WhitmanTrading

How to Trade Options

To trade options, get the appropriate broker approval level, then decide whether you are buying contracts or selling them. Buying risks the premium and needs a move within a deadline; selling collects premium and takes on an obligation whose loss can be much larger.

An option is a contract giving a right, until a date, at a price. That deadline is the whole difference from trading shares, and the second difference — that selling one is a completely different risk from buying one — is why brokers gate access in levels.

Before you start

Approval from your broker, which comes in levels and gates what you can do. Buying is the lowest level; selling uncovered contracts is the highest, and the levels exist for good reasons.

An understanding that every position has a deadline. There is no holding on until it works.

A decision about whether you are buying or selling, because the risk profiles are opposite. One risks a known premium; the other accepts an obligation.

The steps

1. Get the approval level you actually need

A range-bound stretch of price with a defined boundary.
The levels gate what the account can do. Illustrative chart - not real market data.

Buying calls and puts is the first level and enough for most people starting out. Applying for the highest level before you have used the first is asking for permission you cannot yet use well.

2. Learn one position type properly

A slice of price data with a single defined structure.
One structure, understood fully, beats six sampled. Illustrative chart - not real market data.

A long call, or a cash-secured put. One structure, traded until its behaviour is familiar, is worth more than a tour of every spread in the manual.

3. Write the view with a size and a date

A long-horizon price series with a target and a window.
Both halves, every time. Illustrative chart - not real market data.

“It moves 8% within six weeks.” Direction alone is not enough to choose a contract, because the contract needs a strike and an expiry and each comes from one half of that sentence.

4. Check the contract can be traded

A slow-moving stretch of price with participation marked.
Entering is easy; leaving needs a counterparty. Illustrative chart - not real market data.

Open interest and a reasonable spread. On this site’s shared series a round trip on the underlying measures about 2% of the median bar range of 0.493, and an options spread is routinely a multiple of that in percentage terms.

5. Size for the whole premium

The first half of a price series with a fixed commitment.
Defined is not the same as small. Illustrative chart - not real market data.

If you are buying, the maximum loss is everything paid. Defined risk is not small risk, and sizing as though it were is the most common error in the first year.

6. Decide both exits before entering

A section of a price series with two defined exits.
A price to take, and a date to give up. Illustrative chart - not real market data.

The price at which you take the gain and the date at which you accept the view did not happen. Deciding either while holding is deciding under pressure.

7. Close rather than holding to expiry

The first half of a price series with an early exit.
Selling captures the remaining time value. Illustrative chart - not real market data.

Selling the contract keeps whatever time value remains. Letting it expire gives that up and introduces assignment mechanics you did not need.

How to tell it worked

The approval level matches what you actually trade, with nothing unused.

1 position type has been traded at least 10 times before a second was added.

Every contract traded had a spread you checked, rather than assumed.

And both exits were written before entry, in every case.

Three things move the price at once

A candlestick chart annotated with the round-trip cost of a switch.
The spread is charged on entry and exit. Illustrative chart - not real market data.

The underlying moving, time passing, and expected volatility changing. Only the first is the reason most people buy a contract, and the other two act whether or not it cooperates.

A section of a price series drawn without volume context.
And an illiquid contract charges its spread twice. Illustrative chart - not real market data.

Which is why a contract can lose value on a day the underlying rose. Nothing has malfunctioned; two of the three inputs moved against the position while the one you were watching moved for it.

Buying against selling

Buying costs money up front and risks that amount. It needs a move of a certain size within a certain window, and most contracts bought expire worthless — which is the design rather than a failure.

Selling collects money up front and accepts an obligation. The gain is capped at the premium and the exposure below it is substantial, so the arithmetic is a long run of small wins and an occasional large loss.

Neither is safer in general. The buyer knows their maximum loss on day one and pays for that certainty; the seller has a higher proportion of winning trades and a worse tail. Which suits you is a question about what you can hold through.

What the approval levels actually gate

The first level is buying calls and puts, and covered positions against shares you own. Every loss is bounded by something you already have.

The middle levels add spreads, where one contract’s risk is offset by another’s. The maximum loss is still defined, and it is defined by the structure rather than by the premium alone.

The highest level is selling uncovered contracts. Nothing offsets the obligation, and the loss on a sold call has no natural ceiling in the same way a short share position does not.

The levels are a genuine safeguard rather than an obstacle. They stop an account taking on an open-ended obligation before it has demonstrated it understands a bounded one, and applying for the top level early removes a protection you have not yet earned the ability to do without.

The original data

Of the 24,971 unique videos in research/search-study-corpus.jsonl, 279 mention options trading in the title, at a median of 19,999 views across 189 channels, and 57% of those titles are instruction-shaped. Calls appear in 13 at 77,171, puts in 23 at 56,794 and the chain itself in 3 at 1,440. The counts come from site/corpus_count.py.

A candlestick series with several gaps, the largest of them marked.
A gap reprices every contract at once. Illustrative chart - not real market data.

279 videos on options trading and 3 on reading the chain. The strategies have a hundred times the coverage of the screen every one of them is placed from, which is the consistent shape of this corpus and the reason the mechanics pages on this site exist.

A stretch of price bars cut short at a decision point.
A far strike costs almost nothing. Buy 20? Illustrative chart - not real market data.

The answer to the question on that chart is that cheap encodes unlikely. The price is set by people with better models than a chain screenshot — and buying twenty changes the shape of the outcome rather than its expectation, with most of them expiring worthless by design.

When it fails

The failure is the first year spent sampling structures, and it produces no learning at all. A long call one week, a spread the next, a condor after that. Each is entered before the previous one’s behaviour was understood, so nothing accumulates. Twelve months later there are fifty trades, no pattern in them, and no answer to the question of which structure suits the person trading it — because the sample size for every individual one is three.

The second failure is sizing as though defined means small. It is the whole premium.

A third is direction without a deadline. The contract needs both.

A fourth is an illiquid contract. You can enter and not leave.

A fifth is holding to expiry. The remaining time value is given away.

And a sixth is seeking the highest approval level first. The levels exist for a reason.

Options covers what the contracts actually are. Options expiry is the deadline that makes them different. And strike price is the other half of every contract’s definition.

What I actually do

The deadline is what makes options different from everything else, and it is the thing most people underweight. A share can be held until the view works. A contract cannot — being right about direction and wrong about timing produces exactly the same outcome as being wrong.

— Michael Whitman

This page is educational, not financial advice. Test every idea on your own charts before risking money.