I decided to create this thread as a more focused variation of the Option Trading and Advice thread, with that focus on the option strategy known as The Wheel. The thing to understand up front - I'm not a financial advisor, nor am I particularly expert in options trading. So far my experience is almost completely in the options selling side. My forays into option buying either ended in large losses, or are currently losing (index puts). But the option selling has worked great for me! My first and strongest recommendation - if you're new to options trading, or haven't studied it systematically, then I commend the training here: Free Options Trading Course from Option Alpha | Option Alpha This took me about 30 hours to go through all of it (1.25x speed worked great for me). And I urge you not to skimp. This is both general option trading education, along with education about a particular option trading strategy (selling volatility). You're going through that material for the general education, and you'll pick up information about that particular strategy at the same time (it happens to make use of the same edge in the market as The Wheel). From here on, I'm assuming the level of knowledge conveyed in that linked education.