In Part 1 of this series, we looked at where our money beliefs come from — the unconscious “money scripts” we absorb early in life and then perform on autopilot as adults. We walked through the four most common ones: money status, money worship, money avoidance, and money vigilance.

Naming the script is the first step. The harder, more rewarding part is deciding what to do about it. None of these patterns is inherently a problem — each carries real strengths alongside its costs. The goal isn’t to erase them. It’s to keep what serves you and loosen the grip of what doesn’t.

Here’s where to start with each.

Managing money status

When self-worth gets tied to net worth, the drive to prove it can show up as overspending, creeping debt, or a constant habit of measuring yourself against others.

The most useful tool here is a pause. Put intentional space between the urge to buy and the act of buying, and use it to ask one question: am I buying this to meet a real need, or to soothe an emotional one? A luxury purchase isn’t wrong — but it’s worth knowing whether it’s moving you toward a goal you care about or just quieting a feeling for an afternoon.

It also helps to remember that we rarely factor in other people’s debt when we size them up. The neighbors you might be tempted to keep pace with may be stretched thinner than they look, carrying more than their lifestyle can actually support. That’s not a race worth winning.

Managing money worship

Money worship is the belief that enough wealth will finally deliver happiness, freedom, or security. Money certainly helps — it can relieve real stress — but the research on whether more money keeps making us happier is genuinely mixed. Some studies suggest well-being levels off once basic needs and a comfortable margin are met; others find it keeps rising, but slowly. What’s consistent is that money alone is a poor engine for lasting contentment.

The practical move is to take money out of the happiness equation on purpose. Redirect some of that energy toward the things that actually produce joy for you — experiences, relationships, a hobby you keep meaning to start, time with people you love, giving back to your community. Get specific about what matters to you beyond the number, then spend your attention there.

Managing money avoidance

Money avoidance often grows from a belief that money is somehow tainted or shameful. It can look like neglected finances, an unopened-statement pile, or guilt around earning and spending.

The fix is built through small, repeated contact:

Create a habit. Start with 15 minutes a week — review the budget, check balances, glance at where the money went. The more routinely you engage with your finances, the less intimidating they become.
Reframe the tool. Money isn’t good or bad; it’s a tool. Picture what financial security actually lets you do: help the people you love, support causes you believe in, sleep a little easier. Familiarity and a healthier frame slowly replace the shame with a sense of control.

Managing money vigilance

Money vigilance usually produces good habits — diligent saving, low debt, careful planning. Its cost is on the other side: anxiety about spending, and difficulty enjoying what you’ve worked hard to build.

Watch for the signs that vigilance has tipped into something more restrictive:

Are you checking your accounts far more than any decision requires?
Do you feel guilty spending on things that genuinely improve your life?
Are you afraid to spend even when you can clearly afford it and the purchase fits your goals?

Saving matters. So does enjoying the result. Build a little intentional room into your budget for the things that bring you pleasure — and give yourself permission to use it.

Discovering your own script

These four patterns aren’t a complete list, and they aren’t mutually exclusive. Most of us carry a blend, shaped by experience. The work is figuring out which ones pull hardest on you. A few honest questions to sit with:

What did my family and community teach me about money? Was it a source of pride, stress, or something we didn’t talk about? Did financial success signal status?
What did my circumstances teach me? Scarcity in childhood can leave money feeling like something to hoard or fear. Security can make it feel like safety.
What did my culture teach me? In the U.S., talking about money is often taboo — even as the surrounding culture pushes hard toward spending and accumulating.

As you reflect, sort your beliefs into two piles: the ones that have served you well, and the ones that may be holding you back.

Flipping the script

Identifying a script is the beginning, not the finish. Changing one takes ongoing attention and a willingness to try new behaviors.

A good place to start is watching for habit loops. What do you actually do when money crosses your mind? Open a shopping app? Reorganize a drawer to avoid the bank balance? Notice the trigger, the behavior, and the result — bouts of overspending, denied small pleasures you could easily afford, or financial tasks left undone.

Reshaping a money script is a lifelong project. New experiences keep refining how you relate to money, and small adjustments compound into lasting change. If you’ve worked at it and still feel stuck, a financial therapist can help you get underneath the emotions steering your decisions — that’s a real and worthwhile resource, not a last resort.

And as always, we’re here to help however we can. If you’d like to talk through how these patterns show up in your own plan, reach out anytime — we’re always glad to start that conversation.

Related reading

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes only to reflect the current market environment; no index is a directly tradable investment. There may be instances when consultant opinions regarding any fundamental or quantitative analysis do not agree.

The commentary contained herein has been compiled by W. Reid Culp, III from sources provided by TAGStone Capital, as well as commentary provided by Mr. Culp, personally, and information independently obtained by Mr. Culp. The pronoun “we,” as used herein, references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

June 9, 2026June 9, 2026

Published June 9, 2026

At a Glance

Timing is everything. Your Initial Enrollment Period is just seven months around your 65th birthday. Miss it and Part B and Part D surcharges follow you for life.
Higher earners, plan ahead. IRMAA surcharges are based on income from two years prior — so decisions before 65 (Roth conversions, capital gains timing) shape what you’ll pay.
Medigap vs. Medicare Advantage. For affluent retirees the choice usually turns on access and flexibility over premium — the post lays the trade-offs side by side.

Most people spend decades saving, investing, and planning for retirement. Yet one of the most consequential financial decisions of those years has almost nothing to do with your portfolio. It comes down to a government program, a single birthday, and a deadline you do not want to miss.

The program is Medicare, and the window to enroll opens around your 65th birthday. Signing up on time lets you make full use of the coverage you’ve already paid for — and preserves your flexibility as healthcare becomes a larger line item later in retirement. Here’s what’s worth understanding before that birthday arrives.

The enrollment window — and why timing matters

Medicare was created in 1965 to give older Americans access to affordable healthcare. It isn’t free, but if you or your spouse paid payroll taxes for at least 10 years, you’ve already funded a meaningful share of it — a good reason to claim your benefits as soon as you’re eligible.

Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, your birthday month, and the three months after. Miss it, and you can face delayed coverage and permanently higher premiums — surcharges designed to discourage people from waiting until they’re sick to sign up. You enroll through the Social Security Administration’s website.

One important exception: if you’re still covered by a current employer’s group health plan (yours or a spouse’s), you may be able to delay enrollment without penalty. Whether that applies depends on the size of the employer and the specifics of the plan, so it’s worth confirming rather than assuming.

The four parts, briefly

Part A — hospital coverage. Covers inpatient hospital stays, skilled nursing care, hospice, and some home healthcare. For most people there’s no monthly premium, because you prepaid it through payroll taxes. You’ll still owe deductibles — $1,736 in 2026 for the first 60 days of a hospital stay, with meaningful copays beyond that. If you’ve paid in over your career, there’s no penalty for delaying Part A — and no real reason to.

Part B — outpatient coverage. Covers doctor visits, the ER, preventive care, lab work, and medical equipment. The standard 2026 premium is $202.90 per month (higher for upper-income households — more on that below), with a $283 annual deductible and a 20% coinsurance on most services. Missing your Initial Enrollment Period adds a permanent 10% surcharge for every full 12 months you delayed.

Part C — Medicare Advantage. Optional plans from private insurers that bundle Parts A and B, often with Part D, and frequently add dental, vision, and hearing. They typically replace Part B’s open-ended 20% coinsurance with fixed copays and a capped annual out-of-pocket maximum. You still pay your Part B premium, plus any additional plan premium — though some Advantage plans charge none.

Part D — prescription drug coverage. Sold through private insurers; the average 2026 premium is about $34.50 per month, with an annual deductible up to $615 depending on the plan. If you already have creditable drug coverage (through a current employer, say), you can delay without penalty. Otherwise, waiting adds a permanent 1% surcharge for every month you go without it.

Medigap: filling the gaps

Medigap policies are supplemental private coverage that pick up out-of-pocket costs left by Parts A and B. They carry higher premiums — sometimes several hundred dollars a month — but they smooth out the unpredictable copays and coinsurance that can otherwise add up.

The timing here is its own trap. Your six-month Medigap enrollment window opens the first month you’re both 65 and enrolled in Part B. Enroll during that window and you cannot be turned down or surcharged for preexisting conditions. Wait, and that protection may disappear. Note, too, that you can have Medigap or Medicare Advantage — not both.

Medigap vs. Medicare Advantage: which fits an affluent retiree?

For families with substantial assets, this choice usually turns on access and flexibility, not the monthly premium. Here’s how the two approaches compare on the factors that tend to matter most at higher levels of wealth:

Feature	Medigap (Original Medicare + Supplement)	Medicare Advantage (Part C)
Provider access	Unrestricted. See any doctor or specialist nationwide that accepts Medicare — no networks.	Network-based. Limited to local or regional HMO/PPO networks; a preferred specialist may be out of network.
Care approvals	Minimal. Original Medicare rarely requires prior authorization, so physicians drive care decisions.	More gatekeeping. Prior authorization is common and can delay specialist care.
Global coverage	Usually included. Most Medigap plans cover foreign-travel emergencies up to plan limits.	Emergency-only. Typically thin abroad — a gap for frequent international travelers or multi-property owners.
Cost structure	Predictable. Higher monthly premium, low cost at the point of care (Plan G still leaves the 2026 Part B deductible of $283).	Variable. Lower premium, but copays accrue up to an annual out-of-pocket maximum.
Concierge medicine	Compatible. Pairs cleanly with concierge or private-physician memberships.	Often friction. Managed-care network rules can conflict with concierge practices.

Comparison reflects how Original Medicare with Medigap and Medicare Advantage generally work; specifics vary by plan. Sources: Medicare.gov; KFF.

For those who prize unrestricted access to specialists and minimal administrative friction — and who can comfortably carry a higher premium — Medigap (often Plan G) tends to be the better fit. Families who prefer a lower premium and don’t mind network rules may still do well with Medicare Advantage. The right answer depends on your health, how much you travel, and how you like to receive care, and it’s worth weighing alongside the rest of your plan.

A note for higher-income households

For many of the families we work with, the standard premiums are only the starting point. Higher-income retirees pay an Income-Related Monthly Adjustment Amount — IRMAA — on top of their Part B and Part D premiums. The surcharge is tiered, and it can add hundreds of dollars a month per spouse at the upper brackets.

The detail that surprises people most: IRMAA looks back two years. Your 2026 premiums are based on the income you reported for 2024. That lag is exactly why the years leading up to 65 matter so much. Decisions about Roth conversions, when to realize capital gains, and how to time large or charitable distributions can ripple into what you pay for Medicare later. It’s one more reason a thoughtful approach to spending and withdrawals pays off, and a conversation worth having well before your enrollment year.

The takeaway

Medicare has a lot of moving parts, and the penalties for getting the timing wrong follow you for life. The good news is that the decisions are manageable with a little preparation. With some advance planning, many retirees can keep their healthcare costs in check even as their medical needs grow — and avoid the avoidable surcharges along the way.

This is one piece of a larger retirement picture that also includes how your accounts are organized and whether your core legal documents are current. If you’re approaching 65 — or helping a parent who is — we’re glad to walk through how Medicare fits into your plan and to coordinate the timing with the rest of your financial life.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

June 2, 2026June 19, 2026

When families come to us, the conversation usually starts with numbers — accounts, balances, projections, tax brackets. But the more time we spend together, the more another conversation surfaces: the one about how each person thinks about money in the first place.

Psychologist Dr. Brad Klontz calls these underlying beliefs our money scripts — unconscious rules about money that we absorb early in life, usually from family, and then carry into adulthood without ever revisiting them. Some serve us well; others quietly steer us off course. Most of us don’t know we’re running them.

“The problem is that we take these beliefs for granted as adults, and we rarely go back and examine them, let alone decide to change them,” Klontz says. “Instead, they’re kind of like an actor’s script in a movie; we just continue to read the lines in our heads…and believe that they’re true, when in fact, they are often quite distorted and limit our success.”

