At Bsides Vegas, I was inspired to give this talk because we need more career coaching and mentors, and if we don’t address failures and set-backs we are pretending everything is always easy and great. That just creates a false narrative that everyone you see and everyone that is on stage has only had successes and that's nonsense. We all have had serious failures and set-backs. I am here today to discuss some of my professional and personal difficulties and what I was able to learn from them, what impact they had on me and hopefully pass along some lessons learned that will be helpful to you.