The cycle
- Sell a cash-secured put at a strike where you would be happy to own the shares. Collect the premium.
- If it expires worthless, repeat. This is the part that produces a steady, unremarkable income.
- If assigned, you own the shares at the strike. Your effective cost is
strike − premium. - Sell a covered call above that cost. If assigned, the shares go and the cycle restarts.
put return = premium ÷ strike
effective cost = strike − premium
full cycle = (call strike − effective cost + call premium) ÷ put strike
The number that matters is the cost basis, not the premium
A $50 put sold for $1.20 gives an effective cost of $48.80. That is the headline on this page for a reason.
The premium makes the shares feel cheaper than they are. What actually happened is that you agreed to buy at $50 and received $1.20 for the agreement — so if the stock is at $44 when assigned, your position is down $4.80 per share on day one, not up $1.20. The put premium is real and it is small relative to what a genuine decline does.
Judging the wheel by premium collected rather than by cost basis is how a portfolio of "income" positions turns out to be a portfolio of stocks bought above their current price.
The cash nobody counts
A cash-secured put on a $50 strike ties up $5,000 per contract for the duration.
That is the true denominator. A $1.20 premium is 2.4% on that cash over thirty days — roughly 33% annualised if it repeats, which is an attractive number and assumes twelve consecutive uneventful months.
Selling the put on margin instead raises the return by lowering the denominator, and removes the thing that made the position conservative. It is no longer a cash-secured put; it is a naked one with a different name.
Where the wheel stops turning
This is the failure mode, and it is not exotic — it is the normal outcome of a stock that keeps falling.
The stock drops well below your strike. You are assigned at $50 with an effective cost of $48.80, and the shares are now $38. Every call strike with worthwhile premium is below $48.80, so selling one locks in a loss. Selling above your cost collects almost nothing.
The wheel has stopped. You are no longer running a strategy, you are holding a stock and waiting, and the position that was chosen for income is now a directional bet you did not size as one. The calculator warns when the call strike sits below the effective cost, because that is the moment the trade changes character.
The defence is entirely in step one: only sell puts on something you would hold at that price anyway, and size it as if assignment is certain — because eventually it is.