As part of the 1000 Days Challenge, I’m documenting not just my trades but also the systematic framework I use. This guide explains the two core strategies that drive my approach — the 2/7 Double Calendar and the 9/23 Double Calendar — and how they work together to create a disciplined, repeatable trading rhythm.
🔹 Why Calendars?
Options calendars let me:
- Harvest theta decay (time premium from short options).
- Limit exposure by pairing shorts with longer-dated longs.
- Stay flexible in volatile markets.
- Build consistency with rules-based entries and exits.
The core idea: sell time that decays faster, while owning protection further out.
🔹 2/7 Double Calendar
When: Mondays & Tuesdays
Setup:
- Sell options expiring in 2 days
- Buy the same strikes expiring in 7 days
Goal:
- Capture short-term theta during the first part of the week.
- Use long legs to smooth out volatility spikes.
Why I Like It:
- Quick exposure, short duration = efficient capital use.
- Works well when managed with automation (delta rail stops, profit targets).
- Creates early-week structure without holding too long.
🔹 9/23 Double Calendar
When: Wednesdays, Thursdays & Fridays
Setup:
- Sell options expiring in 9 days
- Buy the same strikes expiring in 23 days
Goal:
- Extend theta harvesting into later part of the week.
- Reduce “dead days” when no positions are on.
Why I Like It:
- Complements 2/7 DCs by filling in mid/late-week trades.
- Longer shorts = smoother P/L curve.
- Keeps me engaged without forcing trades.
📅 Weekly Trading Rhythm
| Day of Week | Strategy Used | Notes |
|---|---|---|
| Monday | 2/7 Double Calendar | Start of week exposure |
| Tuesday | 2/7 Double Calendar | Reinforces early-week system |
| Wednesday | 9/23 Double Calendar | Midweek trade |
| Thursday | 9/23 Double Calendar | Keeps exposure consistent |
| Friday | 9/23 Double Calendar | End-of-week setup |
✅ Always in the market
✅ Defined entries & exits
✅ No random trades
📊 Risk Management
- Allocation: ~40% for Mon/Tue trades, ~20% for later-week trades.
- Exits:
- Stop if short-leg delta > 0.70
- Take profit ~5–10% (depending on volatility and conditions).
- Overnight vs. Same-Day:
- Hold if events/volatility favor theta decay.
- Flatten if no catalyst and risk of slow grind.
🧠 The Psychology Behind It
Before building this framework, I struggled with:
- Overtrading (feeling like I had to “be in a trade” daily).
- FOMO (adding trades when SPY, IWM, or other setups looked tempting).
- Buying power misuse (pushing to 100%+ and getting margin calls).
Now, the framework gives me:
- Discipline (clear plan, fewer emotional trades).
- Structure (every weekday has a purpose).
- Confidence (knowing trades are backed by backtests).
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📈 Backtesting & Edge
- The 2/7 DC has shown strong results in past Septembers, reinforcing my automation plan.
- The 9/23 DC is newer, but backtesting indicates smoother decay and better fit for midweek.
- I review historical returns by month and track max drawdowns to understand risk.
⚠️ Important: Backtests are models, not guarantees. They show how a system might have performed, but real results can differ.
⚠️ Disclaimer
The information presented in this blog post is for educational and informational purposes only and is not intended as financial or investment advice. I am not a licensed financial advisor. All trading strategies discussed reflect my personal experience and are not recommendations to buy or sell any security or derivative.
Trading financial instruments such as options, futures, or stocks involves significant risk and may not be suitable for all investors. You should conduct your own research, consider your financial situation, and consult with a licensed financial advisor before making any investment decisions.
Past performance is not indicative of future results. Use of this information is at your own risk.