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

09/07/2026

Labor Day: What Is Your Work Actually Buying You?

Labor Day is usually associated with backyard barbecues, the unofficial end of summer, and one last long weekend before school, football, and fall routines take over. But the holiday has a much deeper meaning. Labor Day was created to recognize the contributions and achievements of American workers. The first Labor Day celebration was held in New York City in 1882, and in 1894, Congress made the first Monday in September a federal holiday.

So this Labor Day, instead of just thinking about work, take a minute to think about what all those years of work are actually buying you. Because a paycheck doesn't just pay the mortgage, buy groceries, or fund the next family vacation. Ideally, a portion of every paycheck is buying something much more valuable: future freedom.

That is really what retirement planning is about. It isn't just about accumulating a certain number in a TSP, 401(k), IRA, brokerage account, or bank account. It is about building enough financial resources that eventually you can decide whether you want to work—not because you have to.
Work has value beyond the paycheck.

Every year you work gives you another year to earn, save, invest, pay down debt, build retirement accounts, increase your future pension or Social Security benefits, and prepare for the next chapter. But the purpose isn't to work forever. The purpose is to eventually turn those years of labor into something that money can't buy directly: choice.

Choice about where you live.
Choice about how you spend your time.
Choice about whether you take another assignment.
Choice about whether you start another career.
Choice about whether you help your kids.
Choice about whether you travel.
And eventually, choice about whether you work at all.

So this Labor Day, (hopefully) enjoy the extra day off. Fire up the grill. Watch some football. Spend time with your family.

But maybe take a few minutes before the weekend is over to ask yourself a different kind of Labor Day question: What is all this work supposed to make possible? Then take the next step and figure out what that life actually costs.

The goal of retirement planning isn't simply to accumulate the biggest possible pile of money. It is to know when you've accumulated enough.

Enough to leave the job.
Enough to take the next assignment.
Enough to slow down.
Enough to travel.
Enough to spend more time with your family.
Enough to say, “I don't have to do this anymore.”

And when you know your number, you don't have to wonder whether you're working because you want to—or because you still need the paycheck.

That's a pretty meaningful way to celebrate Labor Day.

08/31/2026

Back to Basics: Account Types

Some years ago, when some of our fellow steely-eyed killers started swapping paint at 600 knots a bit too frequently, “back to basics” became the method from on high. The Bobs felt that we had lost touch with some basic airmanship and general knowledge. If we went back to the basics, we could save some blood and treasure. But what if no one ever taught us the basics, say about something like the important topic of investing accounts? Enter this article!

Account Types 101

There are only a handful of investing or other types of accounts that most of us need to know about. To avoid clutter, I’m not even going to talk about the others. Here we go!

The five accounts you need to know about are: IRAs, Employer Plans, Taxable Brokerage Accounts, 529 College Savings Plans, and UTMA/UGMA accounts. We’ll skip banking accounts like checking, savings, High Yield Savings Accounts, and CDs for now.

IRA: An IRA is an Individual Retirement Arrangement, but most of us call it an Individual Retirement Account. Let us never speak of this silly distinction again.

An IRA is a tax-advantaged account you set up yourself (or an advisor helps).

It has nothing to do with your TSP or 401(k).

The IRS sets limits on how much you can invest in an IRA each year: $7.5K under age 50 in 2026.

IRAs come in 2 basic flavors, and you can inherit someone’s IRA:

Roth: No deduction on your tax return, but the growth and distributions are generally tax-free.

Traditional: Deduct the contribution on your tax return, subject to limitations, no taxes while the money grows, but pay taxes when you take distributions in retirement.

You can have many IRAs, move money from Traditional IRAs to Roth IRAs, move money from Employer Plans to IRAs, move IRAs to Employer Plans, and consolidate IRAs, subject to various rules and potential tax requirements.

Employer Retirement Plans: Employers can offer various plans to help employees save for retirement. We usually call them the TSP, 401(k), 403(b), SEP IRA, SIMPLE IRA, 457(b or f), etc., but they are probably best aggregated under the term “Employer Plan.”

