FREE Course – Roadmap To Transition Success

Getting out of the military isn’t like flicking a switch. No one turns off the lights and says “bam, you’re a civilian now.”

Yeah, there’s probably an official day in there somewhere when your employment as a servicemember ceases. There will be a date for the files.

But for you, personally, going from a soldier to a civilian is a journey. And it’s one you need a roadmap for.

The Dangers of “Winging It”

A lot of people leave the military with no idea what’s coming next.

And a lot of them say “okay, I’m gonna take these next few months and apply for some jobs, figure stuff out; make a go of it” — and then stop there.

An intention isn’t a plan. A goal isn’t a plan. Saying you’re going to find a job isn’t the same as getting one.

Without a concrete plan you’re just winging it. And that’s how a lot of guys end up blowing through their saved-up vacation days, partying and taking it easy for a month, two months; whatever they’ve got, all in the name of “readjusting” — and then their paid leave is up, and they’re unemployed civilians with no money coming for next month’s bills.

You don’t want to be there. That’s a good way to end up working any job you can get just to make ends meet. It’s starting at a disadvantage — digging a hole that you have to climb back out of, instead of starting on an even plane.

It’s setting yourself up for some early failure. Having to scramble to get a job, any job, locks you into some crappy work for a while, and it’s harder to get out of a lousy work situation than it is to get into it. Your post-military résumé and work experience end up working against you because you had to pay the bills with something unimpressive.

Don’t just wing it. Have a plan. Build a roadmap with concrete, tangible steps that start the moment you step off that base for the last time.

Make Your Decision to Leave as Early as Possible

The transition from military to civilian starts while you’re still in the military.

At some point you’re going to have to make a call on whether you’re staying in or not. Each branch of the service has a slightly different timescale here, and the steps to re-enlisting can vary in complexity depending on your rank and training.

But one way or another, at some point someone is going to hand you a sheet of paper and a pen and say “are you in or out?” — maybe not in quite such blunt terms, but you’ll know it when it happens.

Your goal is to know what your answer is going to be long before that moment.

Knowing When to Get Out: Avoiding the “Prison Sentence” Mentality

Did you ever know someone in the service who talked about his or her enlistment like a prison sentence? They count down the time: “just eight more years ’til I get my pension, and then I can get out.”

If you’re starting to look at it that way, it’s past time for you to be out.

Don’t stick around just for the sake of the benefits. Yeah, they’re nice, but they’re not that nice. There are plenty of twenty-year veterans living on the streets.

If you truly love the military and you feel like you’re in a good place — great. Stay put. Re-enlist, do that extra training, go for a higher rank or pay grade; whatever floats your boat. There’s no reason to quit something you love.

But if you find yourself just plodding along because the military is safe and familiar, and you’re not sure what else you’d do, it’s time to let go and challenge yourself a little. Don’t wait around until you’re one of the grizzled old guys saying “just four more years, just four more years.”

Go Up the Chain of Command: Talk with Your Family

If you’re single and just supporting yourself, the risks and benefits of leaving the military are pretty much your own business. You might want to talk it over with your parents, or a close friend, just to get some outside perspective on the decision, but it’s mostly up to you.

Men and women with a family to support need to do a little more thinking about what leaving the military means. Are there going to be systems in place to keep the family secure while you’re looking for civilian work?

Talk it over. Your spouse is part of your chain of command here! It’s your decision, but when family and kids are on the line with you, it needs to be an informed one. Make sure everyone is aware of what the changes will be not just in your paycheck but in the family’s housing and benefits.

If you need to figure out a system to replace the support the military has been providing for your family, don’t wait until you get out. Know how you’re going to get that support in the private sector before you end your enlistment.

Decide Early; Avoid Wasted Effort

One of the nice things about making a firm decision to leave well ahead of re-enlistment time is that you can avoid wasted effort in the remainder of your service.

If you need another eight months of training for a higher pay grade, and you’re going to be cycling out in six months — don’t go for that training. There’s no purpose to it. You’ll just be wasting your effort and your teachers’ time.

Of course, you might not want to let everyone know. Guys who are definitely on their way out have a strange magnetism for the crap jobs — “oh, he’s leaving soon anyway; give it to him.”

You won’t be able to avoid that entirely. But maybe keep things on the down-low, outside of the people that actually need to know. And don’t bother with extra training or other efforts that won’t pay off before the end of your enlistment.

