can i recieve unemployment benifits if i have been self employed for over five years? by jennifer walker (blountsville, alabama, usa) i have been self employed for over five years, but i file taxes every year, can i draw some kind of unemployment or aid in Alabama? Not likely. Employment must be in “covered employment” (click current year, then coverage) ie., “unemployment taxes” were paid on your earnings. Sole proprietors hardly ever collect unemployment unless they have been working a job in addition to the self employment .. Sometimes a state may provide that corporate officers can collect, but it really does depend on what state is involved.