How to maximize after-tax gains from non-qualified stock options

By Sean Lovison, CFP, CPA

Key takeaways:

● Stock choices: Stock choices in government compensation are promising however unstable and might generally expire nugatory.

● Option sorts: The two predominant sorts are non-qualified inventory choices (NQSOs) and incentive inventory choices (ISOs). This article focuses on the extra frequent NQSOs.

● Essential phrases: Understand grant date, strike value, expiration date, train date, vesting schedule, and truthful market worth (FMV).

● NQSO taxation: Tax applies at train; taxable earnings is the distinction between FMV and strike value, taxed at unusual earnings charges. There is also capital good points taxes if the shares are held after train.

● Tax methods: Optimize by timing the train for decrease tax brackets, contemplate market circumstances, money wants, and danger mitigation when deciding to carry or promote inventory.


Stock choices are undoubtedly one of the crucial intriguing and impactful elements of an government compensation bundle however can be essentially the most advanced. These versatile monetary devices possess the potential to considerably speed up the buildup of wealth and safe your monetary future. However, you will need to perceive that inventory choices include inherent variability, as their worth can expertise dramatic fluctuations, starting from a considerable fortune to doubtlessly nothing in any respect.

There are two major sorts of inventory choices: the easier and extra frequent non-qualified inventory choices (NQSOs) and the extra advanced incentive inventory choices (ISOs). While each kinds can yield important returns for his or her holders, ISOs include further tax advantages. However, this text will particularly consider NQSOs and discover the tax methods that may be employed to maximise their wealth-building potential.

Navigating the advanced realm of inventory choices generally is a daunting job, significantly if you’re new to this type of compensation and lack the time to dedicate hours to monetary analysis. Options include their very own distinct terminology and intricacies that require cautious consideration and understanding.

Terms and examples

When an organization grants an worker inventory choices, it’s primarily compensating the worker with the correct to buy shares of the corporate’s inventory at a predetermined value. Here are the listing of the phrases necessary for understanding about choices:

Grant date: The date on which the inventory choices are awarded or granted to the worker. This is the place to begin for figuring out vesting schedules and different circumstances.

Strike value: Sometimes additionally known as the train value, it’s the predetermined value at which the worker should buy the corporate’s inventory when exercising the choice. The strike value is often set beneath the present market value to supply a chance for potential achieve.

Expiration date: The final date on which the worker can train the inventory choices. After this date, the choices develop into invalid, can’t be exercised, and are actually nugatory.

Exercise date: The date on which the worker chooses to train the inventory choices and buy the underlying shares on the strike value.

Vesting schedule: The timeline or circumstances that decide when the inventory choices develop into eligible for train. Vesting schedules could be primarily based on components like tenure with the corporate, achievement of efficiency milestones, or the passage of a particular time frame. Since most fairness compensation instruments, together with choices, are topic to vesting, a separate vesting article has been created and located right here to keep away from being overly repetitive. Please confer with that part if you need extra info on vesting together with an instance of how a number of years of vesting can construct on one another.

Fair market worth: The present market value of the corporate’s inventory at a given cut-off date. The FMV is used to find out the unfold or the distinction between the strike value and the market value, which influences the taxable earnings when exercising the choices.


The greatest strategy to clarify choices is to work by way of a pair examples. Let’s assume you’re employed for Manatee Corp, a producer of manatee drugs and care merchandise, and as a part of your compensation bundle, you’re granted inventory choices on May 5, 2020 (that is now the grant date). The inventory choice specifies that you’ve the correct to buy 1,000 shares of Manatee Corp inventory at a strike value of $50 per share. The choice has an expiration date of 1 yr from the grant date.

Scenario 1: Stock value will increase

On May 4, 2021, a day earlier than the choice will expire, the inventory value of Manatee Corp rose to $70 per share. Since the inventory value is now larger than the strike value of $50, you resolve to train your choice. You buy 100 shares of Manatee Corp inventory at $50 every, utilizing your choice. May 4, 2021 is now the train date. You now personal 100 shares of Manatee Corp inventory at a value of $5,000 ($50 strike value x 100 shares). If you determined to right away promote the inventory, your achieve can be $2,000.

