Dan Sheridan – Calendars & Double Diagonals

Dan Sheridan – Calendars & Double Diagonals

Trade time, volatility, and structure—not direction.

The Advanced Calendar & Double Diagonal Options Mastery program is a comprehensive, multi-class training designed for traders who want to move beyond basic option spreads and into professional-grade, volatility-driven strategies.

Across eight in-depth classes, this program breaks down how calendars, double diagonals, and related structures actually behave in live markets. Instead of theory-only explanations, each class blends whiteboard instruction, Greeks analysis, live trade placement, and real adjustments based on evolving conditions.

This course is built for traders who want consistency, controlled risk, and flexibility—especially in index and high-liquidity options markets.

What You’ll Learn Throughout the Program

You’ll develop a deep understanding of how time decay, volatility, and structure interact—allowing you to trade with logic instead of hope.

Key outcomes include:

Confident construction of calendar and double diagonal spreads

Clear understanding of how Greeks impact profit and risk

Structured adjustment rules for adverse market moves

Volatility-based entry timing using VIX and ATR

Strategic exits based on probability and capital preservation

Class-by-Class Breakdown
Class 1 – Foundations of Calendars & Double Diagonals

You begin with a clear breakdown of how calendar spreads, double calendars, butterflies, and double diagonals function. The class focuses on comparing structures and understanding why double diagonals act as a powerful alternative to iron condors. Real class trades demonstrate fast profit capture and disciplined exits.

Class 2 – Greeks, Duration, and Trade Selection

This session dives deep into the Greeks as they relate to calendars and double diagonals. You’ll learn how duration impacts risk, how to choose between 7–10 day and 30–60 day calendars, and how to structure trades using real option chains. Risk management rules and adjustment logic are emphasized throughout.

Class 3 – Advanced Adjustments & Volatility Scenarios

You’ll explore double calendars in both short- and longer-term formats, learn how to convert a double calendar into a triple calendar, and understand how to trade calendars when volatility is elevated. The session also introduces reverse calendars and includes live double diagonal execution.

Class 4 – The 9-Day Calendar Strategy

This class focuses on short-duration calendar trading. You’ll learn when short-term calendars outperform, how to compare Greeks across expirations, and how to use ATR and standard deviation to determine trade viability. Adjustment strategies, exit decisions, and nuanced execution rules are covered in detail.

Class 5 – Short-Term Double Diagonals & Ratio Calendars

Here, the focus shifts to aggressive but controlled strategies like 7-day double diagonals and neutral ratio calendars. You’ll see multiple contract sizing examples, wider structures, and live executions. This class emphasizes flexibility and scaling based on account size and risk tolerance.

Class 6 – Double Diagonal Mastery

This session is a full deep dive into double diagonals—why they work, how they profit, and when they fail. You’ll learn strike selection, volatility timing, profit targets, and adjustment pathways. Live trade examples reinforce how to manage positions under real market pressure.

Class 7 – Tactical Calendar Variations

This class introduces guerilla calendars, campaign-style calendars, and bearish calendar strategies. You’ll learn when to deploy each structure, how to manage them over time, and how to align calendars with broader market bias. A live equity calendar trade demonstrates tactical execution.

Class 8 – Portfolio Construction & Strategy Integration

The final class ties everything together. You’ll learn how to allocate capital across calendars and double diagonals within a defined portfolio size. The session also demonstrates how iron condors can be transitioned into double diagonals, creating a more adaptive, volatility-responsive structure.

Why This Program Stands Out

Most options courses focus on single strategies in isolation. This program teaches you how structures evolve, how trades are adjusted rather than abandoned, and how volatility can be exploited instead of feared.

By combining:

Multiple durations

Live trade execution

Real adjustment decisions

Portfolio-level thinking

You gain a professional framework for trading options with discipline and repeatability.

Who This Course Is For

This program is ideal for:

Intermediate options traders ready for advanced structures

Income traders seeking non-directional strategies

Traders who want defined risk with flexible adjustments

Professionals trading indexes like SPX and RUT

Anyone serious about mastering volatility-based options trading

If your goal is to trade options with structure, logic, and control, this advanced calendar and double diagonal course delivers a complete, real-world education.