You need to constantly review your situation. The risks I took in high school, college, my early and mid 20’s and now my mid 30’s all look different. When I was younger, I was more willing to take big financial risks. I would go into the negative often, knowing I could always dig myself out. But that all changed in my mid 30’s. I’m married, I have a lot of employees that rely on my company succeeding, and the downside is greater now than it was in my 20's.