Start Making Your Roadmap While You’re Still in the Service

Here’s an advantage hardly any soon-to-be veterans take advantage of: you can start planning your transition to civilian life while you’re still in the service.

If that doesn’t sound like a big deal, think about this: once you get out, you’ll have to do whatever job-hunting or business-building you’re planning on at the same time as paying your bills, meeting your family’s needs, and taking care of day-to-day life.

While you’re still in the military, on the other hand, you’ve got a roof over your head, three squares a day, and all the other benefits of living within the system. Yes, you have your actual job, but you aren’t constantly dealing with the needs of the moment.

It’s a great time to look ahead and do some long-term planning. Because once you get out, and every day you’re having to figure out for yourself how food’s getting on the table, how the laundry’s getting done, how the dishes are getting washed, and so on, it’s going to be a lot harder to find uninterrupted planning time.

Be Ready for the Boot

The military isn’t set up to help veterans with their transition to civilian life.

When the end of your enlistment rolls around, expect it to be pretty brief and perfunctory.

You’re going to sign a few forms, maybe get the contact info for some support groups or headhunting firms (most of which aren’t very good), and get booted out the door.

The VA does have some resources, particularly if you’ve got a disability rating, but you’re going to have to seek most of that out yourself. There’s no one that’s going to hand you a useful brochure explaining how to claim your benefits.

Be ready to walk out that door with a clear list of the places you need to go for support and benefits. Budget a couple days of phone time if you have to figure out anything through the VA — it’s a giant, bureaucratic mess. And be on the lookout for support groups and websites like this one that are set up to help veterans independent of the military or the VA.

You’re going to be booted out on your own pretty briskly. Take steps before that happen to make sure you’re on your own for as short a time as possible.

Document Your Journey

So what actually goes into a “roadmap” for the military-to-civilian transition?

That’s going to depend a little on what you want to do once you’re out. But for the most part: written steps.

Seriously. Write the biggest damn to-do list you’ve ever put together. Any single useful thought that enters your head as you’re getting ready to leave the service — put it down on paper.

Find a Method and Stick To It

Different people like their data organized in different ways.

Maybe you like to use an online, cloud-based system like Evernote, where you can access notes from any internet-capable device. Maybe you’re more of a pocket journal kind of person. Or maybe notes stuck to the refigerator with Disney magnets work best.

Whatever it takes, find it and stick to it. You want one central location — physical or digital — where you can put everything related to getting a job, paying bills, and doing all the other real-world necessities that were taken care of for you in the military.

Don’t underestimate how much you’re going to rely on a good system. The reality is that there is a lot of stuff to remember in civilian life. You need to be able to look in one spot and see what you’ve done, and what still needs to be done.

When in Doubt, Sort by Date

What needs to be taken care of today? What needs to be taken care of this week? What can wait until next month?

That triage is the easiest way to start sorting your civilian responsibilities.

Take a look at the things you have to do as you’re cycling out — paperwork for benefits, doctors’ appointments for disabilities, etc. — and get them organized in order of what needs to happen first.

Then do the same with whatever real-life needs you’ve got, whether that’s paying rent or a mortgage, paying tuition, or something else.

You don’t necessarily need a huge desk calendar or anything like that. Just a stack of papers works, as long as the stack is in order and you flip through the first few items every day to see what’s coming up.

But when in doubt, get your business sorted in order of immediate versus long-term needs.

You can still work on long-term goals — like getting a better job, or enrolling in a school or training program — while you’re dealing with short-term needs like rent and grocery money. But to avoid slipping into debt or a similar hole, have those short-term needs on top.

Have a Long-Term Plan — And Share It

What you do in your first couple months out of the service does not define you for the rest of your life.

If you’ve got to take a temp job or do some short-term moving around to make ends meet at first, do it. There’s nothing wrong with that.

The key is to not get stuck doing the first thing that comes your way. You need your system to be constantly pushing you onward and upward.

One of the best ways to do that is to have a long-term goal that you share with other people.

Whatever your goal is — law school, a business start-up, promotion at your dad’s old firm; anything — tell people close to you. Let your friends know what you’re shooting for. Let your spouse know (he or she should probably be in the loop anyway, don’t you think?). Let your neighbors and your poker buddies know.