Scenario 2: Stock value decreases

Instead, now on May 4, 2021, the inventory value of Manatee Corp declines to $40 per share. In such a state of affairs, it will be prudent to not train the choice because the inventory value is beneath the strike value. By opting to not train, the choice would expire with none worth, leading to no further prices. However, it is necessary to notice that the choices you had been granted would develop into nugatory, indicating that the compensation initially granted holds no worth.

Here are each eventualities for comparability:

Scenario 1 Scenario 2

Market worth of inventory at train



Strike value



Gain per share



Number of shares



Total Gain



It is value emphasizing that in situation 1, there is no such thing as a obligation to promote the inventory instantly after exercising the choice; we solely demonstrated the sale for illustrative functions to showcase the potential achieve. Should you select to retain the inventory post-exercise, you can be uncovered to future fluctuations within the inventory value, which may have an effect on your achieve positively or negatively.

Related: Using asset location to reduce earnings tax whereas reaching your funding targets

Exercising the choices

Once the choices have vested, you’ll possess full possession rights of the choice contracts and might train them at your discretion inside the choice interval. In our first inventory choice contract instance we used an choice interval of 1 yr for simplicity however the typical time interval for an choice granted as a part of compensation is 10 years (once more, learn your settlement for exact info).

Upon selecting to train the choices, it’s essential to amass the corporate’s inventory by buying it on the predetermined strike value. When you train the choices, you might must have funds accessible for the acquisition. However, some employers provide a cashless train. You primarily borrow the cash wanted to train the choices from the corporate’s dealer, and the dealer instantly sells sufficient of the acquired shares to cowl the price of the train and any related taxes. This methodology does not require you to make use of your personal money however might lead to a smaller variety of shares acquired.

Now, you’re formally the proprietor of the shares, just like every other inventory, and have the liberty to make choices primarily based in your particular person monetary goals and tax planning concerns, which can be influenced by the particular sort of choice concerned.

Up till this level we’ve got described how choices work basically however now let’s talk about how NQSOs specifically work.

Taxes on NQSOs

At their core, NQSOs are similar to the essential choice contract we outlined when explaining choices. Their worth comes from the distinction between the market value of the choice and strike value however you will need to perceive the tax impacts their granting, vesting, and lastly train:

Time of grant: At the time the NQSOs are granted the chief, NQSOs don’t set off any tax implications. The grant itself doesn’t lead to taxable earnings for the worker.

Time of vesting: When NQSOs vest, which means the worker turns into eligible to train the choices, no tax penalties happen. The vesting of NQSOs doesn’t set off any taxable occasions for the worker. This is favorable, it permits extra management for the worker to implement tax planning methods later when the choices are exercised and earnings is acknowledged (see subsequent).

Time of train: Taxation comes into play when NQSOs are exercised. The distinction between the truthful market worth of the inventory on the train date and the train value (also referred to as the “spread”) is taken into account taxable compensation earnings. This unfold is topic to unusual earnings tax charges and is often added to the worker’s W-2 or 1099-MISC type.

Note: If your organization permits an 83(b) election, this will change the tax implications and create a tax legal responsibility when the 83(b) is filed. This submitting may create further danger for the worker as they now have paid tax on compensation which might later be nugatory, however does additionally create the chance to transform a number of the compensation from unusual earnings to capital good points (and be taxed on the decrease charges).

From our earlier instance, if the FMV of the inventory on the train date is $70 per share, and the train value is $50 per share, the unfold can be $20 per share. If the worker workouts 1,000 shares, the taxable compensation earnings can be $20,000. This portion of the achieve can be taxed as unusual earnings at unusual earnings tax charges.

