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The ONE Thing You Absolutely MUST Do Before You Transition Out of the Military


The ONE Thing You Absolutely MUST Do Before You Transition Out of the Military

You are beginning, going through, or completing your transition out of the military, which means that you have a secret that is so deep, so dark, and so scary that you probably haven’t shared it with anyone. But I know what your secret is:

You’re scared.

There ― I said it. Transitioning out of the military is scary.

Why is it that after all the dangerous jobs we do in the military, or the crazy things many of us do in our free time, that we are scared about transitioning back into civilian life? Because we simply don’t know what we don’t know. It doesn’t matter how many transition assistance programs or job fairs that we go to, or how many head hunters we talk to.  We may even feel excited about what’s next; but deep inside we don’t know ourselves yet.  We’ve been wearing a uniform and taking orders throughout our entire young adulthood. We willingly sacrifice our individuality in service to our country, and honorably so. But soon you’re not going to be in the unit anymore, and I’m here to tell you that civilian society is not waiting to step up and automatically fill the void that will be left in you without your unit, your “tribe.”

Transitioning out of the military is scary because we aren’t ready for it. We don’t know what we are transitioning TO. We expect the military or some PowerPoint presentation to do our transition work for us, and we haven’t taken the time to decide or discover what we’re really about. And not only that: we tell ourselves comforting lies.  “Jimmy got a ‘good job’ after the military. I’ll just do the same thing.”  Well, let’s look at the stats of how Jimmy with the “good job” is really doing.

According to the Blue Star Families  survey, only 60% of post 9/11 veterans are employed. 47% are not in their preferred career field, and 34% report they find it difficult to establish a sense of purpose, value, or meaning in post military life.  And that’s just the people who have reported it.

Remember the last time you told yourself that everything would be fine…but it wasn’t? The same thing can happen with your transition.  It certainly happened with mine…

A Transition Gone Wrong

I had just gotten back from deployment, having spent an entire year living with 150 other soldiers in one of Saddam Hussain’s lake houses in Iraq. I was 25 years old, single, making good money as an officer, and living in Germany. For my 26th birthday, I bought a fancy, new German car. Soon afterwards, I met a German opera singer, fell in love, and decided: “This is awesome! I love Germany! I love this girl!” And at that point my decision seemed to make itself; there was no opera in Ft. Bragg, where the military wanted to send me next, so I decided to get out of the Army. I spent the next few years following the opera singer around Europe.

Yeah.  That was a bad plan ― if my decision-making process back then can even be dignified by the word “plan.”

Have you ever had a rough break up?  One that hurt really bad, and may have even been for the best, but that you really weren’t quite ready for? When I was unexpectedly dumped, my plans for the future came to a screeching halt. I had to rethink my personal life, my direction, my career.  It was a wake-up call. I had been in the “wrong” relationship. I had been comfortable, and it seemed like I was living the life that we all think that we are “supposed” to have, so of course I had assumed that I must be doing the right things. But the truth, which became clear to me only in retrospect, was that at that time I lacked any ambition of my own.  I was comfortable in the Army. I had been dependent on the Army. And when I threw the Army away without any forethought as to what I might be transitioning to, what happened next was probably inevitable. I quickly filled the gaping space in my life with a new job and the German opera singer ― but neither of these things were aligned to my true self.

That was the first time that I experienced true, core-rattling fear. I had been lucky on my deployments. I was worried a lot, but I hadn’t experienced the type of fear that I experienced in the aftermath of that breakup. I had given up everything for her: my military career, living in America, getting to spend time with my parents…  Now my world had changed overnight, and I was acting like I hadn’t seen it coming.

For years afterwards, I thought that my issues with finding my true path in life were because I had gotten dumped and stranded in Germany. Sure, my life looked good on Facebook: I was making good money. I was self-employed, living in Europe, and traveling the world. People left comments about how cool it was. But inside ― I can admit it now ― I was miserable.  Looking back at these photos now, I can see it in my face. I was sad, and embarrassed that I was sad, and my guilt about that sadness only added to the fear.

So I went on a personal journey.  I had to do this better; “this” being transitioning to civilian life; because even though I was no longer in the military, I hadn’t actually transitioned. Transition implies forethought. It implies planning. A “transition” is intentional. What I had been doing was more like… flux. As I talked to other veterans, I began to realize that I wasn’t the only one who had gotten out of the Military only to make wrong turns, end up feeling lost, and never really arrive anywhere. In a sad, but kinda good way, I found community in my misery. This is when I realized that it wasn’t the break-up with the German opera singer that had wrecked my world ― it was my break up with the military.

