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Losing Money With Options

A summary of common pitfalls discussed in the book, where losses arise from technical ignorance, errors, and misunderstanding the nuances of options behavior.

1. Directional Trading Pitfalls

Ignoring Implied Volatility

Predicting a price move isn't enough. An adverse shift in implied volatility can crush an option's value, even if your directional bet was correct.

Ignoring Time Decay (Theta)

Options are wasting assets. Failing to account for the daily erosion of value is a fundamental and costly mistake, especially for out-of-the-money options.

Failing to "Speak Greek"

A superficial understanding of option Greeks (like Delta) is insufficient. You must grasp how these sensitivities change with time and volatility for effective risk management.

Ignoring Option-Specific Risks

Theoretical models assume smooth, continuous time. Real-world market mechanics, like opening and closing, can create unexpected outcomes for directional traders.

2. Exercise & Expiration Mistakes

Exercising ITM Options Early

A classic error. This sacrifices the option's remaining extrinsic (time) value. Selling the option is almost always more profitable than exercising it before expiration.

Exercising OTM Options

A "wildly expensive" human error that results in an automatic loss. Requires stringent safety checks to avoid this spectacular disaster.

Not Exercising ITM Options

Throwing away guaranteed profit. This is even worse if the position was delta-hedged, as hedge losses are locked in without the offsetting option gain.

Ignoring Pin Risk

When the underlying closes at the strike price, uncertainty about assignment can leave you with a large, unwanted, and unhedged position over the weekend.

3. Gamma Trading Errors

Not Working a Long Gamma Hedge

Failing to place re-hedging orders misses the opportunity to profit from market moves, especially during sharp reversals.

Putting All Hedge Eggs in One Basket

Using a single, large stop-loss for a hedge is risky. If triggered, it locks in a large loss. Break hedges into smaller orders at multiple levels.

Switch Gamma

Hedging with a correlated but different underlying (e.g., another futures month) can create unwanted synthetic spread positions that move against you.

Selling Gamma, Forgetting the Hedge

If you adjust your gamma exposure but fail to make the corresponding delta-hedge trade in the underlying, you're left with a naked, exposed position.

4. Volatility Trading

Overpaying for Long-Dated Volatility

Overreacting to a short-term volatility spike (like a flash crash) by buying long-dated options locks in an inflated price, leading to losses as volatility inevitably mean-reverts.

5. Option Landmines

Ignoring Corporate Actions

Trading low-risk arbitrage positions (conversions/reversals) without checking for dividends or splits can lead to huge losses as the put-call parity relationship breaks down.

6. Order Entry Errors

"Fat Finger" Mistakes

Simple but costly errors like buying instead of selling, choosing the wrong expiration, or trading the wrong underlying are common and avoidable.

The Devastating Error

Selling a deep in-the-money option for a minimal price (e.g., 1 tick) on an exchange without mistrade protection. This is like giving away a winning lottery ticket. Always know the exchange rules.

How to Prevent These Losses

The path to avoiding these pitfalls is clear and requires a combination of three key pillars:

Technical Knowledge
Alertness & Discipline
Risk Management Systems