Reader Interview: Planning For The Military Transition

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[Today’s military transition advice is brought to you by servicemember Annabel Monroe of Monroe Brothers Investments.  If you’re interested in contributing your interview at, please see our posting guidelines.]


What influenced your decision to join the military, and what’s your transition plan to leave active duty?

I always knew I’d serve in the military. My Dad and Grandpa both served in the Army. My freshman yearbook says I’ll join the Air Force and my veteran Dad led me to consider the Air Force very carefully.

I loved the Air Force so much I actually joined TWICE! After enlisting straight out of high school I was eager to use all of those great education benefits. I started school immediately and pursued the Airman Scholarship and Commissioning Program at my six-year mark. I was selected to finish my degree and earn a commission. In order to do so, I separated completely, finished my degree and, upon graduation, became an officer a year and a half later.

My husband is four years ahead of me in time in service with a 2023 retirement date. I aim to retire from the Air Force in 2027. We’ve decided that as long as the Air Force keeps us together (for the most part) and that we are both still enjoying serving (again, for the most part, haha) and leading our teams well, that we will both pursue military retirements. We will also focus on growing our real estate investing knowledge, business, and portfolio.


How did you prepare for your transition? What was a good idea, and what was a waste of time?

We are preparing for our transition by continuously growing our investment knowledge. I’ve become passionate about increasing my financial literacy, educating our children, coworkers and even Airmen!

We focus on establishing multiple streams of income to ensure our financial freedom AND financial freedom for generations to come.


What military skills helped your transition, and what do you wish you’d learned before you left active duty?

The military literally spends hundreds of thousands of dollars teaching us how to lead, mentor, and manage teams. This is a HUGE advantage and easily traverses civilian employment, property management, contractor management, and many other facets of real estate investing.

With a focus on being spiritually sound, physically fit, resilient and well-adapted to most situations our military training has given us many strengths! Don’t forget them and don’t forget how useful they can be to others!


Looking back on your transition now, what would you advise your younger active-duty self? What lessons did you learn?

We always encourage young service members to do the best they can do in whatever it is they are currently doing. If you’re at work and performing your primary duties – be the absolute best Airman you can be. When you’re spending time with family be present and attentive, build memories that will last a lifetime. And if you’re smart enough to find the path to financial independence early, (which you are – since you’re here) dedicate time away from your other responsibilities to grow and learn – don’t ever feel guilty for your desire to have a “side hustle.” Know that your passion for financial independence directly benefits your family and that it can have a positive example on your troops and our military!

One of the biggest lessons we learned was squashing the idea that you need to be settled in one place, married, with a kid and a dog before you buy a house or use your VA loan.

There is a technique called house hacking, where your VA loan can be used to purchase a home, up to a fourplex, you live in it shortly or live in one unit while renting out the other units.

We rented for nearly five years before using our VA loan for the first time and I’d encourage all service members to learn about their VA loan benefits, research real estate, and buy an investment property! You don’t have to be married, with a dog, and a baby on the way, or settled into your forever home before learning about real estate or purchasing your first home!


Imagine that you’ve been out for a while.  What would you miss about the military? What would you not miss one little bit?

Haha, I’ll save these questions for a later date.


What advice would you give to someone who has 2-3 years left on their active-duty obligation and isn’t sure whether to stay in?

I would say that there is some security and stability in service and retirement form our United States Armed Services, but can also be huge opportunities on the outside. If you plan to get out, use your benefits!!! Use Tuition Assistance and your GI Bill to prepare for your post-service life. Learn about the benefits of using a VA loan! Consider options to earn a commission and serve as an officer. Consider the National Guard or Reserve. Do not get out without a plan. Transition with a plan and be proud that you were among the less than 1 percent to serve!

If you decide to stay, stay because you love leading teams, stay because you find honor in service. And just because you stay doesn’t mean you can’t ALSO begin your investment journey or pursue other educational or career goals.


The Military Guide to Financial Independence and Retirement Price: By Doug Nordman: This book provides servicemembers, veterans, and their families with a critical roadmap for becoming financially independent. The Military Guide to Financial Independence and Retirement All Author royalties donated to military charities. Last Updated: 10/10/2018


Related articles:
VA Loan Eligibility and Service Requirements
VA Loan Guide – What You Need to Know About Buying a Home with a VA Loan
Don’t Buy a Home on Active Duty
VA Loan Property Types – Which Type of Home Can You Buy with a VA Loan?
VA Loan Certificate of Eligibility – Why You Need it and How to Get One

WHAT I DO: I help you reach financial independence. For free. I retired in 2002 after 20 years in the Navy's submarine force. I wrote "The Military Guide to Financial Independence and Retirement" to share the stories of over 50 other financially independent servicemembers, veterans, and families. All of my writing revenue is donated to military-friendly charities.

  1. Best financial decision I ever made was to take $50 from my 1st military pay in 1985 and invested with Vanguard. When retired in 2008, nothing like the magic of time and compounded returns. Pay yourself first.

    Tried my hand a real estate, income properties, in the Navy hub of Hampton Roads. Did not have either the temperament or personality type to do the long distance landlord stuff. Know you strengths and weaknesses as applies to various asset classes, and risks of each. Ask anybody who experienced 2007-09. And yes, the military is likely the only career option in America, outside of maybe Federal Law enforcement, where you can “retire” with benefits with 30, 40 years maybe of productive life ahead. Use it wisely.

    Comment? Question? What's on your mind?