I hadn’t just been comfortable with the military; I had been dependent on it. So when I haphazardly decided that the military wasn’t right for me anymore, I became comfortable and then dependent on the things that came next ― without ever once asking myself whether they were the right things. My life was comfortable and safe. But the safest options in life aren’t necessarily always the better ones, and there came a day when I realized:

SCOTT, dude, you almost settled!!!!

Have you ever “settled” for something?  It’s deflating, isn’t it? I was a person who had been ambitious enough to go to West Point; did I want to end up stuck in an uninspiring career, still driving up to my office just outside of Patch Barracks and going to eat lunch at the same cruddy food court for thirty years? It was when I decided that I didn’t want to live that way that I became intentional about finding the life I was meant to live.

Before I did DEEP work on myself, I did not realize that the source of my unhappiness when I left the military had been the lack of purpose in my life.

I didn’t know, then, how powerful it is to have a mission. But my journey to build a meaningful life has led me to discover some fascinating things about the standard military transition process; about how money and military benefits really work; and about how most military servicemen and women may be doing the “right things” by all conventional standards, yet they are completely unaware of and missing the opportunity that is right in front of them to not just transition into civilian life, but into a new mission, and a new way of serving the communities that we love.

So what’s the “ONE thing you absolutely must do before you transition out of the military?” Essentially, it’s to ask yourself this question:

Do you want to settle for the life that everyone thinks you ought to have, or do you want to make decisions and take actions TODAY that will set you on a course to build a post military meaningful life you can be proud of?

If you want to build a meaningful life you can be proud of ― if you want to start TODAY ― then keep reading, because I’m going to tell you exactly what you need to do.

Your Ideal Future Starts with Intention

If you want to be in control of your destiny, you have to be intentional.

What do I mean by that?

An intentional transition starts by looking at reality, by being present to your current situation, to your current possibilities, and to what YOU want, rather than  “following the orders” of society about how we’re supposed to live as civilians.  Folks, we’re all different from one another, and as veterans, we are different from those who don’t have military experience. It’s time that we honor all of our differences as we transition into a new way to serve our country as leaders.

If you have looked into transition at all, you have probably already figured out that money plays a big role in it. Now… I’m not going to say that everything that your military counselors and financial advisors told you is wrong. Don’t worry; there are sound and accepted financial planning industry standards, and if you are following these widely recommended standards, then you are doing things right! However, as someone who has been in the financial industry for almost a decade, I have found that those standards are just one part of the equation, and nowhere is this more true than it is for someone who is transitioning out of the military.

Truly well-rounded financial planning involves understanding your goals and priorities. As a financial planner, I was taught to ask clients about their goals, and they would always answer in very similar ways: I’d like to buy a house at age such and such; I want to pay for my kid’s college; and I want to retire at 65.  And I’d wonder… are they all the same person?  Of course they’re not.  But society and those who have come before us have told us that these are what our goals should be.

And yes!  We need to plan for these things.  Buying a house ― sure! Own your home!  I think you’ve earned the right to have a place you can call your own! College for the kids ― of course we should take care of our loved ones, our tribe. So we need to plan for that. Retirement ― of course we want financial freedom, so we don’t have to work anymore and we can focus on enjoying our lives.  Of course these things should happen for all veterans.  But we need to shift our mindset about them. These are not really “goals;” they should be more like “inevitabilities” or “supposed to happens.”  If we make them our primary or only goals, then we fall into the trap of comparing our situation or status with that of others. Instead, we need to shift our focus and answer this question for ourselves:

“How do I produce more income for myself and my tribe, so that these inevitabilities aren’t a concern, and I can focus on doing what I was put on this earth to do?”

Another goal that I often hear is, “I want to have a million dollars (or five, or ten, or whatever) by age X.  Then I can retire.”  My good friend and client, a retired Air Force Master chief, had saved a million dollars by age 55, and he was so proud of that. I was proud of him. He had done all the right things. But he was miserable and questioning everything.  His life felt empty because his only fixation was keeping his bank account balance at one million dollars.

Financial Security isn’t about the amount of money you can accumulate. It’s about the money you can produce and then use for something that has MEANING to YOU.

