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The Transition Assistance Program covers a tremendous amount of information.

Employment. VA benefits. Healthcare. Education. Life insurance. Taxes. Retirement pay. Disability claims. Resumes. Networking. Relocation. Survivor benefits.

It can feel like drinking from a fire hose.

You may leave with a binder full of resources, a long list of websites, and several pages of notes. But that does not mean you absorbed everything – or that you were ready to understand why every topic mattered.

That is why I believe one TAP class is not enough, especially for someone retiring after a full military career.

I attended TAP twice, about two years apart. Looking back, that was one of the better decisions I made during my own transition.

Take TAP the First Time About Two Years Out

Retiring service members can generally begin TAP as early as 24 months before retirement. That is not too early. In fact, it may be the best time to attend your first class.

Two years gives you time to act on information that cannot be handled during your final few months in uniform.

For me, one of those areas was my medical record.

Like many service members, I had lingering medical issues that I had learned to live with. Some were easy to put off because the mission, the job, and everyone else’s needs seemed more urgent. My first TAP class helped me recognize that I needed to be seen for those issues and make sure my records were complete.

That does not mean trying to manufacture a claim. It means making sure your medical record accurately reflects the care you needed and the conditions you experienced while serving.

That takes time.

You may need appointments, referrals, follow-up visits, tests, or corrections to incomplete records. Waiting until your final months can leave you scrambling through a process that deserved more attention.

The Department of Defense’s Managing Your Transition Timeline places medical-record preparation, physical and dental checkups, the separation health assessment, and disability-claim preparation across several stages of the transition. It is a timeline, not a single event.

The First Class Helps You See the Work Ahead

The greatest value of an early TAP class may not be remembering every detail; instead, it’s seeing the entire landscape.

At two years out, you probably do not need to make every final election. You do need to know which decisions will require research, conversations, paperwork, or lead time.

The first class can help you begin asking better questions:

What do I want to do after the military?
Where does my family want to live?
What qualifications will I need for my next profession?
What will our income look like after retirement?
What benefits will change?
What expenses will be new?
What decisions could become difficult to reverse?

Those questions begin the mission analysis for your next chapter.

In my case, I began conducting informational interviews as I explored a move into a new profession. Those conversations helped me understand the field before I committed to it. They also helped me learn the language, expectations, and qualifications of a civilian career that did not operate like the military.

Informational interviews are not job interviews. They are conversations with people already doing the work. They can help you understand what the profession is really like, where your experience transfers, and where you may have gaps to close.

That work is much more useful two years before retirement than two months before retirement.

Kirk Windmueller’s Military Retirement Transition Planner makes the same point visually. His planner begins well before the final year and includes networking, informational interviews, mentors, credentials, financial preparation, medical-record review, and determining your post-military pathway. Windmueller describes the planner as a guide rather than a source of definitive information, but it is a valuable way to see how many transition tasks overlap.

The Second Class Lands Differently

When you attend TAP again closer to retirement, you are not the same person who attended two years earlier.

Your retirement date is real.

You may know where you are going to live. You may have narrowed your career direction. Your spouse may be thinking differently about work, family, or relocation. Your children may be approaching college. You may have retirement orders—or at least a much clearer timeline.

The same information now has a different meaning.

During the first class, you may hear “Survivor Benefit Plan” and write it down as something to research later. During the second class, you may be preparing to make the actual election.

During the first class, civilian compensation may feel theoretical. During the second class, you may be comparing a salary, bonus, healthcare package, retirement plan, and stock compensation from a potential employer.

During the first class, taxes may be another slide. During the second class, you may be trying to understand why a civilian paycheck that looks larger on paper does not feel as large after taxes and benefits.

Repetition is not wasted time. Repetition, combined with a new level of readiness, creates understanding.

Retirees Should Look for Executive TAP

Those retiring from senior military positions should ask whether Executive TAP, often called E-TAP, is available.

Executive TAP is designed for senior leaders and retirees whose transition questions may be different from those of someone leaving after a first enlistment. Depending on the installation, it may place greater emphasis on translating senior-level experience, networking, executive resumes, interviewing, compensation, and moving into leadership roles outside the military. Availability and eligibility vary, so ask your local transition office what is offered.

