Your Journey through the Military & Beyond

People don't usually think about the average military career, and how that will set them up for lifelong success. Here's a template that might help.

The Average Military Career in a Nutshell

When someone joins the military, it’s for all sorts of reasons.

You’ve decided to join the military. Either because you heard about the terrific benefits or out of patriotic obligation — or both! — you’re in the process of putting on a uniform and serving the country for some years.

How do you make that work for you — what goals should you be hitting at each stage of your career? While some of that depends on where you are and what you’re doing, it’s possible to generalize to some extent. Here’s a step-by-step schema for how to build a successful career in and out of the military.

Step #1: Sign a 3-4 Year Contract

Your recruiter really only cares about making numbers. That’s fine, that’s what you should want them to care about — it's their job, not yours. But they’re going to push you to take deals that might not be in your best interest, whether you know that or not.

You can sign contracts for up to 6 years, plus an additional 2 years in the IRR (from which you can be recalled at any time. I knew people who got summoned during the surge in Iraq. It happens). That was a very long time.

Sign up for 3-4 years, maximum. One needs 36 months of service to qualify for the Post-9/11 GI Bill, and in most enlisted MOS’s (career fields in the military — pilot, infantry, artillery, etc.) it takes about 36 months to make sergeant. In 36 months as an officer, one will often make captain.

3-4 years is about the amount of time you need to understand if the military’s right for you — and you, for the military. If it suits you, reup for another 3-4 years. If it’s not a good fit, serve your time honorably and get out with full benefits.

Not everybody is not cut out for general, and that’s fine in the U.S.A.

The key is not to be pressured by the recruiters. Look out for your best interests and make sure you advocate for yourself. If you want Airborne school, or to be a Ranger, make sure you get it in your contract.

Step #2: Transitioning out of the Military

For the purpose of this piece, we’re going to assume that you won’t be making the military a career. Few (about 1 in 5) do. So whether you’re getting out after 3-4 years or 7-8 years, you’re looking to move on. What’s next?

If you’re enlisted, the very best thing to do is college. Get your bachelor’s degree while you’re young, and you still remember high school algebra. The longer you wait, the more difficult it will be — or impossible, at smaller liberal arts colleges.

Sign up for Service to School or the Warrior Scholar Project, polish up your academic and application skills, and make your way into the best program you can. If you can line things up so you’re leaving the military in the late spring or early summer, that’ll give you time to prep for undergraduate life, and also enjoy freedom from Brigade staff duty for a month or so.

Preparing for college is not fun, but it’s better than failing college!

Step #3: College

Easy as writing it down and doing it. 36 months — faster if you work hard and skimp on extracurriculars — and you have your B.A. or B.S. That also happens to be the amount of time the post-9/11 GI Bill covers. Convenient! Some people choose to either co-term to be able to complete their Masters at the same time as their undergraduate, or they go into the workforce for a couple of years before returning to school to complete their MBA or other advanced education. 

Key to your time in college: finding your vocation — what you’re interested in doing to help the world and your community, that makes you money. With the Post-9/11 GI Bill you’ll have the ability to study the way college was intended — without having to worry about working, thanks to a full stipend and your tuition, room, and board all being covered. Do you want to go into business? Academics? Teach high schoolers? Write? Work in politics, or abroad? Pick the major that best suits your ambitions. Get internships that buttress those ambitions. And then graduate with a good G.P.A.

Remember to have fun while in college! Sure, you may be a little bit older than the general population, but you can still enjoy your time there. Join clubs, attend events, and meet new people. Solely relying on fellow veterans will isolate you from the vast array of resources on campus. I promise, you learn just as much—if not more—outside the classroom as you do from inside.


Step #4: Career

Starting your career may involve a false start or two — few people end up with the job they start in after graduating college. That’s fine. So long as you keep growing and learning, that’s all part of your path.

Look for a job with a decent salary that affords you the quality of life you require for mental wellness, offers a good health care package, and some form of retirement, and you’ll be in very good shape. And don’t look back. Some people imagine they would have done better sucking it up and staying in the military for 20 years. But if they’re honest with themselves, they always left for very good reasons.

Find a job that lets you do your thang.

And that’s it — that’s what an average career looks like in and after the military. What are you waiting for!


The SEC is investigating claims that its former and current CEO, Sam Altman, misled investors. A serious charge that, to be frank, I don’t expect to go anywhere.

Some of the most prominent companies have been very vocal about rounds of public layoffs. Why have their employment numbers remained relatively stable?

The Fed has a mechanism for gauging underlying inflation — which is still on the rise. This is one reason they haven’t yet acted to cut sky-high interest rates.


Minorities serving in the military and veterans from those groups suffer from disproportionately high rates of suicide, per a new study. And veterans of all races and ethnicities already suffer from higher rates of suicide than their civilian counterparts. Not good.

“But what about special forces?” rhetorical question from a popular ranger school video some years back finally answered by big Army force restructuring.

“Why would the military care about climate change” I ask, somewhat stupidly.

AI is becoming much more widely accepted within the military. But does the military truly understand the potential applications of AI — or its various flaws?


A very consequential case on Presidential immunity now set to come before the Supreme Court.

Friends have an interesting and distorting impact on our finances, by shifting how we perceive ourselves. Except me, that doesn’t apply to me, I’m different.

Over a hundred killed and hundreds more wounded at the scene of a food riot near Gaza, as people swarm aid trucks.


A strange piece on The Onion about time traveling cats.