Conservative option strategies, what did you buy or sell today?

[Kerim]

Thanks! I'm gonna set aside some time tomorrow to dig into this!

[NilesMike]

Building on selling puts on futures contracts; I reviewed 20 years of /ES charts. 240 option expiration cycles- 11 times it dropped 10% or greater and caused assignment. When assigned, 10 times of those 11 the contract became profitable w/in the next option cycle (within 30 days). The one time it didn't was during 2/2020 Covid and likely would have been avoided altogether.

Combining the upward drift built into the stock market, being 10% OTM and using any bit of info about VIX term structure, makes this the safest bet going IMO.

Raw 95.5% winners, after assignment that becomes 1 loser out of 240. 99.6% winners. I can live with that!

[NilesMike]

Update, since 9/20/2022 up 45% on this strategy. That includes a few oops trades.