The good news: once you can name your money script, you can decide whether to keep following it.

Why scripts get written in the first place

Most money scripts are inherited. A parent who grew up with scarcity might raise a child who equates spending with danger, hoarding savings they never feel free to use. A household where one big raise or windfall changed everything can produce adults who treat money as the answer to every problem. Research from the UK found that children who were raised in households where spending was secretive were more likely to develop hoarding and other compulsive money habits as adults.

These patterns aren’t character flaws. They’re scripts — written by experience, performed automatically.

The four most common scripts

Klontz and his colleagues have grouped money scripts into four broad patterns. Few people fit neatly into one. Most of us carry pieces of each, with one or two pulling harder than the others.

Money status. Self-worth gets tied to net worth. People in this pattern may overspend to project success — the right car, the right address, the right watch. They may round up when describing their income or keep purchases hidden from a spouse. The underlying belief: what I have signals who I am.
Money worship. Money is treated as the path to happiness, freedom, and security. The belief that “if I just had more, the problem would go away” keeps the goalposts moving. This script often shows up in high earners who keep working past the point where additional income changes anything — because the script says it should.
Money avoidance. Wealth itself is viewed as suspect or even shameful. People with strong avoidance scripts may sabotage their own accumulation, give too much away, or simply refuse to look at statements. Underneath is often the quiet belief that I don’t deserve to have money, or that having it makes someone a worse person.
Money vigilance. Money is treated as a tool to be managed carefully. Vigilant savers tend to be frugal, private about finances, and uncomfortable spending on themselves — even when spending is clearly warranted. The strength of this script is discipline. The cost is often a reluctance to enjoy what they’ve worked to build.

These categories sound extreme on purpose. Read straight through, none of them are particularly flattering. But that’s the point — extremes are easier to recognize than nuance. In reality, we likely contain a bit of each of these patterns to varying degrees. Some may pull stronger than others, and some that sound overtly negative may offer strengths. For example, a money vigilant saver might also have a little money status running underneath, which is why the same person who clips coupons all year may also buy the flashier car. Both scripts are operating; both are inherited; both can be examined.

Why this matters for planning

With an understanding of the most common money scripts under your belt, you’re equipped to start keeping an eye out for where echoes of each appear in your own life in positive and negative ways. This identification process is important, because it allows you to move away from tendencies that don’t serve you well and toward those that do. In the second part of this series, we’ll offer strategies for flipping the script on these common behaviors and exploring your own personal money scripts. Stay tuned!

And in the meantime, we’re here to answer questions or offer strategies that can help you better reach your long-term financial goals. Reach out anytime — we’re always glad to start that conversation.

1. Confirm your beneficiary designations

Most of your assets pass under your will or trust. But a meaningful share — retirement accounts, life insurance, certain annuities — passes by beneficiary designation, which overrides whatever your will says. That makes these designations one of the most common sources of unintended outcomes.

Check that named beneficiaries still reflect your wishes. Common red flags: an ex-spouse still listed on a 401(k), a deceased relative as a sole beneficiary (which can force the asset through probate), or a custodian arrangement for a child who is now an adult. Most custodians let you update beneficiaries online in a few minutes. It’s one of the highest-leverage estate planning tasks you can do.

2. Revisit your fiduciary appointments

Your fiduciaries — trustees, executors, agents under power of attorney, health care proxies — are the people who carry out your wishes when you can’t. The right choice ten years ago may not be the right choice today. (We walk through each of these documents in The Core Four.)

Health changes, deaths, and shifting relationships are obvious reasons to update. Less obvious: a sibling you named when your children were small may now reasonably be replaced by an adult child. Check in with named fiduciaries each year — and after any plan update — to confirm they’re still willing and able to serve. Don’t forget the backups.

3. Make sure your trust is actually funded

A revocable trust only works for the assets that are titled in its name. We see this often: a client signs a trust, then buys a new home, opens a new brokerage account, or inherits property — and never retitles it. Those assets bypass the trust and often head straight to probate, defeating one of the main reasons the trust exists. Kiplinger has a useful primer on which assets belong in a revocable trust if you want a refresher on the categories.

Each year, walk through your asset list and confirm everything intended for the trust is properly titled. Real estate, business interests, and non-retirement financial accounts are the usual suspects. (Retirement accounts generally stay in your name with beneficiary designations rather than being retitled into the trust.)

4. Reflect recent life changes

Marriages, divorces, births, adoptions, and deaths in the family are all triggers for a plan review. So are larger financial shifts — the sale of a business, a meaningful inheritance, or a significant change in your overall net worth.

Two reminders that often get overlooked. First, moving to another state matters. Estate and probate rules vary, and community property states have particular rules around spousal rights to retirement assets. Second, federal tax law changes can meaningfully alter the calculus on lifetime gifting, the estate tax exemption, and trust structures. When Washington moves, it’s worth checking whether your plan still does what you think it does.

5. Store documents securely — and accessibly

A plan no one can find is a plan that doesn’t work. Originals of your will, trust, powers of attorney, and health care directives need to be stored somewhere safe and somewhere your fiduciaries can actually get to them when the time comes.

A fireproof home safe or your attorney’s secure storage are usually better choices than a bank safe deposit box, which can require a court order to access after death. Digital copies are useful for reference, but courts and financial institutions generally require originals with wet signatures.

Your fiduciaries don’t need a complete list of account numbers. They generally need to know which institutions hold your assets — with that, a death certificate and your Social Security number are usually enough to identify everything.

Estate planning is a process, not an event

Most annual reviews are short. But a regular cadence is what makes the bigger updates — after a major life change, a relocation, or a tax law shift — feel routine rather than overwhelming. For the procedural side of what your family will face after you’re gone, our estate planning framework walks through it step by step. Protection during your lifetime gets its own treatment in Protecting What’s Yours (While You’re Alive).

