This empirical paper aims to cast light on the relatively unexplored field of study of the effects of failure on entrepreneurs. In fact, in the last years different scholars published relevant analyses on the financial, social, and psychological outcomes of this occurrence, but there is still a certain lack of research on the long-term effects of failure on the career choices of failed entrepreneurs.

Thus, we consider relevant existing research on entrepreneurship, failure, and career choices, and come to the conclusion that the Career Construction Theory provides a useful framework to interpret the decision on whether to re-entry or not self-employment following failure.

Combining the existing relevant body of knowledge, through a deductive process, we present hypotheses and empirically test them on a Swedish sample.

The results confirm that portfolio entrepreneurs are more likely to continue, hint that marital roles might affect positively the probability of re-entry, reject the importance of balance between the main roles of the individual at the time of failure for his or her financial performance upon re-entry, and reject that, by including other colleagues in the re-entry, entrepreneurs achieve better financial performances.