CASE STUDY

Rethinking a $4.1M stock position in retirement

A recently retired investor held a significant portion of investable assets in a single, volatile stock position, creating portfolio concentration risk. A coordinated planning approach evaluated options-based strategies, portfolio diversification, and broader estate and tax considerations. 

Senior man sitting down in his kitchen thinking
Challenge

The client’s portfolio included a substantial holding in a single energy stock that generated dividend income but represented a large concentration of overall wealth. The challenge was balancing risk management, income generation, and future liquidity decisions while considering longer-term tax and estate planning objectives. 

At-a-glance

Client
Recently retired investor in the early stages of retirement
By the numbers
~ $10 million in investable assets, including a $4.1M concentrated stock position evaluated for an options strategy
Constraints

Concentration risk, tax considerations, retirement income needs, estate planning complexity

The plan

Covered call strategy, portfolio balancing, and coordination of tax, estate, and legacy planning

Approach

A coordinated planning team developed an investment and wealth-planning framework designed to address both immediate and long-term considerations. 

Options Strategy  
Implemented a covered call strategy on a portion of the concentrated stock position to generate additional income while managing exposure to a single security. 

Portfolio Balance  
Directed generated income toward a moderate-growth allocation to improve overall portfolio balance. 

Tax-Aware Planning  
Evaluated future liquidity and stock-disposition strategies with attention to tax implications. 

Comprehensive Wealth Planning  
Reviewed estate planning considerations, charitable giving opportunities, stock option planning, and potential Roth conversion strategies. 

Outcome

The client gained a more structured approach to addressing concentration risk while expanding planning discussions beyond investments alone. The process helped create greater visibility into tax, estate, charitable, and retirement-planning considerations, supporting a more coordinated view of long-term financial objectives. 

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This case study is based upon real clients. This content is for illustrative purposes only, may not be representative of any future experience of our clients, and is not intended to provide specific recommendations to any individual. Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year you convert, you must do so before converting to a Roth IRA. The writer of a covered call option forgoes, during the option’s life, the opportunity to profit from increases in the market value of the security covering the call option above the sum of the premium and the strike price of the call but retains the risk of loss should the price of the underlying security decline.