If it’s been more than a year since you looked at your estate plan, that’s a reasonable starting point for a conversation. We’re happy to coordinate with your estate planning attorney to make sure what’s on paper still matches what you want for your family today.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

May 19, 2026June 3, 2026

Published May 19, 2026

At a Glance

New in July 2026: Trump Accounts allow up to $5,000 per year per child (under age 18) in contributions, plus a potential $1,000 government seed deposit for eligible birth years.
Tax-Deferred — Not Tax-Free: Growth and most contributions are ultimately taxed as ordinary income unless proactively converted to a Roth IRA after age 18.
Planning Opportunity — But Timing Is Critical: The real advantage is a strategic Roth conversion during a child's low-income, financially independent years. Converting too early — while they're still a student claimed as a dependent — can trigger the kiddie tax and eliminate the benefit.

By now, you’ve likely heard something about Trump Accounts — formally known as 530A accounts. They’re one of the more talked-about provisions in recent tax legislation, and for good reason: they’re a brand-new, tax-advantaged savings vehicle for children, launching July 4, 2026. For families thinking through Trump Accounts tax planning, the details matter quite a bit before you commit. Before your family rushes to open one, here’s what you need to understand.

What Are They?

Trump Accounts are a type of custodial account — owned by the child but administered by an adult until the child turns 18. Family members can open accounts online at trumpaccounts.gov or by filing IRS Form 4547. They’re designed to fill a gap in the planning landscape. Custodial brokerage accounts (UTMAs/UGMAs) allow families to invest for a child, but growth is generally taxable. A 529 plan offers tax advantages, but only for qualified education expenses. And while children can contribute to a Roth or traditional IRA, they need earned income to do so — something most young children don’t have.

Trump Accounts require no earned income. Contributions of up to $5,000 per year can be made by parents, grandparents, adult siblings, legal guardians, or employers, as long as the child has a Social Security number and hasn’t yet turned 18 in the year the account is opened. Employers can also make matching contributions, which are deductible up to $2,500 and count toward the annual limit.

For children born between January 1, 2025 and December 31, 2028, there’s an added incentive: a one-time $1,000 federal seed contribution deposited directly into the account (and not counted against the annual cap). Separately, up to 25 million children age 10 or younger in lower-income zip codes may receive an additional $250 through a charitable contribution from the Michael and Susan Dell Foundation.

Investment options will be limited — likely a narrow menu of low-cost U.S. equity index funds, similar to the federal Thrift Savings Plan, with an expense cap of around 0.10%.

How Withdrawals Work — and Why It Matters

Withdrawals from a Trump Account are not allowed before the child turns 18. Beginning January 1 of the year the child turns 18, the account converts to a traditional IRA — subject to standard IRA rules, including a potential 10% early withdrawal penalty before age 59½.

Like a traditional IRA, growth inside the account is tax-deferred, and withdrawals are taxed as ordinary income.

That’s worth pausing on. A family that instead invested in a taxable custodial account (UTMA/UGMA) would likely see long-term growth taxed at capital gains rates — which, for most long-term investors, are meaningfully lower than ordinary income rates. So without additional planning, a Trump Account can effectively convert what might have been long-term capital gains into future ordinary income. That trade-off isn’t necessarily bad, but it’s not automatically a win, either.

Trump Accounts Tax Planning: The Age-18 Roth Conversion

Here’s where the planning story gets interesting — and where these accounts may offer a genuine advantage for families who think ahead.

Under Notice 2025-68, Trump Accounts are explicitly permitted to be converted to a Roth IRA once they become IRAs at age 18. That’s significant.

At 18, many young adults are in college with little to no income. If a child converts their Trump Account to a Roth IRA during a year when their taxable income is low, they may owe conversion taxes at a very low marginal rate — potentially 10% or 12%. Once converted, the account grows completely tax-free, no required minimum distributions apply during their lifetime, and withdrawals in retirement are income-tax free.

Used intentionally this way, a Trump Account becomes something closer to a delayed Roth funding mechanism for minors — one that doesn’t require earned income during childhood. That’s a genuinely useful planning tool.

The Kiddie Tax Caveat

There’s one important wrinkle families need to understand before assuming an 18-year-old college student can simply convert the account at a low rate.

The kiddie tax is a provision in the tax code that taxes a dependent child’s unearned income at the parents’ marginal rate, rather than the child’s own rate. It applies to children under age 19, and to full-time students under age 24 who don’t provide more than half of their own financial support.

A Roth conversion counts as income in the year it occurs. If a child is 18, in college, and still a dependent, the kiddie tax could cause a large Roth conversion to be taxed at the parents’ rate — potentially defeating much of the benefit.

The planning implication: the optimal time for conversion is likely after the child is working, financially self-supporting, and no longer subject to the kiddie tax. That might mean waiting until age 22 or 23 rather than converting the moment the account becomes an IRA. The account continues growing tax-deferred in the meantime, which softens the delay — but families should be deliberate about the timing.

How Trump Accounts Compare

Account Type	Tax Treatment	Earned Income Required?	Use Restrictions
Trump Account (530A)	Tax-deferred; withdrawals as ordinary income (Roth conversion possible)	No	Cannot withdraw before 18
529 Plan	Tax-free for qualified education	No	Education expenses only
Custodial Roth IRA	Tax-free growth and withdrawals	Yes	IRA rules apply
UTMA / UGMA	Taxable (capital gains rates)	No	None

What Should Families Do Now?

For eligible children born between 2025 and 2028, accepting the $1,000 government seed contribution is a straightforward decision — it costs nothing and gives the account a running start. Over 60 years at a 7% annualized return, that $1,000 alone could grow to nearly $58,000. Add $50 per month in family contributions, and the account could reach close to $550,000 over the same period.

Beyond that, the question of whether to make additional contributions deserves a closer look. The answer depends on your family’s overall tax picture, whether a deliberate Roth conversion strategy is part of your plan, and how the account fits alongside other savings vehicles like 529 plans and IRAs.

These accounts have real potential — but the advantage isn’t automatic. It requires coordination.

If you’d like to talk through how a Trump Account might fit into your family’s financial plan, reach out. We’re glad to help.