This is about incentives. Half of the people you tell are going to smile, nod, and forget, because that’s how a lot of people are, but some of them will remember. Weeks or months down the road, they’ll say “hey, how’s it going with that job you were looking for?” or something like that.

Knowing that other people are interested feels good — and it’s also good motivation. You don’t want to have to shuffle your feet, look away, and say “it didn’t really work out.”

Which, you know what? Sometimes it doesn’t. Once in a while things really don’t work out. But much more often that’s code for “I didn’t try hard enough.” And the potential embarrassment of having to tell people that something “didn’t work out” is a great way to make sure that you, personally, do try hard enough.

On a practical note, letting people know what you’re looking for never hurts job prospects, either. You never know when a friend of a friend’s brother is going to have an uncle who knows someone that’s got an opening in just the field you’re interested in, or something like that.

If you tell people what you’re trying for, it doesn’t necessarily mean they’ll help you get there. But they’re a heck of a lot more likely to than if you don’t say anything at all.

Stay on Top of Your Military Connections

One thing you definitely don’t want to do when you leave the service is lose touch with everyone you knew.

Facebook and e-mail make it easier to stay in touch, of course, but you probably want to get some back-up contact information for everyone you were close with as well. (When in doubt, get their parent’s address or phone number — parents tend to change their contact information a lot less frequently than younger men and women).

Even if you’re not applying to a job or school that requires letters of recommendations right away, get general letters of recommendation from your commanding officers or other superiors anyway. They don’t have to recommend you for a specific job or position — just commend your service and list your merits.

Hang onto a hard copy and a soft copy if possible, and that way you won’t be faced with the prospect of tracking down someone you served with ten years ago who’s been out of the military himself for years when, a decade down the line, you decide to go back to college and they want letters of recommendation.

Your wider network of military friends and associates is going to be a powerful tool once you’re out in the civilian world. As more and more people you served with also join civilian fields, you’ll have an ever-increasing pool of contacts to draw on — and you might end up able to do a buddy a favor, too.

“What Next?” — How to Open Your Mind to Options

Having a roadmap only works if you know where you want to go, right?

One of the problems with military service is that it doesn’t necessarily show you a wide range of options for your life. Unless you’re interested in something pretty specific to the military, you’re not likely to find your passion in the service.

And that’s okay. People who were never in the military take years to figure out what they want to do with their lives, too. You’ve got time.

The key is to have an open mind, and to be continually looking for your passion and your calling in life. That only happens when you’re exposing yourself to new options.

Career Books and Transition Guides

You’re reading a military-to-civilian transition guide right now.

Obviously, we think that’s a good idea! And there are a lot out there, both in online forms and in traditional printed book format as well.

These are not a bad starting place. Some are more mindset-oriented, while others look at how to get jobs in specific fields.

Go ahead and work your way through some military-transition-specific literature. This is a good thing to start on while you’re still in the service, but if you didn’t, don’t panic — you can still catch up on the reading once you’re out.

The main thing to keep in mind here is that any guide you read is going to have the bias of at least the author, and in many cases of a third-party publisher as well. In some cases those third parties also run for-profit businesses like headhunting or talent agent firms, and they’re going to have a vested interest in guiding you toward one specific way of job searching or making your way in the world.

So use some grains of salt, and read with a cautious mind. You should also beware of advice that’s too heavily focused on turning what you already know how to do from the military into a job in the civilian world.

For a lot of guys, that seems logical: if you were EOD, you look into joining the police bomb squad; if you were a communications specialist you end up in IT, and so on.

And there’s nothing wrong with that — but it’s a limiting way to look at your potential.

Think about it this way: when you joined the military, you were probably somewhere between 18 and 25 years old, at least for the vast majority of servicepeople. The choices you made then, both your enlistment and the tests and training you took after it, determined what you learned and what you did for the military.

Now, if you had the chance to go back in time and ask your 18-year-old self what he or she thinks you should do for the rest of your life, would you trust that kid to give great advice?

Probably not, unless you were one hell of a sharp teenager. The truth is, what you wanted to do — or thought you wanted to do — when you were young isn’t necessarily what you’ll want to do for the rest of your life.

So sure, if you love what you did with the military and you want to go on leveraging those skills and learning more and more about them, look for a job in a related field.

But don’t think you have to. There’s always time to learn something new. Men and women are going back to college or to trade school in their 40s, 50s, and even 60s and up these days, learning completely new skills that they’d never touched before.