What is missing from traditional financial planning is being present and aware to what is right in front of us, and for active duty military, the elephant in the room is the transition. And I’m going to show you how to be ready for it by sharing what I call my Transition First philosophy or Transition 2.0.  Basically it’s this: your financial planning shouldn’t be focused primarily on your retirement until you know what you want your LIFE to look like. You need to understand what you can influence NOW to create more certainty around those “supposed to happen” goals, to end any worry about what’s coming after the military, and to truly define what “financial independence” actually means for you. Once you do that, you can brand yourself and position yourself financially to create more opportunities. This means you can create a life you’re proud of THE WHOLE TIME THAT YOU’RE LIVING IT ― not just a life you intend to be proud of thirty or forty years from now during retirement.

I repeat: Financial independence is not defined by how much money you accumulate. You serve your country in the military. You are going to be a veteran. You will always be a leader, and when you lead from your true self while you are accomplishing your post-transition mission, you will actually get paid a lot more.

What to Do Right Now

At this point you are probably asking yourself: What do I do now? Maybe you already know what you want to do after the military and you know you need act on your ambition, but you’re not sure what to do, and you’re worried you may miss opportunities because of uncertainty.  That’s why I started Be Financially Fit and put together a unique and simple system to help you start your journey, and today I’m going to share with you the first steps that I take with ALL of my clients, regardless of where they are in the their financial lives, or in the transition process. In fact, when you complete this exercise, you can fit the outcome on one page and stick it on your refrigerator or bathroom mirror to remind yourself daily what your intention is, so that you can always begin every day focused on WHY you are waking up to go to work for that paycheck. Ready? Here we go!

If you would like some one-on-one support with this process, I’m happy to help you design a customized transition plan for your money and benefits so that you can have the confidence to make the decisions that are best for you after the military. Click here to request a personalized “blueprint” of your complete financial picture as it pertains to your transition.

First, Face Reality

The first thing you need to do right now is to face reality. We need to know exactly what we are we working with ― that’s all.  Don’t overthink it.  You are exactly where you are financially today.  And realistically, you’re exactly where you need to be. It’s what brought you here today. As we follow the next steps, you’ll be able to align your true intentions with some hard data to make a simple decision about whether or not you need to make adjustments that will allow you to execute the opportunity you are creating for yourself by being intentional. That’s all. Don’t worry about any past financial mistakes.  Yes, you need to deal with them, but I am going to teach you how to see that those mistakes were valuable, and with that value comes opportunity.

What is your income?  What are you spending?  What’s the relationship between them? That’s called cashflow.  We look at cash flow to determine the health of a business.  If we have negative cash flow ― if there is more money going out than there is coming in ― eventually our business will go bankrupt.

You are your own business. You are the Brand of YOU.

So your first task is to look ― really look ― at your financial situation. Understand it. Own it. Think about what you want your life to look like. Ask yourself, and answer honestly, whether or not the way that you handle money today is truly honoring and respecting the YOU that you want to be, the Brand of YOU.

Become Profitable

Next, we’re going to turn the idea of budget on its head.

The problem with a typical budget is that it focuses on expenses. This is a mistake.  When we focus on things that are outside of ourselves, we lose control. And sometimes there’s not enough money left to save for the future. So let’s simplify and shift how we do this.  You’ve heard of paying yourself first? Yes? You are a business. You work for a salary right? You are an income-producing entity. I say that budgets should put Profit First. Make your budget about the Brand of You.

You need to be profitable! Guess what a salary is, especially a military salary? It’s guaranteed profit! Holy COW! Just by joining the military you became a profitable business. Explain that to someone who went to college and racked up $100,000 in debt and then needs to “find a job!”

Let’s look at a scenario.  Let’s say a LCDR makes the equivalent of $100K including his housing allowance.  Can he take a 20% profit every year and live a nice life on just 80%?  $80K?!  Yeah! Then why do I see so many senior officers struggling? Because they are living their financial lives without intention, and they aren’t paying themselves first.

The clients I’m lucky enough to work with are COMMITTED to themselves. They find ways to take their 20% profit. What changes can you make in your life right now that will allow you to set aside 20% of your income in profit every month? Can you drive a used car? Subscribe to Netflix instead of cable? Stock up on the things you need when they are on sale or purchase things from thrift stores? Eat in more than you eat out? Examine your life, and find ways to pay yourself first with PROFIT. Then invest that profit back into the “Brand of YOU.”

Stop Focusing on Something that is 20, 30, or 40 Years Away!

Related: The Tax Breaks and Special Mortgage Programs Available to Our Military Forces

Finally, I’m going to tell you something no other financial planner will: do not make your financial planning about retirement.


