Five Year Plan-Why It’s Important For Every Military Family To Have One

14,542 grads of the Ultimate Military Credit Cards Course already know why
The Platinum Card® from American Express is my #1 recommended card

Military Money Manual has partnered with CardRatings for our coverage of credit card products and may receive a commission from card issuers. Some or all of the cards that appear on this site are from advertisers and may impact how and where card products appear on the site. This site does not include all card companies or all available card offers. Any opinions, analyses, reviews or recommendations expressed in this article are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed by any card issuer.

I was catching up with an old friend the other day, and he told me that his favorite question to ask Sailors is, “What is your five year plan?” That question immediately resonated with me in so many different ways, because it’s a philosophy that I've adopted throughout my career, even if I never thought of it in terms of that exact question.

This article serves to outline some of the dimensions in which you could (and probably should) think about in terms of a five year plan. JW-Thanks for the idea!

What Should I Include in My Five Year Plan?

You Five Year Plan should be personalized to your specific needs. But if you are still in the military, you can use this outline as the basis of your Five Year Plan. Just make adjustments according to you specific needs. If you are no longer in the military, you can omit the “Military Career” section. But you should replace it with what is applicable in your life right now – whether that is your current career, your education, your business, or whatever is most important in your life right now.

Military Career

Obviously, since this blog is focused on military personnel and their families, the immediate thing to consider in your five year plan is what the next five years of your career will look like. If you just enlisted or got your commission, you should think about:

  • What tours will I have accomplished over the next five years? Most officers I know are trained to think of where they should be two tours removed from their current one. This is good advice for enlisted personnel, as well.
  • If I’m thinking two tours ahead, what am I doing now that will qualify me in my next tour & subsequent tour? Every tour I’ve been in, I’ve spent time trying to figure out what skills I need for that tour after my next.
  • If you’re nearing the end of an enlistment, will you re-enlist? If you re-enlist, what tours would you want under your belt in your next enlistment? Are you re-enlisting for a technical school, to complete your college degree, or something else?
  • Will you be able to make your goal over the course of those five years. If you’re a career track officer, is there a promotion board or admin screening in your near future? If so, what do you need to accomplish to be ready for it? Whether you’re enlisted or officer: are you near 20? If so, are you going to keep going?

At the very least, you should have a five year plan by the 15-year mark so that you can tell whether you’re going to try to stay in past 20. If you don’t plan to stay in, that brings us to your post-military plan.


Despite what you may think, you CAN plan a parallel track of professional achievements/accomplishments outside your military career. In fact, you should, for several reasons:

  1. If you’re in a technical field, you may be able to get a certification that industry values, but the military doesn’t.
  2. You may find that when you leave, there isn’t a whole lot of demand for the skills that you’ve been trained in. I worked with a lot of hard-working ship’s servicemen & cooks…they have some of the heaviest sea/shore rotations in the Navy, but there isn’t a whole lot of formal military training which prepares them for the civilian world.
  3. You might end up in a completely different career field from the one that you were in. It’s not that having done some additional training or going to school on the side could make you competitive…not doing so could make your resume less impressive than it should be.
  4. If you’re nearing the end of your career, you might need to focus on community relationships and networking—this all counts as the stuff that can help make or break your post-military career.


This almost goes hand-in-hand with your post-military five year plan, but not quite. You can pursue a formal education that has nothing to do with the training you may have done on the side.  For example, post-military training might be to obtain the Program Management Professional (PMP) designation. However, getting an MBA or a Bachelor’s in Business Management would be the educational portion. College education is a much longer-term commitment…even more than your five year plan.

However, keeping a ‘steady strain’ approach will help you manage that education in five year increments, so that you can finish a 20-year career with your degree or advanced degree, even if you didn’t get a formal opportunity to do so through the military.

Personal Finances

You should track where you are financially throughout the course of your career. If you get reenlistment or retention bonuses—where do they go? Where does your deployment or combat pay go? Ideally, it goes less to shiny rims and new cars and more towards investments that grow over time. If you’re in debt, you should work with your base’s financial aid office to help you with a cash management plan to get you in the clear. That could be the basis of your five-year plan.

If you’ve saved a bunch of money, but don’t know where to begin planning for the future, you should sit down with a fee-only financial planner who specializes in working with military personnel. Financial planning doesn’t have to be expensive, and having a long-term relationship with a fee-only financial planner can make a huge difference in your net worth over time. Once you start, being able to look back and notice the increase in your net worth can be a huge incentive to keep going.


This should be the most important aspect of your five-year thinking. If you don’t think about your family first, you may or may not have a successful career—but you will almost definitely ruin your family. Every person in the military is replaceable. Let me repeat this for those of you who feel like you need to put in 80 hour work weeks at every tour: every person in the military can be replaced. In fact, every person will be replaced at some point.

However, your position as a member of the household cannot be replaced.  Part of your five year plan needs to include

  • Important family milestones and events, like high school graduation & college.
  • Elder-care issues:  Is it possible that you'll have to take time off to take care of a parent?

So, what does your five-year plan look like for your family? When you’re young, this is pretty easy. When your kids are young, this could be pretty easy as well. However, many families reach a point where the toll is just too much for the children to take. You need to pay attention to when this may happen to you. My tour in Tampa was not coincidental—it was an opportunity for Tania and I to have a clear crossroads: do we stay in & try to make O-6, or do we retire from here? After our oldest son, who had just made his 5th move in 9 years, started missing friends he had two tours ago, we realized our decision was pretty easy.

It’s important for you to take some time to think about each of these aspects and build your own five year plan.  You may find that some of them seem mutually exclusive, especially when you look at your military career, family planning, or post-military ambitions. In some cases, you may be able to establish priorities that allow you to achieve all of them, while in others, you may decide to put something on the back burner because of another priority. However, if you take the time to think about these things, you’ll be more likely to succeed—even if you decide that the military stops being your top priority.

As always, this blog serves to answer your questions and address concerns.  If you like this blog, please forward it on to other people who may benefit.  If you have issues or concerns, or if you have a question you'd like me to answer, please feel free to contact me.

Forrest Baumhover is a Certified Financial Planner™ and owner of Westchase Financial Planning, a fee-only financial planning firm in Tampa, FL. As a retired naval officer, Forrest helps veterans, transitioning servicemembers and their families address the financial challenges of post-military life so they can achieve financial independence and spend more time doing the things they love.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.