Rank may open a door in the military, but it does not automatically translate into the civilian role you want.

You still need to explain the value you bring in language a civilian employer understands. You need to build a new network. You may also need to let go of the assumption that your title, clearance, or years of service will speak for themselves.

E-TAP can be much better aligned with that reality for someone completing a full career.

Take TAP at Two Different Locations When Possible

There is also value in attending TAP at more than one installation.

Every class should cover the required core material, but the instructors, guest speakers, local resources, and employment connections can vary. A class near a large military installation may have a different perspective from one in the community where you plan to settle.

When possible, take at least one TAP class near the place you intend to live after leaving the military.

That can help you learn about:

Local employers and industries
State veterans’ benefits
Licensing and credentialing requirements
Regional salary expectations
Housing and commuting realities
Local networking organizations
Nearby VA and military healthcare resources

Transition is not just about leaving your current duty station. It is about entering a new community and finding a new tribe.

Learning the local landscape before you arrive can make that next chapter feel less like stepping into the unknown.

Do Not Miss the New Expenses

The financial portion of TAP deserves more attention than many service members give it.

Military retirement may bring a pension, but it also brings costs that were easy to overlook while serving.

Healthcare costs change

Active-duty families are accustomed to healthcare operating in the background. After retirement, you may have TRICARE enrollment fees and cost-sharing that did not exist in the same way while you were on active duty.

You also need to take action to enroll in an eligible retired TRICARE plan. Retirement is a qualifying life event, and TRICARE advises retirees to complete enrollment within the applicable post-retirement window.

The important planning point is not merely knowing that TRICARE continues. It is understanding what the specific plan will cost your family and how copayments, deductibles, prescriptions, and the catastrophic cap may affect your budget.

Dental and vision may become separate decisions

Routine retiree dental coverage is generally available for purchase through the Federal Employees Dental and Vision Insurance Program, or FEDVIP. Eligible retirees may also purchase vision coverage through FEDVIP. These are separate coverage and enrollment decisions, not automatic extensions of active-duty benefits.

That means new premiums need to be included in your retirement spending plan.

Life insurance may cost more

Servicemembers’ Group Life Insurance does not simply continue forever after retirement. You will need to evaluate Veterans’ Group Life Insurance, private insurance, or whether you still need the same amount of coverage.

This decision should begin early.

Private life insurance may become more expensive – or unavailable – if your health changes. The right amount of insurance may also depend on your pension, Survivor Benefit Plan election, debts, children’s ages, spouse’s income, and the life you are trying to protect.

Insurance is a tool. The question is not how much you can buy. The question is what job the insurance needs to do for your family.

Taxes may rise more than expected

Military families often underestimate the tax change that comes with retirement.

Basic Allowance for Housing and Basic Allowance for Subsistence are generally not included in taxable income. Military retirement pay is generally taxable at the federal level. Civilian compensation may also include bonuses, stock compensation, or other income that creates withholding and tax-planning challenges.

Your gross civilian salary may look attractive, but gross salary is not the number your family gets to spend.

You need to estimate the after-tax income, subtract new benefit costs, and compare the result with the lifestyle you are trying to support.

Money is a tool, but you need to understand how much of that tool will actually be available.

Include Your Spouse

Your spouse should attend TAP whenever possible. Military retirement affects the entire family.

The decision about where to live may affect a spouse’s career. Survivor Benefit Plan and life insurance choices affect the family’s long-term security. Healthcare, dental, and vision elections often cover the entire household. Education benefits may influence college decisions. A new civilian career may change schedules, travel, and family responsibilities.

It is difficult to align money with your values when only one person hears the information.

Your spouse may also hear something you miss. Remember, you are both drinking from the same fire hose.

TAP Is a Starting Point, Not the Whole Plan

TAP is valuable, but it is not designed to make every decision for you.

It gives you information, tools, and access to resources. You still have to decide how those pieces fit together for your family.

That is where a financial mission statement can help.

What matters most in the next chapter?
Is it maximizing income?
Having more control over your time?
Living near family?
Helping children through college?
Starting a business?
Continuing to serve in a new way?
Finding work that provides purpose and a new tribe?

