52 Learnings from a Conversation with Robert Greene

I recently had the privilege of speaking with New York Times bestselling author, Robert Greene, who you might know as the man behind books such as the 48 Laws of Power, Mastery and the Art of Seduction.

We had a one-hour long conversation for the Future Squared podcast, exploring themes from his brand new, and sixth book, The Laws of Human Nature. The episode was so jam-packed with learnings that I decided to distill my notes of key learnings from the conversation into this blog post. I’ve sprinkled my own observations and examples of how these learnings apply across a number of domains.

You can listen to the entire episode below or find Future Squared wherever you get your podcasts.

The Value of Broad Experiences

  1. Greene had almost 80 jobs before he became an author, including construction worker, translator, Hollywood movie writer, skip tracer and magazine editor. Greene credits these broad experiences with providing countless inspiration for his writing, having brought many of these experiences to his first book, The 48 Laws of Power. . “You want to know as many different people as possible and have broad experiences”.
  2. While operating as a skip tracer, Greene learned about the power of deception, a discovery that would later inform much of his work, especially his third book, the Art of Seduction.
  3. “Everything is material”: Greene says that he can use almost anything he sees or talks about in his work, including things I might’ve said during our conversation, sometimes years later. Comedians such as Steve Martin say the same thing when it comes to collecting material for bits. There is humor everywhere, you just need to look for it.
  4. Like former Future Squared guest Mick Wall, Greene says that grimy jobs, such as his skip tracer role, helped to develop his resilience and patience.
  5. By having many broad experiences you not only get closer to learning what you do like and where your natural strengths and inclinations lie, but you also learn what you don’t like (in Greene’s case, the ‘politics and bullshit’ that underpinned Hollywood scriptwriting).

The Power of Purpose

  1. Greene says that he got closer to his true purpose thanks to his broad experiences. He says that the empathy he built for common people forced him to want to help them via his books.
  2. Too many people go through life with a false purpose, driven either by money, social status, ego, a sense of self-worth and so on. What they do usually doesn’t align with their natural inclinations or strengths so they ultimately wind up miserable and unfulfilled.
  3. Following your passion isn’t practical, as more often than not, it’s probably not something that will make you any money.
  4. In order to follow your purpose, go where your brain naturally heads, what excites you and what you love to invest countless hours learning about.
  5. “You can’t learn quickly unless you’re excited about the subject”.
  6. Sometimes you need to become ‘very frustrated’ to learn what you don’t like and take action. “In my early 30s, I was writing screenplays for directors and realized that this wasn’t where I wanted to be. I was given a chance to write a book and I was so motivated, so hungry, so desperate (that I made it the best book I could write). Sometimes you need to feel a sense of urgency or as rapper 50 Cent put it, you have to find it ‘or die trying’. This also echoes what Plato put forward in The Republic on the notion of ‘no philosophy before 30’ because you hadn’t struggled enough yet.

On Business and Creativity

  1. Build a business around what makes you different from other people, not similar.
  2. Use your twenties as an apprenticeship and accumulate skills, perhaps two or three strong skills, work across different fields and have broad experiences. This will make you more creative and help you determine where your purpose, strengths and true inclinations lie. Take advantage of that.
  3. Your prime creative years are your early 30s.
  4. If you persist at a problem long enough, you will solve it. This could take hours, days, weeks, months or years. It’s how Einstein and Edison did their best work.

On Unmasking Someone’s True Character

  1. About one in ten people you meet will be toxic people. You will inevitably encounter them and they will make you miserable. You need to develop social intelligence to better navigate the world and toxic people.
  2. Most people are wearing a mask (how we show up most of the time) and we all have a shadow (our true self that sometimes makes an appearance).
  3. Be observant of what people say and do to become a better judge of their true character.
  4. ‘Out of character’ moments are often a revelation of one’s suppressed true self, when the mask essentially falls off.
  5. To help identify one’s true character, watch out for micro-expressions, contradictions, words used, their tone of voice, their smile or lack thereof in the split second they first see you, the way their eyes and body posture respond and so on. This can often tell you a lot more about a person than what they tell you themselves ever could.
  6. Watch out for the counterfeit “yes”, when people say yes to something because they have an innate desire to be liked and to not hurt your feelings or feel uncomfortable. This often shows up in business where a prospect might say that they are interested in working with you but never return your calls or emails after your initial meeting.
  7. We are all voyeurs — which is why we have a natural inclination to people watch.
  8. Try to glean something from someone every time you interact with them, particularly from their non-verbal cues. Make it fun. You’ll be surprised how much you can learn about people you’ve known all your life. Practice this skill. Like training a muscle, it requires many reps before it starts to become second nature.


  1. People fail at the influence game because they are too focused on themselves.
  2. Focus on the target and their self-opinion (eg. “I’m smart, in control, moral”) and play to that when trying to influence them.
  3. Never outshine the master.
  4. With ego comes insecurities. You can influence people and get buy-in by focusing on what they are uncertain about, things they are unsure are true. For example, former Disney executive Michael Eisner valued creativity but was insecure about his own creativity (or lack thereof) so if you wanted to get him on board you’d play to that insecurity by talking up his creative talents. On the flipside, you don’t want to use this where somebody is absolutely sure they don’t have the requisite attribute because then they’ll see right through it.

