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General What is Your Approach to Taking Risks?

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Some people take bold leaps, others prefer calculated steps. I fall somewhere in the middle. How do you decide when a risk is worth taking, especially with work or long-term plans? Let's say you took a risk but it didn't go well, what next now? Or you didn't take risk and now now you are regretting about it. How do you handle thinks like these?
 
I am a great risk taker but I always take risks that are deeply calculated. I always make sure to examine all variables before I step into unknown or uncertain territory. I always make sure that I know what to expect with every venture that I enter.
 
I try to take calculated risk, I also try to minimize my risks. But despite being cautious, I frequently get into a lot of troubles because of the losses from the risks I took. There is no safety net even when I take calculated risks.
 

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