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Humana Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Humana is one of the largest health insurance companies in the United States, primarily offering a range of Medicare Advantage plans, individual and family health insurance, and group health plans for employers. As we look towards 2026, healthcare costs are expected to rise significantly, with many experts forecasting increases in health insurance premiums across various states. For Humana, the pressure stems from a confluence of factors including the anticipated expiration of enhanced federal premium subsidies under the Affordable Care Act (ACA) and rising medical costs. The Kaiser Family Foundation projects that without renewed subsidies, a staggering 92% of ACA policyholders could face premium hikes of over 75%, making 2026 one of the most challenging years for consumers navigating their healthcare finances. Factors like escalating hospital and drug costs, aggressive rate increases by insurers, and overall economic conditions contribute to this inflationary trend. Click here to learn more

'Humana 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.

'Humana 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:

How taxes can affect investment returns, particularly on concentrated stock positions.
Exchange funds and options-based strategies as methods for tax deferral and diversification.
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.' Humana 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. Humana 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 Humana 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 Humana 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 Humana 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 Humana 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 Humana 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 Humana 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 is the purpose of Humana's 401(k) Savings Plan?

The purpose of Humana's 401(k) Savings Plan is to help employees save for retirement by allowing them to contribute a portion of their salary to a tax-advantaged account.

How can employees enroll in Humana's 401(k) Savings Plan?

Employees can enroll in Humana's 401(k) Savings Plan through the company’s benefits portal during the open enrollment period or within 30 days of their hire date.

Does Humana offer a matching contribution for its 401(k) Savings Plan?

Yes, Humana provides a matching contribution to the 401(k) Savings Plan, which helps employees boost their retirement savings.

What types of investment options are available in Humana's 401(k) Savings Plan?

Humana's 401(k) Savings Plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles tailored to different risk tolerances.

Can employees change their contribution percentage in Humana's 401(k) Savings Plan?

Yes, employees can change their contribution percentage at any time through Humana’s benefits portal.

What is the minimum contribution required to participate in Humana's 401(k) Savings Plan?

The minimum contribution required to participate in Humana's 401(k) Savings Plan is typically set at 1% of an employee’s salary, but employees can choose to contribute more.

When can employees access their funds in Humana's 401(k) Savings Plan?

Employees can access their funds in Humana's 401(k) Savings Plan upon reaching retirement age, or in cases of financial hardship, as defined by the plan.

Are there any fees associated with Humana's 401(k) Savings Plan?

Yes, there may be administrative fees and investment-related fees associated with Humana's 401(k) Savings Plan, which are outlined in the plan documents.

How does Humana educate employees about the 401(k) Savings Plan?

Humana provides educational resources, including workshops, webinars, and one-on-one consultations, to help employees understand and maximize their 401(k) Savings Plan benefits.

Can employees roll over funds from another retirement account into Humana's 401(k) Savings Plan?

Yes, employees can roll over funds from other qualified retirement accounts into Humana's 401(k) Savings Plan.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Humana provides a defined benefit pension plan and a 401(k) plan with company match.

Humana grants RSUs to its executives and certain employees. RSUs vest over several years, aligning employee interests with the company's long-term goals.