I believe you may be mistaken about how these plans are taxed. Assuming the stock is sold for a set discount off of the price at the end of the offering period, that discount you received is taxed as regular income
regardless of when you sell. Your basis is then set to the fair market value at that time. So if you sell right away, you pay essentially no capital gains taxes, and regular income tax on the discount. If you wait, the stock could go up or down. If it goes up, you'll pay long-term gains on the increase, sure, but you'll still be paying your regular marginal rate on the discount you received. So the question really is: do you have some reason to believe that your employer's stock will beat the market, and are you willing to bear that risk? If not, just sell right away and invest in an index fund.
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Thats not true for my ESPP. We get a 15% discount when we purchase. if we sell in less than 2 years that 15% discount is treated as income, if we sell in more than 2 years it is treated as capital gains.
Either way. Max it out man, just make sure to diversify as soon as you can.
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Yup that is the way it worked when I was doing them. The laws may have changed in the last 15 years, and the 2 year starts at beginning of the period so it is generally 18 months after the shares are purchased.