I’m looking for some input from people who actively run covered call strategies because I THINK that is my best strategy during sideways/bearish market.
Background on my strategy: Professionally, I’ve spent \~15 years in the transportation industry in senior finance roles, so I’m pretty familiar with how these cycles actually play out—capacity expansion/contraction, pricing lag, broker vs asset dynamics, etc.... I focus on things I understand.
If you are familiar with trucking/transportation, you will understand it's very cyclical and the cycle is typically 18-24 months long. Look at a few transportation stocks: you can see there was a boom in 2017-18; bust in 2019-2020. Boom in 2020 & 2021; bust in 2022-24. We began price appreciation in late 2025 and beginning a boom now in 2026 which I expect to last into 2027 (I have my own internal data I've turned into buy/sell signals based on market conditions). I am long pretty much all major transportation companies (SAIA, JBHT, CSX, XPO, EXPD, RXO, KNX, TFII, FWRD, ARCB). I wish there was a good ETF but IYT has too much airline and uber.
Anyway, later this year or early next I believe the market will flip back to bearish in transportation. What would be the best strategy if I were to hold onto some of the more quality names? I was thinking of buying long term put and selling short term calls over a 12- 18 month period and then buy back into the market. A more concrete back test type of example: for those names above - Sell signal: 10/1/21; Buy signal: 7/1/23