The FITools methodology

What makes an option worth selling.

The full approach, from the first screen to expiration, laid out so you can judge the method before you judge the tool.

Advice about selling options tends to arrive in two registers: the trading crowd shouting about premium, and the prudent crowd warning you away from the whole category. Neither is much help to an investor who already researches businesses carefully and wants to know whether selling calls against them can be held to the same standard.

What that investor is missing is not enthusiasm or caution but a method: a repeatable way to decide which options are worth selling, at what price, and what deserves attention after the trade is open. This page lays that method out in full. It is the process FITools is built to run, and it works by hand before it works in software.

Why sell options at all

A portfolio's job changes as you near the point of living off it. Through the accumulation years the goal is growth, and the standard advice serves it well. Close to financial independence the need inverts: cash flow starts to matter more than additional gains, and selling shares to raise it defeats the purpose of holding them. Dividends and bonds are the conventional answers. Selling options is the third: early in a career it means selling upside you still need, but near retirement it means selling upside you no longer need in exchange for income you do.

It helps to know who is on the other side. Option buyers are, broadly, two kinds: funds paying to protect large positions, and speculators paying for long shots. The seller writes the insurance and prints the lottery tickets, and the individual seller holds advantages the professionals lack: no clients to calm, no quarterly benchmark to chase, a time horizon measured in years, and access to contracts too small to matter to a fund. You are not competing with the professionals here; you are supplying them.

None of it is free money. The premium is payment for real risk: you still hold the stock through its drops, and you will sometimes watch a capped winner run on without you. This is a long-term discipline, closer to running a small insurance book than to trading, and it suits the investor who can be paid today and judged over years.

Which is why one principle governs everything that follows: take measured risks, and insist on being paid fairly for every one.

The trade itself, plainly

A covered call is a contract sold against shares you already own: the buyer pays you cash now, the premium, for the right to purchase your shares at a set price, the strike, before a set date. If the stock stays under the strike, the contract expires and you keep the shares and the premium. If it rises past the strike, you sell your shares at that price, keeping the premium and the gain up to the strike while giving up the gain above it.

The payment is real in either ending; what has to be earned is the judgment about when that trade-off is worth taking, because the stock can always move against the position. A cash-secured put is the sibling trade, cash paid to you now for the standing willingness to buy a company at a lower price, and the method treats it as its own decision, judged fresh on its own merits, never a step in a loop.

Where this method came from

I spent my first years as an investor certain that options were gambling. I started with The Intelligent Investor in 2003, while working as a patent examiner. Its author, Benjamin Graham, the value-investing mentor Warren Buffett credits for his approach, drew a hard line between investing and speculating, and that line became the foundation for everything I did; options sat squarely on the wrong side of it. I only learned them because work put them in front of me: I had to market Motley Fool Options, and you cannot market what you do not understand. Most of what I saw confirmed the reputation. The exception was covered calls, which jumped out immediately, because they were income from shares I already owned, without selling them. I had been right that most options activity is speculation. What I had missed is that selling premium to speculators, on companies chosen the way Graham taught, is taking the other side of their bet. If I had not been forced to learn, I would still think options were gambling, and most buy-and-hold investors are stuck exactly there.

— Don Lair, FITools

The method, in three decisions

  1. 1

    Screen the business.

    Decide which companies you would own at all, before any option enters the picture.

  2. 2

    Judge the contract.

    Decide whether the premium pays you fairly, against what the trade has to beat.

  3. 3

    Follow the position.

    Decide in advance what deserves your attention, and check for it on a schedule.

Each step is a judgment you make. The tool's job is to make each judgment cheap to repeat across the whole options market.

Step one: screen the business

The method begins where your investing already begins, with the question of what you would own. A covered call puts you on both sides of ownership: if the stock falls, you still hold it, and if it rises past the strike, you part with it. So the only comfortable position is a company you would be glad to keep and content to sell, and no premium is rich enough to make a shaky business meet that bar.

In practice this means running your fundamental criteria before anyone mentions an option: valuation, profitability, growth, balance-sheet health, whatever standard you would apply before buying a share outright. Only the companies that clear it deserve a look at their option chains. FITools runs this step as a screen of twenty-two fundamental filters you set yourself, but the judgment is portable: a watchlist built by hand against the same criteria serves the same method.

Step two: judge the contract

A premium is never good in isolation; it is only good against the alternatives. The same capital could sit in Treasury bills, and the same strategy could run passively on the S&P 500, so a covered call has to be judged on its edge over the higher of those two bars. That comparison is the heart of the scoring math: a contract earns income credit only for what it pays beyond that hurdle, a fat premium that fails to clear it earns nothing, and the bar rises when market volatility runs high, because wilder markets demand a wider margin.