As with many new legislative programs, details are still being finalized — for a full legislative overview, the Congressional Research Service published a comprehensive summary in April 2026.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

May 12, 2026June 2, 2026

Spring is graduation season, and that means it is also the season when we hear a version of this question almost weekly: parents and grandparents asking how to give the young people in their lives a real head start with their money — not just a check tucked into a card, but something with staying power.

It's a thoughtful instinct. Children and grandchildren have one asset working in their favor that no investor can buy back later: time. A modest contribution made when a child is five or ten years old has decades to compound before it's ever drawn down. That is the entire engine behind multi-generational wealth, and it's available to any family willing to start.

The challenge is choosing the right vehicle. Each account type below carries trade-offs — tax treatment, control, financial aid impact, flexibility — and the right answer depends on what the money is for and how much control you want to keep. Here is how we typically frame the choices for clients.

529 Plans: The Workhorse for Education

For most families, a 529 plan is the first account we'd consider. It's built for one purpose — education — and the tax benefits are hard to beat: tax-deferred growth, tax-free withdrawals for qualified education expenses, and no federal contribution limits. Annual contributions above the gift tax exclusion ($19,000 per donor per beneficiary for 2026) start to use lifetime gift exemption, but a five-year "superfunding" election lets grandparents accelerate up to five years of gifts into a single year — a useful tool when timing matters.

Qualified expenses have broadened meaningfully. In addition to college, families can use up to $10,000 per year for K–12 tuition, fund graduate school, or apply $10,000 (lifetime) toward student loan repayment. Unused balances can be rolled to another family member or, in some cases, into a Roth IRA for the beneficiary. We covered the broader question of how to sequence different education dollars in How to Pay for College.

One caveat worth flagging: 529 ownership matters for financial aid. A 529 owned by a parent generally has a smaller impact on need-based aid than one owned by the student or, historically, by a grandparent. Recent FAFSA changes have softened the grandparent-owned 529 penalty, but the rules continue to evolve — coordinate before opening accounts in a grandparent's name if aid eligibility is on the table.

Custodial Accounts (UGMA/UTMA): Flexibility With Real Trade-offs

Not every gift to a child is meant for tuition. For families thinking about a future car, a wedding, a down payment on a first home, or simply a longer-horizon investment account, a UGMA or UTMA custodial account is often the right tool. These accounts are simpler than a trust to set up and can hold a wide range of investments — stocks, bonds, mutual funds, ETFs — and, in the case of UTMAs, even more complex assets like real estate, art, or intellectual property.

There are no contribution limits, and the money can be used for anything that benefits the child while they're still a minor. But here is the trade-off we make sure parents understand before they fund one: at the age of majority — typically 18 to 21, depending on the state — the child takes full ownership and can use the money however they choose. We've seen this work beautifully when families pair the account with conversations about money. We've also seen it become a teachable, expensive lesson when those conversations don't happen. (We've written before about why those conversations matter and how to start them in Family Conversations About Money.)

Custodial accounts also trigger the "kiddie tax," which applies to a minor's unearned income. For 2026, the first $1,350 is tax-free, the next $1,350 is taxed at the child's rate, and amounts above that are taxed at the parent's marginal rate. And because these accounts are considered the child's asset, they typically reduce financial aid eligibility more than a parent-owned 529 would. None of this disqualifies them — but it does mean they should be funded with intention, not as an afterthought.

Custodial Roth IRAs: The Long Game

For the family that wants to give a young person a true generational gift, it's hard to compete with a custodial Roth IRA. Decades of tax-free compounding, followed by tax-free withdrawals in retirement, is precisely the kind of asymmetric outcome time can produce. A child who funds a Roth at age sixteen and never contributes again can still reach retirement with a meaningful balance — without ever paying tax on the growth.

The catch: a Roth IRA requires earned income. Babysitting, lifeguarding, tutoring, a summer job at the family business — all qualify, but the contribution is capped at the lower of the child's actual earnings or the annual limit ($7,500 for 2026). Documentation matters. We typically recommend keeping a simple log of hours and pay, particularly when the earnings come from informal work, so the contributions are defensible if questioned.

Don't Skip the Other Half of This: the Conversation

Setting up accounts is the easy part. The harder, more valuable work is the financial literacy that goes around them. The young people in our clients' families who arrive at adulthood prepared to handle money tend to share a common experience: they grew up in households where money was discussed openly, where investment statements were reviewed at the kitchen table, and where they were brought into decisions early — not handed a portfolio at twenty-two.

Reviewing a 529 statement together is a free lesson in compounding. Letting a teenager help allocate a custodial Roth across a few low-cost funds is a free lesson in diversification. The accounts are the vehicle; the conversations are the road.

One Note on What's Coming

There is one more account type worth flagging that the original framing here didn't anticipate: Trump Accounts, a new vehicle created under recent legislation that adds another option to this toolkit. They have their own contribution rules, tax treatment, and trade-offs, and they fit alongside — not in place of — the accounts above. We'll cover them specifically next week.

How We'd Approach This With Your Family

There is no single right answer to "how should I invest for my kids." The right answer is the combination of accounts that fits your goals, your tax picture, and the role you want money to play in the next generation's life. For families with meaningful gift capacity, the question is often less "which one" and more "in what order, and how do they coordinate with the estate plan." That coordination is where we add the most value — and it's the same lens we apply to estate planning more broadly (see Protecting What's Yours (After You Pass)).

If you're thinking about funding accounts for children or grandchildren this year — particularly before a graduation, a wedding, or a year-end gifting deadline — we're happy to sit down and walk through which combination makes sense. Reach out and we'll set up a time.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

May 5, 2026May 14, 2026

If it feels like the headlines have been relentless lately, that's because they have been. Over the past year, investors have had to process an ongoing trade war, sharp market swings and now the geopolitical shock of a war in Iran—all while trying to stay focused on their long-term financial goals. As we discussed in our Q1 2026 quarterly letter, economic news in the first quarter was dominated by the conflict in the Middle East and its effects on markets.

