Winged Wealth Management and Financial Planning, Niceville, FL (2026)

10/12/2026

The CFO vs. the Hostage

There's a financial planning concept you'll never find in a Monte Carlo projection: both people in the relationship need to know what's going on.

You can have the perfect allocation, airtight insurance, and a beautiful estate plan — but if one spouse is the CFO and the other is basically a hostage at the budget meeting, you have a problem.

You know the dynamic. One person knows every account, password, and TSP allocation down to the percent. The other knows approximately where the credit card lives. Ask "how are we doing financially?" and the CFO pulls up a spreadsheet with 14 tabs. The hostage starts eyeing the exits.

Nobody plans this. One spouse just got more interested in spreadsheets, and efficiency took it from there. The problem isn't the division of labor. It's when one person has zero idea how the system works.

Picture a military spouse whose partner deploys — and then they're the one who gets sick, or is traveling, or is just unreachable. Suddenly someone needs to find the life insurance, access the TSP, and figure out who the advisor is. "Somewhere in the cloud, password involves the dog's birthday" is not a continuity of operations plan.

Being on the same page doesn't mean both people become financial experts. Nobody needs two spouses who can calculate a Roth conversion. But both should know the big picture: what you have, what you owe, what happens if one of you dies, and who to call. Above all — what is the money actually for?

Because a real financial plan isn't a document one spouse nods politely at once a year. It's a shared roadmap you can both explain.

That doesn't mean you'll agree. One of you may think $90K of extra cash flow from a deployment is a lot of extra TSP and IRA savings while the other sees a gleaming new truck as a deployment survival reward. Better to have that fight before the deployment than after.

The goal isn't identical attitudes about money — it's understanding each other's priorities well enough to decide together. Maybe that's a "conversations required above spending $X" rule. Maybe it's a monthly 30-minute money meeting. Maybe it's the CFO staying the CFO while the other spouse handles literally anything else, as long as both understand the whole picture.

The CFO can keep the job. Just don't let them be the only one who knows where the financial oxygen masks are.

Money stress rarely comes from having too little — it comes from mismatched expectations. One of you thinks you're saving for retirement; the other thinks it's a house fund. One thinks the pension means you're set; the other is quietly panicking about every dentist bill. A spreadsheet won't fix that. Communication will.

The goal isn't turning the hostage into a CFO. It's giving them a financial security clearance — read-in access to the accounts, the plan, the passwords, the professionals, and the right to ask questions without feeling like they're interrupting a classified briefing.

Financial planning isn't really about money. It's about running a life together — and having a plan for when the CFO suddenly goes dark.

Cleared to Rejoin

The best plan isn't the one with the fanciest spreadsheet. It's the one where both people know the mission — so if the CFO goes offline, nobody's standing in the command center asking "uh… where's the money?"

Fight's On!

10/05/2026

Monday Money: Super-Maxing Your TSP While Deployed

Maxing out the TSP is already a flex. For 2026, the employee deferral limit is $24,500 for anyone under age 50, and the list of folks who do it may be distinguished, but it isn’t terribly long. A combat-zone deployment unlocks some extra stages of afterburner, allowing servicemembers to “super-max” their TSP contributions, saving as much as $72K.

Unfortunately, the list of ways the super-maxing process gets confusing is long and distinguished. Let’s simplify it.

Start With the Two Limits:

There are two different ceilings to keep straight.

The first is the normal $24,500 “employee deferral” limit. Roth contributions count toward that limit, as do ordinary pre-tax traditional contributions when you’re not deployed.

The second is the much larger $72,000 “annual additions” limit for 2026.

That limit counts nearly everything going into the account, including your own contributions and BRS (blended retirement system) government contributions.

If you're in BRS, the government can add up to 5% of base pay: a 1% automatic contribution and up to another 4% in matching contributions.

Combat-zone pay creates the opportunity to use the space between $24,500 and $72,000 that you can’t touch in a non-deployed month.

Traditional TSP contributions made from tax-exempt combat-zone compensation do not count against the normal $24,500 employee deferral limit, although they do count toward the $72,000 annual additions limit.

