My wife has the opportunity to buy stock through her employer, which is a legacy tech company (and has a sluggish stock price at the moment). She can purchase between one and ten percent of her salary, and she buys it at a 15% discount from the current market valuation. Since we hit fifty, we’ve begun to max out our 401K plans, with mine through my S-corp, so I’m also kicking in a sum of money through profit sharing.

On the one hand, we are already saving plenty and are in a good position for my wife to retire in a few years, and I wonder if it will really make a big difference in the long run if we go chasing after that extra return offered by the discount. On the other hand, it is 15%, so why not max it out if we can. I’ve never been a fan of buying stock in the company one is working for, as you’re already exposed financially via your paycheck, but maybe that’s an unnecessary worry. We could always just sell the stocks after one year, when any increase would be counted as capital gains.

How would you weigh this decision?