Employer Plans are tax-advantaged accounts only your employer can set up unless you’re self-employed. The rules for employer plans are a mix of what the IRS allows and what the employer chooses to pay to offer. The more complex the plan, the less likely you’ll find it at a small employer because employers pay handsomely to offer these plans.

Employer plans can also offer Roth or Traditional options based on the same tax treatment as IRAs.

The IRS sets the contribution limits for employer plans, but they are much higher than IRAs.

Employers usually match employee contributions to a certain point and can share profits into the plans.

You can usually keep your employer plan after leaving the job, but you may not want to.

Taxable Brokerage Accounts, or taxable accounts, are just “regular investing accounts” in that you don’t get a tax break when you contribute; you pay tax on some of the earnings each year, and you pay tax on the gains when you sell investments.

Taxable accounts are often used for extra retirement savings, savings goals short of retirement, and even for “early retirement.” The “taxable” moniker may sound like a bad deal, but generally, the tax burden is modest and manageable. Usually, the tax rate on a taxable account is lower than the tax rate for other types of income.

Taxable accounts create flexibility because you don’t have to wait until retirement to use the money.

Taxable accounts generally allow access to the entire universe of publicly traded securities.

Taxable accounts can be jointly or individually owned.

Taxable accounts can have beneficiary designations to make estate planning easier.

Taxable accounts get a “step-up in basis” when you die, which usually means that any built-in taxable gains go away.

Families that save a lot usually max out their IRAs and employer plans, so a taxable account is the next logical place to put money to work.

529 College Savings Plans: 529 plans are like a Roth IRA for college. They are only a few decades old and have lots of great upsides, but there is one major downside. 529 plans are the de facto savings option for college expenses, and they can help with K-12 expenses and loan repayment too. Features include:

No federal tax deduction for contributions, but many states with income taxes allow a state deduction.

Growth is tax-free.

Distributions for qualified (most college-related) expenses are tax-free.

You can change the beneficiary to another family member (even grandkids).

You can roll over leftover money to a Roth IRA, subject to restrictions.

The downside is that if you can’t or don’t use the money for a qualified expense, you’ll pay income tax plus 10% on the earnings.

UTMA/UGMA Accounts: Uniform Transfer/Gift to Minors Act accounts are taxable accounts with modest tax advantages that we can set up for our kids. It’s probably best to think of these as wealth transfer and gifting accounts, but some families use them as college savings accounts. Key features include:

The custodian (usually the parent) operates the account for the child’s benefit until the state age of majority, usually 18-25, then the child takes it over.

The first few thousand dollars of income are tax-free or at low tax rates, but accounts earning lots of dividends or capital gains can start weighing on the parents’ tax bill.

The investment options are generally the same as any other taxable account, but these can hold more “exotic” investments.

Because these must be transferred to the child at a young adult age, many families defer funding until they know what path their child is on to avoid pouring gas on a fire.

Cleared to Rejoin

That’s it. There are really 5 account types you need to care about. Yes, the financial industry gives other names to these basic accounts. Yes, there are many other account types, but the vast majority of us will only ever need to interact with these five and probably not even all five. These are the account type basics, should you ever need to go back to basics.

Fight’s On!

08/24/2026

Understanding Required Minimum Distributions: The Retirement Tax Bill Many People Forget About

For decades, you've done exactly what financial professionals tell you to do. You contributed to your 401(k), Thrift Savings Plan (TSP), or Traditional IRA. You received tax deductions along the way, watched your investments grow tax-deferred, and built a retirement nest egg that hopefully gives you financial confidence.

Then, one day, the IRS comes knocking.

Not because you've done anything wrong—but because the government would like its share.

That's the basic idea behind Required Minimum Distributions, commonly referred to as RMDs. While they aren't particularly complicated, they often catch retirees by surprise because they represent a shift in mindset. During your working years, the goal is to put money into retirement accounts. Eventually, the government requires you to start taking money back out.

Why Do Required Minimum Distributions Exist?

Traditional retirement accounts were never intended to be permanent tax shelters. When you contribute to a Traditional TSP, Traditional 401(k), or Traditional IRA, you generally receive a tax deduction upfront. Your investments grow tax-deferred for years, sometimes decades, without generating annual taxable income. Eventually, however, the IRS expects to collect the taxes that were postponed.

