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Appraising one position: maximum loss, break-even, cost and what you are really betting on

Before any derivatives trade, write down five numbers. If you cannot fill them in, you are not evaluating a position - you are guessing.

11 min read · Level 5

The point

Most derivatives strategies sold to individuals are ways of trading one risk for another and relabelling the result. Covered calls convert upside into income; protective puts convert a known cost into reduced downside. Both are legitimate. What I would push back on is the framing that either makes money appear from nowhere, because once the five numbers are written down, the trade-off is usually clear and often not worth it.

What is it?

Every derivatives position can be reduced to five numbers:

1 Maximum loss in money, not percentage 2 Break-even the price needed at expiry to lose nothing 3 Total cost premium, spread and commissions 4 Time available days to expiry, and when decay speeds up 5 What must happen the move, by when, for this to work

Two common structures show how the numbers change.

Protective put. You own 100 shares at 100 and buy a put, strike 90, premium 2, costing 200. If the share falls to 70:

Loss on shares -3,000 Put pays (90 - 70) x 100 +2,000 Premium paid -200 Net -1,200

The maximum loss is capped at (100 - 90) x 100 + 200 = 1,200, however far the price falls. If the share never falls, you lose the 200 premium.

Covered call. You own 100 shares at 100 and sell a call, strike 110, premium 2, receiving 200. If the share rises to 130, your gain is capped at (110 - 100) x 100 + 200 = 1,200, compared with 3,000 had you just held. If the share falls to 90, you lose 1,000 on the shares, offset by 200: a loss of 800.

Why does an investor care?

Because derivatives magnify the gap between having a view and having a plan. Most losses come from positions opened on a directional hunch without anyone writing down how much could be lost or what had to happen.

The five numbers also expose trade-offs that sales pitches blur. A protective put is insurance with a cost. A covered call earns income by giving away upside. Neither is free money.

This is educational information, not investment, securities or financial advice. Rules differ by country and change — get advice from a qualified professional in your jurisdiction before acting.

Educational, not personalised financial advice. Nothing in the Investor Academy is a recommendation to buy, sell or hold anything — what is right for you depends on your own circumstances and the rules where you live.

Sources: U.S. SEC - Investor.gov, protecting your investments; FINRA - investor information; UK FCA - information for consumers

Example

An investor considers a protective put on a 20,000 holding of 200 shares at 100.

Put strike 90, premium 2, two contracts Cost 2 x 100 x 2 = 400 Share of holding 400 / 20,000 = 2.0% Days to expiry 90 Maximum loss on the position (10 x 200) + 400 = 2,400

If they rolled similar puts every quarter, the cost would be around 1,600 a year - 8% of the holding - before any payout. The investor concluded that permanent insurance at that price was too expensive, and that reducing the position size would limit risk more cheaply.

The common mistake

Calling a covered call strategy income without counting the upside given away, or treating a protective put as free protection without counting the premium paid every period.

How it works

Step 1: Fill in all five numbers before trading

If any is missing - especially maximum loss - do not open the position.

Step 2: Annualise recurring costs

For insurance-like strategies, multiply the premium by how often you would repeat it and compare to the holding's value.

Step 3: Compare to a simpler alternative

Ask whether holding less of the share, or holding cash, achieves the same risk reduction more cheaply.

Step 4: Set the exit before you enter

Decide the price or date at which you will close the position, and write it down.

When to use this

Before opening, adjusting or rolling any derivatives position.

When not to use it

Do not use the five-number check as a reason to trade. It is a filter that should stop most positions, not a template for making them feel safe.

How investors actually did it

A recurring pattern: covered call funds in strong markets

Funds that systematically sell call options against their holdings have been widely marketed for income. Performance data published by index providers over long periods show such strategies generally lagging the underlying index in strong rising markets, because gains above the strikes were given away, while holding up somewhat better in flat periods.

An income figure from option premiums should always be compared with the upside surrendered to earn it.

Do this now

  • Write the maximum loss in money for every derivative position you hold
  • Annualise the cost of any recurring hedge

Create a free account to read the rest and apply it to your own investing.

Related lessons

  • You pay for intrinsic value, time and uncertainty - and time runs out — An option's price has two parts: what it would be worth if exercised now, and extra value for the time and volatility left. That second part shrinks to zero by expiry. (12 min)
  • Position sizing: how much of it to own — Sizing is where conviction gets converted into consequences, and it is the one variable in investing that is entirely within your control. Most people set it by feel and discover afterwards what they actually decided. (12 min)

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