If you think you’ve got time, think again. Transitioning out of the military isn’t something you wing—it’s something you plan, and that plan should start earlier than you think.
After 20 years of active-duty service, my husband and I can look back to the beginning and almost laugh at how naive we were. The rose-colored glasses were thick, and the lenses with which we saw the world around us certainly didn’t account for blind spots. We looked at our parents’ generation of military retirees and daydreamed of campers, summers spent on boats, and a financial freedom that I can barely fathom today.
Don’t get me wrong—we tried to save and plan for the future. Much of my background is in insurance and financial planning, so we had a fundamental knowledge of budgeting, financial health and investing. But every time we attempted to save or prepare, a crisis would hit and wipe out our savings. The rising costs of raising children and living expenses also impacted our ability to keep up. Not to mention the costs of trips home to see family and other odd military lifestyle expenses—like replacing all of my spices every two to four years—took a toll on our bottom line.
Why does all of this matter? Now that we are at the finish line, we are nowhere near where we wanted to be. We can’t make it on one income like we had hoped. We also aren’t as comfortable as we thought. The planning and preparation aren’t just about handling the money. Some of the biggest challenges I’m finding in this season are repairing the damages to our connections and dealing with my career.
Two years ago, I launched a nonprofit so that I would be a couple of years ahead of his transition. My logical thought was that I would be steady and settled. Yeah… That is not at all what happened. The chaos of active-duty military life is still sucking the life out of me. I wish I would have planned long-term for the upheaval this retirement transition has caused.
Here are 3 things you need to know as you plan for retirement:
Prioritize your health early
My family should have been in therapy way before we were, and I wish I would have focused more on our collective mental health. I was nearly 37 when I was diagnosed with ADHD because I never had the time to get evaluated. Recently, I was also finally diagnosed with depression. Once I received treatment for these things, I regretted putting off the treatment. I should have cared for myself this way earlier.
So, evaluate your health—physical, mental, emotional, and spiritual—and get taken care of. Prioritize yourself. Plan to be exhausted, over-taxed, and frustrated. Maybe explore therapy or other forms of support to develop healthy coping mechanisms. The mental toll of military life is real, and it doesn’t just go away when the uniform does.
Set up your own retirement account or one for your spouse
The second thing I wish I would have done is to set up my own retirement account. The moment I realized I had served my family for the last two decades working odd jobs, building my life around the mission, and sacrificing my own needs for the military—and had no retirement of my own, I was extremely discouraged. I opened an account the next day so that in 20 years, I won’t feel the same way.
It’s easy to get caught up in the day-to-day demands of military life, but don’t neglect your future self. Even small contributions to a retirement account can make a huge difference down the line. Don’t wait—start now.
Prepare for the job hunt
Lastly, I wish I would have felt more prepared on the job front. I have had so many jobs over the years and made so many career moves. Honestly, I am tired. I would have loved to have a 20-year track record in a career field and a retirement account. Instead, I have the craziest patchwork of weird income streams and bootstrapped efforts. Now, we need two incomes to support our growing family, and I find myself entering the career field at a disadvantage.
What I thought would be a dreamlike experience of smoothly transitioning together, getting meaningful jobs, and riding off into the sunset has been more like a nightmare of struggling to connect, lacking desirable options, and feeling stuck. I wish I had planned more strategically for this, understanding that my career path wouldn’t be linear and that I would need to adapt constantly.
The clock’s ticking, and the sooner you start planning, the smoother the landing. Transition isn’t just an event—it’s a long-term mission.
The reality of military retirement is that it’s not the idyllic picture we once imagined. It’s a complex, challenging process that requires more planning and preparation than we ever thought possible. The earlier you start, the better off you’ll be when the day finally comes. Don’t wait—start planning for your retirement now. Because when the time comes, you’ll want to be as ready as possible to navigate the transition with confidence and security.