Sixteen rules. Follow them and the strategy almost doesn't matter; break them and the strategy can't save you. Every rule below is a guardrail against the same enemy: your own discretion.
IV Rank above 50 is the green light for selling premium; 80+ is extreme and pays the richest. When IV Rank is low, you're selling cheap insurance — reduce size, sell further out in time, or step aside.
45 days to expiration is the standard entry. Nuance for precision: consider 60 DTE when IV Rank is below 30 and 30 DTE when IV Rank is above 30 — higher IV lets you enter closer and still get paid.
Strikes around 16 delta carry roughly a 16% chance of finishing in the money — the market's one-standard-deviation boundary. This is where probability and premium balance best for systematic sellers.
Buy the position back for half the credit you received. Exceptions: ratio spreads at 30%, butterflies and diagonals at 25%. Taking profit early is what converts a good win rate into a great one.
Never hold short premium inside 21 days to expiration. Gamma risk accelerates near expiry; the last few dollars of premium aren't worth the tail risk. Close it or roll it out.
Undefined-risk trades: 3–7% of net liquidation value each. Defined-risk trades: 1–3% each. Position sizing is the single biggest determinant of survival — more on that in Mistakes Futures.
No more than 15% of net liq in any single underlying. One ticker going wrong should be an annoyance, never an event.
Maximum buying-power allocation rises with fear — but it's a ceiling, not a target:
| VIX level | Max buying-power used |
|---|---|
| 10 – 15 | 25% |
| 15 – 20 | 30% |
| 20 – 30 | 35% |
| 30 – 40 | 40% |
| 40+ | 50% |
Allocate roughly 75% of options buying power to undefined-risk strategies (strangles, naked puts) and 25% to defined-risk (condors, spreads). The undefined side earns more; the defined side keeps the book balanced.
Do not hold short premium through earnings or other binary events. The tail is asymmetric — most earnings moves land inside the expected move, but the ones that don't can erase months of premium.
Tight bid/ask spreads are non-negotiable. Wide spreads are a hidden tax on every entry, exit, and roll — they quietly destroy the edge that the whole system is built on.
The wings are the management. Let defined-risk losers ride to the 21-DTE exit. For undefined-risk losers, roll — the untested side closer, or the whole position out in time. Use time-based exits, not P/L stops.
Beta-weight your deltas to SPY and keep the book roughly neutral. Diversify across sectors and expiration cycles — but remember that in volatility spikes, correlations run toward 1.0, so watch gamma and stress scenarios too.
Take profits when they're offered and extend duration when you're in the trade. A small edge repeated hundreds of times is a business; a small edge traded twice a year is a lottery ticket.
Judge trades by probability of profit, return on capital, and cost-basis reduction — not by headlines, narratives, or how you feel about a company. Strategy and duration beat direction.
Naked positions' margin requirements can more than double under stress (worst case ~3.6×). Size for the stressed margin, not the entry margin — or a volatility spike will size you out at the worst moment.
The books and desk gear behind this site. No courses for sale here — just the tools.
The options bible. Natenberg explains volatility, pricing models, and how market makers actually think — from basic spreads to advanced volatility trading. If you only read one book on options, this is it. Dense but readable, and every serious trader I know has a worn copy.
See it on Amazon →
The encyclopedia of options strategies. McMillan documents every spread, hedge, and combination in exhaustive detail with real-world examples and risk graphs. It's the reference you reach for when building or dissecting any position. Not a cover-to-cover read — a lifetime desk companion for strategy builders.
See it on Amazon →
The Greeks, finally made practical. Passarelli translates delta, gamma, theta, and vega from textbook math into trading decisions — when to be long gamma, how theta really decays, what vega means for your P/L. The perfect companion to this site's Greeks page, written by a former market maker.
See it on Amazon →Ultrawide monitor, mechanical keyboard, a chair you can sit in for six hours — the unglamorous edge.
See desk gear on Amazon →Affiliate disclosure: links above are Amazon affiliate links. As an Amazon Associate I earn from qualifying purchases — it costs you nothing and keeps this site free.
Weekly: one options trade idea with the math, one casino truth, one comp-cruise deal. Free forever. Unsubscribe anytime.