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Harvard Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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'Harvard employees with concentrated stock positions may benefit from thoughtful tax planning that allows for tax deferral while balancing liquidity, compliance, and long-term compounding,' Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Harvard employees who hold highly-appreciated stock may want to consider tax-efficient strategies that help mitigate their liabilities while aligning with their overall retirement goals,' Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

  1. How taxes can affect investment returns, particularly on concentrated stock positions.

  2. Exchange funds and options-based strategies as methods for tax deferral and diversification.

  3. Alternative planning techniques outside ETFs, including charitable trusts and gifting strategies.

By Carlos Hernandez, Wealth Enhancement advisor

When it comes to driving portfolio returns, many investors aim to keep management fees low by investing in low-cost index funds and exchange-traded funds (ETFs). While fees matter, however, the real culprit for lower-than-anticipated performance is taxes. 1

Wealth Enhancement advisor Carlos Hernandez explains: 'By losing less to taxes each year, investors have access to more capital that can continue to compound over time. This makes tax deferral an important part of an effective financial plan.' Harvard employees looking for long-term growth strategies could benefit by understanding how to better manage their investment tax burdens.

Trade Money

One area where taxes can take a toll is on the sale of company stock or other concentrated investment positions. Harvard professionals looking to diversify could face significant capital gains taxes on an outright sale. One way to diversify without triggering immediate capital gains is through exchange funds. By contributing their highy-appreciated stock to a pooled fund, investors can trade their concentrated holdings for shares in a diverse basket of securities. This method can be used by Harvard employees who want to diversify while postponing taxable events.

Although this method allows for tax deferral, it also requires investors to hold the exchange fund for a period of time, typically seven years. 2  This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Harvard executives should carefully evaluate.

Funds Based on Options

Another way to mitigate taxes on the sale of highly-appreciated stock is by using options contracts. The idea is to hedge risk with put options while covering the cost of those puts by selling call options—a strategy called 'collaring'. From there, the strategy reverses, with investors selling put options and using the proceeds to buy call option on an equity or bond index. 3  If managed effectively, this helps to diversify a concentrated portfolio while still maintaining liquidity.

Given the complexity of this strategy, meticulous planning is necessary. It's generally recommended that investors work with an experienced financial advisor before pursuing this approach.

Things to Be Aware of

Although these strategies can be beneficial for Harvard employees who hold highly-appreciated stock, caution is recommended. There are costs associated with these approaches, and potential liquidity risks. Additionally, the IRS may eventually contest such arrangements because their tax status has not been thoroughly examined—something Harvard retirees should keep top of mind.

'Tax drag reduction strategies can be effective, but they must be assessed through the lens of risk, liquidity, cost, and compliance,' warns Carlos Hernandez. What is appealing in theory must hold up to inspection in the real world.

Alternative Strategies

Although they show promise, investors with highly-appreciated stock or those looking to postpone gains have other alternatives besides exchange funds or options. Other tactics could include:

  • - Prepaid variable forwards (subject to IRS regulations, contracts to sell at predetermined terms in the future).

  • - Charitable remainder trusts (CRTs), which allow investors to donate appreciated stock to a charitable trust and receive a stream of regular income in return.

  • - Donor-advised funds (DAFs), which provide investors with a tax deduction for the fair market value of the appreciated stock they donate.

  • - Other gifting techniques, such as direct donations to charity or family.

  • Each has its own set of guidelines, advantages, and disadvantages. To limit unnecessary taxes or violating the constructive sale regulations, careful planning is necessary for Harvard professionals managing complex portfolios.

The Bottom Line

Although the movement to mitigate the tax burden on investments is not new, the instruments are changing. Both exchange funds and options-based structures offer investors a way to manage tax liabilities, especially for Harvard employees who hold highly-appreciated stock.

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In the end, taxes are unavoidable. However, with the correct set of instruments, they can be controlled and postponed. 'The real value comes from aligning tax strategy with investment strategy,' summarizes Carlos Hernandez. 

Sources:

1. BlackRock Advisor Center. ' Investing for After-Tax Returns ,' 2025. 

2. Kiplinger. ' Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings ,' by Robert Waskiewicz. Sep. 11, 2025.

3. Financial Planning Association. ' Tax-Efficient Ways to Diversify Concentrated Stock Positions ,' by Peter Lazaroff. Oct. 2024.

What are the key distribution options available to employees at Harvard University upon retirement, and how do these options differ regarding tax implications? Employees should understand both the annuity options and lump-sum distributions available under the Harvard University Retirement Plan, as these can significantly affect their financial outcomes in retirement. Harvard University provides various choices depending on the lump-sum value, and it's essential to analyze each choice carefully to maximize retirement benefits.

Key Distribution Options: Upon retirement, Harvard University employees can choose between a lump-sum distribution, a rollover to another retirement account, or an annuity with different options, including a single-life annuity or joint and survivor annuity​(Harvard University Reti…). Lump-sum payments may lead to immediate tax liabilities, while annuity options offer more tax-deferred growth​(Harvard University Reti…).

