<prompt> Human: My company offers an employee stock purchase program, which is as follows: every 6 months, the employee purchases stock at a price that is 85 of the current stock price, or 85 of the stock price 6 months prior, whichever is cheaper.I thought this was a great deal, but now Im re-thinking. Im already over-leveraged in company stock. Id rather have the money in index funds. Would I be better off just applying the same money to the direct purchase of index funds?  <response>: Do it! Max out the ESPP, but sell immediately.You would be turning down a minimum annualized 90 return. Its that big because that money that you contributed the week before the end of the period is coming back to you 1.85 bigger 17.6 increase. You only had to wait 3 months on average to get that money back, so the annualized payoff is great.The only way that you could possibly lose any money is if the stock drops 17.6 between the purchase and the time that you are able to sell. The purchase date is usually a few weeks after quarterly results, so there is no chance for a bad quarter to strike. Ive been doing it for 20 years and never lost money.The only thing to watch out for is to be sure that the shares are immediately available. If you company makes you hold for a while, thats a big red flag. 