Brigadier General Michael Meese details the critical decisions military families must make before retirement.

Transitioning into retirement is a major life change for anyone.

But for military families, that transition isn’t just about leaving a job. It’s about moving from one entire system of life into another.

As Brigadier General Michael Meese explained, this shift requires more than just paperwork. It requires understanding your benefits, your options, and your goals—before the transition begins.

“Understanding all of the military benefits and the circumstance that you’re in… and then aligning that with the goals that you might have” is essential to getting this right.

That alignment is where good planning begins.

Why Military Transitions Are Different

Most civilian career changes are relatively straightforward. You move from one company to another, often with similar systems, benefits, and expectations.

But transitioning out of the military is fundamentally different.

You’re not just changing jobs.

You’re shifting from a structured environment—with defined benefits, systems, and support—into a civilian world where many of those decisions are now your responsibility.

That’s why preparation matters so much.

This isn’t something you want to figure out for the first time when someone puts paperwork in front of you.

You want to understand your options before that moment arrives.

The Decisions That Matter Most

There are several things that all former service members and their families need to evaluate before jumping into retirement.

The Survivor Benefit Plan

One of the most important decisions is whether to elect the Survivor Benefit Plan (SBP).

This plan provides ongoing income to a surviving spouse, but it comes with trade-offs.

While this benefit is valuable, it doesn’t fully replace income:

The maximum your survivor can get is a 55% payout once you’re gone. How confident are you that your survivor’s bills will drop by more than 45% when you’re gone?

That means SBP should be viewed as part of a broader plan—not the entire solution.

Coordinating SBP with Social Security, savings, and other assets is essential to ensuring a surviving spouse is truly protected.

Life Insurance Decisions

Another key transition happens with life insurance.

Many service members are covered under SGLI (Servicemembers’ Group Life Insurance) while on active duty. After leaving the military, they may transition to VGLI (Veterans’ Group Life Insurance).

But that transition often comes with higher costs.

The key insight is that timing matters.

If you’re in good health, you may be able to secure more affordable coverage through private insurance—but that process takes time and underwriting.

That’s why planning ahead is critical. You don’t want to wait until after separation to explore your options.

Don’t Overlook Your TSP

The Thrift Savings Plan (TSP) is another major asset for many service members.

One of its biggest advantages is cost.

It offers low expenses and access to unique investment options like the G Fund, which provides a stable return without the same price volatility as traditional bonds.

That makes it a valuable component of a retirement strategy—even after leaving the military.

The key decision isn’t simply whether to keep money in the TSP or move it elsewhere.

It’s understanding how it fits into your overall plan.

Advocate for Yourself

Another important topic in the conversation was VA disability benefits.

These benefits are designed to compensate service members for conditions developed during their time in the military.

But receiving them requires active participation.

This is a moment where service members need to shift their mindset:

You’ve taken care of everybody else. It’s time to make sure you get that disability determination.

This isn’t about taking advantage of the system.

It’s about receiving the benefits you’ve earned.

Preparation Is the Advantage

One of the most powerful insights from the episode came from a military principle itself.

Preparation.

When I was in ROTC training, a significant portion of time was spent preparing and rehearsing before any action took place.

That same mindset applies to retirement.

You don’t want to improvise your transition.

You want to prepare for it.

Because when you understand your benefits, align them with your goals, and make decisions ahead of time, you reduce the chances of regret.

And that’s the goal.

Not just to retire—but to transition with confidence into the next chapter of life.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Brigadier General Michael Meese on LinkedIn
Retirement Transition Timeline – Armed Forces Mutual
Armed Forces Mutual

Connect With Jeremy Keil:

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