You can too, if you want to. So read the military-to-civilian guides — but read them with an open mind, and don’t get too caught up in what you did in the military. Maybe it’ll come in handy in civilian employment and maybe it won’t, and both are fine.

Start Reading about Different Careers

If you have a passion you want to pursue, you’re ahead of the game.

Get down to the library, grab some books on the subject and start reading. You’d be amazed how quickly you can become an “expert” in something, at least relative to people who’ve never done any reading on it.

But if you’re not 100% sure what you want to do — which is the case for most folks, military or not — you should start looking at a broad spectrum of things that seem potentially interesting.

Don’t worry too much up front about what you’re trained to do or qualified to do, or what you think you can get a job in right away. If the idea of being a brain surgeon seems interesting, go pick up a few back issues of their academic journals and start reading. It’ll be jargon-heavy and you won’t understand all of it, but it’ll give you a sense for what their lives are really like.

This has the obvious benefit of exposing you to a lot of new ideas and teaching you a little bit about a number of different careers. But it’s also just a good object lesson in how many different ways there are to make a living out there.

Think about it: if you read, for example, a leisure magazine about SCUBA diving and underwater photography, a literary magazine, a trade publication for automotive engineers, and the blog of an ACLU lawyer, you’re not just learning about those careers. You’re learning how a guy who wants to take pictures underwater for a living has to go about turning his work into a saleable product, versus how publishers find a month’s worth of writing to sell, versus how one auto mechanic can sell his knowledge to others, and so on.

In the first months and years out of the military, when you’re still figuring out how you want to make a go of civilian life, having that extra perspective is a huge help. It really gets you believing that yeah, people can make a living doing what they love — that just requires different stragtegies for different people.

Books can be good for this, but keep yourself especially open to magazines and websites. We’re living in an age where things change so quickly that a book can become outdated after just a few years. Think about former Florida governor Jeb Bush — the poor guy published a book last year, and by the time it hit the stores he’d already had to change his position on immigration, disavowing what he’d written less than a year ago.

You never know what’s going to spark the lightbulb — the “aha” moment — so keep yourself immersed in as much as possible.

Examine Your Motives

Think long and hard about what you want out of life, and why you want it.

It’s easy to end up in a lousy job — or a lousy life — because of false motives.

Money is probably the number one thing to think about here. There are a few people out there who are genuinely happy when they are making as much money as humanly possible. It’s how they keep score. That’s their thing. And if that’s your thing, then go for the best-paying career you can. Milk it for all you’re worth.

But for most of us, money is only really important as a way to do or have other things that we like. It’s not the cash value that matters — it’s what you can do with it, whether that’s support a family, travel the world, or drive really flashy cars.

Don’t get caught up in money for the sake of money. If you go into a career you find yourself hating, get out of it. Don’t tell yourself “I’ll just stick around for a couple years and make a comfortable stash, and then I’ll quit.” What pile of money is worth a couple years of your life being unhappy?

You can always make more money, but you can’t get time back.

None of that is meant to steer you away from high-paying jobs. If you think you’d enjoy the challenge of hedge fund or asset management, or of law school and court cases, or of highly-specialized surgery, go for it.

But if you hate those jobs, the fact that you’re getting paid well for them isn’t going to matter — and you’re probably not going to be energized enough to do a great job, either, meaning you’ll never rise to the top.

There’s a lot of depressed, unhappy lawyers out there barely making enough to pay off their student loans. Don’t go that route.

Career Progression: Understand Your Path

Not all careers progress equally.

A medical doctor follows an extremely structured path from undergrad through med school and residency on up to private practice; a freelance photographer not so much.

There’s no right way or wrong way — but once you pick a career, there is probably going to be a best way. You should figure out what’s best for your needs and your interests so that you know what’s coming.

Education and Certification

A job that requires a specific degree or certification is one you need to do a lot of advance planning for. How are you going to pay for school? How long is it going to take? What work can you do in the meantime?

Questions like that need answering before you lay the money on the table. Even the shortest degrees usually take a year or two to complete, which means you need to have at least a year or two of meeting your basic needs mapped out before you enroll.

Keep in mind that not all jobs require formal schooling, even if it’s common. You don’t have to go to business school and get an MBA to start your own company. It’s not a bad route, and you’ll probably learn some useful things and make some useful contacts along the way, but plenty of guys make do without.

