Prepaying Tax for the Next Generation

Prepaying Tax for the Next Generation

by Luke Brooks, CFP®, CEPA®

Educational white paper | Federal-law references reviewed April 22, 2026 Educational material only. Federal income-tax, estate-planning, retirement-plan, and charitable-planning rules are summarized at a high level and should be coordinated with each client’s tax, legal, and estate-planning advisors before implementation. This analysis is intentionally framed around a controlled set of assumptions and planning objectives. Outcomes may differ—potentially materially—based on tax conditions, legislative changes, investment results, and individual family circumstances.

For affluent families, the retirement-account planning discussion often evolves beyond simple tax deferral and toward a broader question of balance-sheet design: whether tax should be prepaid deliberately so that children and grandchildren inherit a better category of asset. In that setting, the practical comparison is often not between spending and saving, but between Roth conversion and taxable reinvestment once the family has already agreed that recognizing income now may improve long-term after-tax family wealth.

This paper concludes that, under that controlled comparison, Roth conversion can often have a stronger multigenerational profile, depending on the specific circumstances and assumptions involved. If the same pre-tax dollar is distributed from an IRA or pre-tax 401(k), taxed at the same marginal rate, and the same after-tax amount is then positioned either inside a Roth account or inside a non-qualified brokerage account, the Roth will often produce a more favorable long-term family asset under the stated assumptions because it preserves tax-free compounding during the original owner’s lifetime and also preserves an additional inherited tax-free growth window for many beneficiaries.

Taxable accounts nevertheless remain essential. They support household liquidity, basis management, charitable gifts of appreciated securities, concentrated-position management, and broader asset-location design. Even so, once a family has consciously chosen to prepay tax within a selected bracket corridor in order to improve the quality of the family balance sheet, Roth is often a compelling destination for dollars that are meant to compound across generations, particularly under the framework described here.

A useful family-office framework is to separate wealth into three planning buckets: lifestyle capital, family compounding capital, and philanthropic capital. Taxable accounts often serve the first bucket because they provide flexibility and access; Roth capital often serves the second because it shelters long-duration compounding; and unused pre-tax retirement assets are frequently among the most efficient assets to direct to charity, especially when a private foundation or the sponsoring charity of a family donor-advised fund is part of the family’s long-term legacy plan.

1. The Core Planning Question

Traditional IRAs and pre-tax 401(k) balances are valuable because they defer tax while the assets grow. Deferral, however, is only one stage of the analysis. Under current beneficiary rules, most non-spouse designated beneficiaries of post-2019 defined-contribution plans and IRAs are generally subject to a 10-year payout framework, and taxable distributions from inherited pre-tax retirement accounts are included in the beneficiary’s gross income. As a result, a large traditional retirement balance can be a less attractive inherited asset than many families first assume.

Roth IRAs change the character of the asset in a meaningful way. Qualified distributions are tax-free, the original Roth IRA owner does not have lifetime required minimum distributions, and heirs generally inherit an asset that can continue to compound tax-free within the inherited Roth for the applicable inherited-account period, even though many non-spouse beneficiaries must ordinarily empty the account by the end of the tenth year.

Taxable brokerage accounts occupy a different place in the planning architecture. They are flexible, familiar, and free of retirement-plan contribution limits and many inherited-account operating rules, and inherited property generally receives a basis adjustment to fair market value at death. At the same time, taxable accounts re-enter the tax system every year through dividends, interest, and realized gains, which means that a basis adjustment can erase historical appreciation but cannot preserve future appreciation from tax in the same way a Roth wrapper can.

The planning question can therefore be stated in a direct and practical way.

If a client has already decided to accelerate income recognition now for estate, family-balance-sheet, and multigenerational-planning reasons, should those dollars generally be moved into Roth or reinvested in a taxable brokerage account?

For families whose priority is long-term family compounding rather than near-term spending flexibility, Roth will often be a more compelling answer, depending on individual circumstances.

