In my primer, Selling Options...Simply Called and Simply Put, I insist that my strategy eliminates the need for guesswork. All I need to do is select an expiration - I use monthly options; & a strike price that's attractive to me - a strike price at which I don't mind a put or call assignment. I.e., I'm amenable to being put-assigned to buy or call-assigned to sell at my strike price. Of course, the premium that I receive for selling the put or call must be attractive compensation for my obligation to buy or sell the underlying. I have no need to guess the future direction of the underlying's price (I even admit that I'm not good at doing so).
- through the roof.
- up modestly.
- flat.
- down modestly.
- into the tank.
If the market for my ETF goes through the roof, my option selling strategy will do very well, but not as well as buy & hold. If the market goes into the tank, I'll also lose, but not as much. But if the ETF's market is flat, or up or down modestly, option selling is often a real winner.
No need to guess? I sell the put or call & often hope for 3 outcomes: up or down modestly, or flat. But if the underlying goes through-the-roof, even though I do very well, I am often disappointed to leave money on the table - to not get it all! And if the underlying tanks, even though I lose less, I'm often disappointed about the loss! That's when, at times, I apply a repair strategy (a roll strategy). It's my sometimes-mistaken effort to out-guess the market.
On 12/23/19, I began using XLE - the energy ETF - exclusively in my sell puts, then calls strategy. Starting with $467K. In almost all of the 19 months through 7/16/21, my option selling strategy's performance compared as expected versus a buy & hold performance vis-a-vis the 5 market outcomes above. But my overall 19 month option selling strategy dismally under-performed buy & hold. During this 19 month period, XLE dropped 13%, from $61.67 to $53.65 (including the $4.97 in divs). My option selling strategy lost 18%, down to $382K! I would have expected a single digit loss.
Although I had some successful repair strategies, I made 2 critical errors using them. In March, 2020, I repaired my strike price from $32 to $26, when XLE was around $23. I guessed that XLE would stay (COVID-) weak, but it moved to nearly $34. In March, 2021, I repaired from $47 to $55, when XLE was around $53. I guessed that XLE would remain strong, but it dropped to around $49.
The March, 2020 error cost me $41K & the March, 2021 error cost $21K! Without these mistakes, my 7/16/21 value would have been $444K, down only 5% & in line with my expectation.
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