The 7 Options Trading Books That Will Actually Make You Money Trading Options

Look, I'll cut straight to the point. Most options "education" out there is garbage. YouTube gurus selling courses, Twitter traders hawking alerts, "options millionaire" webinars—it's all noise.

If you want to actually make money trading options (and keep it), you need to understand the math, psychology, and market mechanics behind these instruments. That means reading books. Real books. Written by people who've made real money over real time periods.

Here are the seven books that separate profitable options traders from premium donors.

The Foundation: Start Here or Don't Start at All

"Options as a Strategic Investment" by Lawrence McMillan

This is the bible. 1,100 pages of everything you need to know about options. McMillan covers every strategy, explains the math behind pricing, and shows you how each approach works in different market conditions.

Yes, it's intimidating. Yes, it's dry in places. But if you only read one options book, make it this one. Everything else builds on concepts McMillan explains here.

Best for: Anyone serious about options trading. No exceptions.

Understanding Volatility (AKA The Only Thing That Matters)

"Option Volatility and Pricing" by Sheldon Natenberg

Once you understand basic options mechanics, volatility becomes everything. Natenberg wrote the definitive guide on trading volatility rather than direction.

This book transforms you from someone who buys calls because "the stock will go up" to someone who understands implied vs. realized volatility relationships. Game changer.

Key insight: Options are volatility instruments that happen to have directional exposure, not directional instruments that happen to be volatile.

Risk Management (Or Why Most Traders Fail)

"Trading Options Greeks" by Dan Passarelli

Delta, Gamma, Theta, Vega—these aren't just abstract concepts. They're risk management tools that determine whether you make or lose money.

Passarelli explains how to use Greeks for position sizing, when to adjust trades, and how to hedge portfolio-level risk. Most importantly, he shows you how Greeks change as markets move.

Reality check: If you don't understand Greeks, you're gambling, not trading.

The Psychology of Winning

"Market Wizards" by Jack Schwager

Options trading is 20% strategy, 80% psychology. Schwager's interviews with legendary traders reveal the mental framework required for long-term success.

Several profiled traders made fortunes through options strategies. Their insights about risk management, position sizing, and maintaining discipline apply directly to options trading.

Money quote: "The key to trading success is emotional discipline. If intelligence were the key, there would be a lot more people making money trading." - Victor Sperandeo

Option Premium Selling Strategies That Actually Work

"The Complete Guide to Option Selling" by James Cordier and Michael Gross

Most options education focuses on buying options. Most professional traders focus on selling them. This book explains why and how.

Cordier and Gross provide systematic approaches to selling puts, calls, strangles, and straddles. More importantly, they explain risk management for premium sellers (spoiler: it's different from buying options).

Warning: The authors later blew up their fund, which actually makes this book more valuable. Learn the strategies, but implement better risk controls.

Strategy Implementation

"The Options Playbook" by Brian Overby

Theory is useless without execution. Overby provides step-by-step instructions for implementing common options strategies, complete with real-world examples and common mistakes.

This book bridges the gap between understanding concepts and placing actual trades. Essential for translating book knowledge into profit.

The Classic on Market Psychology

"Reminiscences of a Stock Operator" by Edwin Lefèvre

Written in 1923, still relevant today. Lefèvre's chronicle of Jesse Livermore's trading career provides timeless lessons about markets, psychology, and risk management.

The principles apply directly to modern options trading: cut losses quickly, let winners run, size positions appropriately, and recognize when you're wrong.

Event-Driven Options Trading: An Advanced Strategy

Books provide excellent foundational knowledge, but there's an advanced strategy that deserves special attention: positioning around specific corporate events rather than relying purely on technical or fundamental analysis.

Modern options success increasingly involves timing positions around catalysts that create volatility opportunities. Corporate earnings, merger announcements, CEO changes, and regulatory decisions often drive the price movements that make options strategies profitable, yet this approach requires systematic monitoring beyond what most traders attempt.

For example, companies announcing earnings results, breakthrough developments, or leadership changes often experience 5-20% stock price movements, creating substantial options profits for those who can capture a majority of the price swing.

LevelFields AI tracks these corporate events across thousands of stocks, providing backtested data on how different event types typically impact stock prices and sending automated alerts when events occur. This systematic approach helps identify when to deploy the strategies you've learned from books and their analytics make is super easy to pick entry and exit points for options trades. Those wanting more education on options trading can sign up for the Level 2 service, where they break down options trade ideas each week.

TradingView offers advanced charting tools and community insights that help time entries around catalyst events, with customizable alerts for technical breakouts that often follow major announcements. Their social platform aggregates trader sentiment and analysis around upcoming events, while their screening tools help identify stocks approaching key catalysts like earnings or product launches.

Benzinga Pro provides real-time news feeds, earnings calendars, and audio squawk services for catching breaking announcements as they develop. Their platform excels at delivering the immediate notification needed for event-driven strategies, with customizable alerts for specific companies or event types that can trigger options opportunities within minutes of announcements.

This systematic approach to catalyst identification often separates consistently profitable options traders from those who rely solely on technical analysis or hope to time markets perfectly.

Your Options Education Roadmap

Here are the rundown of education roadmap:

Months 1-2: Foundation Building

Read "Options as a Strategic Investment" cover to cover. Don't skip sections. Take notes. This is your options university.

Months 3-4: Volatility and Risk

Study "Option Volatility and Pricing" and "Trading Options Greeks" simultaneously. Practice calculating theoretical values and Greeks for real positions.

Months 5-6: Psychology and Implementation

Read "Market Wizards" for mindset, then "The Options Playbook" for execution. Start paper trading to apply concepts without risk.

Months 7-12: Advanced Strategies

Tackle "The Complete Guide to Option Selling" and "Reminiscences" while beginning live trading with small positions.

Common Reading Mistakes That Cost Money

Mistake #1: Rushing to Advanced Strategies Don't try iron condors before mastering basic calls and puts. Complexity without foundation equals losses.

Mistake #2: Reading Without Practice Books teach concepts. Markets teach reality. Combine reading with paper trading, then small live positions.

Mistake #3: Ignoring Risk Management Chapters Everyone wants to read about profitable strategies. Winners focus on risk management sections.

Mistake #4: Stopping After One Book Options trading requires understanding multiple perspectives. One book gives you one viewpoint.

The Hard Truth About Options Education

Reading these books won't make you profitable overnight. They provide the knowledge foundation required for long-term success, but markets will still humble you regularly.

The difference: educated traders lose money temporarily while learning. Uneducated traders lose money permanently while hoping.

These seven books separate serious options traders from gamblers. They explain the mathematical foundations, psychological requirements, and strategic frameworks necessary for consistent profitability.

Start with McMillan. Everything else builds from there.

But remember: the best options education combines theoretical knowledge with practical experience and systematic opportunity identification. Books teach you how options work. Markets teach you when to use them.