2. Tax-Law Baseline for the Comparison

A traditional IRA is tax-deferred. Contributions may be deductible, and amounts in the account, including earnings and gains, are generally not taxed until distributed. Under current law, the applicable required beginning date depends on birth year. For many current retirees and near-retirees, required minimum distributions generally begin at age 73, while for individuals born in 1960 or later the applicable age is 75. Workplace retirement plans follow parallel rules, subject in many cases to the later-of-retirement rule for non-5% owners and any plan-specific provisions.

A Roth IRA operates under a different tax bargain. Contributions are not deductible, but qualified distributions are tax-free, and the original Roth IRA owner may generally leave amounts in the Roth IRA for life without lifetime required minimum distributions. Conversions from traditional IRA money to a Roth IRA are not subject to an income cap, but since 2018 a conversion generally cannot be recharacterized back to traditional IRA treatment, which makes the tax decision materially more permanent once it is executed.

For employer plans, Roth planning depends on plan design and distribution eligibility. Some 401(k), 403(b), and governmental 457(b) plans include designated Roth accounts and may permit in-plan Roth rollovers or other Roth features; under current law, pre-death required minimum distributions are no longer required from designated Roth accounts in those plans. In other situations, the client may need a distributable event or a rollover to an IRA structure before the desired strategy can be implemented. This paper uses 457(b) references only in the governmental-plan sense. Non-governmental 457(b) arrangements, which are common in certain tax-exempt institutions, are fundamentally different unfunded deferred-compensation arrangements and require separate analysis.

Beneficiary rules matter because this is not merely an owner-lifetime question. Under current IRS guidance, most non-spouse designated beneficiaries of post-2019 deaths generally fall under a 10-year distribution regime, while eligible designated beneficiaries—such as surviving spouses, minor children of the decedent, disabled or chronically ill individuals, and individuals not more than 10 years younger than the decedent—can in many cases use life-expectancy-based payouts for a period of time. Final regulations also clarified that when a designated beneficiary subject to the 10-year rule inherits a pre-tax account from an owner who died on or after the required beginning date, annual distributions may still be required in years one through nine, with the balance fully distributed by year ten. Inherited Roth IRAs follow a different practical pattern because the original Roth IRA owner had no lifetime required minimum distributions, although many non-spouse beneficiaries must still empty the account by the end of the tenth year. Taxable brokerage assets follow a different regime. Investment income is taxable, and gains and losses on disposition are reportable. Property acquired from a decedent’s estate is generally received with basis equal to fair market value at the date of death, or the alternate valuation date if applicable. That basis adjustment is unquestionably valuable, but it addresses gain that accrued before death; it does not shelter future returns from tax.

3. The Critical Analytical Mistake in Many Comparisons

One of the most common analytical errors in this area is to treat a basis adjustment at death as though it were functionally equivalent to Roth treatment. The comparison is appealing because both concepts improve after-tax wealth, but they address different tax burdens at different points in time. A basis adjustment deals with appreciation that accrued up to the date of death. Roth treatment protects future growth from current income taxation. When the family’s objective is multigenerational compounding rather than immediate liquidity, that distinction becomes outcome-determinative.

The difference becomes even clearer once the family’s actual objective is stated plainly: to create a better inherited asset for children or grandchildren. A taxable account may receive a favorable basis adjustment when the senior generation dies, but from that point forward the heir’s dividends, interest, and realized gains are once again subject to tax.

If the same pre-tax dollars are instead converted to Roth at the same tax rate, the family generally preserves tax-free growth during the owner’s lifetime and then preserves an additional inherited tax-free runway during the heir’s inherited-account period. That second layer of sheltered growth is the feature that many simplified step-up analyses underweight. Step-up therefore remains important, but it rarely replicates the full economic effect of Roth treatment in a true multigenerational compounding case. It can make taxable reinvestment more competitive than many families initially expect, yet it does not recreate the Roth’s ability to continue sheltering future returns after the owner’s death. That conclusion should still be applied with nuance in affluent-family planning: some families combine taxable assets with trust and estate-inclusion planning designed to preserve or improve basis results at death, and those structures can narrow the gap further. They do not, however, eliminate the basic analytical difference between a one-time basis adjustment and an ongoing tax-free wrapper. That conclusion is not universal; differing tax conditions, liquidity needs, or beneficiary behavior may lead taxable or pre-tax structures to be equally or more appropriate.

