President Obama is expected to sign an executive order which would prevent federal contractors from discriminating against their employees on the basis of their gender identity or sexual orientation.

Gay rights advocates say this could provide employment protections for about 11 million workers who currently don't have any. But even with new guidelines in place, there are still huge challenges to face in the workplace, which Jacob Tobia knows well. He's a self-described gender non-conforming man who feels more comfortable dressing in women's clothing.

The recent graduate of Duke University, who wrote about the challenges of dressing for success for the Huffington Post, joins the show with more.