Retired, 450k fun money, lets see what happens - SPY Options

Will I be successful and outperform the S&P 500?


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I am confused; the wheel assumes assignment and instant calling away (weekly options). Are you saying cover the puts before they are exercised? Then it is not the wheel. Otherwise, I see your point. Even in a bear market, stocks can advance to be called away...granted one has to be a decent stock picker.
If one is a decent stock picker, then why do options?
 
To clear things up - my goal is to be invested in the market and get a little premium on the side. If the market tanks, my account will tank with it. I'm bullish on the market and want correlated exposure to it.

My plan with this account is a bit different from the traditional way of running the wheel. I'm going to sell very short term premium at close to the money levels that I would want to enter if the market dipped a little bit. Once that dip happens and I get assigned, I'll sell covered calls where I want to take profits, expecting the market to bounce back up. If the market continues to fall and I can no longer sell covered calls above my strike price, I wait it out. If it doesn't recover right away, I'll be happily sitting on a beach, drinking beer and fishing.



I'm no stranger to markets and managing money. Having a goal of building wealth has always been a personal challenge of mine that I find exciting.
The problem with the wheel strategy is that once assigned, the call premium that you collect will necessarily be reduced from where it would have been had to just started out with a simple strangle.
 
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