When is the Best Time to Sell Options?

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Most people make money when the market trends. And we know that market doesn’t trend most of the time. Side-way markets are boring and traders felt devoid of profits. One of the ideas to trade a side-way market is to sell options. WRONG! To me, this is the worst time to sell, unless it is a covered call. Selling options during a quiet market is courting death, and that is why most traders warn against selling options in general.

Let me explain.

3 Main Factors of Option Pricing

Those who are not interested in options are unlikely to have read the article to this point, and if you did, I assume you have some knowledge about options and I am not going to repeat what other sites have been explaining about the basics. I will just go through a truncated explanation.

Time Decay (Theta)

The natural advantage going for the option seller is time decay. All options have an expiry date and the option premium will reduce day by day if other factors are kept constant.

Underlying Price Movement (Delta & Gamma)

Second element of option pricing is commonly known as the intrinsic value, measured by the price difference between the underlying price and strike price. The option will be more expensive when the underlying price is moving closer to the strike price, and the contrary is true.

Volatility (Vega)

Third element is volatility. In a side-way and quiet market, volatility is low and option premium is cheaper, with all other factors being equal. When the underlying price moves wildly, volatility increases and will be priced into the option premium.

Interest rates and dividends are less significant in affecting option premiums. There aren’t dividends for commodity options at all.

When to Sell or Short an Option (and when not to)

When you sell options, you want the option premium to decrease. The best time to sell an option is to counter a trend. Yes, not follow the trend or in a side-way market.

Counter Trend

When an underlying is rising in price, the call options will become more expensive. When the underlying is falling in price, the put options will become more expensive. In addition, the volatility has also increased, leading to higher option premiums. The mantra to successful investing is to buy low and sell high, or sell high and buy low. Hence, shorting (selling) high option premiums is a logical point of entry, and usually counter trend has high option premiums.

(I must clarify that traders may view trends differently because of a time-frame difference. My time-frame of trend is the price direction in the past 1-2 months.)

Trend Following

It is less lucrative to sell a put option when the underlying is rising in price, or sell a call option when the underlying is falling in price. It is mistakenly perceived as safer than a counter trend trade. To me, it is riskier because the option premium is likely to be lower and have the potential to become more expensive when the market changes direction.


Another misconception is selling options during a side-way market. Most traders need price movements to make money. Side-way markets are boring and traders yearn for profits during the quiet times may resort to selling options. This is the most risky time to sell options. This is because options prices are cheap due to low volatility and the option prices would jump when the market starts to move, amounting to losses very quickly.

In essence, sell options when they are expensive, and avoid selling when options are cheap. Wait for the market to make a move and we react. Do not predict and make a move first, because other traders may react against you. Sun Tzu has a wise saying for traders:

“The opportunity to secure ourselves against defeat lies in our own hands, but the opportunity of defeating the enemy is provided by the enemy himself.”

Margin, Margin, Margin

The problem with selling options is that the broker will require you to put up a high margin. And to make things even more complicated, this initial margin is not fixed and will increase correspondingly with the increase in options price. Hence, maintaining sufficient margin in your trading account is of utmost importance. Trade small. You are not trying to make a fortune with selling options. It doesn’t matter whether you are right on your trades, but whether can you survive till the trades are closed. John Maynard Keynes said,

“The market can stay irrational longer than you can stay solvent.”

Cutting Losses

You may not always be right with the counter-trend trades and sometimes, the trend can be stronger than it appears to. Hence, there will be times when the trader must take the loss and close the position. The problem with selling options is that an automated stop loss order cannot be used. It requires manual closing and because of that, it requires much more discipline to overcome the emotions of loss aversion. To me, this is the most risky element of options selling. The first part of Sun Tzu quote is so true, “The opportunity to secure ourselves against defeat lies in our own hands…”

  • Join AFACT (Association for Financial and Commodity Traders), there will be a free course coming out soon for our members.

    • yes Patrick! I wanted to join but until now I have not done it. I will fill up the form and get down to it! can’t wait to network with you guys!

  • Can you elaborate a bit on the time decay (theta)? A book showed an option value of underlying stock ABC having a time decay 0.5. What does it mean compare to another option having time decay 5? How can one compute the eroding values of these option?

    • Time decay of 0.5 means the options would lose $0.50 the next day.
      An option seller prefers to have high time decay.

      I won’t bother calculating but just understand that OTM options decay faster above 30 days to expiry. Time decay slows down for OTM options in the last 30 days.

  • Alvin, do you normally wait for the options you sell to expired worthless or do you actively manage them? Like if it goes negative, you close them. How far into the future do you sell the options?

    • I often close the option positions before they expire, either cut loss or take profit. within 1-2 mths to expiry.

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