These are the kinds of disruptive forces that test our patience as investors. And while the current backdrop may feel uniquely unsettling, it's worth stepping back and asking: how does this moment compare to other periods of disruption? And more importantly, how should you respond?

Disruption itself is not new. It could come from government policy like tariffs, from geopolitical crises, from unexpected shocks like the Covid pandemic, or even from something as improbable as one of the world's biggest container ships blocking the Suez Canal for a week. History can give us a clue as to how events like these have shaken out—though, as the SEC likes to remind us, past performance is not indicative of future results. There's no way to know what will happen six days, six months or even six years after a disruptive event takes place.

What History Can Teach Us

Let's start with tariffs, since they've been a persistent feature of the economic landscape since early 2025. When the Trump Administration announced sweeping tariffs on Canada, Mexico and China—with rates ranging from 20% to 25% and climbing higher in subsequent rounds—markets reacted sharply. A series of stutter steps followed as the Administration alternately paused tariffs on some goods while increasing them on others.

History offers useful context. The Smoot-Hawley Tariff Act of 1930 is the most cautionary example: enacted during the Great Depression, it triggered retaliatory tariffs from Canada and European countries, contributed to a collapse in global trade and deepened the economic downturn. The first Trump Administration's 2018 tariffs told a different story—they didn't spark the same cascade, though they also didn't achieve their stated goal of reducing the trade deficit with Mexico, which actually increased by 159%.

As for the 2025 tariff round—we now have the benefit of hindsight. Markets absorbed the initial shock, experienced significant volatility and, true to form, began recovering as investors recalibrated. This is consistent with what more than a century of market history has shown: disruptions are painful in the short term, but markets have generally found their footing.

That said, it's worth being honest about what "long term" really means. The NASDAQ didn't reclaim its dot-com-era peak until 2015—15 years after the bubble burst. The S&P 500 delivered a negative annualized return for the entire decade from 2000 to 2009, underperforming both bonds and cash over that stretch. The long-term direction of markets has been upward—but the path can be grueling, and it can test even the most patient investors. This is precisely why a properly diversified portfolio matters as much as it does.

The same perspective applies to the Iran conflict that has dominated headlines in 2026. As we explored in When Geopolitics Rattle the Markets, geopolitical crises are unsettling by nature and their market effects can be sharp in the short term. But looking back at major geopolitical events over the past century—World War II, the Korean War, the Gulf Wars, the September 11 attacks—markets have ultimately found their footing, even when the recovery took longer than anyone expected.

Your Next Steps

None of this is to say that disruptions won't touch your daily life—they may. Rising prices from tariffs, energy market volatility from geopolitical conflict, uncertainty about future policy—these are real concerns that may warrant a closer look at your budget and spending, particularly if you're on a fixed income.

When it comes to your investment portfolio, though, remember that it's been designed with disruption in mind. Research shows that diversified portfolios—those that combine stocks, bonds and other asset classes—have historically experienced significantly less pain during downturns than all-equity portfolios, and have recovered more quickly as a result. Proper diversification and disciplined rebalancing are built to help you navigate uncertainty without having to make reactive decisions in the heat of the moment.

We've worked together to create an investment plan that's structured for tax efficiency and allocates your assets according to your need, willingness and ability to take on risk. If your goals or circumstances have changed, we can revisit your allocations. But if nothing fundamental has shifted, you may not need to make any changes to your strategy at all.

The noise can feel deafening right now. That's normal—and expected. Disruptions are, by nature, jarring. So if you have questions about what's happening in the markets, the economy or your own portfolio, please reach out. That's exactly what we're here for.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

April 28, 2026May 14, 2026

If you’ve opened your homeowners insurance renewal lately, you’ve probably done a double-take. Premiums are up — sharply — and the pressure isn’t easing. Across the country, homeowners have seen their rates climb by 24% over the past three years, with some states seeing rates climb by more than 50%. As of last summer, insurance now accounts for more than 9% of the average single-family mortgage payment — the highest figure on record.

For families in the Southeast, this is more than a national headline. Hurricane Helene in 2024 left a trail of damage from Florida through eastern Tennessee and western North Carolina, including places that historically didn’t consider themselves catastrophe-prone. Reinsurance costs have followed, and they get passed through to homeowners, whether or not your roof has ever seen a named storm.

Insurance isn’t part of TAGStone’s licensure, and we’re not here to recommend a policy. But where insurance touches your financial plan — your cash flow, your real estate exposure, your retirement geography — it absolutely matters. Here’s how we think about it.

Start with your primary residence

If you’re facing a renewal hike, work the problem from a few angles before you simply pay the new bill.

First, re-read your policy. Coverage levels often haven’t kept pace with rebuild costs, and standard policies don’t cover everything: flood and earthquake are typically separate, and wind exclusions are common in coastal markets. Being under-insured at renewal time is a quieter risk than the sticker shock, but it’s the more expensive one if something happens.

Second, get a fresh quote from another carrier. The market has fragmented — some insurers have pulled out of certain ZIP codes, others are aggressively pricing in markets they want. A good independent insurance broker is worth their fee here.

Third, consider raising your deductible. A higher deductible lowers the premium, but it shifts more risk onto your balance sheet. That trade is worth it only if you’ve actually built — and earmarked — the cash to cover it.

Now consider your real estate investments

If you own rentals, vacation properties, or commercial real estate, rising premiums hit you twice: directly, through your own policy, and indirectly, through tenant economics and property values. Single-family rental investors have already seen carriers tighten in coastal markets. Commercial leases that don’t pass insurance through to tenants are renegotiation candidates at the next reset.

A more strategic question: if you’ve built real estate exposure concentrated in one geography — particularly a coastal or fire-prone one — your “diversified portfolio” may not actually be as diversified as the spreadsheet suggests. Insurance pricing is the market telling you something about correlated risk, and it’s worth listening.

A note on retirement geography

For clients planning to relocate in retirement, insurance cost has quietly become a meaningful line item. Florida’s tax and lifestyle case still pencils for many retirees, but the all-in cost of homeownership there isn’t what it was five years ago. The Carolinas, Georgia coast, and Tennessee mountains have their own evolving risk pictures. None of this rules anywhere out — it just means the “where” question deserves a fresh look in your retirement cash-flow plan.

