As the sole proprietor of an unincorporated business the law does not require you to insure yourself. However, under a recent change to the law, sole proprietors and partnerships (that have no employees) can now obtain insurance if they so choose. If you do work for a general contractor they may want you purchase a policy in order to work on a particular job they are overseeing.

(this is from the Mass.gov site. Do you we need to list this as the source? And how do we keep this updated? We’ll have to know if the laws change…)

Yes, but only if it is provided for in the contract they have with you, or otherwise explicitly provided. General contractors have legitimate concerns about whether you have WC insurance since they can be found liable for claims against them by a subcontractor or their employees. Therefore, you may find that the general contractor requires you to provide proof of coverage, or that you agree to come under their workers’ comp policy with such costs passed on to you.

With limited exceptions, every employer in the Commonwealth with one or more employee(s) is required by law to have a valid workers’ compensation policy at all times. This “no fault” insurance not only provides injured workers with medical care and partial wage replacement, but also protects the policyholders from potentially damaging lawsuits. Although most companies in Massachusetts purchase a traditional commercial insurance policy, there are alternative methods of coverage which include licensing as a self insurer, gaining membership in a self insurance group, or obtaining coverage in the Assigned Risk Pool.