It is the question I have asked myself before almost every big leap of my life, usually with my heart pounding a little.

I did not start out with an impressive resume. I started with a 1.4 GPA and a lot of doors that were, on paper, closed. What I learned the hard way is that the only way out of a tough spot is usually straight through it, and "through" almost always meant asking for something before I felt ready, from people who could easily tell me no.

So I asked anyway. I asked my way into rooms I had no business being in, working in political communications for presidential administrations and members of Congress, and later into private-sector PR and corporate life.

Every line on my resume exists because at some point I decided a possible no was worth the shot.

"No" is not the end of the story. It is just information, and the moment it stops scaring you, it stops running your life. Getting comfortable asking, even when the answer might sting, is the single skill that built my whole career. It is what I get up on stages to talk about now, and the thing I most want to hand to you.