The bottom line

Insurance is a household expense in name only. In practice, it’s a financial planning input — and a growing one. If your premium is up materially this year, that’s a signal to re-run a few numbers: cash flow, emergency reserve, the cost basis of any property you own, and whether the structure of your real estate exposure still matches your goals.

If you’d like to walk through any of those numbers together, please reach out. Insurance decisions are for your insurance broker — but the rest of the plan is what we do.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

April 21, 2026May 14, 2026

It has never been more tempting to spend money. Every day, we’re pressured to buy something, whether through traditional ads, targeted recommendations or the curated lifestyles of online influencers. The messages are constant and persuasive.

Financial professionals like us spend a lot of time talking about how to save. But knowing how to spend well is equally important. And for many, spending is surprisingly fraught, wrapped up in behavioral biases and the psychological imprints of past experiences.

Unexamined spending can lead to extremes. On one end of the spectrum, you find overspenders who rack up debt and land in financial hot water. On the other end are those afraid to spend, depriving themselves of things they can afford that would give them pleasure.

Ultimately, spending is unavoidable. Ideally, we find a middle path that allows us to cover necessities and spend on the things that truly bring joy, whether that’s hobbies, travel, experiences with your family and friends, or simple everyday pleasures.

So how do you engage in thoughtful spending? These tips can help.

Consider Your Values

One of the best ways to become a mindful spender is to spend in line with your values. Take the time to identify what matters most to you. These could be things like health, family, community, security or creativity. Before making a purchase, consider whether it supports one or more of these values. Doing so can help you avoid potential behavioral traps, such as signaling—spending money to shape how other people think of us.

It’s one thing to buy a nicer car because you need it. It’s another to buy one because you want to broadcast status to neighbors.

If you can truly afford to do this, there’s not necessarily a lot of harm done financially speaking. But it’s still worth asking whether the motivation reflects something you truly value or simply a desire to impress others.

And if the purchase stretches your finances, the irony is clear: Spending to appear wealthy actually undermines your financial security.

Compare and Despair

Closely related to signaling is the phenomenon of keeping up with the proverbial Joneses.

Morgan Housel, partner at The Collaborative Fund and author of The Psychology of Money puts it well: “There are two ways to use money. One is as a tool to live a better life. The other is as a yardstick of status to measure yourself against others. Many people aspire for the former but get caught up chasing the latter.”

When we see other people spending freely—neighbors renovating their kitchen or friends taking pricey vacations—it can create subtle pressure to match their choices. After all, we humans are deeply wired to avoid appearing like outsiders.

But appearances can be misleading. The people you’re comparing yourself to may be financing those purchases or stretching their budget to maintain a perfect front.

So again, before trying to match anyone’s spending, revisit your own priorities. You may find that the security of living within your means is much more important to you.

Be Mindful of Hedonic Adaptation

Besides being a bit of a mouthful, hedonic adaptation is the tendency for humans to return to a baseline level of happiness even after major positive or negative changes in their lives. In other words, the emotional impact of these events fades quickly over time.

This can have important implications for spending. Many purchases—the latest smartphone, a luxury car, a bigger home—promise lasting happiness. These items might provide a short-term boost in satisfaction, but that feeling typically fades faster than we’d expect.

Understanding this tendency can encourage a bit of pause before making big purchases. If it’s greater happiness you seek, whatever you’re considering buying likely isn’t the solution.

Being mindful of hedonic adaptation can also help guard against lifestyle creep, where spending gradually increases as income rises without necessarily improving long-term happiness. Buying that bigger home requires spending more on things like taxes and upkeep, which may quickly make you feel out of control. Or as Housel puts it: “Sometimes the stuff you spend money on has so much influence over your autonomy…that it’s not clear whether you own things or the things own you.”

On a more reassuring note, just as we adapt to positive changes, we also adapt to setbacks. Difficult events like a job loss or a financial downturn can feel overwhelming in the moment, but emotional recovery tends to be swift.

Think Before You Carpe Diem

Popular aphorisms encourage us to “carpe diem,” “YOLO” or “live for the moment.” And on a fundamental level, that message has merit. Life is unpredictable, and it’s important to enjoy it.

However, the idea also can be used to justify impulsive spending, allowing our present selves to win out over our future selves.

Consider a simple example: Spending $200 on a new pair of boots now may not seem like a major decision. However, if that same amount were invested and allowed to grow for decades, it could be worth thousands of dollars in the future.

This doesn’t mean you should never buy those boots—especially if you can afford them. The key is considering the trade-off and making that decision consciously.

Interestingly, carpe diem—often translated as “seize the day”—may have originally carried a more nuanced meaning. Some scholars suggest it would be better translated as “pluck the day,” an allusion to picking fruit or flowers at harvest time. Seen this way, the phrase originally may be more about appreciation and enjoying opportunities when the moment is right, rather than an exhortation to take impulsive action. That, perhaps, is a useful way to think about spending as well.

A Plan That Makes Room for Living

It might be easy to think that financial advice is all about pushing you to cut back and save more. In reality, it’s about finding balance. Together, we can build spending strategies that reflect what matters to you most, so you can feel confident about your future without putting your present happiness on hold.

At TAGStone, our planning conversations aren't just about accumulating wealth, they're about deploying it in ways that reflect what matters most to you. If you'd like to talk through how your spending fits into your broader financial picture, we'd welcome that conversation.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

April 14, 2026May 14, 2026

Published April 14, 2026

At a Glance

Consolidation simplifies your financial life and can trim duplicate fees — but a few 401(k) features (the Rule of 55, plan loans, some institutional share classes) disappear the moment you roll those dollars into an IRA.
There is no universal right answer. The best path depends on your age, your retirement timing, and what each of your existing accounts actually offers.
For most clients, the real payoff isn’t simplicity — it’s getting every retirement dollar aligned to one coherent investment strategy, instead of scattered across five versions of whatever seemed like a good idea in 2014.

