I agree. You should always try to wear bigger shoes. It's the learning process.

But I claim that (bigger) deviations are the ones that kill you.

If you have no experience and suddenly get to step in too big shoes (CEO and Jackpot) you suddenly find yourself surrounded with much bigger fish you are used to deal with.

For example in a corporate environment, one level below you (as a new CEO), most of the managers want to get to your seat and are willing to play dirty. And you're fighting in a unknown foreign territory.

Yes, fine-tunning your risks assessment skills can be greatly rewarding.