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At their most basic level, executive compensationplans are designed to attract, retain and motivate top talent and leadership. But truly successful plans are designed to be much more than providing a high salary to a key employee – they support the business’s philosophies, values, and mission. .
The surtax will increase the Massachusetts tax liability by $68,000 on the sale of their home. Further, if you weren’t planning to sell the asset, it’s usually not advisable to do so for tax reasons alone. But if a sale is in process, wrapping it up before 12/31 would be advantageous (all else equal).
While it’s not always advisable to sell investments at a loss, it may make sense in your situation to consider selling underperforming assets, especially if you’re willing to invest in alternative assets that provide similar exposure without triggering a wash sale.
Reason #2 – A Belief that the Stock Will Go Up: Fear of missing out, or fear of making a mistake on the sale of your stock (particularly if it has been outperforming), may influence your decision not to sell and diversify. These factors might lead to overconfidence in the stock, and its future price expectations. Proceed more gradually?
However, if you are seeking a qualified sale in pursuit of more favorable tax treatment, and you are willing to evaluate AMT and AMT credit (if applicable), an exercise and hold of some or all your ISOs may be your best bet. Some might be typical financialplanning goals like: I want to buy a house (or a vacation home).
While AMT and holding periods for qualified sales may be important from a tax-reporting standpoint, they may be irrelevant if you simply exercise and sell your ISOs in a cashless transaction. When you do, the sale is either a qualified or disqualified sale, and is taxed accordingly.
The standard, however, is often used haphazardly, invoked as a sales tool by dual-registered advisors who want to virtue signal, only to be abandoned in a legal context by those same advisors who backpedal into being “just a salesperson.” Let’s talk about it. It’s about how you behave and the operational standards you follow.
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