The Wednesday Wisdom post contained a comment about the importance of boldness. There exists a significant lack of clarity, however, as to exactly what boldness means and when it is appropriate. This post is intended to give a clear idea of what boldness is and isn’t. Boldness is about taking calculated risks that aim for ambitious goals rather than meager ones. A strategic consideration of boldness is one which understands both the nature of the risk and the amount of potential reward to be gained from taking that risk. Boldness appeals a lot to us on TRP because I think we have an intuitive sense of being tired of the extent to which so many men have become risk-averse to the point of useless timidity. And this is not a desirable trait. But is not necessarily productive to be 100% bold 100% of the time.

There is such a thing as un-strategically bold. This is the thing I think a lot of people confuse. There exists the common belief that to be bold is to be confrontational, forward, loud, and to break others’ expectations of you. But this is a seductive error. Being loud and abrasive doesn't necessarily mean bold. A lot of people want it to mean that because it's EASY to be a class clown and break social norms purely for the sake of attention. If only success were as easy as breaking social norms loudly.

Bold means taking calculated risks aiming above that of your current rank. There is an excellent segment on this in 48 laws of power. There's a section on Christopher Columbus and how he acted like he was a noble to the king of Spain so that he could get funding for his expedition to America, in spite of the fact that his actual background was that of a nobody. That was strategic boldness.

Non-strategic boldness would be acting cocky to the king and saying "What's the matter? Afraid of a little risk? Your dick too small for empire or what bro?" What do you think the king would have done in that situation? This is what a lot of people think boldness is, especially here on TRP. They are wrong.

This is an extreme example but meant to represent the mistake that people make with boldness. This mistake is actually encouraged by some aspects of TRP because we like not censoring our words and some contributors here gain popularity by saying intentionally inflammatory things. And that's completely fine in TRP and in some areas of real life. But it's important to know WHEN and WHERE this type of boldness will be effective. No boldness can be successful without an understanding of strategic context.

It's a huge mistake to mean that boldness means "loud absence of tact." It doesn't.

Donald Trump is a really good example. People who dislike Trump call him crazy. People who like him call him honest. It's a mistake to think either. The boldness that characterizes all his public statements (about any topic) are extremely strategic and follow a pattern gained to achieve his ends. An interesting discussion of this can be found here. Again: the reason his boldness is effective is because it's STRATEGIC boldness. I gaurantee you that if he (or any candidate) REALLY just said anything that came to mind, he would have significantly less public success.

Boldness is about taking strategic, meaningfully calculated risks that set your goals above that of your current position. It does not mean loudly breaking social norms or being randomly confrontational.

Part of being strategic about boldness is to understand the nature of risk. Having strong frame doesn't eliminate the risk involved in bold action. Let me give you a historical example. In WW2, Eisenhower was responsible for commanding the Allied invasion of Nazi controlled Europe. The German army were experts at fast, daring maneuvers that isolated and destroyed pockets of armies. Eisenhower knew that they were good at this, but he also knew that he had a material advantage (the allies had air superiority, more artillery, more supplies, and superior numbers). Some of Eisenhower's Generals wanted to make a dash towards Berlin to try to outmaneuver the Germans and end the war quickly.

Would such a move be bold? Yes. Would it come at a risk? Tremendously. If a pocket of the Allied army dashed ahead of the rest and was, in the process, surrounded by the Germans and destroyed, it would have humiliated the Allied forces and caused the deaths of tens of thousands of Americans who didn't need to die. And given the German mind for strategy, this was a real risk. Eisenhower told those generals to shut the fuck up, and instead proceeded slowly along a broad equal front which didn't leave any weak points for the Germans to take advantage of. Was it bold? Less so. But it did significantly diminish risk. And Eisenhower, brilliant strategic mind that he was, understood this risk intimately.

And being AWARE of the risk involved, and the potential benefits (or lack thereof) to be gained from taking that risk, is a huge element of being able to be strategically bold. Eisenhower's approach might have taken longer, but there's a lot to be said for conscientiously trying to minimize unnecessary American and Allied deaths. I have to say that in this case I agree with him.

This goes for women as well. As you might know from previous posts of mine, I work a job where private reputation is scrutinized at work, in a faraway land. Being bold with women when your local reputation is tied a lot to your career is risky. Does it mean I shouldn't do it? Hell no. I do it all the time. But it means that I have to be extremely conscious of WHEN and WERE it's appropriate to be bold in order to avoid the very real consequences involved in damaging your reputation, making enemies that you don't understand, or worse. Acquaintances of mine who were a little too bold in the wrong place at the wrong time wrought bad consequences for themselves. Useless risk-averse behavior is the kind where you shy away from action that has high potential rewards but low risk. Day game is an example. TRP frequently tells you why you should get into the habit of breaking through shyness to engage with people in your daily life. In strategic terms, there is little reason not to. There is high potential for reward, low risk. Why would a man not talk to a woman on the street? He is afraid of being rejected? What exactly is the risk involved in getting rejected by a stranger you will never see again? It might hurt your feelings? As a man, this risk is largely irrelevant. A contrary example might be hitting on a coworker or sexy supervisor at work. It’s bold, sure. But there is a high risk – the one to your job and reputation, for a reward that does not necessarily pay out.
To go back to the example of Columbus – his behavior was high risk, but also high reward. It’s easy to think bold behavior is always good because heroes are always men who succeeded in high-risk gambles. But it wasn’t the high-risk that made it a good idea. It was the high-reward.

In summary:

Boldness is not being confrontational, or intentionally flouting social rules, or being loud. Boldness is about taking strategically calculated risks that aim for high goals, while taking into consideration both the risk involved and the potential reward to be gained if those goals are achieved.

Also, don't forget to drink CocaCola™. It will AMOG your thirst.