“When should I sell my stock options?” you might ask. We’ll answer that in this post and discuss some relevant information while we’re on the topic.
Our talking points include:
- Stock options meaning
- Selling stock options tax
- What are the risks of holding stock options long term?
- Can we hold stock options till expiry?
- Are stock options transferable?
- How to sell stock options
If you are looking to invest as an expat or high-net-worth individual, which is what I specialize in, you can email me (advice@adamfayed.com) or WhatsApp (+44-7393-450-837).
Seeking counsel from an expert might help you resolve your individual questions, some of which we’ll cover here, if you’re not sure when to sell your stock options.
Stock options meaning
Investors can bet on or protect themselves against changes in stock prices with the use of these flexible financial tools called stock options.
Companies frequently adopt stock-based remuneration, which gives employees equity ownership as a means of retention and incentive.
The right to purchase or sell a specific quantity of shares in the business at a fixed price is granted to the holder.
When should I sell my stock options?
Different considerations ought to be kept in mind when thinking about selling options.
The tax implications of holding restricted stock units, qualified stock options, or incentive stock options might vary depending on the kind of options and how long you’ve got them.
You can benefit from a reduced long-term CGT rate if you hold stocks for a minimum of one year before selling them. It’s crucial to understand trading windows and blackout periods, which are times when you are not allowed to sell.
Financial objectives are still another important consideration. Depending on your priorities, you may require the money for retirement plans or for immediate needs. If you own a lot of stock in the business you work for, selling options can diversify your basket.
The standing of your firm also matters. You will have to bear the risk of keeping illiquid stocks and pay personally to execute the options if your company is private. It may be possible for you to meet the holding time requirements for advantageous tax treatment by exercising ISOs just prior to an initial public offering.
In terms of option value, you should only exercise your options when the strike price is less than the going rate. Retaining options extends the period the share price can climb, but there’s a chance they could expire worth nothing.
It is essential to keep an eye on stock pricing. Gains can be locked in or more losses can be avoided by selling the stock when it reaches a certain price. You might also decide to drop weaker holdings in response to unfavorable corporate news or general market developments.
The ideal moment to sell ultimately relies on your targets, financial status, and perception of the business.
Selling stock options tax
The tax treatment of stock option sales varies depending on whether the gain is capital or ordinary income.
The gain from exercising is taxable as regular income for Non-Qualified Stock Options. In addition, the gain is subject to ordinary income tax if you sell the shares during the holding period.
If you sell Incentive Stock Options within the holding period, the gain is subject to ordinary income taxation. Long-term capital gains are taxed on gains made on shares held for a longer period. Gains from the sale of NQSOs after a year are considered long-term capital gains.
The wash sale rules, which prohibit losses if you purchase an equivalent option within 30 days of selling, are additional considerations.
What are the risks of holding stock options long term?
Holding onto your stock options for too long can lead to several disadvantages.
First off, if exercise is postponed, the final tax burden may be greater. The ordinary income tax rates on your gains from Incentive Stock Options are often lower than the long-term capital gains rates. This is because you will not be able to keep your shares for the required 24 months after the award date or for more than 12 months after the exercising of your option.
The difference between the strike price and market price of non-qualified stock options is subject to ordinary income tax at the time of exercise; capital gains tax implications are not realized until the option is eventually sold.
Additionally, delaying exercise could mean that you lose out on possibilities. A lot of employers only provide a short window for exercise, usually 90 days after termination of employment. If the options are not exercised within this window of time, you run the risk of losing all of your equity.
A further risk is an excessive concentration of corporate stock. Concentration risk arises when you own a sizable percentage of your net worth in a single stock. You can experience a sizable loss of wealth if the stock’s value drops.
Moreover, you lose out on chances to distribute risk across other investments if you hang onto your options without expanding your investments. You can receive less than ideal investment returns if you don’t sell or exercise and sell shares.
Can we hold stock options till expiry?
Options will expire worthless and you will lose the entire premium amount if you stick onto them until expiration without selling or exercising them.
Should your options be left unmanaged, there’s also a chance of automatic exercise. In the event that you do not have the money to make the acquisition, you can find yourself in an undesired stock position.
You also run a higher risk overnight and over the weekends if you retain options until expiration because the market has less liquidity.
If you believe that the underlying stock will see a large price gain, holding your options until expiration may maximize your upside.
If you have a long-term bullish forecast for the underlying stock, you can use long-term options with more than 12 months till expiration as a tactical play.
Are stock options transferable?
Depending on what kind of options are held, there are certain issues when transferring stock options. It is usually not possible to transfer Incentive Stock Options (ISOs) while the optionee is still alive; transfers of ISOs are only permitted when the optionee passes away.
Subject to the conditions specified in the stock option plan and agreement, transferability of NQSOs may be permitted. Nevertheless, transfers—even for NQSOs—are frequently limited to certain family members or trusts and frequently need board permission.
How to sell stock options
As far as the mechanics of options trading are concerned, option holders primarily employ two tactics. First off, by exercising the option, the holder can profit from any rise in the stock price past the strike price by buying the underlying shares and selling them right away on the open market.
So as to profit from the option’s current market value without having to purchase the underlying shares, holders may also sell the option contract itself to a different bidder on the options exchange prior to expiry.
In general, selling options involves risks, which sellers need to successfully manage. Unfavorable market fluctuations might result in losses if there is no clear exit strategy or safeguard in place.
To leverage option premiums while limiting risk, traders sometimes use techniques like combining long and short contracts with different strike prices and expiration dates. This strategy, which functions as a tactical hedge in unpredictable markets, entails simultaneously acquiring and offloading options to maximize profits and protect against prospective losses.
You need to set up an account with a brokerage business before you start trading options. In this process, you will have to provide personal financial data, describe your trading history, choose the options you want to trade, and indicate your investing targets.
This fundamental step guarantees that traders are ready and able to successfully negotiate the intricacies of the options markets.
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Adam is an internationally recognised author on financial matters, with over 760.2 million answer views on Quora.com, a widely sold book on Amazon, and a contributor on Forbes.