4. The Controlled Comparison: Same Dollars, Same Tax Cost, Same Year

The decisive insight in this planning debate emerges only after the variables have been held constant and the family has clearly defined the decision being made.

Assume that the client has already decided to move a given amount out of a traditional IRA or pre-tax 401(k) this year, that the amount is limited to a chosen bracket corridor such as the top of the 24 percent bracket, that the tax cost is the same whether the dollars are converted to Roth or withdrawn and reinvested in taxable brokerage, and that the family’s objective is long-term wealth compounding rather than present consumption. That assumption is intentionally narrow. Outside this controlled comparison—particularly where the senior generation faces materially higher combined federal and state rates than likely heirs, or where heirs are expected to liquidate shortly after inheritance—the relative advantage can be closer and, in some cases, the answer can change.

Under those assumptions, Roth will often have a structural advantage over taxable reinvestment under these assumptions because the family has already accepted the income-recognition decision and is now choosing between two very different destinations for the same after-tax capital.

Once the tax is paid, the Roth remains inside a tax-favored wrapper and the taxable account does not. Even a highly efficient taxable portfolio still faces some degree of ongoing friction from dividends, future gain realization, rebalancing, turnover, and other income events. The Roth largely removes that friction, and after the owner’s death it generally offers an additional inherited tax-free growth period that a taxable account cannot reproduce.

That advantage is often most meaningful when the assets expected to live inside the Roth are growth-oriented holdings with meaningful appreciation potential. Diversified public equities, private equity, venture capital, and similar long-duration return-seeking allocations can benefit disproportionately from a tax-free wrapper because the economic value lies primarily in protecting compounding, not in merely sheltering current income.

There is also a structural option-value benefit that is difficult to quantify fully in a spreadsheet. Eligible IRA and pre-tax employer-plan dollars can be converted into Roth status, but appreciated brokerage assets cannot simply be rewrapped into Roth treatment on demand. Existing pre-tax retirement balances therefore represent a rare reservoir of capital that can still be repositioned into a tax-free environment if the family is willing to bear the current tax cost and comply with the relevant plan rules.

Once the family has already agreed to pay the tax cost of leaving the pre-tax system, the remaining question is what type of capital it wants to own going forward. A Roth often produces a cleaner long-term compounding asset in this context, while taxable brokerage provides greater day-to-day flexibility and access.

That framing should anchor the analysis. In many affluent households, the more useful question is not whether taxable brokerage is valuable in general, but whether it is the best destination for dollars that the family has already decided to tax now for multigenerational purposes. In that narrower and highly practical comparison, Roth is usually the stronger answer.

5. Where Taxable Brokerage Still Retains an Important Role

Taxable brokerage remains indispensable, although its role in the family balance sheet is distinct from the role of Roth capital.

Taxable accounts are the most flexible capital a family owns. They can fund spending, opportunistic investing, concentrated-stock diversification, family gifts, tax-loss harvesting, and charitable gifts of appreciated property, and they do so without inherited-account distribution rules, five-year qualification issues, retirement-plan distribution procedures, or contribution-eligibility constraints.

Taxable assets are also often the best liquidity reserve for paying conversion tax itself. In many cases, the strongest Roth-conversion math occurs when the tax is paid from outside assets rather than from the retirement account being converted, because that approach preserves more capital inside the tax-free wrapper the family is trying to build.

Basis adjustment at death also continues to matter. If the family expects certain taxable assets to be held until death, the basis reset can be economically significant and remains one reason taxable accounts continue to occupy a central place in advanced wealth planning even when Roth is favored for intergenerational compounding.