Those dollars are tracked as tax-exempt contributions. The contributions themselves have already avoided federal income tax and generally aren't taxed again when distributed. The investment earnings generated by them, however, are maintained in the tax-deferred part of the TSP and remain taxable unless later moved to Roth (and taxed in a Roth Conversion).

Officers, take note: the combat-zone exclusion for officers is capped at the highest enlisted rate plus hostile fire or imminent danger pay.

Traditional contributions attributable to taxable compensation above that amount are regular pre-tax contributions and therefore use part of the $24,500 employee deferral limit.

What a Full-Year Deployment Could Look Like:

Assume you spend the entire year in a combat zone and earn $100,000 in base pay.

A $24,500 Roth contribution spread across the year would require 24.5% of $100,000. Because TSP elections use whole percentages, electing 24% would produce $24,000 of Roth contributions.

If you're receiving the full BRS contribution, another $5,000 goes into the account from Uncle Sam. That puts you at $29,000 toward the $72,000 annual additions limit.

That leaves $43,000 of additional room.

A 43% traditional election on $100,000 of base pay would add another $43,000.

Under these simplified assumptions, the result is $24,000 Roth, $43,000 traditional (tax-exempt), and $5,000 (pre-tax, eventually taxable) from the government: exactly $72,000.

Saving 67% of your own base pay obviously requires both a handlebar mustache and substantial cash-flow capacity, but you’re still reading, aren’t you?

The important point is how the two limits interact. Roth contributions continue to count against the $24,500 employee deferral limit even when the contribution comes from tax-exempt combat-zone pay. Once you reach $24,500, additional Roth contributions aren't allowed for the year.

But reaching $24,500 does not shut down traditional contributions made from tax-exempt combat-zone compensation. Those can continue until you reach the $72,000 annual additions limit.

That doesn't mean contribution timing stops mattering. If you're in BRS, you still want to avoid maxing the normal employee deferral limit, the $24.5K of Roth contributions, so early that you interfere with contributions later in the year and potentially lose part of the government match.

In other words, don't firewall the Roth in January. Meter it across the year.

Real Deployments Require More Mission Planning:

A January-through-December deployment makes for a clean example. Your mileage probably varies.

Suppose instead that you deploy in April and return in the middle of October. Keeping Roth contributions steady throughout the year is good practice in most years anyway. The traditional side requires more attention.

Traditional contributions made before or after the months of combat-zone pay are ordinary pre-tax contributions. Those dollars share the same $24,500 employee deferral limit as Roth contributions. You almost certainly don’t want that to happen.

This creates some notes, warnings, and cautions for an uncertain deployment year.

Don't turn on the traditional contribution too early. If you increase traditional contributions in March and the deployment doesn't begin until May, those March dollars are taxable traditional contributions. You've now used part of the $24,500 limit and reduced the room available for Roth contributions.

Allow for payroll processing time. You should make your pay and TSP changes by the 15th of the month prior to the month you want the change. E.g., 15 March for a 1 April effective date.

Pick a target that fits your actual goals. There is no requirement to hit $72,000. You may decide that contributing an additional $10,000 or $20,000 during the deployment is enough. Determine the amount first, translate it into a contribution percentage, and use that rate during months in which the pay qualifies for combat-zone treatment.

Manage the return home carefully. If you leave the combat zone in mid-October, October still qualifies as a combat-zone month for purposes of the exclusion. Once the return date becomes reliable, reduce the traditional election so that taxable contributions in later months don't unexpectedly consume your remaining $24,500 deferral room.

The real planning risk isn't that you'll somehow lose access to the TSP entirely. It's using too much of the $24,500 employee deferral limit on pre-tax traditional contributions outside the deployment window. That can reduce the amount available for Roth contributions and make the BRS match harder to manage.

Deployment dates move. Contribution percentages should move with them.

Guard and Reserve Members Have Another Limit to Watch:

For Guard and Reserve members with civilian employment, there's an additional wrinkle.

The $24,500 employee deferral limit applies to you across plans, not separately to every employer. Contributions to a civilian 401(k), 403(b), or another TSP account can therefore consume part of the same annual limit.

If you're trying to super-max during a deployment while also funding a civilian retirement plan, this is one of the easiest places for the numbers to get complicated.

