I try to listen to my gut. Most of the most important decisions in my life were made based on instinct, not lists. Lists are BS, if you ask me. If I had made a list, I never would have married my husband. Hell, I never would have met him. I listened to my gut, and that was that. Almost 11 years later, and I couldn't imagine life without my hubby. He is terrific.
So, if you feel deep down that you need to go for it, go for it, just as long as no one will get hurt, yadda, yadda, yadda. Try to find your center, listen, and just jump. Leaps of faith are necessary for so many things. But I agree with Jim, it's all about regret with me too. I have no desire to die with regrets. So, which will you regret more, not trying or having to live with a terrible outcome?