I am over-biased against risk. I usually take the safer option even when it's the wrong one. When I was 18 I stumbled across this paragraph.
You must do everything that frightens you…Everything. I’m not talking about risking your life, but everything else. Think about fear, decide right now how you’re doing to deal with fear, because fear is going to be the great issue of your life, I promise you. Fear will be the fuel for all your success, and the root cause of all your failures, and the underlying dilemma in every story you tell yourself about yourself. And the only chance you’ll have against fear? Follow it. Steer by it. Don’t think of fear as the villain. Think of fear as your guide, your pathfinder… ― The Tender Bar by J.R. Moehringer
I followed this paragraph to the letter. Whenever I was torn between two choices and didn't know what to do I'd just take the scarier option. I recorded my results until I had accumulated 30 decisions. 28 of them (93% of the time) the scarier choice was the correct one. This immediately improved my quality of life. The two decisions where I chose wrong by doing the scarier thing were inconsequential.
I continued using fear to tiebreak my decisions for another two years. It worked great until I negated my aversion to fear. My sense of fear has become subdued outside of immediate physical danger.
I make far better decisions then I did before I deconditioned myself, but I'm still over-biased against risk. I'm not literally afraid of taking risks. I'm just overly-conservative in expected value calculations. I'm too cautious.
Having identified this problem I'm going to try something similar to what I did last time. I'm going to increase my risk tolerance slightly and record my results.
December 13, 2019 update: Apparently my last trial at this years ago wiped out most of my fears. Increasing my risk tolerance helped me write more but otherwise had little effect on my life.