Although I have been known to analyze my losing trades like a crime scene investigation, I tend not to do this with my profitable trades. There can be be gold in analyzing winning trades, especially when things did not go as planned. There may be refinements or positive changes to my system that may be gleaned from this analysis. Below I analyze four option trades that were either closed out at a profit or are currently profitable.
A few weeks ago, I decided to buy a short term ES put calendar spread well below the current market earlier that week with the front option expiring that Friday and the back option expiring the following Monday. The basis for the trade was my expectation for a significant market decline and increase in volatility. On the second day, ES rallied 2%, but my calendar spread actually appreciated a bit. The next day, with ES market action basically a non factor, I closed out this calendar spread at nearly double what I paid for it. So I made a very bad directional call and still made money. Good money. I am now picturing in my mind that new dart board! It turns out I was a beneficiary of changes in term structure, where the very soon to expire front contract saw a major decline in implied volatility versus the next expiration series. The beauty of being aware of implied volatility term structure is that it may be useful as a sentiment indicator as well as a tool for finding trades with unusually favorable risk to reward and profitability percentage metrics.
I am currently long the ES 2675 Dec 17, 2018 put, short the ES 2675 Dec 14, 2018 put calendar spread from the beginning of this week at a debit of 2.65. In contrast to my prior calendar spread, the market moved favorably, but the results so far are only similar to my prior calendar trade. The overall small decline in volatility has been a negative, as normal with this type of trade, of course. I will may close this position tomorrow regardless of what the market does. If the market rallys, this spread becomes more profitable, but any deviations from being near the strike price are negative. If the market declines, the value of my long option decreases and the chance of favorable prices near expiration go down. The key again seems to be term structure. The volatility margin between Friday's option expiration on Monday's is still inverted and about unchanged if not even less favorable to my position. I must note however, that Friday's option series goes bye bye in two trading sessions, potentially leaving me with a put with a very low basis to hold over the weekend. My takeaway is that trader confidence is not high right now. I am not ready to use this term structure "indicator" as a contrarian signal right now because of other multiple market negatives. Although the US economy is still very strong, I may have read somewhere the market has been known to discount the future. I plan to use this latest correction as an opportunity to go short, possibly with a put purchase or keeping the long put of my calendar spread over the weekend after the front option expires.
The last two days, I have traded hedged straddles on ES and SPY. Although both trades were modestly profitable, I definately feel like a bull in a china shop. With the ES straddle I hedged my accumulated deltas using spy. The ES straddle was based on options that expired next day, and it was bit of a challenge keeping up with the rapidly changing deltas due to high, near expiration related gamma. Today, I traded a spy straddle with options that expired today. I chose SPY for Its lower notational value as a risk mitigation strategy for anticipated crazy expiration related delta swings. I need to reorganize and streamline my workflow to accomodate the particular needs of this type of trading. In addition, I really need to review my hedging strategy. On the prior trades, I managed my deltas at about the 20 level and in 10 point increments at times. I am missing a ton of positive expectation by mechanically hedging accumulated deltas. Therefore, I will give my straddle hedging strategy 20 delta of descretion for now. As I gain more experience, I will increase my descretionary amounts.