To me, Boldness integrates a few different qualities: Motivation, Risk Tolerance, and Ambition. Those who embrace Boldness are those who are willing to take big risks to achieve big outcomes. Rather than focusing on incremental improvements, Boldness strives to make leaps forward, such as taking on ‘Moon Shot’ projects. This tends to require much more effort, as well as a general holistic understanding of the problem, but potentially has a big payoff.
A different connotation I think of when I hear ‘Boldness’ is volume. Bold is loud. To rise about the noise of convention, ‘bold’ leaders get up on their apple box and shout their bold assertions. But can Boldness also be quiet? I think so. One interesting finding is that it is often better to not share your goals out loud to others. Your body gives you a dopamine hit when you do, but counterintuitively it acts a little like you already accomplished the thing, making it harder to do to the hard work. So perhaps, in this light, Boldness may be better suited through quiet toiling than bombastic gestures.
Lastly, the word comes from the Old English beald or bald, meaning ‘stout-hearted, brave, confident, or strong’. Later in the 13th century it came to mean ‘requiring or exhibiting courage’, though it could also be used negatively as ‘audacious, presumptuous, or overstepping usual bounds‘. So I think the main takeaway is the Boldness requires Courage, both to take on a challenge, but also potentially to take on societal norms in a way that might be seen as ‘overstepping usual bounds’. It is tossing off the yoke of tradition in favor of a new path.