Bear markets can make money quickly – and lose it just as fast. This chapter shows how to trade them properly: when to enter, when to get out, and what to buy to stay on the right side of the move.














Here is the glossary for Chapter 15. Trading the bear is a completely different beast, so let’s cut the fluff and get straight to the new terms:
Bear Market: Not your slow, predictable bull. These drops are short, sharp, and unpredictable.
Christmas / New Year Rule: Stay off the trading floor. Low volume and erratic prices make our signals totally unreliable during the holidays. If you aren’t already in a trade, wait until January.
Exercising Puts: Selling 100 shares at your strike price. Your broker handles the math and the T+1 settlement behind the scenes, so you never actually need a mountain of cash sitting in your account to pull it off.
Intrinsic Value (Puts): Your strike price minus the current stock price. It is that simple.
ITMB IN Signal: Your green light to enter a bear trade. It requires four strict criteria: SPY is officially in a 20% bear market, SPY is below the 100-day SMA, a 5/20 SMA death cross hits, and the MACD histogram is red. No gut calls.
ITMB OUT Signal: A simple 5/20 SMA Golden Cross. It is a highly sensitive, hair-trigger alarm designed to get you out fast and protect your capital the second momentum turns against you.
ITMB Put Selection: The exact contract we buy to short the market. We hunt for a put option with 5 to 6 months until expiry and a strike price roughly 30% above the current SPY price, making sure the time value is firmly under 1%.
Put Option: The exact mirror image of a call option. It gives you the right to sell shares at a fixed price, allowing you to actually profit when the market tanks.
Time Value (Puts): The option premium minus its intrinsic value. Thanks to simple supply and demand, deep in-the-money puts carry almost no time value compared to calls, largely because institutions just use them for boring portfolio insurance rather than risky leverage.
ITMB Execution
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Please note that Heather answers all questions at the end of the ITM Blog.
Happy trading!