3 Things I Wish I Had Planned Before Leaving Military Service

Most don’t do #3

Your time in the military is coming to an end.

Maybe you have a couple years left.

Maybe it’s 12 months.

Or perhaps you’ve got just a couple months before you start the separation process.

Whatever your situation is you’ve probably had the butthole puckering thought “What’s next?”

For some people it’s an easy decision while others it’s a difficult and emotional decision.

For me it was an easy decision.

I wanted to be a cop since I was in 5th grade.

So the military was a stepping stone to get there while gaining one of a kind experiences, seeing new places, and venturing off on my own.

I served six years active duty in the Air Force as Security Forces and an additional three years in the reserves.

But as my active duty time came to an end, things didn’t go as planned.

I failed the California Highway Patrol’s testing process and was stuck with no job.

I was also applying to several agencies but the hiring process takes so long that I couldn’t afford to stay on unemployment (California is expensive as fuck in case you didn’t know…).

Since the military paid decent, I decided to sign up for the reserves while I was going through the testing process for a few agencies.

Looking back I realized that the military didn’t prepare me to enter the civilian world.

Now that I think about it, they hardly did anything, aside from taking my gear and signing off on papers.

Why should they?

It’s their mission to retain members, not lose them prematurely to retirement.

At best I was supposed to attend a week long transition assistance program (TAP) but that never happened.

I was the only certified Security Forces Controller on my shift and they couldn’t find a replacement.

So in order to rush and get someone certified I had to remain working to train the next person.

I literally had to out process on my own days before ETSing with almost no assistance.

If I got a chance to re-do the last twelve months of my military service here is what I would do differently:

1. Actually this one should start way before 12 months but I would make sure I would’ve taken advantage of the tuition assistance program.

Each year active duty members receive a limited amount of tuition money to pay for college.

This is in addition to your GI Bill, but you only get it while you’re active duty.

If you’re guard or reserve and on active orders, or you’re on deployment orders under U.S. Code Title 10, then you should be eligible for TA.

At the time we got $1,200/year but now I believe it’s up to $4,500/year.

These numbers may be different as I researched several sources and each one had a different answer.

To get the right information of course just visit or call your education office.

You get the idea…

I would try to knock out as many courses as possible because once you’re out and decide to continue with school, you use your GI Bill (which you may want to pass down to your kids).

You’re also eligible to receive a book stipend and BAH, depending on how many credit hours you’re taking and other factors.

Again, these are in addition to your GI Bill.

2. Start a side project that will be an extra revenue stream.

Many service members don’t think about the business owner or entrepreneurship journey.

I think it’s mostly due to the push from everyone and their mother for you to get your degree or finish school and get a job afterward.

No one ever talks about starting a business.

But in today’s economy, many military members are struggling to find work, regardless of the industry.

Having “veteran” status might give you a slight edge against other applicants, but don’t think that just because you can check that box means job hunting will be a breeze, or that you’re guaranteed to land that job over everyone else applying.

Spend some time in veteran Facebook groups or on LinkedIn and browse all the posts of veterans struggling to find work and you’ll see what I’m talking about.

It’s sad honestly.

I hate to see veterans struggling.

Especially after all we went through and served our country.

But that’s the reality unfortunately.

Here’s my tip: I would’ve started a side hustle as early as possible.

Here’s why…

Let’s say you did take advantage of the TA program, got your degree, your resume is all squared away and looking pretty, and are all set to land your dream job…

But if you’re unfortunate not to land a job after 6 months of applying to more than 200 jobs like I’ve seen a few veterans post about, now what?

Unemployment doesn’t pay shit and neither does hitting the “super size” button on the cash register in the drive-thru.

Inflation is sky-high for everything.

Literally everything.

The struggle is real.

And unfortunately many veterans, and spouses, are struggling to find jobs that pay enough to support them and their families.

This is the reason why I encourage you to start something on the side as early as possible and get it going.

Business takes time to grow, especially with a limited marking and advertising budget, and inexperience.

And if you want to write to earn money on platforms like SubStack or Medium like I do now, then expect to be writing for a while before you make your first penny, unless you have a marketing strategy in place.

If you want to become a content creator, the same applies.

These all take time to build an audience and gain trust.

Social media is saturated with content and it’s hard to stand out unless you’re entertaining, uniquely you, have a strategic marketing plan, and can create attention grabbing videos and posts.

The content creator industry is exploding and is expected to hit between $450 billion to $480 billion by 2027.

Some colleges even have course now on how to become a content creator (although I wouldn’t recommend wasting your money on them and instead get a YouTube education, it’s free-ninety nine).

You’re probably thinking, is this for real? Are people actually making money being a content creator? And if so what types of content?

In order to keep this article short, yes it’s real, yes you can make a lot of money (I know some who are mid to high six-figures per year), and the types of content is everything. Literally.

If there’s an interest in it there’s money to be made.

But that’s for another article.

Whether you’re active duty or are a veteran, check out John Kerkhoff, PMP, CPLC who is a retired Army vet and now owns Frago22 . They help veterans and military members prepare for employment through coaching and consulting services while helping businesses attract, hire, and retain quality service members.

3. Get my finances in order.

Again this may take more than 12 months but I would make sure whatever debt I could pay off I would.

That would mean being extremely frugal.

Stop spending money on stupid shit like going to the bars, tittie clubs, a new car, expensive dinners, and whatever else you don’t need.

You don’t know how long you’ll be out of work after you leave if you don’t have something lined up.

And even if you do, in today’s economy, you could be laid off as fast as they hired you.

I spoke to two veterans last week who lost their jobs out of the blue (re-read #2 above again where I mention having “veteran” on your application doesn’t guarantee anything).

Credit card debt is the highest it’s been in years.

People are dipping into savings just to pay bills.

House prices and interest rates are astronomical.

Don’t be fooled by some of the shit you see posted from lenders, real estate agents, and bankers saying “Now is the best time ever to own a home!”

If you can afford it, great!

But do a quick search online and compare housing prices in 2024 to 2020.

We had our house built in 2013 and in just 11 years it went from $250k to now being able to sell for almost $470k if we wanted to (although we have no intentions of moving).

Most of that increase came in just the last 4 years.

F'n insane wouldn’t you agree?

Are people still buying and selling homes?

Yes of course.

But I just wanted to give you a reality check on how serious the world is outside of military life.

Pay off as much as you can.

Save as much as you can.

You’ll be glad you did, trust me.

Start venturing off into other things of interest such as starting a business, investing, buying/selling businesses, buying/selling commercial real estate, content creation, writing/blogging…

Life after the military can take some time to adjust.

It can be stressful.

But what’s even more stressful is if you don’t have your shit in order when it comes time for you to ETS.

There are many more I could add to this list but looking back over 20+ years ago these three things top my list.

Like I said I hate to see veterans struggle.

Especially on things that could’ve been prevented or had a lesser impact if they had just been told or prepared.

It is my hope that this touches just one military member and changes their life.

If it does that makes me happy.

Please share this with other military members.

Are you a veteran?

Do you have anything to add to this list for others to learn from?

Let me know in the comments!