Roth Conversions- the Bonus Plan:

Beginning in 2026, the TSP permits in-plan Roth conversions.

That can be especially relevant during a combat-zone year because your taxable income may be unusually low. A conversion pays tax at today’s rate to convert traditional TSP money into Roth money (usually never taxed again).

It’s possible, but rare, for steely-eyed killers to have a higher tax rate in retirement than during a deployment year. You’ll need both an abacus and a crystal ball to be sure.

You Can't Simply Convert Only the Tax-Exempt Dollars:

The “pro-rata rule” matters. It states that when you do a Roth Conversion, whether inside the TSP or a Traditional IRA, the conversion is always a pro-rata mix of the pre-tax and after-tax (tax-exempt) dollars. You can’t only convert the pre-tax dollars inside the TSP.

Assume your TSP contains:
• $100,000 of Roth money
• $100,000 of pre-tax traditional money
• $100,000 of tax-exempt combat-zone contributions

The existing $100,000 Roth balance has nothing to do with the conversion calculation because the conversion is coming from the traditional side of the account.

That traditional side totals $200,000 and, in this example, is split evenly between pre-tax money and tax-exempt contributions.

Ignoring the TSP's required source minimums for the moment, a $20,000 conversion would therefore generally consist of about $10,000 of pre-tax traditional money and $10,000 of tax-exempt traditional contributions.

The $10,000 pre-tax portion would be taxable. The $10,000 representing tax-exempt contributions would not.

If your account contains a large amount of pre-tax money, a conversion can still generate a substantial tax bill. That's a situation where professional tax help may be worthwhile.

Younger Service Members May Have an Unusual Opportunity:

Someone who has contributed primarily to Roth TSP throughout a relatively short career may not have accumulated much pre-tax money.

A portion of the traditional balance may simply be BRS government contributions, since automatic and matching contributions currently go into the traditional side of the TSP.

Combine a relatively small pre-tax balance with unusually low taxable income during a deployment, and a Roth conversion may occur at lifetime low tax rates.

In the right situation, a younger service member could return from deployment with a TSP that is nearly-all Roth by performing in-plan conversions every pay period.

There is one operational limitation. Active participants generally must leave at least $500 in each applicable non-Roth payroll source, including tax-deferred employee contributions, tax-exempt employee contributions, automatic 1% contributions, and matching contributions.

So, while you're still actively contributing through payroll, you may not be able to convert every last traditional dollar.

Cleared to Rejoin:

You can super-max your TSP with as much as $72,000 (2026), but measure twice with your Roth and Traditional percentages and timing.

The key is understanding that the $24,500 employee deferral limit and the $72,000 annual additions limit are different limits serving different purposes. Combat-zone traditional contributions t allow you to operate in the space between them.

Don’t skip the opportunity just because $72K feels unrealistic. If the deployment simply gives you the cash flow to max the normal $24,500 limit for the first time, you still get a gold star.

Finally, even if you don’t super-max your TSP, take a look at in-plan Roth conversions to see if they might lower your lifetime tax bill.

Fight's on!

09/28/2026

Health Spending Accounts and TRICARE: Why Military Families Have a Different Option

Healthcare is one of those expenses that can be easy to underestimate when building a financial plan. We tend to think about the monthly premium, perhaps glance at the deductible, and move on. But over the course of a year, the costs of prescriptions, copays, dental work, vision care, braces, medical equipment, and other healthcare expenses can add up quickly.

One way to make some of those expenses less expensive is by using a tax-advantaged health account. For many employees, that might mean a Health Savings Account, or HSA. For eligible federal employees and service members, it may instead mean a Health Care Flexible Spending Account, or HCFSA. And for military families using TRICARE, understanding the difference is particularly important because TRICARE generally does not qualify as an HSA-eligible high-deductible health plan.

An HSA is one of the more powerful accounts available in the tax code. When you are eligible, contributions can receive favorable federal tax treatment, the money can be invested, and withdrawals can be tax-free when used for qualified medical expenses. The account belongs to you rather than simply being an annual benefit that disappears if you don't use it. For 2026, the HSA contribution limit is $4,400 for self-only coverage and $8,750 for family coverage, assuming you meet the eligibility requirements.

