Before you start compiling ways to convince your boss, you must first convince yourself. Why do you want to work from home and telecommute? You should have good reasons to want to work from home, such as saving on commuting costs and clothing costs. You may also want to spend more time with your kids. Less time driving will help you do just that. You will have a little bit more freedom working from home, but you will need to be self-disciplined to get the work done without a boss looking over your shoulder. If you want to cut childcare costs and keep your kids home with you, working from home may not be the best choice for you. Imagine taking your kids to work with you all day, every day. It is far from easy and convenient. It is distracting, time consuming, draining, and you'll barely get any quality work done. Ponder your reasons to ensure they are good ones.