Careers like law and medicine, on the other hand, typically have an explicit requirement for a certain level of schooling. You’re stuck planning for those years of education if you want the career. Plan on it in advance.

On-the-Job and Self-Teaching

Fields that don’t require a specific degree are ones you might be able to learn as you go .

The cheapest way to learn something is always to teach yourself, with publicly-available materials (which there are more and more of thanks to the internet) and hands-on practice at home.

Obviously, that works better for some careers than others. You can become a pretty decent “shade tree” mechanic just by reading some books and tinkering around on an old car — good enough to get an entry-level job at an auto shop and start working your way up, certainly.

If, on the other hand, you want to do underwater welding, you’re probably going to have to go through some training courses and apprenticeships first.

The more you can learn while getting paid to, the better. Unfortunately, “paid internships” and “on-the-job training” were both hard-hit by the economic crisis. You may need to have some skills to bring to the table — either self-taught or acquired at an unpaid apprenticeship while you worked a second job — before you can get a salary for doing what you love.

Don’t be alarmed by setbacks or delays. Just have an eventual goal for how you want to get paid for your skills (wage job, salary, contract work, freelancer, etc.) and take the steps to get there, even if they involve working some other jobs on the side and doing some self-teaching at home in your limited free hours.

Understand the Return on Investment for Education

Not all degrees are created equal.

Occasionally your highest level of education will be tied to your salary — many police departments, for example, incentivize education by giving employees with a Master’s degree a higher pay grade than those with a Bachelor’s, and those with a Bachelor’s more than those with an Associate’s, and so on.

For the most part, though, the relationship will not be that direct. You’ll want to figure out what a degree is actually going to be worth to you before investing your time and money in it.

Getting a B.A. from a good liberal arts college might be a really good education — and if you’ve got the time and money to invest in it, it may well be worth your while. Schools like that are focused on teaching you how to think creatively and evaluate critically, which are skills that everyone can use.

But if you’re short on cash and need a good, reliable trade, it may not be the best investment for you. You’ll end up smart but poor. Someone who’s short on free time or who doesn’t have the cash for a residential college tuition might be better off taking night classes to earn an Associate’s degree or a trade certification.

In the longest term, and speaking very broadly, people with higher levels of education tend to make more money. But that doesn’t mean you’re going to get a good return right away if you just pursue the highest degree available with no real plan for how to turn it into a career.

Look at your needs and look at what gets you to them. A one-year course that ends in a trade certification might be more valuable to you than a Master’s with a $40,000 price tag on it.

Look at What Others Have Done

When in doubt, look at the place you want to get to, and then look at the guys that are already there.

What did they do to get there? That’s what you need to find out.

Read the blogs, subscribe to the magazines, watch the interviews, or heck — just write a personal letter to the successful role model of your choice. See what it took to get them there.

Your path is ultimately going to be your own, but it can’t hurt to know what routes have worked for other people.

Veteran Psychology — How You See Yourself, and How the World Sees You

Less than 1% of the American population serves in the military.

It’s hard to understand how profound that fact is until you go from a world where literally 100% of the people you’re interacting with know what military life is like to a world where less than 1% does.

Be Ready to Be “That Guy That Was in the Military”

Even if you don’t have your unit’s insignia tattooed on your hand or something, expect to be recognized as a veteran in your first few years out.

Part of that is going to be purely physical: you’re going to look like a soldier, at least at first, and you’re going to move like one for years. They train that into you pretty hard, and it sticks.

A larger part is social. People naturally ask “what did you do before this” in just about every professional situation there is, and for a while your main answer is going to be “I was in the military.” As you get further and further out and add more and more experiences that will become less true, but for a while you’re going to have to either lie, be very quiet, or deal with everyone knowing that you’re a veteran.

And that’s okay. There’s nothing wrong with being known as a veteran, especially if people asked you first (it’s kind of rude to flaunt it unprompted).

But it is a “brand” you’re not going to be able to get away from, at least at first. Embrace it — because if you don’t, you’re just going to be pissed off at people all the time for pointing it out, and that’s not good for anyone.

Have a Reply to “Thank You For Your Service”

People are going to say it to you.

No, really — people are going to say “thank you for your service.” Strangers on the train, bosses at work, people you’re flirting with in bars; whoever. Everywhere you go, someone’s going to do it once they learn you’re a vet.