Required Minimum Distributions are simply the government's way of ensuring retirement accounts don't continue growing tax-deferred forever. Think of it as deferred taxes finally coming due—not a penalty, but the final chapter of the agreement you made when you accepted those tax deductions years ago.

When Do RMDs Begin?

Current law generally requires most retirees to begin taking Required Minimum Distributions during the year they turn age 75. (If your birth year is between 1951-1959, it's actually 73, but we'll assume you're at least a late-stage Boomer, Gen-X'er or later...) If Congress changes the rules in the future, that age could change again, but for today's retirees, age 75 is the key milestone.

Your first RMD can be delayed until April 1 of the following year. While that sounds appealing, delaying isn't always the best strategy because you'll also need to take your second RMD before December 31 of that same year. That means two taxable distributions could occur in one calendar year, potentially increasing your tax bill.

For many retirees, taking the first distribution during the year they turn 75 results in a smoother tax picture.

How Are RMDs Calculated?

Many people assume there's a complicated formula.

Fortunately, it's much simpler.

Each year, the IRS publishes life expectancy tables. Your retirement account balance as of December 31 of the previous year is divided by your life expectancy factor to determine the minimum amount that must be withdrawn.

For example, suppose you have $1,000,000 in a Traditional IRA on December 31. If your IRS life expectancy factor is approximately 26.5, your Required Minimum Distribution would be about $37,700 ($1M/26.5).

That amount becomes taxable income for the year, assuming the account consists of pre-tax contributions.

The following year, the process repeats using your new account balance and updated life expectancy factor. Because investment values fluctuate, your RMD changes every year.

It's a Minimum—Not a Recommendation

One misconception is that retirees should only withdraw their Required Minimum Distribution. That's not necessarily true. The RMD simply establishes the minimum amount you must withdraw to satisfy IRS rules. If your retirement spending requires larger withdrawals, you can certainly take more. Conversely, if you don't need the income, you're still required to withdraw at least the minimum amount.

Many retirees find themselves withdrawing money they don't actually need for living expenses.

Fortunately, you aren't required to spend it.

After paying any taxes that are due, the remaining funds can be invested in a taxable brokerage account, gifted to family members, donated to charity if appropriate, or used for other financial goals.

Why Large RMDs Can Create Tax Problems

One challenge many retirees face is success. Imagine diligently saving for forty years. Your investments perform well. You retire with several million dollars in pre-tax retirement accounts. While that's certainly a good problem to have, larger account balances often lead to larger Required Minimum Distributions. Those distributions increase taxable income, which can create several unintended consequences. You may move into a higher tax bracket. A larger portion of your Social Security benefits may become taxable. Higher income could also trigger increased Medicare Part B and Part D premiums through Income-Related Monthly Adjustment Amounts (IRMAA).

In other words, Required Minimum Distributions can create a ripple effect that extends beyond simply paying income taxes.

Planning Ahead Can Make a Difference

The good news is that Required Minimum Distributions don't have to become a surprise. In fact, many of the best tax-planning opportunities occur before RMDs ever begin. Some retirees intentionally perform Roth conversions during lower-income years between retirement and age 75. By voluntarily paying taxes on smaller portions of their retirement accounts over several years, they may reduce future Required Minimum Distributions while increasing tax-free assets inside Roth accounts. Others strategically withdraw money from Traditional retirement accounts before RMD age to smooth taxable income across retirement instead of allowing large mandatory withdrawals later. The best approach depends on your pension, Social Security benefits, other income sources, and long-term estate planning goals.

What About Roth Accounts?

One of the advantages of Roth IRAs is that they are not subject to Required Minimum Distributions during the original owner's lifetime. That's one reason Roth accounts have become increasingly valuable in retirement planning. Money can continue growing tax-free for as long as you live, giving you greater flexibility over when—or whether—you withdraw it. Beginning in 2024, employer-sponsored Roth accounts such as Roth 401(k)s and Roth TSPs are also no longer subject to lifetime Required Minimum Distributions for the original owner. That change eliminated one of the biggest differences between Roth workplace plans and Roth IRAs.

