For me, the biggest challenge is getting used to having to take my own taxes out of my paychecks, which will amount to around 25% of most freelancers paychecks. But for others, the number one issue involved with freelancing is maintaining the self-discipline necessary when you don’t have someone telling you when to work and what to do. On the upside, some freelancing problems can resolve themselves in time. For example, while affording medical insurance is currently a major issue for many freelancers in the U.S., Obamacare’s healthcare mandate comes into effect next year, which means, if nothing else, you can at least buy affordable insurance through the state.