In addition, thoughtful asset-location design usually requires both structures. A family may intentionally place its longest-duration dynasty capital into Roth, preserve a taxable pool for lifestyle spending and flexibility, and allow the pre-tax bucket to shrink over time as disciplined annual conversions are executed.

The stronger conclusion, therefore, is not that taxable brokerage loses relevance, but that Roth is typically the better home for dollars specifically intended to become the family’s highest-quality long-term inherited compounding asset once the tax has already been prepaid.

6. Key Things Families Should Know

Families evaluating this strategy should keep several practical considerations in view as they decide how much capital belongs in each wrapper and what role each wrapper is expected to serve over time.

Roth conversion is often most compelling when the dollars being repositioned are intended to do the family’s longest-duration growth work. The more the allocation is centered on appreciation-oriented assets such as diversified public equities, private equity, venture capital, and other return-seeking holdings, the more valuable the tax-free wrapper may become over both the senior generation’s lifetime and the beneficiaries’ inherited period.

Taxable brokerage nevertheless continues to play an essential role in a sound plan. It provides liquidity, can fund taxes, supports gifts of appreciated securities, and gives the family an accessible reserve for spending, rebalancing, opportunistic investments, and changing family needs.

The strategy is also most powerful when the family truly intends to preserve and reinvest inherited wealth rather than treat it as near-term spending capital. The inherited Roth window becomes especially valuable when children or grandchildren are likely to steward the assets as continuing family capital rather than consume them shortly after receipt.

Execution quality matters as much as strategy selection. Annual tax corridors, plan-specific conversion mechanics, beneficiary designations, and the source of tax payments can each materially affect the long-term outcome, which is why the strongest results usually come from multi-year implementation rather than a single isolated transaction.

Families should also recognize the qualitative advantage of Roth capital. Roth assets are generally easier for heirs to understand and easier to use well because they do not require the next generation to manage annual tax friction, estimate future capital-gain exposure, or worry that a necessary distribution will create a tax surprise. The most durable plans typically emerge when Roth and taxable accounts are treated as complementary tools rather than interchangeable pools of capital. In that structure, Roth often becomes the preferred home for long-horizon family compounding, while taxable brokerage remains the preferred home for liquidity, flexibility, and day-to-day control.

7. Medicare, NIIT, and Other “Hidden” Costs of Conversion Planning

Even when a family is entirely willing to prepay tax, conversion decisions should not be modeled by reference to the federal ordinary-income bracket alone.

Roth conversions can increase modified adjusted gross income for purposes of Medicare income-related monthly adjustment amounts. For 2026 premiums, Medicare and Social Security look to prior-return income information, and higher MAGI can drive higher Part B and Part D costs. The net investment income tax adds another layer of analysis: although IRA and many retirement-plan distributions are generally not themselves net investment income, they can still increase MAGI and thereby affect whether other investment income becomes exposed to NIIT.

The practical implication is that an “acceptable tax rate” should be defined broadly. For affluent retirees, the real marginal cost may include federal tax, state tax, IRMAA effects, and downstream NIIT consequences on other investment income, even when the conversion itself remains attractive on a long-term basis.

Disciplined annual bracket management therefore still matters. The central point of this paper is narrower and more precise: once the family has chosen to prepay tax within the desired corridor, Roth will typically offer the superior long-term destination for dollars intended to build family capital.

8. A Quasi-Family Office Framework for Multi-Generational Planning

Families with substantial wealth often benefit from thinking about asset location by purpose before thinking about it by account label. That shift in perspective tends to produce a more coherent planning architecture and a more useful conversation around what each dollar is actually meant to accomplish.

One practical framework is to separate the family balance sheet into three pools of capital, each with a different objective, time horizon, and governance expectation.

Lifestyle capital is meant to fund the senior generation’s spending, reserves, taxes, opportunistic needs, and gifting flexibility. Taxable brokerage is often the natural home for much of this bucket because it provides ready access and operational flexibility.