If tax season left you digging through 1099s from three old employers, two IRAs, and an account you inherited from a parent, you’re in good company. Some version of this question hits my inbox almost every April: “I’ve got retirement money in six different places. Do I need to pull it all together?”

It’s a fair thing to wonder. After a career of job changes, firm mergers, plan rollovers you meant to finish but didn’t, and a Roth IRA you opened in your thirties, a lot of successful savers look up in their fifties and realize they’re managing more accounts than they intended. The Bureau of Labor Statistics reports that the youngest baby boomers had held an average of 12.9 jobs by age 58. If even half of those came with a workplace retirement plan, you can see how the pile grows.

So: should you consolidate? As with most decisions in planning, the honest answer is it depends — but the factors that matter are knowable, and worth walking through.

The Case for Pulling Things Together

The most obvious benefit of consolidation is simple and not to be underestimated: fewer moving parts. Fewer statements to open. Fewer usernames to remember. Fewer beneficiary forms to update when life changes. When your retirement picture lives in one or two places instead of six, we can actually see it — and so can you.

Cost is the next layer. Multiple legacy accounts often mean multiple sets of administrative, custodial, or advisory fees, quietly compounding against you. Consolidating into a single custodian frequently eliminates that redundancy. It also expands your investment menu. Many old 401(k) plans offer a handful of pre-selected funds; an IRA opens the door to nearly any publicly traded security.

Consolidation also gets easier to appreciate as you approach required minimum distribution age. Calculating and executing one RMD, from one custodian, is meaningfully less error-prone than coordinating three. And on the estate side, fewer accounts across fewer institutions makes life dramatically simpler for whoever has to settle your affairs one day — which is a gift to them, even if it doesn’t feel like one to you today.

What You Might Quietly Give Up

This is where I slow people down. Consolidation isn’t always the right call, and a few specific features can vanish the moment funds leave an old 401(k):

The Rule of 55. If you separate from your employer in or after the year you turn 55, you can take penalty-free distributions from that 401(k) before age 59½. Roll those dollars into an IRA and the exception is gone. For anyone considering early retirement, this is a detail worth protecting.

Plan loans. A 401(k) can be borrowed against in a pinch; an IRA cannot. I’d never recommend borrowing from retirement savings as a first move, but if a current plan has loan provisions you value as a last-resort emergency tool, be thoughtful before rolling that flexibility away.

Institutional share classes. Some large employer plans give participants access to low-cost institutional share classes — share classes you often can’t buy individually, even with a sizable IRA balance. If your old plan’s expense ratios are genuinely lower than what we can replicate elsewhere, staying put can be the right answer.

Before we consolidate anything, I want to compare the expense ratios and fund menus in every account you’re considering moving. Sometimes the old plan is quietly the cheapest and best option you have.

Three Ways to Simplify (Without Doing Too Much)

If consolidation makes sense, you generally have three paths:

Roll everything into an IRA. This tends to offer the broadest investment flexibility and the cleanest administrative picture, and it’s the right move for most people.

Roll into your current employer’s 401(k). If your current plan accepts incoming rollovers and offers strong, low-cost investment options, this preserves 401(k)-specific features (Rule of 55, plan loans) while still reducing the account count.

Same custodian, separate accounts. A middle path: move everything to one institution without commingling account types. You still get one login, one statement, one phone call — but your traditional IRA, Roth IRA, inherited IRA, and rollover IRA each stay in their own lane. This matters more than it sounds; for example, commingling an inherited IRA with a contributory IRA can create tracking and distribution headaches you don’t want.

The Bottom Line

The goal isn’t to own the fewest retirement accounts. The goal is to make sure every retirement dollar you’ve worked for is being managed deliberately — aligned to a single long-term strategy rather than whatever each plan’s default allocation happened to be the year you left that job.

For some clients, that means five separate accounts collapsing into one. For others, it means keeping a legacy 401(k) in place for its unique features while consolidating the rest. The right answer is the one that fits your circumstances — your age, your retirement timeline, your estate plan, and what each of your current accounts actually offers.

If you’ve been meaning to take inventory, this is a good time to do it. Pull your most recent statements together and send them over. A forty-five minute conversation is usually enough to tell whether consolidating is worth your effort, or whether you’re better off leaving things as they are.

This post is part of our Client Questions series. See also: Lump Sum vs. Dollar-Cost Averaging.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Money Scripts, Part 2: How to Rewrite the Ones That Don’t Serve You

Managing money status

Managing money worship

Managing money avoidance

Managing money vigilance

Discovering your own script

Flipping the script

Related reading

The enrollment window — and why timing matters

The four parts, briefly

Medigap: filling the gaps

Medigap vs. Medicare Advantage: which fits an affluent retiree?

A note for higher-income households

The takeaway

Why scripts get written in the first place

The four most common scripts

Why this matters for planning

Related reading

1. Confirm your beneficiary designations

2. Revisit your fiduciary appointments

3. Make sure your trust is actually funded

4. Reflect recent life changes

5. Store documents securely — and accessibly

Estate planning is a process, not an event

What Are They?

How Withdrawals Work — and Why It Matters

Trump Accounts Tax Planning: The Age-18 Roth Conversion

The Kiddie Tax Caveat

How Trump Accounts Compare

What Should Families Do Now?

529 Plans: The Workhorse for Education

Custodial Accounts (UGMA/UTMA): Flexibility With Real Trade-offs

Custodial Roth IRAs: The Long Game

Don't Skip the Other Half of This: the Conversation

One Note on What's Coming

How We'd Approach This With Your Family

What History Can Teach Us

Your Next Steps

Start with your primary residence

Now consider your real estate investments

A note on retirement geography

The bottom line

Consider Your Values

Compare and Despair

Be Mindful of Hedonic Adaptation

Think Before You Carpe Diem

A Plan That Makes Room for Living

The Case for Pulling Things Together

What You Might Quietly Give Up

Three Ways to Simplify (Without Doing Too Much)

The Bottom Line