Bought 600 shares near the open as planned and sold 1 call. Tomorrow, most likely sell 5 puts near the open. I see some threads looking for tops, but we are not near a cyclical top. Garden variety 10% corrections can happen at any time, but for a longer term macro trader, they are gifts to be bought. The ingredients are just not there yet for a prolonged or painful 20%+ correction/bear market.
Current fears over the very low volatility and crappy quality IPOs (Lyft lol) are understandable, but they aren't catalysts for a bear market. They are signs of complacency, like umbrellas being really cheap, but it doesn't mean it's about to rain.
I am thinking of trying it from the short side with LYFT.
I have never done the wheel from the short side, but I can't imagine it to be too different, as long as you understand the innate risks of shorting. At least with selling calls, I imagine vol to mostly decrease as prices rise, but these IPOs are so volatile, that probably doesn't hold.
First, do you have a plan to get out or stop trading if SP 500 enters a bear market?
I never predict a bear market per se, just like a poker player doesn't predict what card will come up next. It's all a game of probabilities. If I see risks rising, I respect that by lowering my position sizing. Taking the 2018 Q4 mini bear market as an example, my thesis was that we may have entered a bear market and my model told me to drastically cut back on position sizing by early October (1/3-1/2 the position size). However, I saw a few things that got me bullish on a short term basis so I was holding onto shares, waiting for a pop to sell into that never materialized. By January rolled around, I was so shell-shocked that I sold too many shares near the bottom.
When the smoke cleared, I was down 3% for 2018 and am up only 9% for 2019. A huge part of me wanted me to trade bigger once I got bullish in Feb/Mar to "get back" what I lost in 2018, but I know that's the wrong road to take, even though with hindsight, that was the correct call. This was the reason for the journal: to force me to stay disciplined.
My spreadsheet is manually updated. I only trade a few times per day at most so it's easily done.