Is the tax advantage of holding onto ESPP shares for a "qualifying disposition" worth it?

Clients often ask, “Is it worth holding onto my ESPP shares longer for the tax advantage?” Generally, no. This article gives that question a thorough treatment, showing you that the tax advantage of holding onto shares may not be much of an advantage after all.

Congratulations, your employer has an Employee Stock Purchase Plan (ESPP)!

What’s that you say? You’re not sure congratulations are in order? That’s understandable. It’s easy to know what to make of excellent healthcare or an annual bonus. It’s harder to wrap your head around how to participate in a well-managed ESPP.

The Inner Workings of Your ESPP

Tricky Taxes

Using ESPP Proceeds to Fund Your Financial Goals

Planning To Benefit From Your Company ESPP

An ESPP (short for Employer Stock Purchase Plan) is a super valuable benefit offered by your company that allows you to purchase your company stock at a discount. With the recent drop in the US stock market however, you might find that the price of your company shares is now below even the discounted purchase price. That may have you wondering if it is worth continuing to participate in the ESPP.

Taking a look at your lookback provision

What to do with shares acquired through the ESPP

Tax considerations with selling ESPP shares

Learn the basics of Employee Stock Purchase Plans.

An ESPP (short for Employer Stock Purchase Plan) is a super valuable benefit offered by some publicly traded companies. The plan allows employees to purchase their company stock, often at a guaranteed minimum discount.

Learning the Lingo

Savings Specifics

Contribution Considerations

Limits to ESPP Contributions