Family compounding capital is meant to outlive the first generation and arrive in the next generation in the cleanest possible form. Roth is often a preferred home for this bucket within this framework because it minimizes future income-tax friction for both the original owner and the heirs and preserves the compounding quality of the asset over time.

Philanthropic capital is meant to support charitable purpose, family mission, and legacy. Pre-tax retirement assets often fit this bucket particularly well because a tax-exempt charitable recipient can receive assets that would otherwise create ordinary income if left to individual beneficiaries.

Once families view the balance sheet through that lens, the planning logic becomes much more coherent. The exercise becomes a redesign of the family’s asset mix so that each dollar is placed in the vehicle best suited to its ultimate purpose, rather than simply left where it happens to sit today. This framing is especially valuable for affluent families who want planning to feel coordinated rather than product-driven. It elevates the conversation from a yearly conversion amount to a broader design question about what type of capital each generation should inherit, steward, and deploy.

9. Charitable Overlay: Why Unused IRA and 401(k) Assets Are Often the Best Assets to Leave to Charity

For charitably inclined families, one of the cleanest asset-location decisions on the balance sheet is to direct unused pre-tax retirement assets to charity rather than to taxable individual beneficiaries.

The tax logic is compelling. Distributions from inherited traditional IRAs and other pre-tax retirement accounts are generally includible in the beneficiary’s gross income, while qualified charitable organizations are tax-exempt. A pre-tax IRA or 401(k) that would create ordinary income in the hands of a child or grandchild can therefore pass to charity with materially less income-tax erosion.

This point becomes even sharper when likely individual beneficiaries are in the second or third generation. Qualified charitable distributions are generally available only from an IRA owned by an individual who is age 70½ or older. Non-spouse beneficiaries of inherited IRAs generally do not solve the inherited-account income problem by attempting to use QCD rules on inherited-account distributions. As a result, children and grandchildren who inherit traditional retirement assets will often face taxable distribution requirements during the inherited-account period without an equivalent charitable-release valve.

For families that use a donor-advised fund, beneficiary design requires precision. The beneficiary designation is ordinarily made to the sponsoring section 501(c)(3) organization that maintains the family’s donor-advised fund, not to a family-owned account in the same sense as a private foundation. Once the transfer is made, the sponsoring organization has legal control over the assets, while the family retains advisory privileges under the sponsor’s policies.

A private foundation offers a different form of legacy infrastructure. It can create a formal family-governance platform for grantmaking, education, mission setting, and intergenerational stewardship, although it also brings annual filings, distribution requirements, self-dealing restrictions, excise-tax considerations, and other compliance responsibilities that should be weighed carefully.

In either structure, the qualitative benefit can be as important as the tax result. A charitable beneficiary designation places real capital behind family values, creates a setting in which children and grandchildren can practice judgment together, and turns charitable intent from an abstract aspiration into an active part of family culture and governance.

For families that want legacy to include both capital and character, directing unused pre-tax retirement assets to philanthropy can become one of the most meaningful planning decisions on the balance sheet. It mitigates tax friction, strengthens the family’s mission, and can give future generations a funded platform through which values are not merely discussed but exercised.

10. Practical Implementation Principles for Families

Families considering this strategy usually achieve the best results when implementation is deliberate, coordinated, and revisited over time as family circumstances evolve.

It is wise to begin with purpose. Before any conversion calendar is built, the family should decide how much of the retirement balance is intended to support the senior generation’s own lifetime spending, how much is intended to become long-term family compounding capital, and how much may ultimately be reserved for philanthropy.

An annual tax corridor should then be established with the family’s advisors before conversions are executed. The relevant number is broader than the headline federal bracket and may include state income tax, Medicare premium effects, and NIIT interactions, all of which can materially affect the economic cost of the strategy.