FITools compresses the full judgment into one score with a letter grade, A to F, built from five weighted components:

Component Weight What it measures
Income edge 30% What the premium pays beyond the hurdle for that duration, with diminishing credit as it grows
Assignment safety 20% How far the contract sits from likely assignment: the option's delta, at most a rough proxy for assignment odds, held near a conservative target, plus the cushion between the stock price and the strike
Liquidity 20% Whether you can enter and exit at a fair price: bid-ask spread, open interest, trading volume
Volatility quality 20% Whether the option's implied volatility, the movement the market has priced in, is generous next to how the stock has actually moved, and how stable that pricing has been
Tenor 10% How the expiration fits the method, favoring middle distances around a month and a half out and penalizing the shortest-dated contracts

The score is built to argue against trades, too: named warning flags ride with every result, calling out premiums that fail the hurdle, thin edges, wide spreads, short expirations, and implied volatility running below what the stock has actually been doing. When volatility data is missing, that component scores below neutral rather than assuming the best. And every result shows its work: the component scores, their weights, and a written rationale for the grade.

In the app, these five components surface regrouped into four labeled panels, Vol Edge, Protection & Return, Time Decay, and Liquidity, each with its own subscore; the arithmetic above is the engine underneath them. The grade ranks candidates; it does not make the decision. Whether you want to own more or less of a company this month is a judgment no score can hold, and it stays with you.

Step three: follow the position

Selling the call is the middle of the trade, not the end. The method's third decision is made in advance: name the conditions that deserve your attention, then check for them on a schedule instead of by mood. FITools evaluates every open position against its rules on a five-minute cycle. The rules, and when each one fires:

Profit target
fires when the position has captured your chosen share of the premium, the signal that most of the trade's value is already banked.
Expiration window
fires when the position enters its final stretch, where time decay does its fastest work.
Expiration floor
fires when days to expiration drop below your minimum.
Breakeven approach
fires when the stock price closes in on your breakeven.
Strike crossing
fires when the stock moves into the money, the zone where assignment becomes live.
Stop loss
fires when the position's loss crosses your limit.
Earnings ahead
fires when an earnings date lands before expiration, the event risk the screen let you avoid up front.
Dividend assignment risk
fires when the option's remaining time value falls below a pending dividend, the point where early assignment becomes economically rational for the buyer.

Alerts carry three severities, from informational to urgent, with per-rule cooldowns so a persistent condition does not become noise. When market data goes stale, urgent alerts wait for fresh quotes rather than firing on old ones.

The rules keep watch; the decisions they set up remain yours. A decay gauge shows how much time value each position has left, and the method's standing preference is to close early: once most of the premium is captured, the remaining pennies rarely pay for the final days, when small stock moves swing the position hardest. When expiration approaches instead, a roll view lays out candidate replacement contracts side by side, scenario by scenario, so rolling is a comparison you make rather than an emergency you improvise.

One trade, run through the method

Take a single trade end to end. You hold 100 shares of a company at $50, and it clears your fundamental screen, so it stays in the field. The option screen surfaces a one-month call at a $52.50 strike paying $0.60. The judgment: $60 collected against $5,000 of stock is 1.2% for that expiration period, the premium clears the hurdle for that duration, the spread is tight enough to exit, and no earnings report lands before expiration. The contract grades well, and you decide this is a company you would be content to sell at $52.50. You sell the call and log the position.

For a month the rules watch it. Three weeks in, the stock has drifted to $51, the option has decayed until most of the premium is captured, and the profit-target rule fires; you close for a few cents, bank most of the $60, and are free to shop the whole market again rather than sweating the final week. Run differently, the stock jumps to $54 and the strike-crossing rule fires instead, and you choose between rolling and letting the shares go at $52.50, keeping the premium and the gain up to the strike while giving up the rest. Every number in that story is arithmetic you can re-run, and none of it says anything about what any portfolio will earn.

Where the method bends

Selling premium puts the odds on your side the way an insurer's book does, and insurers still pay claims. Some positions will be assigned. Some months the market will not pay fairly for any risk you are willing to take, and the correct trade will be none at all. The method's discipline is refusing to lower the bar in those months, which is easier to say than to do: the expiration clock gives options an urgency stocks never have, and that urgency amplifies every behavioral bias you brought with you. A method you can inspect, and rules you set while calm, are how you keep your own temperament from becoming the biggest risk in the book.

None of this requires software. If you are new to covered calls, the better first step is the free FITools handbook, and a few trades run by hand in a spreadsheet; the friction teaches you what the premium is paying for. FITools exists for the point where you understand the problem, and the manual process is what stands between you and running the method across the whole market.

That is the method, start to finish.

If the approach holds up to your judgment, the remaining question is whether it fits you: your holdings, your experience, and what the work is worth. The next page asks that question plainly.

See whether this is for you

Prefer to learn the strategy first? Start with the free FITools handbook

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