That can feel pretty weird, especially if you don’t feel that you, personally, did anything particularly significant or special (which is easy to think when you’ve spent the last couple years being “normal” by military standards — just doing what everyone else around you is doing too).

Try to have a default response, so that you’re never flat-footed and awkward when someone says it. You don’t have to go “aw, shucks, ’tweren’t nothing,” but a simple “I was glad to serve” is always good.

 Be Prepared for the Major Stereotypes

You’re probably going to bump into all of these at some point:

  • People who think you’re a dumb musclehead. They’ve got an idea of the military as purely a physical job, and they think everyone in it was a jock with a gun. They might even think that and respect it — like “damn, you guys are hardcore.” But they’re not seeing you as a creative, independent person.
  • People who think your training is responsible for your successes. “Wow, nice effort — must be that military training, right?” The idea that you work hard because you’re a hard worker, rather than because you went through boot camp, can take a while to get through to people.
  • People who think you’re a gun-toting, gay-hating conservative. This can be awkward both from vehement liberals who get on your case and from guys who want to buy you a round and show you their confederate flag tattoo. They’re both probably working on a mistaken assumption of who you are and what your beliefs are.
  • People who think you’re unstable and possibly dangerous. Everyone knows veterans are troubled by what they’ve seen and jump at loud noises, right? Some people are going to tiptoe around you like they’re walking on eggshells no matter what your actions say about you.

Any or all of these can be incredibly frustrating to deal with. Unfortunately, the solution for all of them is a tough one: patience and setting a good example.

If it’s really bad, you can gently correct someone by saying “look, that was a while ago — I’m just me, you know, not me-the-veteran.” But most of the time the best way to dispel the stereotypes is simply to go about life as a calm, normal person.

Be Aware of Your Weaknesses

That said, there are a few weak spots that military training tends to leave a person with. They’re not hard to overcome, but they are natural products of the military life, and if you’re pretending you don’t have any of these flaws, you’re probably not examining yourself closely enough:

  • Overconfidence – Let’s face it, you can probably walk into a room and figure out how to kill everyone in it with a glance. Which is all well and good, and makes you feel pretty powerful, but that’s not actually a useful skill in civilian life! Veterans need to adjust to the idea that they have done amazing things — but that those amazing things don’t necessarily buy a cup of coffee in civilian fields.
  • Lack of empathy – There’s a definite “suck it up and move on” attitude in the military that doesn’t always go over well in civilian life. If someone is having a bad day at the office, you probably don’t want to tell them how much worse it could be, or that they’re being a wimp. Learn to put up with more complaining than you maybe had to in the service — and to do it nicely, and with sympathy.
  • Taking on too much – Yes, you got more done before breakfast than most people did all day. But you also had a massive support system behind you the whole way. You don’t have that in civilian life, so learn to pace yourself. You’ve got to save energy for simple domestic tasks as well as professional responsibilities.
  • Inability to ask for help – When your CO tells you to do a job, you do it, and you do it right. All well and good when it’s something you’ve been trained to do, but not all expectations in the civilian world are going to be reasonable ones. You’re going to have to learn to stop and ask for help when it’s needed — otherwise you end up doing jobs badly, because you weren’t sure how to do them right, or didn’t have the resources to all on your own.

These show up to greater or lesser degrees in most veterans, especially in their first few years out. Don’t let them get you down — just be on the lookout for them. Be self-aware, know that your training and your experiences have given you certain habits of thought that might not always be useful, and have the flexibility to change as needed.

Recognize How Well-Prepared You Are

Finally, when things are feeling insurmountable, always remember: you’re better prepared for life than most guys out there.

Military training isn’t always practical in the real world. But it is intense, and it does teach you to overcome adversity. However bad things get, you’ve probably seen worse, or at least been trained for worse.

Everything from the rigorous standards of punctuality and manners (“yes sir” and “yes ma’am”) that the military drills into you to the experience of dealing with its massive and antiquated bureaucracy has made you a stronger candidate for civilian jobs.

You’re an asset. Think of yourself as one.




Make The Decision To Leave – Weigh Your Options, Avoid The Prison Sentence Mentality, Look At Those Above You and ask to discuss the future with them. The decision is yours, but include your spouse, family, and any advisors you trust in the decision.