Don't Let the Tax Tail Wag the Dog

It's easy to become so focused on avoiding Required Minimum Distributions that you lose sight of the bigger picture. After all, paying taxes often means you've successfully accumulated significant retirement assets. The goal isn't to eliminate taxes completely. The goal is to manage them intelligently over your lifetime. Sometimes paying a little tax today prevents paying much more later. Sometimes leaving money in a Traditional account makes perfect sense.

Every retirement plan is different.

Cleared to Rejoin!

Required Minimum Distributions aren't something to fear, but they are something to prepare for.

Understanding how they work gives you decades to make thoughtful decisions instead of rushed ones.

Whether that involves Roth conversions, adjusting withdrawal strategies, or simply knowing what to expect, planning ahead can help reduce surprises and potentially lower your lifetime tax bill.

Retirement planning isn't just about building wealth. It's also about deciding how—and when—that wealth will be taxed.

The sooner you understand Required Minimum Distributions, the more options you'll have when retirement arrives.

Fight’s On!

08/17/2026

What Does the Top 10% Retirement Saver Look Like at Ages 30, 40, and 50?

One of the biggest problems with retirement statistics is that they often compare you to the average American. Unfortunately, "average" isn't always a useful benchmark. Many Americans have little or no retirement savings, which makes it easy to feel like you're ahead—even when you may still be behind your long-term goals.

A better question is this: What do the top savers actually look like?

Not billionaires. Not people who inherited wealth. Just disciplined, educated professionals who consistently save, invest, and allow compound growth to work over decades.

Let's take a look at what that journey often looks like.

By Age 30: Building the Habit

By age 30, the top 10% of retirement savers usually haven't accumulated extraordinary wealth yet. What separates them isn't necessarily the account balance—it's the behavior.

Most have been contributing to a workplace retirement plan since their early twenties. They've taken advantage of employer matches, increased contributions as their salaries grew, and resisted the temptation to dramatically increase their lifestyle with every raise.

A typical top saver around age 30 might have between $150,000 and $250,000 invested across retirement accounts and taxable investments, depending on when they started working and how aggressively they've saved.

Their retirement savings rate is often 15% to 25% of gross income, and many save even more after receiving bonuses or promotions.

At this stage, time is their greatest asset. A dollar invested at age 30 has decades to compound, making consistency far more valuable than chasing the hottest investment.

By Age 40: Compound Interest Starts Showing Up

Something interesting happens during the fourth decade of life. Many people assume their investment returns come from new contributions. Increasingly, that's no longer true. For top savers, investment growth begins doing much of the heavy lifting.

Someone who has consistently invested throughout their twenties and thirties may now have $500,000 to $900,000 accumulated across retirement and brokerage accounts.

While they're likely earning more than they did ten years ago, they often continue living below their means. Bigger homes and nicer vacations may appear, but savings typically increase alongside income.

Many are maximizing retirement plans, funding Roth IRAs through Backdoor Roth strategies when appropriate, investing in taxable brokerage accounts, and building additional wealth through home equity or real estate.

The remarkable thing isn't that they found a secret investment. It's that they simply stayed invested through bull markets, bear markets, and everything in between.

By Age 50: Wealth Becomes Noticeable

By age 50, the effects of three decades of disciplined investing become difficult to ignore. Top retirement savers frequently have $1.5 million to $3 million invested, although the exact number depends heavily on income, market performance, pensions, and career choices.

Perhaps the biggest difference is that annual market gains often exceed annual contributions.

Imagine contributing $40,000 per year to retirement while your investments increase by $180,000 during a strong market year. Compound growth has officially taken over. This is when financial flexibility begins to emerge. Some people start working because they want to rather than because they have to. Others begin thinking about second careers, phased retirement, or simply knowing they could retire if circumstances changed. Money provides options long before it provides retirement.

What Do These People Have in Common?

