<prompt> Human: So for the past year Ive worked as the only employee for a man who runs his own events business. He is trying to start another business and so we are in negotiation for me to take over more responsibilities and earn a higher percentage of the events I run. The original idea was for me to remain an employee, bump up from 45 to 55 of events I run this year and then 60 next year, and I would be in charge of client expenses estimated at about 10 of my income before taxes. Apparently that would be a bit tricky tax wise though so he has suggested that I fill out a 1099 and become an independent contractor making 65 this year and next year and then renegotiating at the end of the 2019 season. The contractor route seems like a much better option, but Im wondering if theres something obvious Im missing? Ive never had to write off business expenses or really do anything trickier tax season than fill out a couple w2s on turbo tax, so Im a bit worried about the meticulous bookkeeping required for paying my own taxes and business expenses, but Im certainly up for a challenge if it means more money for me overall.Thank you, Ive learned a lot following rpersonalfinance and appreciate everyones advice in advance!  <response>: you pay your own taxes at tax time, you wont be eligible for workers comp if you are hurt, or unemployment if you loose the job, and you might need to be insured at your own expense. 