The company I work for offers an Employee Stock Purchase Plan. We get a substantial discount on purchasing company stocks. They also offer a 401k plan, though they haven’t said anything about any kind of matching (probably because they want us to take part in the ESPP). Should I invest in both simultaneously to take advantage of the tax benefits of the 401k and diversity, or should I invest all into the ESPP to get the benefits of the discount. I know that most people suggest being wary of putting all of your stock into your employer’s company, and I don’t intend to. My idea is to participate in the ESPP and then after the purchase, sell the stock, and then re-invest it into something with higher growth and diversity.