Families should also confirm what each account can actually do before relying on a planning model. IRA assets are generally easier to convert than employer-plan assets, while 401(k) and similar balances depend on the plan’s actual distribution provisions, Roth features, and administrative rules. Governmental 457(b) plans may present Roth opportunities under their own rules, but non-governmental 457(b) arrangements should be analyzed separately because they are a different form of deferred compensation.

When feasible, paying conversion tax from assets outside the retirement account itself often strengthens the result because it preserves more capital inside the Roth, which is the very account the family is attempting to fortify for long-term compounding.

Beneficiary designations deserve the same level of attention as wills and trusts. Many sophisticated families have carefully drafted estate documents but outdated beneficiary forms that no longer reflect the balance-sheet design, charitable intent, or multigenerational strategy the family now intends to implement.

Families should also decide explicitly how philanthropy fits into the plan. If charitable legacy matters, pre-tax retirement assets are often strong candidates for that role, while Roth and taxable assets can be allocated more deliberately across the family’s spending, compounding, and governance objectives.

Finally, the strategy should be reviewed regularly. Asset values, family goals, tax law, liquidity needs, market conditions, and the maturity of the next generation all change over time, and the best long-term results usually come from a disciplined multi-year process rather than from a single transaction viewed in isolation.

Conclusion

The most useful planning insight in this area is also the simplest: once a family has already chosen to pay tax now on a given dollar at a given rate, Roth will often be a more effective destination for dollars intended to compound across generations, particularly under the assumptions outlined in this paper.

Taxable accounts remain indispensable for liquidity, flexibility, basis management, and broader household planning, and a basis adjustment at death still matters. The more decision-relevant point is narrower: a basis reset does not recreate the Roth’s ability to continue sheltering future growth, including the additional inherited growth window available to many beneficiaries.

For families that want to convert a present tax payment into a better category of inherited capital for the next generation, Roth conversion is often the most coherent and durable answer.

For families that are also charitably inclined, the design can be even more elegant. Taxable assets can continue to serve flexibility and liquidity needs, Roth assets can serve family compounding, and pre-tax retirement assets can be directed toward philanthropic legacy in a way that reinforces both tax efficiency and family purpose.

Viewed together, that architecture turns retirement-account strategy into a broader exercise in multigenerational wealth design, family governance, and legacy planning.

Sources and Authorities

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Compliance Disclosure

This material is provided for educational and informational purposes only. It is intended to illustrate high-level planning concepts involving retirement accounts, Roth conversions, taxable brokerage accounts, charitable beneficiary designations, and multigenerational wealth planning. It is not a recommendation to implement any specific transaction, strategy, account structure, security, or charitable arrangement, and it should not be construed as individualized investment, tax, legal, accounting, or estate-planning advice.

Any forward-looking statements, projections, illustrations, or examples are hypothetical in nature, are included solely for discussion purposes, and are not guarantees of future results. Actual outcomes will vary based on tax law, investment performance, fees and expenses, state law, beneficiary circumstances, liquidity needs, plan-document provisions, charitable-organization rules, and other factors that may change over time. References to private equity, venture capital, concentrated equity positions, or other growth-oriented assets are illustrative only and should not be interpreted as a recommendation, endorsement, or suitability determination for any particular investor.

Retirement-plan and Roth-conversion rules are complex and may change through legislation, regulation, administrative guidance, or judicial interpretation. Beneficiary-designation planning, charitable-planning structures, qualified charitable distribution rules, and employer-plan conversion features should be reviewed with the client’s tax advisor, estate-planning attorney, and other relevant professionals before implementation. An RIA or its personnel should also review any client-facing use of this material for consistency with the firm’s Form ADV disclosures, policies and procedures, advertising-review standards, and applicable federal and state regulatory requirements.

This document does not constitute an offer to buy or sell any security, an offer of advisory services where such services are not permitted, or a solicitation relating to any private fund or other investment vehicle. Past tax treatment and historical market behavior do not ensure similar outcomes in the future. Families should make implementation decisions only after considering their own objectives, risk tolerance, cash-flow needs, estate-planning goals, and professional advice.