How does the choice of an annuity payment method impact the long-term financial security of retirees at Harvard University? Employees need to weigh the advantages and disadvantages of single life versus joint and survivor annuities, considering not only their own financial needs but also those of potential beneficiaries. The decision can affect monthly income levels and the benefits passed on to surviving partners or dependents.

Impact of Annuity Payment Method: Choosing a single-life annuity maximizes monthly payments but provides no benefits after the retiree’s death. A joint and survivor annuity reduces monthly payments but ensures ongoing income for a surviving spouse or beneficiary, offering more long-term financial security for both parties​(Harvard University Reti…).

What specific conditions must be met for a retired employee of Harvard University to elect the Consolidated Harvard Annuity Option (CHAO), and what benefits might this offer? Understanding the eligibility criteria for CHAO and its implications on retirement planning will help employees make informed decisions. The CHAO allows for a potential increase in annuity benefits, but there are specific deadlines and requirements that participants must adhere to.

Consolidated Harvard Annuity Option (CHAO): To elect the CHAO, employees must terminate their employment after April 30, 2006, and have a Basic Retirement Account balance exceeding $1,000. They must elect the CHAO within 60 days of termination to exchange their investment account for a higher annuity​(Harvard University Reti…)​(Harvard University Reti…).

How can employees at Harvard University ensure that they have properly designated beneficiaries within their retirement plans, and what are the ramifications of failing to do so? The importance of keeping beneficiary designations up to date cannot be overstated, as it impacts how benefits are distributed upon the participant’s death. Employees must familiarize themselves with the required forms and the potential consequences of having outdated or incorrect designations.

Beneficiary Designations: Employees should ensure their beneficiary designations are up to date by completing the appropriate forms. Failure to do so could result in benefits being distributed according to marital status or to unintended recipients​(Harvard University Reti…).

In what ways do the spousal consent rules affect the retirement options for married employees of Harvard University, and why is this a critical aspect to consider when planning for retirement? Understanding the spousal consent requirements is vital for retirees since failing to adhere to these regulations can lead to unintended consequences, including issues related to benefit disbursement. Employees should seek to navigate these requirements carefully to secure their desired benefit structure.

Spousal Consent Rules: Married employees must obtain spousal consent, witnessed by a notary or plan representative, if they choose a retirement distribution option that does not provide survivor benefits to their spouse​(Harvard University Reti…). Failure to adhere to these rules can result in complications with benefit disbursement​(Harvard University Reti…).

How does the $1,000 threshold affect retirement distribution choices for employees retiring from Harvard University, and what specific options are available once this threshold is considered? Employees need to be informed about the options that arise based on the value of their Basic Retirement Account when making distribution decisions. Knowing whether an annuity or lump-sum option is available can significantly influence retirement planning and benefits.

$1,000 Threshold: If an employee's Basic Retirement Account value is $1,000 or less, they must take a lump-sum payment or rollover, as annuity options are unavailable. The lump-sum is subject to tax withholding unless rolled over​(Harvard University Reti…).

What steps should employees at Harvard University take if they wish to defer their retirement distributions, and what factors should they consider before making this decision? Deferring distributions can offer various tax advantages and impact retirement income strategies. Employees should evaluate their financial situations, anticipate future needs, and understand the timelines involved in the deferment process to make sound choices.

Deferring Distributions: Employees can defer their distributions until the April 1st following the year they turn 70½. Deferring can offer tax advantages and allow time for the value of retirement funds to grow​(Harvard University Reti…).

What are the consequences of electing a lump-sum distribution from a retirement account at Harvard University, particularly in terms of immediate and long-term tax implications? Employees considering a lump-sum distribution must recognize that such options can lead to significant tax liabilities and potential penalties, especially if improperly managed. A thorough understanding of these financial repercussions can aid in making choices that align with retirement goals.

Lump-Sum Distribution Consequences: Opting for a lump-sum distribution can result in substantial tax liabilities, including early withdrawal penalties if under age 59½. However, rolling the distribution into another retirement account can mitigate tax impacts​(Harvard University Reti…).

How can employees contact the Harvard University Retirement Center to learn more about their retirement plan options, and what information should they prepare before reaching out? Understanding how to access information and ask the right questions is crucial for employees looking to navigate their retirement options effectively. Having personal details and specific inquiries ready when contacting the Harvard University Retirement Center will facilitate a more productive dialogue.

Contacting the Retirement Center: Employees can reach the Harvard University Retirement Center at 800-527-1398 for information. They should have their pension statement, retirement account details, and any specific questions prepared​(Harvard University Reti…).

What should employees at Harvard University consider when choosing whether to roll over their retirement benefits into another employer's retirement plan or an IRA? The decision to roll over retirement benefits comes with various implications, including investment choices, fees, and the overall management of retirement funds. An in-depth understanding of the pros and cons of rollover options will empower employees to make informed decisions that best suit their financial futures.

Rollover Options: Rolling over retirement benefits into another employer’s plan or an IRA allows employees to maintain tax-deferred growth. It is crucial to compare fees, investment options, and withdrawal rules before making a decision​(Harvard University Reti…).

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