Your financial mission statement gives you a filter. It helps you evaluate opportunities rather than simply chasing the first salary, location, or shiny object that appears.

The goal is not just to finish a retirement checklist.

The goal is to enter your next mission with clarity and confidence.

Take It Twice

My recommendation is simple:

Take TAP for the first time about two years before retirement. Use it to see the full landscape and begin the long-lead-time work.

Then take it again closer to retirement, preferably both should be E-TAP classes if it fits your situation. When possible, attend the second class near the community where you intend to settle.

You will hear some of the same information twice – that’s the point.

The first time, you learn what you need to do.

The second time, you are ready to make the decisions.

One TAP class may satisfy a requirement. Two can help you build a better transition.

Working with a financial planner who understands the unique challenges and benefits of military families can prove invaluable. The financial planners at Military Financial Advisors Association understand your life and can help you develop a personalized financial plan, navigate complex financial decisions, and stay on track toward your family’s goals.

For my friends who live under a rock as far as tax law goes, the recent passage of the OBBBA spending bill creates a new type of child-focused investment account, literally named a “Trump” account. It might have been possible to come up with a more polarizing name for a savings vehicle, but I’ll leave that musing for another time. Let’s focus on what these accounts are and whether you should consider them or not.

Trump Account 101

These accounts won’t be available until mid-2026, so cancel panic and anxiety about them for now. They are essentially non-deductible Traditional IRA accounts, but the list of known unknowns regarding them is long and distinguished. Here are the basic known features:

$5K Annual contribution limit, until age 18, starting in 2026, with inflation increases starting in 2027.
$1K one-time government contribution (tax-free) for children born between 2025 and 2028.
No tax deduction for contributions, but the contributions are not taxable when distributed.
Earnings are taxed at ordinary income rates: 10% to 37%.
Distributions are not allowed prior to age 18, but after that, there is no 10% penalty like with other IRAs.

At face value, these accounts seem like a good way for military families to stash away additional savings to help their kids get ahead. Grandparents could help with the funding, too.

But let’s take a look at some of the pros and cons of these new savings vehicles.

Trump Account Pros and Cons

Any tax-advantaged savings vehicle is worth exploring, but there’s no free lunch. Pros of these new accounts include:

$5K more of tax-advantaged savings per kiddo is on the table.
IRA/Roth IRA contributions are still allowed.
UTMA/UGMA contributions are still allowed.
529 contributions still allowed.
Free $1K for kids born in one 4-year period of time…
Accounts must invest in low-cost, US-focused index funds.

We’ll look at tradeoffs in a minute, but let’s consider the Trump account cons, acknowledging the triple-entendre there…

The tax treatment is the same as a non-deductible Traditional IRA, which means:
- You must track the basis until the account is emptied, or you could pay tax twice on the contributions. (Remember how much fun it’s been tracking basis in your Traditional IRA?)
- Earnings will be taxed as ordinary income, which could be much higher than capital gains rates or the potential 0% rate of a Roth IRA, UTMA, or 529.
Lack of diversification. While I’m a fan of US equities as a core holding of young retirement savers, and this rule is meant to keep insurance-sales-foxes out of the hen house, it’s a bit “big government.” What’s more, being forced into US equities during certain periods (2000-2010) was pretty toxic to returns. Hopefully, this will get a re-look.
Uncertain financial aid and other government aid treatment. It’s likely that these accounts will look like an IRA for the education financial aid process, but it’s also possible these accounts will weigh against low-income families for other aid programs.
Uncertain Roth Conversion. Usually, we want to Roth convert non-deductible Traditional IRAs as soon as practical to get tax-free earnings going. It’s uncertain if this will be allowed for these accounts.
The $5K contribution would compete with the $19K gift limit, thus lowering what could be contributed to a 529 account or UTMA/UGMA. (Gift splitting from a couple would mitigate this.)
Naming… Trump tends to be a love him or hate him personality. You can probably call it a Section 408f account (like a 529 account) you aren’t a fan.

Now that we know the ins and outs, let’s take a look at alternatives and potential COAs.