  • Do not underestimate the power of your gut. It has guided many people to success in life, and away from disaster.
  • There is great power in the the advice of peers, mentors, and loved ones, but in the end this is your life (and your families if applicable) and you need to do what feels right.


  • Early is good (1 year out) – a focused concerted effort though can make up for lost time.
  • Start writing down goals, aspirations, dreams. Then start taking the necessary steps to acquire the knowledge necessary to achieve these goals, aspirations, and dreams. Google is the only starting block you need, the rest is waiting for you to uncover and unlock its potential.

Document Your Journey

  • Good ole fashioned Paper
  • Evernote/Google Docs/Word/OneNote
  • Bookmark sites that update frequently in your desired niche and visit them often.

Open Your Mind To Options

  • Career Books Are The Start – In my opinion very limiting as they assume you want to leverage your experience/background. If you do – great. However the reality is that most opportunities are going to be outside your scope of expertise in the military.
  • Subscribe to a wide range of magazines and explore them with the mindset of understanding how the people featured make a living.
  • Join groups and masterminds with like minded people who are in similar situations as you currently are. Pool your knowledge.
  • Entreprepreneurs – Mixergy, EntrepreneurOnFire, Smart Passive Income

Veteran Psychology – How You See Yourself, How The World Will See You

  • Less than 1% of the population serves in the military – it will define you for many, especially if you are fresh out.
  • You are better prepared than you think – the little things will separate you – confidence, leadership, punctuality, manners, dealing with bureaucracy.
  • You have faults – learn humility, empathy, overconfidence, taking on too much, inability to ask for help.
  • Be the one to dispel stereotypes – both with the liberal professor or ultra-conservative.
  • You need to do this yourself – not your staff or fire team.
  • Not everyone loved it – but we do share that bond and we can look at fellow Vets with respect and dignity.

Explore Your Options

  • Medical, Legal, Academic? There is a defined path for this.
  • Business? Not so much.
  • Further Your Education – Entrance Exams, Letters of Rec, Specialized Training, Associates, Trade Education, BA/BS, Masters, JD (Law), (MBA) Business
  • Measure the Return On Investment! What will your benefits cover and what are their placement stats (speak to the school & alumni).
  • Headhunters: Bradley Morris, Cameron Brooks

Commit To The Transition

  • Everyone who matters should be on board: Family
  • Take advice from others, but again, trust your gut and commit to your decision: Friends, Chain of Command, Peers

Preparation For A Smooth Transition

  • Start Saving
  • Cut Expenses
  • Create a budget and start tracking all expenses
  • Plan for new expenses and forecast those out in your long term budget: Housing, healthcare, clothing.
  • Build a support network – there will be dark times.


  • Veteran Bibliographies – Read their stories (create list)
  • Written interviews
  • Podcast interviews

Understanding The Rank & Pay Structure In The Civilian World

  • Under The Table Jobs
  • Hourly Jobs
  • Contract Work
  • Salary Work
  • Consulting
  • Commission Work
  • Business Ownership

Begin Your Job Search In Earnest

Understand that most of the information out there is Bullshit and not applicable to you. Every situation is unique – our goal is to give you a solid foundation in the principles vs. telling you your resume needs to be written in times new roman vs verdana vs arial. Focusing on these details is only .01% of the game.

  • Resume:
  • Clothing:
  • Language:
  • Networking:

You are ALWAYS interviewing.

Make no mistake here – you are always interviewing. Your brother-in-law you’re meeting for coffee to better understand how things work at AT&T – he’s sizing you up. Whether he tells you or not he is thinking that 1) we sure could use a guy like you or 2) he’s hoping that you won’t ask him for help finding a job at his office. And he’s family.

  • Developing Your Interview Skills
  • Learn to sell yourself

Negotiating Salary, Benefits, and Hours

  • Military = Complete transparency when it comes to who makes what.
  • Civilian world = A cloud of mystery and intrigue.
  • Use sites like,, and others to judge what level you should expect/demand before accepting a job.
  • 30 days a year off no longer. 2 weeks on the high end when starting.
  • Make sure the health care is what you and your family needs.
  • Look into their matching 401k programs and be sure to take full advantage of the “free money”.
  • Negotiate hard, be ready to walk away from the table with no job. They will respect you for that.
  • A salary job means you will work until the job is done, regardless of the hours.