve regretted staying in many days. Not because it’s really that bad in the military. But with my increasing self-confidence, I realized that the Army needs me much more than I need the Army. But taking the safer, more responsible path for my family always seemed like the right thing to do.

To do what I felt was the logically sound choice, I had to give up on my own identity and just suck it up. This haunts me, but I’m hopeful that once I get some years on me in retirement, I’ll be able to let go of those feelings of regret and wondering what could have been.

I like my life now and am proud of who I’ve become. I wouldn’t change anything. I’ve always ended up exactly where God needed me to be at the time.

Final Reflections on 20 Years of Service

I’ve had a love-hate relationship with the Army as long as I’ve been in. Overall, I think I’ve gained a lot from my time in service and made some exceptionally impactful contributions. I’ve had the distinct honor of being a small part of many Soldiers’ lives – from their first interaction as their recruiter, to draping a flag over the casket of the fallen when I was on honor guard detail.

I had no idea what life would be like when I started, but I’m going to walk away with confidence in myself, a deeper love and appreciation for my country, and friends scattered all over the world.

A Stable Base of Pension and Healthcare

I’ll also have healthcare for my whole family and a steady income for life. These two key benefits will help us have the flexibility and confidence to build a meaningful and enjoyable life. Only time will tell how valuable this solid base to work from will be. I’ve already built some amazing stuff outside the military, “in the margins” while on active duty. I’m excited to see what devoting my full time and attention will yield.

The Army Goes Rolling Along

At the end of the day, we’re all just a small piece of a bigger puzzle. I’m proud of my service and those I’ve served with. But when I exit service, as The Army Song so playfully tells us, “And the Army goes rolling along…”

And so will I.