Strong Opinions, Weakly Held

  1. Greene has a background in history and philosophy and credits the likes of Socrates’ “the more I know, the more I know nothing” in shaping his world view. He subscribes to theories like Marc Andreesen’s ‘strong opinions, weakly held’, as well as Plato’s dialogs, in asserting that we are ultimately ignorant and that the path to wisdom is understanding that we don’t know anything.
  2. It takes time to arrive at the truth and oftentimes we only end up being ‘more right’ than before but not ‘absolutely right’. There are so many variables that it is almost impossible to be absolutely right. You must assess all of the variables to move to the best version of the truth.
  3. Despite all of his success, Greene is humble and says that although he has done his best to avoid it, there is a possibility that some of his work has fallen victim to the narrative fallacy.
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  1. Greene is an advocate of Sun Tzu’s concept of a position of ‘shi’ — putting yourself in a position of strength where you can execute on plan A, B, C, D. For example, a boulder atop a hill that can be rolled down in multiple directions in the path of unsuspecting adversaries. In the investment world, having a balanced, diversified portfolio of liquid assets might be an example of this, and better than having all of your eggs in one illiquid basket.
  2. Great generals succeed by harnessing the unorthodox and coming in at an angle that others don’t expect or haven’t though of. For Rocky fans, Rocky fighting right-handed when his adversary, Apollo Creed, expected him to go left-handed, is a simple example of throwing your opponent’s gameplan off with the unexpected.
  3. Former US fighter pilot and military strategist, John Boyd, coined the term OODA which stands for ‘observe, orient, decide, act’. The shorter your OODA loop, the faster you learn and make decisions. In strategy, you want to shorten your OODA loop to get inside your competitor’s loop and outflank them.
  4. French military general, Napoleon Bonaparte, was a practitioner of ‘controlled chaos’. A well thought out strategy for the French, but chaos for adversaries. He often did this by leveraging a tight OODA loop and empowering his men on the ground with a mission but leaving the details on execution up to them. In the entrepreneurial domain, this amounts to rapid experimentation across your business model, sales strategies, marketing strategies and so on, in order to figure out what works the best.
  5. The source of Napoleon’s brilliance was his organization. “His brain worked like a modern computer and he could take vast amounts of info and organize it in a meaningful way and make vastly better decisions as a result”.
  6. Strategy is not the same as tactics; strategy is art.

On Activism and Moral Righteousness

  1. Many people are looking for a fast-track to moral righteousness without doing the work. This can show up by way of activism for a cause as well as putting people who have achieved great things down by pointing out some flaw that may be true or not. Fans of Ayn Rand’s Atlas Shrugged will have observed this in Hank Rearden’s family’s behavior.
  2. Conviction Bias: when we say something with conviction we assume it’s true; the more outrage and anger, the truer I am, however…
  3. The more certain and loud someone is, the more suspicious you should be. Nobody should be that certain of the truth, because the absolute truth — more often than not — is beyond our reach. This is especially poignant in an age of divisiveness between the far left and right.
  4. Humans are essentially irrational and 95% of our decisions are governed by emotions. This is in large part driven by the primal fight or flight parts of our brain that evolved over thousands of years to help us detect threats and quickly respond. This is also why our brains become aware of negative stimuli faster than we become conscious of it and why we hold on to negative emotions for longer than positive ones.
  5. To be truly rational in the face of external stimuli or the need to make a decision, you need to take a step back and increase your reaction time. By doing so, you allow the emotional cobwebs to clear and then you can use your pre-frontal cortex to make more rational decisions. For example, don’t respond to an email that irks you immediately, instead sit on it for an hour or more and come back to it when you are thinking clearly. Throwing fuel onto a fire rarely has positive outcomes.
  6. Greene is an advocate of Ancient Greek politician Pericles who put rationality above all else and knew that emotion often clouded our judgment, critical in a domain awash with emotion and public sentiment.
  7. Emotions lead us inward, not outward. Pericles worked to remove himself from tribalism, and instead focus on best outcome for people of Athens.
  8. Train yourself not to react. Resist it.
  9. It is not worth getting into fights with people who are more passive aggressive than you.
  10. ‘Focus, focus, focus’: The motto for most successful people, be it Leonardo Da Vinci, Thomas Edison, Steve Jobs or Warren Buffett.

On Focus, Technology and Social Media

  1. If you can’t focus in today's world you are doomed. Social media is a detriment and hurts your ability to focus. You should be intentional about creating time away from it. Facebook, was about capturing attention and keeping them addicted,d not connecting people.
  2. Greene practices Zen Buddhism to give him a clear head and help him to focus.

On Leadership and Entitlement

  1. “Make them want to follow you”. As with Queen Elizabeth I or Marcus Aurelius, it comes down to the examples you set, not what you say.
  2. Get over the sense of entitlement that comes with the power of a leadership position. You have to earn that privilege every single day by what you do and say.
  3. The moment you feel you’re entitled, you are doomed. People hate entitlement and want to follow empowering leaders
  4. People who inherit power are usually the worst kinds of leaders

This is just scratching the surface of what you will learn from Greene’s books, including his latest magnum opus, the 600-page Laws of Human Nature, which The Guardian called “illuminating”. To find out more and pick up a copy of the book, head to Amazon.

January 15, 2019




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