It's tempting to assume the top 10% are investment geniuses. Most aren't. They simply demonstrate several habits consistently over decades. First, they save a significant percentage of their income—often 20% or more. Second, they increase savings whenever income increases rather than allowing lifestyle inflation to consume every raise. Third, they invest primarily in diversified, low-cost index funds instead of chasing speculative investments or trying to time the market. Fourth, they remain invested during downturns. Every major bear market has felt different, but the disciplined investor continues buying through uncertainty instead of waiting for the "perfect" time. Finally, they understand that retirement planning is less about finding the highest-performing investment and more about avoiding costly mistakes.

Don't Chase Someone Else's Number

One caution about comparing yourself to others: everyone's path is different. The account balance itself isn't the goal. The goal is building enough assets to create financial independence. If you're consistently saving, investing in diversified funds, increasing contributions as your income grows, and avoiding unnecessary debt, you're likely moving in the right direction—even if your timeline looks different from someone else's.

Cleared to Rejoin!

The top 10% of retirement savers aren't defined by extraordinary investment returns. They're defined by extraordinary consistency.

They save early. They save often. They keep costs low. They ignore market noise. They let compound interest do what it does best.

Whether you're 30, 40, or 50, the next decade of your financial life will be shaped less by what you've already accumulated and more by the habits you practice from this point forward.

The best time to become a top saver was twenty years ago. The second-best time is today.

Fight's On!

08/10/2026

Should You Leave Your Retirement Savings in the TSP After Military Retirement?

One of the most common questions military retirees face is what to do with their Thrift Savings Plan (TSP) after leaving active duty. For many, the assumption is that retirement means it's time to move everything into an IRA or transfer assets to a new employer's 401(k). While those options may make sense in certain situations, it's important to recognize that the TSP remains one of the most competitive retirement plans available—even after you've hung up the uniform.

The TSP's biggest advantage has traditionally been its low costs. Every dollar not spent on investment expenses stays invested and working for you. While investment costs across the industry have fallen significantly over the past two decades, the TSP still offers some of the lowest expense ratios available. For retirees who value simplicity and efficiency, that's a meaningful benefit.

Another reason many retirees choose to keep funds in the TSP is the straightforward investment lineup. Rather than sorting through thousands of mutual funds and ETFs, participants can build a diversified portfolio using a handful of core funds or simply utilize the Lifecycle (L) Funds. For those who prefer not to spend their retirement years constantly tweaking investments, simplicity can be a feature rather than a limitation.

The TSP also offers access to the G Fund, a unique investment option that cannot be replicated elsewhere. The G Fund provides a government-backed return without the market risk associated with stocks or longer-term bonds. While it won't generate eye-popping returns, it can serve as a valuable tool for retirees looking to balance growth and stability within their portfolio.

In 2026, the TSP began offering in-plan Roth Conversions, which many civilian plans do not offer. This can drastically lower the lifetime tax bill for many families and is a reason to consider rolling money INTO the TSP in retirement.

That said, keeping your money in the TSP is not automatically the best choice for everyone. Some retirees may benefit from rolling assets into an IRA if they want a broader range of investment options, more sophisticated tax planning strategies, or greater flexibility for beneficiaries. IRAs generally provide access to thousands of investment choices and may offer estate-planning advantages that are important for certain families.

Retirees who continue working after military service may also want to evaluate whether consolidating retirement accounts could simplify their financial lives. Over a career that includes military service, civilian employment, and perhaps a second career, it's easy to accumulate multiple retirement accounts. In some cases, combining accounts can make investment management easier and reduce the chances of losing track of assets over time.

One of the most common reasons retirees consider moving their TSP assets is the belief that firms such as Vanguard or Schwab offer better investment options. While those firms certainly provide more choices, the reality is that many of their core index funds are remarkably similar to what is already available inside the TSP.

The TSP's primary stock funds—the C Fund, S Fund, and I Fund—are built around broad market indexes and carry extremely low expense ratios. Comparable offerings at Vanguard and Schwab often track similar benchmarks and, in some cases, have slightly lower costs. However, the differences are generally measured in hundredths of a percent rather than whole percentages.