The catch is that you have to be eligible to contribute to an HSA. The primary requirement is that you be covered by a qualifying high-deductible health plan, or HDHP, and not have other disqualifying health coverage. For 2026, an HSA-qualified HDHP generally must have a deductible of at least $1,700 for self-only coverage or $3,400 for family coverage, while also staying within the applicable out-of-pocket maximums. There are additional rules, including restrictions involving other health coverage and certain FSAs or HRAs.

This is where military families sometimes get confused. You might hear someone say, “I have a high deductible, so I should be able to contribute to an HSA.” But having a deductible does not automatically make a health plan an HSA-qualified HDHP. The plan has to meet the specific requirements established under federal tax law. TRICARE does not qualify as an HSA-eligible HDHP. TRICARE itself specifically states that HSAs don't work with TRICARE because TRICARE doesn't qualify as a high-deductible health plan.

That means a service member or military family covered by TRICARE generally can't simply open an HSA and start making tax-deductible contributions because they wish to. The HSA rules are determined by federal tax law, not by whether the healthcare plan feels like a “high deductible” plan. And this distinction matters because an HSA is not just another savings account. Making contributions when you are not eligible can create tax problems and potentially require corrective action.

So what can military families use instead?

For eligible service members, the Health Care Flexible Spending Account, or HCFSA, can be a valuable alternative. The HCFSA allows eligible participants to set aside money from their paycheck before taxes and then use those funds for eligible healthcare expenses. For 2026, the HCFSA contribution limit is up to $3,400. The account can be used for a broad range of eligible medical, dental, vision, prescription, and certain other healthcare expenses.

This can be particularly useful for military families because TRICARE can cover a significant amount of healthcare costs, but it doesn't necessarily cover everything a family might spend on healthcare. Depending on the TRICARE plan and the particular service, families may still encounter copayments, deductibles, coinsurance, prescriptions, dental expenses, vision expenses, braces, and other qualified expenses. TRICARE itself points out that an HCFSA can be used for costs that TRICARE doesn't cover.

The HCFSA can be useful even if you think, “We have TRICARE, so we don't really spend much on healthcare.” Maybe your family doesn't have many medical bills. But perhaps one child needs braces. Someone needs new glasses or contact lenses. You have recurring prescriptions. You use an eligible wellness service. Or you simply want to purchase qualified over-the-counter healthcare products with pre-tax dollars. Those expenses can add up.

TRICARE specifically lists examples of HCFSA-eligible expenses including medical copayments, coinsurance and deductibles, dental exams and braces, vision exams and eyeglasses, contact lenses and supplies, certain wellness services such as chiropractic care, acupuncture and massage therapy, prescription medications, prescribed over-the-counter medications, and eligible over-the-counter healthcare items such as bandages and blood-pressure monitors. The IRS ultimately determines which expenses qualify, so it is important to check the current eligible-expense list rather than assuming something qualifies simply because it is related to health or wellness.

There is another important distinction between an HSA and an HCFSA: the money works differently. An HSA is designed to be a long-term health savings vehicle. If you don't spend the money this year, it generally remains in the account and can continue growing. An HCFSA is much more focused on using pre-tax dollars for eligible healthcare expenses during the applicable plan period, subject to the plan's carryover and other rules. In other words, an HSA can become a long-term asset; an HCFSA is primarily a way to reduce the tax cost of healthcare spending you expect to have.

That difference makes planning especially important with an HCFSA. You don't want to put $3,400 into an account simply because that's the maximum contribution and then discover that you only have $500 of eligible expenses. The rules governing unused balances, carryovers, and grace periods can vary, so you should understand the current FSAFEDS rules before making your election. The better approach is to estimate your family's predictable eligible healthcare expenses for the coming year and use the account strategically.

Think about it like any other part of a financial plan. If you know your child is getting braces next year, you have predictable prescription expenses, your family regularly purchases eligible vision products, or you know you're going to have recurring qualified medical expenses, an HCFSA may allow you to pay those bills with pre-tax dollars instead of after-tax dollars. That difference can effectively reduce the true cost of the expense.

