Wheel Strategy & Options Guides

Practical, plain-English articles for people who sell cash-secured puts and covered calls. Start at the top if you are new, or jump to what you need.

Calculators

Cash-Secured Put Calculator

Collateral, premium income, return on capital, annualized return, breakeven, and max profit. No sign-in.

Covered Call Calculator

Premium yield, annualized return, profit if called away, breakeven, and downside protection from your cost basis.

Wheel Strategy Calculator

Chain a cash-secured put into assignment and covered calls to see the cost-basis reduction and total return.

Start here

The Wheel Strategy Explained

The full cycle — cash-secured puts, assignment, covered calls — with a worked example and the real risks.

Cash-Secured Puts vs. Covered Calls

How the two legs of the wheel differ in risk, capital, and what each one is really betting on.

How to Track Your Wheel Strategy Trades

What to record for each leg so you can see a wheel’s true return instead of disconnected trades.

How to Choose Stocks for the Wheel

A checklist for picking underlyings you can live with owning: liquidity, volatility, fundamentals, and what to avoid.

Common Wheel Strategy Mistakes

The errors that quietly cost wheel traders the most, from oversizing to chasing premium to bad record keeping.

Making decisions

How to Choose Strike Prices and Delta

Using delta, premium, and your own assignment tolerance to pick strikes for puts and calls.

Rolling Options: When and When Not To

What a roll actually does, the main kinds of roll, and the traps that make rolling look better than it is.

Early Assignment and Ex-Dividend Risk

When short options get assigned before expiration, and how dividends change the odds.

Position Sizing for the Wheel

How much capital to commit per ticker, and how cash-secured collateral limits what you can run.

Implied Volatility and Option Premium

Why premium is high or low, what IV rank tells you, and why rich premium is a warning as much as an opportunity.

Running the Wheel in a Down Market

What to do when assigned shares keep falling: calls below basis, patience, rolling, and knowing when to exit.

Returns and taxes

Cost Basis in the Wheel Strategy

How premium lowers what you effectively paid, and why tracking basis differs from tax basis.

Annualized Return on Options Premium

Why 2% in 30 days is not 24% a year, and a calculator for return, breakeven, and annualized yield.

How the Wheel Strategy Is Taxed (US)

How premiums, assignment, and holding periods flow into capital gains, plus wash-sale and covered-call pitfalls.

Comparisons

Compare wheel trackers

OptionsLoop next to a spreadsheet, WheelTracking, WheelTracker, and Option Wheel Tracker. Competitor details are cited, as of October 2026.

OptionsLoop vs a spreadsheet

What stays manual when the wheel lives in Excel or Google Sheets, and what OptionsLoop links for you.

OptionsLoop vs WheelTracking

Price, accounts, export, community, and how each privacy policy treats trade data.

OptionsLoop vs WheelTracker

A synced Google account compared with the local-first tracker at yourwheeltracker.com.

OptionsLoop vs Option Wheel Tracker

A free plan and a Premium subscription compared with a one-time license.

Reference

Options Trading Glossary

Plain-English definitions of the wheel, assignment, rolling, spreads, implied volatility, and theta decay.

For educational purposes only, not financial advice, and not tax or legal advice. Options trading involves substantial risk, including the potential loss of your entire investment. OptionsLoop is a tracking tool, not a broker or investment adviser, and does not recommend specific securities or strategies. Examples use made-up prices for illustration.