Coming out as transgender is a life-changing experience, but as freeing and exciting as the process can be, it's also one commonly riddled with fear and guilt. Dr. Jenny Boylan knows this firsthand .

Boylan is a professor, activist and best-selling author who is now recognized often as Caitlyn Jenner's mentor on "I Am Cait." When Boylan transitioned more than 15 years ago, she worried how her identity would affect her family -- particularly her two sons. Sean and Zach were both under the age of 6 at the time and their young age was a central point of concern.

As it turns out, Boylan didn't need to worry about her transition shaping Sean and Zach negatively. In fact, as she states during an interview for "Oprah: Where Are They Now?", Boylan actually believes that her transition has in some ways helped both boys become better men.