Enrollment generally occurs through FSAFEDS during Federal Benefits Open Season, with qualifying life events providing certain opportunities to make changes during the year. Think of TRICARE as the healthcare coverage and the HCFSA as a tax-advantaged account that can help you pay certain eligible expenses that arise alongside that coverage.

Cleared to Rejoin!

Tactical takeaway: Before the next benefits enrollment period, look at your family's expected medical, dental, vision, prescription, and other eligible healthcare expenses. If you're eligible for an HCFSA, consider whether putting some of those predictable expenses through a pre-tax account could lower your overall tax bill. And if you think you might be eligible for an HSA because of another health plan, verify your eligibility under the IRS rules first.

Fight's On!

09/21/2026

Is A Roth IRA Better Than Life Insurance?

Most of us don’t have enough life insurance. We should fix that before topping off retirement savings.

My daughter is allergic to peanuts. Like many Gen-Xers, I don’t think I met a single person with a food allergy growing up, but when my own kids came along, it seemed all too common to hear that our friends had kids with food allergies too. Unsurprisingly, I’ve started to notice allergies more since a lethal one became part of our family. But the allergy I encounter most these days is to life insurance. We love to fund our TSP and Roth IRAs, but ask us to fund sufficient life insurance? Cue the hives and itching!

Why is the Military Allergic to Life Insurance?

I mainly serve military and veteran families, and most show up with too little life insurance. I have a few thoughts on why.

1. We already get SGLI/FSGLI (Servicemembers Group Life Insurance and Family Servicemember Group Life Insurance) on the cheap. The $500K of SGLI seems like a lot, but for officer families with kids and aspirations for a home, a mostly-stay-at-home parent (often mom), and education for the kiddos? It’s simply not enough.

2. Cost. We may not know what coverage costs, but we watch every dollar, and we know there aren’t spare dollars in the month for something that doesn’t have immediate value.

3. Horror Stories. We’ve heard about comrades who got swindled by an insurance salesman masquerading as a financial advisor (or relative/friend) and now pay hundreds or thousands every month while wearing the handcuffs of punishing surrender charges.

4. Ghoulish. To wake up and pledge our lives to defend democracy and the rule of law every day requires that we know death is an ever-present possibility. We compartmentalize that and avoid thinking about it. Life is hard enough without dwelling on death.

5. Math. If we do any math about our life insurance needs, it’s often wrong-math. We leave out inflation and skip the variables that skew our numbers in the wrong direction.

Let’s take a look at each of these underlying causes and see if we can’t recalibrate our immune systems a bit.

SGLI is NOT Enough

A retired O-5 with a 90% VA rating wakes up with about $100K of annual income. A post-military job likely pays about another $200K. Active Duty income was probably closer to $150K-$175K, yet lifestyle needs almost always shift towards that new $300K standard of living. Common rules of thumb about life insurance needs quote 8x to 16x annual income.

Thus, nearing the end of active duty, said O-5 could need somewhere between $1.2M and $2.4M, and his retired self could be looking at $2.4M to $4.8M. The latter is probably high, but maybe not.

Life insurance rules of thumb are just that, but let’s consider some realities. Assume a family with two kids and a stay-at-home parent who hasn’t worked in 6-9 years due to raising the kids while their servicemember wins bread.

If we think about what we need life insurance to do for us, it’s usually the following:

1. Pay for a house. If we die, we probably want our family to always have a home and not have to worry about losing it. Home prices have exploded since COVID. This is probably $500K to $1M or more, depending on the locale.

2. Pay for education. If we want our kids to attend college, we may need life insurance to foot the bill. If we die on active duty, the Fry Scholarship essentially provides the Post-9/11 GI Bill to our whole family, but if we die after active duty, the best case is usually that our GI Bill covers one kiddo. Public universities average $30K a year, and Private school bills are $65K+. Let’s call this $120K to $400K.

3. Living expenses. It may not be practical for our stay-at-home spouse to never work again, but s/he almost certainly needs time to grieve, adapt, and retool for the workforce. A good rule of thumb is that we need living expenses until the last kiddo is at least in full-time school, if not driving. If we were living on $150K a year, and our youngest is, say, 6, this might be 2-3 years or as much as 10. So, let’s add $500K to $1.5M

All told, our O-5 needs a minimum of about $1.2M and as much as $2.9M. Double those numbers if we want to cover the lifestyle of the retired O-5 with $300K of income. Surprisingly close to the 8x-16x numbers…

Cost

Almost all service members and their spouses should only consider Term Life Insurance. If someone is advocating Whole Life, Variable Life, Universal Life, or even worse, Indexed Universal Life, trap them at your six and light the wick.

