I am going to be selling some employee stock later this year. Is there an alternative investment I can use to defer taxes. Like adding it to my 401K?

[RichardG · Accepted solution]

If you're asking about contributing the stock to a retirement plan, that is not an option.  Only cash contributions are permitted.  If your shares have not vested, they are not transferable,  and any permitted transfer would trigger taxable income, anyway.

There are several options you can consider for increasing your tax deductions to offset this added income: 

• charitable giving

• cash contributions to qualified retirement plans

•  selling investments at a loss

Another option to consider is forming a charitable remainder trust and contributing the vested shares to the trust prior to selling.  Please follow this link for more information.  https://www.fidelitycharitable.org/giving-strategies/give/trust.shtml