Tax methods for NQSOs

The standard 10-year expiration date (not the one yr used within the easy instance) comes into play right here, permitting for multi-year tax planning. It places the chief accountable for once they train the choice and soak up the rise in taxable unusual earnings.

One tax technique is to easily wait and defer the entire taxes till simply earlier than the choices expire. This is extra of a passive technique and might be not the neatest because it may discover you getting ran into the next tax bracket as a result of train of all of the choices in the identical yr.

A greater tax technique that may be employed is to “full up” a decrease tax bracket earlier than crossing over into the following larger bracket by exercising choices. Years when firm efficiency is decrease and different variable compensation elements similar to money bonuses are decrease are glorious years to think about this technique.

Let’s have a look at the present unusual earnings tax charges for a taxpayer submitting as Married Filing Jointly in 2023:

  • 10% for incomes as much as $22,000.
  • 12% for incomes from $22,001 to $89,450.
  • 22% for incomes from $89,451 to $190,750.
  • 24% for incomes from $190,751 to $364,200.
  • 32% for incomes from $364,201 to $462,500.
  • 35% for incomes from $462,501 to $693,750.
  • 37% for incomes over $693,750.

If the taxpayer is at present within the 24% bracket with a predicted family earnings of $250,000, they might need to train NQSOs to generate further unusual earnings of $114,000. This would deliver their complete earnings to $364,000, slightly below the beginning of the 32% tax bracket. It is particularly useful to replenish these decrease tax brackets if they’re forecasting larger salaries or further bonuses in future years.

Other than taxes, there could also be different causes to train the choices ahead of later as soon as vested, these embrace:

  1. Market volatility: If you anticipate the inventory value to say no considerably within the close to future, executing a disqualifying disposition permits you to lock within the achieve on the present market worth earlier than potential depreciation happens.
  2. Cash stream wants: If you require fast money and should not have the monetary means to carry the inventory for the required holding interval, a disqualifying disposition allows you to entry the proceeds from the inventory sale promptly.
  3. Risk mitigation: Holding firm inventory carries dangers, similar to focus danger or modifications within the firm’s monetary stability. Opting for a disqualifying disposition permits you to diversify your investments and cut back publicity to a single inventory.

After exercising the NQSOs, the worker assumes possession of the acquired inventory. They have the choice to retain the inventory or promote it. If the inventory is bought sooner or later, any income or losses can be topic to both long-term or short-term capital good points tax, relying on the holding interval and the distinction between the sale value and the truthful market worth on the train date. If you resolve that you simply need to maintain onto the shares after exercising the choices and the inventory does enhance in worth, you’ll want to maintain the inventory for a minimum of a yr and sooner or later to appreciate the decrease long-term capital good points tax fee. If bought for lower than that, the good points can be thought-about brief time period capital good points and taxed on the identical charges as unusual earnings.

Remember, the tax canine will not be the information canine to your life. There is much more to your monetary independence than decreasing your current-year taxes. Risk mitigation, together with avoiding a probably highly-concentrated place in your organization inventory, must be thought-about.


Please understand that tax laws and charges can differ primarily based on numerous components, together with the worker’s tax bracket and the period for which the inventory is held. Seeking steerage from a tax or monetary skilled advisor is crucial to make sure adherence to tax legal guidelines and achieve a complete understanding of the tax penalties related to NQSOs, tailor-made to at least one’s particular circumstances.

It can’t be repeated sufficient, it’s of utmost significance to fastidiously overview the plan paperwork or, alternatively, share them together with your adviser for an intensive examination, whereas concurrently establishing a strong, long-term tax technique.

Congratulations in your success and being granted these thrilling compensation automobiles, you earned them by way of your whole onerous work. Now be certain they’re used to their fullest to supply you a path to monetary independence and objective.

About the writer

Sean Lovison, CFP, CPA is a Principal with Purpose Built Financial Services, LLC. 

Editor’s Note: The content material was reviewed for tax accuracy by a TurboTax CPA skilled for the 2022 tax yr.