Trump Account Options and Alternatives

An entry into this merge starts with answering some of the following questions:

Do we/I actually have extra money to save after taking care of retirement, college, and other savings? If not, no need to consider these accounts. Put your own mask on before helping others…
Are we hoping to help Junior with lifetime wealth transfer? “Twenty’s Money” to start a business, buy a home, or dodge debt? Are we trying to run up the scoreboard on what accounts can be in Junior’s name? Is education funding our priority?
Will we proactively manage the tax consequences of the account?

Alternative accounts to consider include:

UTMA/UGMA: The contribution limits are essentially $19K per parent, the first $1,350 of income is tax free and the next $1,350 taxed at the child’s rate, often 0%. Tax-gain harvesting can whittle away at a potential tax bill. Earnings are at capital gain rates, which are usually lower than ordinary income rates. There are no penalties for early withdrawal nor RMDs.

As a child-owned asset, they “harm” education financial aid considerations. The main downside of a UTMA/UGMA is that it must be turned over to the child at the state’s age of majority, usually about 21, but ranging from 18 to 25. Also, while a high enough balance to cause a “kiddie tax” is somewhat uncommon for middle-class families, the income above $2,700 is taxed at the parents’ capital gain rate, probably 15% to 23.8%.

Roth IRA: If a child is working, then a Roth IRA should probably be first in the order of operations. Contributions can be withdrawn tax and penalty free at any time, and assuming these dollars are for retirement, the earnings should be tax free after age 59.5. The main downside is that many kids don’t earn income outside the home or in a family business.

Teen Brokerage Account: Fidelity (not a recommendation) offers a brokerage account that is not a UTMA, but has parent guardrails until 18. It would not offer UTMA/UGMA tax provisions, and would also “harm” financial aid, but if you’re in the Fidelity ecosphere, it’s a consideration.

So, to simplify, let’s say a family has $7K to help a child out financially in the future, a good order of operations might look like:

Retirement Focus

Roth IRA if the child is working and qualifies to contribute.
If Roth IRA isn’t an option, then $5K into a Trump account and $2K into a UTMA whilst planning to tax-gain harvest and hopefully Roth Convert the Trump Account after age 18.

Twenty’s Focus

$7K into a UTMA/UGMA would seem straightforward, but if the Trump account could be Roth converted after age 18, it’s possible the tax bill on earnings would be lower over a series of Roth Conversions than it might be significant capital gains later in life.
Focusing on the UTMA/UGMA account requires intentionality. Gains should be harvested when the tax bill will be $0 so that the account has the highest possible basis when it’s needed for “Twenty’s Money.”
A hedge would be to put $5K into the Trump account and $2K into the UTMA/UGMA. This could lower any workload from tax gain harvesting in the UTMA/UGMA and defer any tax gymnastics on the Trump account until age 18 or later.

Education Focus

A 529 account is already the gold standard for education savings. Some states offer a tax deduction for contributions; the money grows without taxation; and the list of ways to use the money without paying any taxes is, you guessed, long but distinguished and growing each time Congress tinkers with the tax code.
A UTMA/UGMA is a sound second place for education, primarily if families are allergic to the education focus and restrictions of a 529 account. Because UTMA/UGMA accounts must eventually be turned over to the child, mind the risk of pouring gas on a future fire.
A Trump account is in last place here. The funds can’t be used for K-12 education, and the child has full control at 18. Most UTMA/UGMAs can be extended to age 21+, so a young adult who’s off the path could start doing some damage a few years earlier while starting a bogey-gathering turn for the taxman.

Cleared to Rejoin

The intersection of investing, saving, and taxes is literally what brought me to my second career, so anytime a new financial tool arrives, I’m admittedly excited. The Trump accounts are a bit of a head scratcher, but they do offer some opportunities, especially to wealthy families on the hunt for tax strategies. Expect to learn more about them as they become available in mid-2026. Until then, if you have $5K to save for junior, no need to wait!

Do you need help figuring out how you should save for your children or for your own retirement? The MFAA Advisors are an excellent resource to help you answer these questions or any other financial topics you’d like to discuss. Find an MFAA advisor here.