<prompt> Human: My monthly stipend doesnt get taxes taken out so I have to pay quarterly or annually. Im saving an extra 400 a month for this. Im thinking of putting that money into a dividend yielding stock and selling it when I have to pay taxes. Its risky but I have some cash savings that I can use to cover me if Im in the red. What do you guys think, too risky? What companies do you suggest? Edit Thanks yall, great advice. Not worth the risk for little gain.  <response>: Generally you shouldnt invest money that you will need within the next 5 years. 