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Layin’ It on the Line: Three decisions military retirees only get to make once

By LYLE BOSS - Special to the Standard-Examiner | Nov 11, 2026

Photo supplied

Lyle Boss

Drive past Hill Air Force Base on any weekday and you’re looking at one of the reasons Northern Utah works the way it does. Generations of families here have worn the uniform, and a good number of the people I sit down with in Ogden retired from it.

So this Veterans Day, along with a sincere thank you, I want to offer something more useful than a discount on breakfast. Military retirees face a handful of financial decisions that civilians never do. A few of them are made once, early, and are very hard to undo.

First, the good news

If you retired with a military pension, you’re already holding something most of my clients would trade a lot for: a lifetime check that rises with inflation. Military retired pay gets the same cost-of-living adjustment Social Security announced last month, every January, for life.

Stack that on top of Social Security, and many military retirees have more guaranteed, inflation-protected income than most civilians ever will. That changes the planning math, and it’s why the rest of this column matters.

Decision one: The Survivor Benefit Plan

When you retire, you choose whether your spouse keeps a portion of your pension after you’re gone. The Survivor Benefit Plan costs 6.5% of the base amount you choose and pays your surviving spouse 55% of that base for life, with the same annual inflation increases.

That decision is largely permanent. And every year I meet a widow whose husband declined SBP decades ago because a salesman told him term life insurance was cheaper.

Sometimes it was. Then the term policy expired at 70, the premiums to keep it became impossible, and she was left with no pension at all. Life insurance has its place. But a lifetime, inflation-adjusted income for a surviving spouse, with no medical exam and no expiration date, is very hard to replicate privately at any price. One more improvement worth knowing: the old offset that reduced SBP for widows also receiving VA survivor benefits, the so-called “widow’s tax,” was fully eliminated in 2023.

If you’re still serving and approaching retirement, talk through this one carefully with your spouse at the kitchen table. It’s their paycheck you’re deciding.

Decision two: Medicare Part B, even if you think you don’t need it

TRICARE For Life is one of the best health benefits in America. But it comes with a condition that catches people every year: To keep TRICARE after 65, you generally must enroll in Medicare Part A and Part B and pay the Part B premium.

Skip Part B, and you can lose your TRICARE coverage, then face a late-enrollment penalty to get Part B back. That penalty can follow you for life.

And since Medicare enrollment season runs through Dec. 7, a related warning. If you have TRICARE For Life and someone on the phone is urgently pushing you into a new Medicare Advantage plan, slow down. TRICARE For Life already works as your secondary coverage. Make sure any change actually adds something before you sign.

Decision three: VA benefits, and the people who sell them

Wartime veterans and their surviving spouses who need help with daily living may qualify for a VA pension with Aid and Attendance, a meaningful benefit for families facing assisted living or in-home care costs. It has income and asset limits, and since 2018 it has a three-year look-back. Move or give away assets to qualify, and you can face a penalty period of up to five years with no benefit at all.

That rule exists because of a cottage industry that told veterans to reposition savings, sometimes into annuities, to fit under the limits. I sell annuities for a living, and I’m telling you plainly: Be very wary of anyone who pitches a financial product as the way to qualify for VA benefits.

Two simple protections. You never have to pay anyone to file an initial VA claim. And anyone helping you should be VA-accredited, which you can check on the VA’s own website.

Where that leaves the rest of the plan

Because a military pension already covers so much of the base, many veteran households need less additional guaranteed income than civilians do. Sometimes the right answer is a smaller Fixed Index Annuity than you’d expect, or none at all, with the rest of the plan focused on taxes, legacy and keeping a surviving spouse secure. A good adviser should be just as willing to tell you that as to sell you something.

You signed paperwork once that said you’d go wherever you were sent. These forms deserve that same seriousness, because the person they protect is usually the one who waited at home.

Thank you for your service. Now let’s make sure your family is protected the way you protected ours.

Lyle Boss, The REAL BOSS Financial, a native Utahn and retirement specialist who has spent decades helping families across Utah and the Mountain West build secure, income-focused retirement plans. Boss Financial, 955 Chambers St. Suite 250, Ogden, UT 84403. Telephone: 801-475-9400. https://www.safemoneylyleboss.com

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