Saving for education can feel overwhelming, especially when you’re juggling military life, moves, and everything in between. Whether it’s understanding your military benefits, choosing the right savings plan, or figuring out how to afford college for multiple kids at once, it can get complicated quickly.
In this episode, Joe Brown shares strategies to help you plan for education expenses while making the most of your military benefits. We talk about how to use the GI Bill smartly, what to know about Chapter 35, and why scholarships and merit money should be a big part of your family’s game plan. Plus, Joe breaks down 529 plans, education savings accounts, and tips for blending everything together without the stress.
Joe is a CFP® Professional, an MQFP®, and a visiting professor of personal finance at the U.S. Coast Guard Academy, where his work is supported by the USAA Educational Foundation. He’s the founder and lead planner at Always Ready Financial Planning. After a 25-year Coast Guard career filled with deployments, leadership, and teaching, Joe now helps military families and retirees plan with purpose. When he’s not teaching or planning, Joe enjoys golfing, woodworking, ocean adventures, and working toward his goal of exploring all seven continents.
Map Out the Life You Want First
When Joe started planning his life after the Coast Guard, he didn’t just look for a civilian job that mirrored his military role. Instead, he sat down with his wife and thought about what kind of life they wanted: flexibility, the ability to move if needed, and meaningful work. That big-picture thinking led him to financial planning, where he could continue to help others in a way that aligned with their values.
Career transitions shouldn’t just be about finding “the next thing”. They should be about building the kind of life you truly want.
Use Military Education Benefits Strategically
Joe shared that there are three main education benefits military families need to know:
- the Post-9/11 GI Bill (Chapter 33)
- Chapter 35 benefits for dependents if the service member is 100% permanently and totally disabled
- Vocational Rehabilitation and Employment (VR&E) for veterans who need to transition into a new career
Timing is critical. For the GI Bill, you want to transfer benefits as soon as you hit six years of service if you plan to use it for your dependents. Waiting too long can mean losing the opportunity to share those valuable months of education support.
Chapter 35 offers monthly payments for dependents pursuing education, and VR&E can be a lifeline if you need to pivot careers due to service-connected injuries.
Related: Mapping Out a Plan for Your GI Bill
529 Plans Are Still One of the Best Tools
For non-military-specific savings, 529 plans are the most flexible and powerful tool available. They offer potential state tax benefits, allow for large contributions, and cover a wide range of education expenses, including private K-12 schools in many cases.
Joe pointed out that even if you didn’t start saving early, you can still benefit. In some states, you can contribute to a 529 and immediately use the funds to pay tuition, capturing a tax deduction in the process. And if you move duty stations, you aren’t locked into one state’s 529 plan. You can transfer or leave it where it is, depending on the investment options and benefits.
Related: Why Military Families Should Use 529 College Savings Plan
Equal Isn’t Always Fair When Dividing Education Benefits
One of the most powerful lessons Joe shared is that trying to split GI Bill benefits equally among children might actually cost you (and your kids) more money in the long run.
He explained how families can sometimes use the full GI Bill and Yellow Ribbon benefits for one child attending an expensive private school while helping cover another child’s less expensive state school education through other means, like housing stipends or Chapter 35 benefits.
It’s not about treating everyone exactly the same. It’s about maximizing the benefits and resources available to help the whole family succeed financially.
Applying Smartly Can Make College More Affordable
Joe encourages families to think strategically about college applications. Applying to multiple schools, even some you may not plan to attend, can create leverage for better financial aid offers. Some colleges openly publish their merit scholarship criteria, allowing families to make informed choices based on grades, test scores, and available awards.
Planning for What’s Next After the Military
Beyond college planning, Joe emphasized the importance of figuring out how much is enough when transitioning to civilian life. It’s not just about finding a job with a certain salary. Taxes, healthcare, and lifestyle choices can dramatically shift the financial picture.
Starting early, developing a financial mission statement, and breaking down big goals into small, actionable steps can make the entire transition smoother. Whether that means starting a new career, pursuing core passions, or simply aiming for financial independence, the goal should always be to create a life that fits your personal values and not someone else’s definition of success.
Wrapping It Up
Planning for college, career transitions, and life after the military doesn’t have to be overwhelming if you take a strategic approach. Using benefits wisely, understanding your financial picture, and focusing on building the life you want makes all the difference.
As Joe reminds us, money is just a tool. The real power comes from knowing how to use it to support the mission you have for your next chapter. Start early, ask for help, and remember, you don’t have to figure it out alone.
Resources
- Joe Brown’s Linkedin
- What the Happiest Retirees Know by Wes Moss
- Always Ready Financial Planning
- USAA Educational Foundation
MILMO Show Sponsor
Support for the MILMO Show is provided by Navy Federal Credit Union. We’re all living life and taking things day to day, but life often doesn’t leave a lot of free time. That’s why Navy Federal Credit Union created an all-in-one banking experience that saves you time and money with fast direct deposit setup, checking accounts with ATM refunds and no service fees. You can also get access to real financial counselors to help you budget, pay down debt and monitor your credit score. You can learn more at navyfederal.org.
Got Money Questions?
If you have questions about money or entrepreneurship, please fill out this form, and Lacey will answer them on the show and send you a free MILMO t-shirt!
