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Is wheeling worth it?

S
Apr 25, 2026 · 19:08

I have been doing wheeling for some time but feels like not worth the time and work.

Also it is difficult to select good and stable stocks to wheel on. I have been doing telecommunications stocks like AMT, VZ, comcast and Chtr but was burned by chtr and “riskier” stocks like robinhood and other LETFs.

How do you really know the stocks you selected won’t suffer from declining business and therefore declining stock price?

If the stock you selected is volatile enough you might as well just buy on dip or do some swing trading.

Usually stocks with higher Iv come with higher risks, stocks that are more stable has less IV.

Wheeling also takes significant effort up to like 10x work vs just buy the dip and hold. It is also difficult to truly master the skills and understand the technicalities / nuances of options. There are just too many variables. Know when to cut when to accept assignment when to roll. Just too much skills to learn

It is difficult to execute wheeling in practice.

If you decide to roll, you may end up with multiple open positions over some time and you need to keep track of them and manage them. It’s too much cognitive load. Often the rolled positions may get worse over time, ie the loss becomes greater. And when you decide to cut loss, you basically undo a few weeks of gains

When a stock crashes down hard you cannot sell CCs as your cost basis is way out. If you do sell CCs below your cost basis then you risk selling the stock at a loss when it gets called away or missing out on gains when the stock rebound strongly. There are couple of times I missed out gains when the price shot up above my CCs. The opportunity cost is significant enough to be several weeks worth of wheeling premiums.

If you sell CSPs, you may end up buying a stock at a much higher price.

The risk and reward ratio is like picking pennies while potentially losing thousands.

I think wheeling only makes sense for a stock that is on the uptrend or sideways, otherwise can easily wipe away your gains .

Has anyone compared the returns of wheeling vs buy&hold / buy on dips or DCA?