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No company would approve of you having two jobs that overlap. That being said, go for it and know what DD is right: You WILL burn out and you could get caught if a 1099 client sees you with your DM and says something. Your other issue is how successful can you really be at TWO jobs unless you are willing to work 90 hours a week? What about space in your car for all the stuff? Better not leave something in there for your DM to see. Money is not the be all and end all. It sickens me how many people would sell their soul and all their free time just to make an extra 50K. Go for it but in the end, you will wish you had spent your time in school, with your family or on more worthy pursuits. (Unless your 1099 can turn into a business that you own with residual income.)