Options Education.
Written from a Live Portfolio.
Every guide here is based on concepts I use in my real-money portfolio. I am a long-term buy-and-hold investor who uses covered calls, cash-secured puts, and LEAPS to enhance my broader investment strategy. These guides explain the mechanics, risks, and decision-making behind the options strategies I actually use.
My Approach
First and foremost, I am a buy-and-hold investor. I use covered calls, cash-secured puts, and LEAPS to enhance my portfolio.
I generally sell options around 0.10 to 0.20 delta, favor shorter expirations, and review earnings and major macroeconomic events before opening positions.
I do not sell naked options or use margin. I also do not believe an option needs to be sold every week simply because capital or shares are available.
Start Here
The Expired Options Strategy: Long-Term Investing and Options Premium
Learn how I combine long-term stock ownership with covered calls, cash-secured puts, and LEAPS while managing more than 100 tickers in a real-money portfolio.
Managing Risk When Selling Options
Learn how I think about position sizing, assignment obligations, multiple simultaneous assignments, event risk, and why I do not use margin.
How to Read an Options Chain: Strike, Premium, and Greeks Explained
The options chain is the dashboard of the derivatives market. Learn what every column means — from the bid/ask spread to open interest, implied volatility, and the Greeks that define your risk.
Options I Sell
Cash-Secured Puts: Premium and Potential Stock Entry
Learn how cash-secured puts work, how I evaluate strikes and expirations, and why I only sell puts on companies I am comfortable owning if assigned.
Covered Calls: Generating Premium on Shares You Own
Learn how covered calls generate premium, why they cap upside, and how I evaluate delta, expiration, and my willingness to sell the underlying shares.
The Wheel Strategy: Cash-Secured Puts and Covered Calls
Learn the mechanics of the wheel, including put assignment, covered calls, call-away risk, and why I do not manage my portfolio as a rigid wheel system.
Rolling Options: Strike, Expiration, and Premium
Learn how rolling closes an existing option and opens a new contract, and how I evaluate strike, expiration, and premium when managing a position.
Long-Term Options
What Are LEAPS Options and How Do They Work?
I began using LEAPS in 2023 as another way to gain long-term exposure to companies I am interested in owning. Learn how I treat them as a trial period towards share ownership.
Poor Man's Covered Call (PMCC)
Learn how a long call diagonal spread uses a longer-dated call and a shorter-dated short call, along with the additional theta, volatility, expiration, and assignment risks involved.
Options Mechanics
Understanding Options Greeks: Delta, Gamma, Theta & Vega
Learn how Delta, Gamma, Theta, Vega, and Rho describe an option’s sensitivity to stock movement, time, implied volatility, and interest rates.
Implied Volatility: Understanding Option Premium
Learn how implied volatility affects option pricing, the difference between IV Rank and IV Percentile, and why elevated premium often reflects elevated risk.
Expired Options publicly documents portfolio performance, options activity, and LEAPS positions from a real-money portfolio.
⚠️ All content on ExpiredOptions is for educational and informational purposes only. Options trading involves substantial risk. Past performance is not a guarantee of future results. This is not financial advice.
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