This chapter investigates the experiences of female Icelandic marketers and their employment; more specifically why they choose to leave their corporate roles, and the challenges they face when establishing their company. Iceland has been identified as the country with the world’s smallest gender gap, but at the same a time very small proportion of women can be classified as entrepreneurs. Little research has focused on the reason why Icelandic women decide to leave the corporate world and become self-employed. The findings reveal that the financial crisis has affected the majority of these women and their career choices, and that some of these women had no plans to be self-employed for the rest of their working lives. The Icelandic welfare system seems to favour employment, but it also looks like the women themselves prefer the security of employment even though all of them had a positive experience of running their own company.