Robert Greene is my favorite author.
I found Robert while browsing a Barnes & Noble bookstore around the year 2000 and found his book The 48 Laws Of Power. Years later I read Niccolo Machiavelli’s The Prince. Yesterday I watched this video by Alain de Botton where he referenced Machiavelli.
Michavelli’s philosophy, and by extension de Botton’s video and Greene’s first four books (about Power, Seduction, War, and Fear), all situate around one idea, perfectly captured in a quote by Niccolo Machiavelli himself.
“Any man who tries to be good all the time is bound to come to ruin among the great number who are not good. Hence a prince who wants to keep his authority must learn how not to be good, and use that knowledge, or refrain from using it, as necessity requires.”
You are trying too hard to be too good.
You are trying too hard to be too good." There are many good people out there, people who have good, rational ideas, and intentions to use those ideas for helping other people. You’re probably one of those people. Since you’re one of those people, you probably know this: your bright ideas and positive intentions are rarely sufficient to get your goals accomplished.
But, you’re far from lazy. Your ideas are indeed good (you even have proof of it). And your intentions are pure.
Here’s a short list of your possible challenges, then; see how many apply to you.

Shallow-thinking people who just don’t get what you’re trying to do or convey.
Shallow-acting people — competitors for attention — who don’t have half your value or depth, but seem to be getting double your results.
Shady tactics that you’re too ethical to get involved in, but that have proven to work for others. You’re not tempted to jump in that pool, but you are a bit annoyed that that stuff actually works.
The realization (which may have hit you already) that doing things the right way, and having those right intentions of yours, will produce only a certain level of results — a level that you’ve either convinced yourself to be OK with it you’re still living with the frustration of.
Machiavelli understood in 1532 what Robert Greene furthered 1998 in their respective books: playing the game the right way all the time will leave you unfulfilled, underpaid and somewhere other than the winner’s circle.
I’ll use an example that everyone is aware of: Donald Trump.
(Some people just deleted this email or used the Back button on their browser at the mere mention of this name. Those people will continue to have the 4 problems laid out above. For the rest of you, read on.)
The first 2020 Democratic debates (for choosing a candidate who’ll try and unseat Trump next year) took place this past week, just up the street from me in Miami. There were 20 candidates involved, who were spread out over two nights of debates.

How hard do you think it is to convey your most important ideas when you’re sharing a stage with 9 other people? And when you’re given a time limit in which to respond to questions?
Brevity is a skill — actually, it’s more an art.
I couldn’t name all the candidates who were in the Democratic debates. What I’m sure of, though, is that there are good candidates who have really good ideas — ideas that we’ll never know about — because their ideas don’t fit into 30-to-60-second soundbites.

These candidates' ideas and proposed policies are probably outlined in detail on their websites, in their YouTube videos, in local speeches they give while out campaigning, and in the emails they send to supporters.
Problem: Most voters will never consume any of that shit. Thus, these voters won’t know where a candidate stands on anything outside of the soundbites produced in the debates. And this anonymous candidate thusly won’t receive donations, votes or poll support — and they’ll soon drop out of the race.

I mentioned President Trump.
He mastered the soundbite during his campaign. Because he understood point #1 above.

Trump knew that most people — the voters — would do no research beyond the soundbites (have you EVER read the proposed policies on a political candidate’s website? If so, explain them without looking at the site again). Just in case he missed some with the soundbite, though, he took to 280-character mini-speeches via Twitter.

Trump knew that he didn’t need to go deep on policy. He knew that the details and facts didn’t actually matter to his supporters (whose votes he’d need to win). He bet that his lack of political experience wouldn’t hurt if he could capture enough people’s attention and touch their emotions, bypassing the many logical arguments against him. He turned his many supposed weaknesses into strengths by doing the opposite of what the reasonable person would do.

Like it or not, it worked.
Sometimes it seems like the least-deserving people are doing the most winning. Even when a “deserving” person wins, it’s not long before the stories leak out about how they were never so noble in the first place themselves.

Bill Clinton admitted to smoking weed in his youth (back in the 1990s, when smoking weed was a big deal). He received oral sex from a White House intern while serving as President. Upon his exit from office in 2000, long before we’d heard of Obama, the African American community jokingly called Bill “The First Black President.”
When his wife Hillary came up for the Presidency less than twenty years later, the Clinton mystique had flipped. Many people whom I’ve heard bash Trump also admit that they weren’t too thrilled about President Hillary either.
This is not about politics. Admittedly, I hardly pay attention to it myself. What I do notice are the actions people take and the words they use, and I try to understand what may have been the thought process behind those actions and words.
I don’t know if Donald Trump has read Machiavelli or Greene. But he apparently understands, inherently, that good ideas and positive intentions are never enough. To win in a world as cutthroat as politics (it was cutthroat and dirty before Trump, believe it or not), or whatever industry you’re in, you have to know how and when to play dirty.

When to quietly bend the rules.
When to create and/or leverage an unfair advantage, win because of that advantage, then pretend like it was a fair fight all along so you look like a hero (everyone does this. This is the pro basketball player who tells a room full of teenagers that hard work was the key to his success, while conveniently ignoring the fact that being 6’9” helped a bit).
When to use aggression to back people down and move them out of your way (if you’ve never done this, you probably need to start using it).
When to lie and cheat and steal — not to harm anyone else, just to help yourself (you don’t have to admit it out loud).

When to prioritize doing the thing that works over the virtuous and just thing — so you have the time and space to eventually do the virtuous and just thing (this is how Lincoln got the Civil War to happen, and used the war as his pretext for ending slavery when it looked like the Union had the win in the bag).
The truth of life is, the players who are willing and able to play dirty are the players who often win.

"The truth of life is, the players who are willing and able to play dirty are the players who often win." 

WRONG, Dre!!! What about those who do things the right way — and have a clean, positive image to back it up?, You retort. You even go so far as to name names.
Read Law #24 of The 48 Laws Of Power.
These “clean image” people aren’t innocent — they just, unlike Trump, know how to keep their hands clean when playing with dirt.
Even better, they get other people to handle that dirty stuff, while they continue playing up the squeaky clean good guy/girl image to the public.
Don’t feign offense at the idea.

If we were to dig deeper into the biggest successes of your life, I’m sure we’d find something objectionable about it that you wouldn’t want on the homepage of CNN tomorrow morning. Nothing illegal or against the rules, per se — but something that you’d rather take with you to your grave than make public.
Go ahead, tell me I’m wrong.

(waiting…)

The winners in life can be hard-working, positive, helpful, and good-spirited. I’m not telling you to lose those qualities of your character. I’m telling you that that stuff by itself will leave you frustrated and coming up short to people less worthy, in your estimation, of success.

Learn to play the game. Then, learn when (and when not to) play a little (or a lot) dirty.
Your victory depends on it.

"Learn to play the game. Then, learn when (and when not to) play a little (or a lot) dirty. Your victory depends on it." 
#929: How To “Cheat” To Win