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services to others), and assuming those are not your core
business activities. Gray areas abound. If you operate a
restaurant, it is likely that you can hire a webmaster as an
independent contractor, but if you operate an online
store, an argument could be made that the website is part
of your usual course of business, and therefore should be
managed and staffed by employees under the law.
It is truly surprising how many businesses in
Massachusetts get this wrong, so you should not assume
a practice of using independent contractors instead of
employees is lawful, even if it is common in your
industry.
The measure of damages in misclassification cases
depends on the circumstances, but can include the value
of benefits that W-2 employees receive, the amount of
self-employment tax liability the employee has incurred
57| Rules of the Road
