It’s good to have options. It’s also kind of confusing. When you’re trying to figure out when to exercise stock options, it’s smart to consider how you’ll be taxed, and that depends on the type of options you have and whether you satisfy the holding period for capital gains. If the exercise of your options doesn’t qualify for long-term capital gains treatment, you may have to pay the dreaded income tax rate.
Type of Option
The IRS distinguishes between statutory and nonstatutory stock options. Generally, options you got as part of an employee stock purchase plan or incentive stock option plan are statutory stock options. Everything else is a nonstatutory option. But even if you got the option as part of a plan, if you didn’t remain an employee of the company granting the option or a related company from the date of the grant through three months before you exercised the option, or if the option is transferable, it is a nonstatutory option.
Nonstatutory Stock Options
Nonstatutory options have no special tax treatment and no holding period. They count as income, not capital gains. If the option is traded on an established market, or you can otherwise determine its fair market value, you must treat the option like any other compensation at the time it is granted to you, but you won’t have to count it as income when you exercise the option. If the fair market value isn’t readily determinable, the opposite is true: you do not have to count the option as income until you exercise or transfer it.
Statutory Stock Options
If you have statutory stock options, you don’t include them as income either when you receive the options or when you exercise them (except to calculate the alternative minimum tax). Instead, you determine the tax treatment when you sell the stock that you got by exercising the option. This could be years down the road, and whether you owe the ordinary income tax rate or the lower long-term capital gains rate mostly depends on whether you satisfied the holding period or not.
Holding Period for Statutory Options
To satisfy the holding period for statutory options, you must hold the stock for one year after you received the stock itself and two years after you received the option. If you have to sell the stock sooner to remove a conflict of interest, you are considered to satisfy the holding period. For the most part, if you meet the holding period, your sale is a long-term capital gain or loss, but if the option was granted under an employee stock purchase plan and at a discount, a portion of it may be considered income.
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