If you were reading this blog post three years from today, and you were looking back at what happened to you over those three years both personally and professionally, what kinds of things would you need to see in order for you to be happy with the progress you have made?

I’m going to give you a few minutes to think about it.

The things that came into your head just now ― and I have no doubt that whether or not it seems so at first glance, they all have a financial aspect ― THOSE are your real financial goals, and the goals of your transition back into civilian life, not the “inevitabilities” and “supposed to haves” that I talked about earlier. Do you want to start a business? Travel the world? Write a book? Become a Nutritionist? A teacher? A martial artist?

Cast your mind back to that reality check you did on your financial situation. Focus on your strengths; don’t worry about your weaknesses.  Let me explain one strength that most career military misunderstand.  They think of their military pension as a “buffer” for their next job. NO! Your pension is not a buffer, it’s an ASSET that you EARNED.  It has value.  Honor your service, realize that value, and recognize the impact it can have in your life.  Be aware of the risk of not protecting it.

Then, try to brainstorm what dangers you might face in the next three years. It’s more realistic to plan to risks and challenges within 3 years than it is to try to anticipate dangers over a 10 or 20 year period.  Most of the dangers you’ll experience will have to do with money. One of the dangers is what happens to that pension ASSET if you get hit by a bus during your retirement? Does the military take care of your wife?  What about the danger of a stock market crash? Are you set up to protect yourself from that?  Do you know how you’d respond emotionally? What if you get sued?  Can someone just take your money from you, all that money that you organized and saved with intention so you could capitalize on an opportunity? What if you did everything right, and then someone cracked their skull because they tripped on a crack in your driveway? Figure out what these dangers are, so that when you talk to a financial advisor you can be very specific about what you are trying to protect yourself from.

With a solid understanding of your opportunities, your strengths, and the dangers you may face, it becomes much easier to set an intention, and that’s what you’re going to do now.

A Successful Transition from the Military Starts with Setting Your Intention

All of that thinking that you have done is now going to get boiled down into a single statement that you can post on your refrigerator or your bathroom mirror and check in with every day. Basically, all you need to do is fill in the blanks, based on your own soul-searching. Some people would call this an affirmation:

I am committed to do __________ so that I can ______________, by ________(date).

Now think about the three years that you have ahead of you today. What opportunities are available to you in the next 3 years that NOW ― with intention ― you can say YES to?

When you have a clear intention, you’ll know what to do in the next three years to realize it.  Maybe you need to go to school and get a specific degree like my buddy Pete West. That guy wouldn’t shut up about getting into physical therapy.  Now he changes people’s lives everyday by helping them deal with serious injury.

Now that you know what you want to transition INTO, set a long term goal for your transition out of the military. Pick a date. It’s okay if it changes! Wake up every morning and review your intention, and the date you set for your transition, while you’re getting ready to go to work. Is it still the plan? Still the plan! Or, nope, I need a new plan. Okay, cool. Change it.  Either way, you have made a choice and created a new intention. Use your intention to give yourself the strength you need to make tough choices so that you can be profitable ― NOW ― in the business of managing the Brand of YOU, because when you are profitable, you can say YES to opportunities that will get your closer to your goals.

Don’t Get Left Behind!

As an active duty service member or veteran, you have a unique opportunity in today’s America, but only if you take responsibility for your future ― the military can’t and won’t do it for you. You CAN shift your mindset around money, your military career, and your ambitions as a veteran. Using simple and modern tools, techniques, and strategies you can stand out from your peers, experience financial confidence and continue to lead as a successful veteran. Honor the struggle, seek your personal truth, embrace your tribe and the financial freedom will follow.

Are you ready to get involved?

I am proud to be leading a community of veterans and soon-to-be veterans who are committed to serving our country in this next new and exciting phase of their lives. Our FREE Military Transition 2.0 Training in San Diego, CA is already a huge hit! This one-of-a-kind seminar is uniquely designed for service members and veterans who want to transition with intention. Our webinars offer next-level information about financial planning and the transition process. Participate as the starting point in discovering your next mission, or build upon what you learned at one of our seminars. We are going above and beyond financial planning 101 and really digging into the realities of what money means to our service people today. On our Facebook Live shows, we discuss anything and everything around Military Transition 2.0! Enjoy book recommendations and discussions, interviews with top military transition experts and fellow veterans, and much more! I’m also available for one-on-one consultations. Take a step towards your future and connect with me today!

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