Or sometimes you have an approach that is high risk/reward. That's totally fine to take as long as your aware of the risk and have mitigations or offramps at the right points if you find the path isn't viable.
If we take your first statement to be a "rule of wisdom" then it is either false, or all roads lead to disaster anyway.
If you leave off the rest of my post, you're likely to misunderstand it :-)