The fear of not taking (calculated) risks is the same as any other fear. It stems from lack of certainty. Certainty comes from knowledge.
Basically saying, fear is caused by lack of knowledge, a feeling of not being in control because you don't know all the variables in the equation.
Decrease your fear of risks by increasing your knowledge. That is why the best risk you should take is called calculated risk. Because you've worked out all the equations.
Another powerful way forward is to take mentors - people who have achieved the level of success that you want to achieve. Your mentors need not be business gurus who charge you thousands of dollars per hour of their time. They can even be people you already know but haven't thought of tapping their expertise for your benefit, learning and growth.
Ask yourself - do you want to continue living the way you are right now? Do you want to remain stuck in your present level of circumstance? How much do you really, really want to get to the next level - whatever that is for you?
What will you lose if you don't get to the next level? What is required to get to the next level? How much risk is needed? Would you rather lose a little by risking (calculatedly) or lose even more (maybe even everything) by staying in your comfort zone?
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