Term Life Insurance is very inexpensive if we’re healthy. If we’re not healthy, that’s another story, and we may not even be able to qualify for life insurance anyway. A common range for a 20-year term policy for a healthy person in their early 40’s is $8-$15 per $100K per month. So, a $1M policy might cost $80-$150 per month, and it’s often less.

I won’t finger-wag about how many trips to Starbucks equals a monthly insurance premium, but it suffices to say that most of us could find this amount in our monthly spending and trade it for the assurance that our family will be okay if the worst happens.

Personally, I would shave that premium amount off TSP or IRA savings before I would go without adequate life insurance.

Compounding is great, but it won’t provide enough until we’re retirement-ready, at which point we can (and often do) surrender any remaining insurance policies.

Horror Stories

Term Life Insurance is meant to be bought. Whole Life and its cousins are meant to be sold. Plenty of us wake up and think, “I need to cover my spouse and kids if I die.” So we seek a product that will meet the need. We search out the cheapest Term Life policy and buy it. No one gives us a slick pitch about it because Term Life doesn’t pay squat for commissions. It sells itself and doesn’t need to be sold.

Whole Life Insurance, along with Variable Life, etc., must be sold. No one wakes up and thinks, “I need to partially cover my spouse and kids if I die, and perhaps in 20 years if interest rates go up and if the insurance salesman didn’t lie about policy performance, I can take a loan against the policy for a need I can’t even fathom today…”

Whole Life policies cost 10-20x as much as Term Life policies for the same coverage, so we rarely get the same coverage because we can’t afford those premiums. Yet, many of our peers get hornswoggled by insurance salesmen and buy paltry coverage for premiums that would easily buy enough Term Life coverage for our needs with plenty left over to invest; thus the adage: “Buy Term, invest the rest.”

When we hear about policies that cost a car payment and don’t provide a year’s worth of income, it’s hard to consider buying life insurance. We don’t have to be that horror story. Buy Term.

It’s Morbid

Yes, thinking about death is unpleasant. There’s no sugarcoating that. But I have spent too much time in the room with a grieving widow who’s trying to breathe and wonder how to feed and clothe her kids, and when she’ll have to explain why we can’t afford the things we used to afford since daddy died… I will take thinking about death long enough to get an insurance policy in place, rather than thinking about my wife and kids struggling every day of the week.

We show up to defend our nation and its founding ideals. We can show up to defend our family. Until our nest grows enough from decades of compounding, we need enough life insurance. There’s just no way around it. Cowboy up.

Math

We’ve covered the basics of how much we need based on giving Momma and the kids a chance to have the life we’d planned together, but another reason for being underinsured is that we don’t consider other math.

Inflation erodes the utility of life insurance. A 20-year $1M policy might buy a house in year 1, but by year 20, it only buys a $570K house if inflation is 3%. ($395K if it’s 5%). Education inflation is typically 5%+.

Thus, we may need to say $1.5M of coverage when we first decide to address this need, but we could need to layer on additional coverage some years later as life changes.

The amount of life insurance we need isn’t fire and forget. Slimy insurance salesmen know this and use it to try to sell us more coverage every time we PCS (this is actually the model for a certain company…). We often need more as we experience peak vulnerability, e.g., when expenses are growing, but income and savings haven’t caught up. We need less as the kids leave the payroll, the house is on glidepath for payoff, and the nest egg has compounded nicely.

Cleared to Rejoin

If I had a nickel for every family I meet that’s underinsured, I’d have enough to pay premiums on an appropriate-sized amount of Term Life Insurance. I would absolutely pay for enough Term Life Insurance before topping off my Roth IRA, TSP, or 401(k).

There are few better ways to tell your family that you love them than to ensure they don’t have to worry about money on their worst day.

It’s time to get enough life insurance. Get ‘er dun!

Fight’s On!

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https://www.wingedwealth.com/

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