Winged Wealth Management and Financial Planning

Winged Wealth Management and Financial Planning Winged Wealth serves the military and veteran communities, specializing in pilots and their families with fee-only, fiduciary planning and advice.

Monday Money: I Know How Much You Spend.  Do You?Of the hundreds of families I’ve served, there is a 99.99% common trait...
06/01/2026

Monday Money: I Know How Much You Spend. Do You?

Of the hundreds of families I’ve served, there is a 99.99% common trait and my family shares it too: we don’t know how much we spend. As virtuous as Davey Ramsey’s “plan and track” every nickel (since pennies aren’t a thing) advice is, it’s tedious at best. If we don’t know what we spend, it’s really hard to plan for the future, especially when the paycheck switch flips to the OFF mode.

Why We Don’t Track Spending:

Even with slick tools like Monarch Money and other financial aggregators, you must review, categorize, process, and acknowledge every electronic transaction in a day/week/month/year. Most families have hundreds of transactions per month, and many transactions span multiple categories. Even if you’re a bookkeeper, you’d be getting paid to do this for someone else. Where’s the compensation for your time, energy, and attention when you track spending in your own home?

Reviewing spending induces lots of emotions, and few of them are “spender’s joy.” It’s all but impossible not to reflect on a month’s worth of spending without thinking things like:

“Where did it all go?”

“Did we really (need to) spend so much at Target/Amazon/Costco?”
“When did things get so expensive?”

“We probably need to start talking before we do some of this spending … and that’s probably an argument…”

Unless we’re one of those rare types who just likes having a tidy profit and loss statement for the household, tracking spending ranks right up there with cleaning gutters and picking weeds.

Here’s What You Spend:

There is actually a really simple way to know what you spend, and it’s how I know what you spend.

Gross Income minus taxes minus savings, divided by 12.

In most cases, this really is the number. But let’s slice this elephant into some mouth-fitting chunks:

1. What was your gross income on your last tax return? Add any VA disability pay and, if you received any significant gifts, those amounts too.

2. What was your tax bill? This one is a little trickier because your 1040 tax form doesn’t show Social Security and Medicare taxes, so you’ll need to pull those numbers from your W-2s. Don’t forget state taxes, but those might be on Schedule A.

3. What did you save (and not pull back out of savings)? For a lot of us, this is two helpings of the IRA annual limit, plus some amount into the TSP/401(k) and maybe some college savings too. If you max out retirement savings and automate college savings, your only homework here might be a review of your year-end taxable brokerage account contributions.

Divide that number by 12, and that’s your average monthly spending.

Is It Really That Simple?

Yes and no. It might be helpful to parse out non-discretionary spending, such as mortgage/rent, insurance, education costs, and any charitable giving—expenses you’re probably going to fund in almost all circumstances. But everything else: food, transportation, clothing, utilities, shopping, subscriptions, personal care, pets, hobbies, travel, etc, it fits inside:

Gross Income minus taxes minus savings (minus must-spend spending), divided by 12.

If it doesn’t, we’re pulling money from savings to get through the year, carrying credit card balances, or taking out new loans. Those factors usually don’t escape our attention, so add them to the math if needed.

Does it Matter What We Spend?

No one is still reading unless they answer yes. So here’s why we probably want a decent sense of this number:

1. Are we saving enough? We save so we can spend later. We need to know spending now because it’s probably what we need to spend later. We need some compounding returns to help bridge this gap.

2. Are we saving too much? If we don’t spend much and we save a lot, we’ll probably have trapped gas because of compounding—we’ll have lots of money when we don’t have lots of health and energy in our 70’s+.

3. How much do we need to retire? This is really the same question, but if our current spending is $10K per month, we probably don’t want to tighten our belt in retirement—at least not in the early go-go years.

4. Can we afford to buy an “X?” If we want an RV/boat/vacation home, we need to know where the money comes from for it. Where is the “squish” in the spending that we can reallocate?

