When making a decision, what is more important to consider?

Is it more important to make the decision based on the safest, no risk route OR is it better to take the harder, less trodden on route, which could be more beneficial in the long run? The former (simpler route) means having 100% guarantee of reaching the “next step” in your career/ambition/goal but perhaps not being as prepared. And the latter means maybe not making it to the next step at all, but if you do, you will be better prepared to face the hurdles and perhaps will be more successful in the long run.

Does any of this make sense to you?