To give a comparison, the top TSP investments to their Schwab and Vanguard counterparts highlight distinct differences in cost, variety, and structure:

1. Large-Cap / S&P 500 Funds
• TSP (C Fund): Tracks the S&P 500 Index. It is an excellent core holding, but with total expense ratios historically around 0.035%.
• Vanguard Counterpart: Vanguard 500 Index Fund Admiral (VFIAX) or VOO ETF. Offers the same S&P 500 exposure at a 0.03% - 0.04% expense ratio.
• Schwab Counterpart: Schwab S&P 500 Index Fund (SWPPX) offers an even lower 0.02% expense ratio.

2. Extended Market / Mid-Small Cap Funds
• TSP (S Fund): Tracks the Dow Jones U.S. Completion Total Stock Market Index and has a total expense ratio around 0.051%.
• Vanguard Counterpart: Vanguard Extended Market Index Fund Admiral (VEXAX) or VXF ETF, which provide similar small-to-mid cap exposure at roughly 0.05%.
• Schwab Counterpart: Schwab Small-Cap Index Fund (SWSSX) comes in at around 0.04%.

3. International Stocks (NOTE: I fund changed in 2024 to exclude China and Hong Kong, but there are not true proxies on the market at this time. Replicating the I-Fund will take a bit more approximation.)
• TSP (I Fund): Tracks the MSCI ACWI IMI ex USA ex China ex Hong Kong* has an expense ratio of 0.048%
• Vanguard Counterpart: Vanguard Total International Stock Index Fund (VTIAX) or VXUS ETF, which includes emerging markets like China for broader global coverage at a 0.09% expense ratio.
• Schwab Counterpart: Schwab International Index Fund (SWISX), which tracks the MSCI EAFE** Index, has an expense ratio of 0.06%.
• * - MSCI ACWI is the All-Country World Index, with the TSP I Fund excluding the US, China, and Hong Kong markets
• ** - MSCI EAFE includes Europe, Australasia, and the Far East (excluding the US, Canada, and emerging markets).

4. Bonds and Safe Assets
• TSP (G Fund): Backed by the U.S. government, it yields Treasury interest without risk of principal loss. This fund is unique to the TSP.
• Vanguard & Schwab: Equivalent safe havens include Treasury bills or money market funds like Vanguard Federal Money Market Fund (VMFXX) or Schwab Government Money Fund (SNVXX). These yield market rates but have no principal guarantee.

To put expense ratios into perspective, a fund charging 0.02% would cost approximately $20 annually for every $100,000 invested. A fund charging 0.05% would cost about $50 annually for the same balance. While those differences can add up over time, they are relatively minor compared to factors such as asset allocation, savings rate, and investor behavior. For a $2 million portfolio, the annual difference between a 0.02% and 0.05% expense ratio would be roughly $600.

Because the costs are so similar, retirees should focus less on whether a fund is housed at TSP, Vanguard, or Schwab (or insert your preferred firm here) and more on what additional flexibility they gain—or give up—by moving their money.

You may gain access to more investment choices, Roth conversion flexibility, easier account consolidation, and specialized ETFs or mutual funds. On the other hand, you may lose access to the unique G Fund, the simplicity of the TSP structure, and one of the lowest-cost retirement plans available.

Perhaps the most important thing to remember is that transferring money out of the TSP isn't automatically an upgrade. Too often, retirees are approached by financial firms eager to manage a newly available retirement account. While many advisors provide tremendous value, others are more interested in gathering assets than improving outcomes. Before making any move, understand exactly what you're gaining, what you're giving up, and what the costs will be.

The decision ultimately comes down to your goals, preferences, and overall financial plan. If you value low costs, simplicity, and access to the G Fund, leaving your money in the TSP may be an excellent option. If you need greater flexibility, advanced planning opportunities, or specialized investments, a rollover could make sense. The good news is that retirement doesn't force you to make an immediate decision. You can leave your assets in the TSP and revisit the question later as your circumstances evolve.

For many military retirees, the solution is not an all-or-nothing decision. Keeping part of your portfolio in the TSP—especially if you value the G Fund or in-plan Roth Conversions—and rolling other accounts to Vanguard or Schwab often provides the best of both worlds.

Fight's On!

Winged Wealth Management and Financial Planning

09/07/2026

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