5. Is this okay? Sometimes we just want a sense of well-being from knowing that our money is going to the missions we support.

Cleared to Rejoin:

Detailed dollar tracking isn’t for most of us, but we should know what we spend in a year to make sure our money takes care of our needs, wants, and some wishes, too. The math is bar napkin easy. Give it a shot. What do you think about your number?

Monday Money: Free Financial Planning After SGLI/VGLIWhen a service member or veteran passes away, the system usually mo...
05/25/2026

Monday Money: Free Financial Planning After SGLI/VGLI

When a service member or veteran passes away, the system usually moves quickly. Claims get filed. Benefits get processed. Paperwork flows.

But there's one benefit that consistently slips through the cracks — not because it doesn't exist, but because almost nobody mentions it.

What You're Entitled to After an SGLI or VGLI Claim

Once a beneficiary receives an SGLI or VGLI payout, a quiet clock starts ticking. For two years from that date, they're eligible for something most people never use:

Up to 40 hours of free financial planning with a fee-only, fiduciary Certified Financial Planner (CFP®).

No products. No commissions. No sales pitch dressed up as advice. Just a credentialed professional who is legally required to act in the client's best interest.

It's called the VA Beneficiary Financial Counseling Service, and you can find it here. The catch is that you must know to look for it in the first place.

Why Most Families Miss It

The VA doesn't proactively connect beneficiaries with a financial planner. There's no warm handoff. No automatic follow-up call. No "here's your next step."

Instead, there's usually a brief mention buried in the Explanation of Benefits package — the same paperwork people are sorting through in the middle of grief, logistics, and a hundred other decisions.

What often happens instead: weeks pass, financial decisions start piling up, and MAYBE someone eventually mentions the program — a casualty assistance officer, a fellow beneficiary, or a follow-up letter from the VA. Only then does the survivor realize the opportunity was there the whole time.

By some estimates, only 30–40% of eligible beneficiaries ever hear about it. That number should be much higher.

Even the Professionals Don't Always Know

Here's what I find particularly striking: many of the people closest to this process have never heard of it either.

Installation financial counselors. Casualty affairs teams. Even financial advisors who specifically serve military families (especially those tied to large national firms selling annuities and whole life policies).

If the professionals in the ecosystem don't know it exists, families are working with a pretty significant information disadvantage.

How the Program Actually Works

The VA sponsors the benefit but contracts administration to a company called ComPsych, which runs the program under the name "Financial Point." They match survivors with fiduciary planners in their area — sometimes within one to two weeks, though timing varies because of the time delays between the loss, the VA claim, the VA’s notification to the survivor and the VA’s notification to its contractor.

That structure is relentlessly confusing. You receive a benefit from the VA, then get handed off to a company you've never heard of, under a program name that's different still. It's easy to see why people hesitate or disengage.
But if you push through the friction, what's on the other side is genuinely valuable.

Over up to 40 hours, a planner can help with cash flow and budgeting, investment decisions, tax considerations, debt management, and longer-term planning. All of it without any product being sold. The conflicts of interest are about as low as possible on the advisor’s side.

Why This Matters

When a large lump sum arrives at the same time someone is processing loss, the wrong kind of attention tends to follow: Sales-driven firms, Insurance products, Advisors whose interests may not line up with the client's, Scammers, Fin-fluencers—basically the part of the industry that belongs in the dust bin of history.

A fiduciary advisor gives the survivor a trusted voice in their corner before the decisions get made. In many cases, the most valuable thing isn't a complex financial strategy. It's having someone objective help you avoid a costly mistake.

If You're Connected to the Military Community

Whether you're a service member, a spouse, a veteran, or someone who advises military families — this program is worth knowing about and worth sharing.

The benefit exists. The funding is there. The advisors are fiduciary.

The only thing missing is awareness.

And that part, we can fix.

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Why IRA Rollovers Matter — and How to Avoid a Costly Mistake
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$240K is the new $100K: The New Financial Reality
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Don’t Rush the Switch

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