The art of truth, awareness, and the perils of prescriptions


Last weekend, I listened to an 1 illuminating conversation between famed entrepreneur/investor, 2 Naval Ravikant, and his personal coach, Kapil Gupta, and it inspired me to turn the insights into a summary.

What’s interesting about Kapil is that he has a no-bullshit, unrelenting approach towards the truth. Even though I’ve read all his books and I been listening to him for a couple of years now, he makes me uncomfortable with his directness and he is not the easiest person to stomach. And this is why I like him. You get the sense that he genuinely doesn’t care what you think of him and therefore isn’t playing any games whether it’s persuasion or status. What a breath of first air.

I wouldn’t recommend him to most people but if you’re into truth-seeking and awareness, then you just might find this thought-provoking and challenging.

You can read the original thread on Twitter

P.S. All inaccuracies and misinterpretation are my own.


1/ Seeking the truth is not an abstract, intellectual concept but utilitarian in nature. It’s an essential pursuit if you want to perform at the highest level.

2/ To excel in anything you do, you must ignore prescription and explore the edge of your art, where you are creating and forging your own path.

3/ Prescriptions are how-to, hacks, techniques, and methodologies to help you get somewhere. They are useful for mechanical tasks, e.g. learning to ride a bike, but if futile you want to be at the tip of the spear. Don’t mistake the finger pointing to the moon for the moon.

4/ Greatness is murky, non-linear, and unpredictable (possibly by design). The way to get to it is by jumping in, flailing about, and living in its confusion. If the obsession is there, through a messy process you will find a way.

5/ Ask someone to retrace their steps to success by mimicking themselves and they will fail. Whatever people can articulate is merely a sliver of what’s conscious and available to them. Often, there are important details that are invisible to even the person themselves.

6/ If you follow the highlight you will miss. Mastery lies in the small details and they are usually unknowable or untransmissible.

7/ The thing you do greatest you know not how to do them. One can argue that you are not even there. Often, what arises from authentic self-expression is spontaneous and it is surprising to us as much as it is for the audience.

8/ Everyone is looking for truth whether they profess it or not. We are all looking for a way out of our problems. One does not need to have the desire to be the best in the world to be held back by prescription.

9/ What we really want is freedom from our problems but we’ve been sold (and bought into) the idea that prescriptions are the cure.

10/ Truth is a demanding discipline, especially in the public domain, because it requires vulnerability, to say things that are socially unacceptable, and to disregard scripts. It’s tough to do this because the voice in our head wants the audience to understand and to like us.

11/ A person asking for how-tos usually isn’t serious; if you’re serious you’ll find a way. Even though we may beg for the prescription, we inherently resist being told what to do. You can observe this by why we don’t change despite having the necessary information.

12/ The prescriptions themselves aren’t bad or useless: if you want to feel calm for 20 minutes then meditation might be a good tool for that. However, if the desire is to be at peace all the time, it is fundamentally a different question that leads to a different answer.

13/ It’s never about the words, but where the words are coming from. Don’t try to find out what to do but seek to understand through quiet, serious examination on what’s being said.

14/ The remedy is found by examining the truth. To discern the truth, begin with what’s always true and go from there. For example, a truth is that every person has problems in life and everyone has specific problems that are more acute to themselves than others.

15/ Any freedom that leads to the desire for more freedom is not freedom. We think of freedom in material and physical terms and rarely in the form which ails us: the persistent, ambient level of anxiety that follows us no matter where we go and what we have achieved.

16/ The problem always arises in the individual. There is no problem outside of yourself. All conflict is self-conflict. Notice how whenever you have a problem in life, you’re there?

17/ Circumstances do not cause pain, it reveals it. As long we are invested in the belief that circumstances cause our suffering, we will be trapped in a vicious loop of trying to fix the circumstances – which is a fool’s game because it is always changing.

18/ The solution to any problem is never the solution — it’s always the problem. Nature has hidden the solution within the problem and if you want to find a way out you have to go deep into it.

19/ Freedom comes from the understanding of where things come from, not the conscious attempt to end them. Often, a prescription is so subtle that any attempt to follow it removes you from the solution.

20/ Invariably, we treat the symptoms and not the disease. The point is not to find different ways to soothe the wound, it is to close the wound permanently and directly.

21/ Society has normalized the idea of endless treatment and practicing forever. We have accepted that self-improvement means working on ourselves continuously with no arrival.

22/ Contrast that with making money. Money is practical, we want to make money to spend it while we’re young and alive. No one wants to wait for eighty-years to make money. We want to arrive.

23/ Contrary to popular self-help/spiritual advice, it’s not the journey but the destination that matters. Everything you do in life is defined by the destination. If there is no compulsion to arrive, there is no journey.

24/ The real problem is that most people have prescriptions as the destination. Everyone is trying to dive into the prescription. Everyone’s impetus into the game is the should and the should not, the good and the bad.

25/ The truth requires transcending concepts and shared narratives such as duality (right or wrong) and morality (good or bad). Authentic self-expression is limited in tight, predefined boxes.

26/ If you possess the genuine desire to solve a problem, rules are to avoided at all costs, e.g. Stoicism has rules. When we follow rules, we not only cede our locust of control but we are also being disingenuous in the pursuit of truth.

27/ All progress seeking is pleasure-seeking. We are trying to get pleasure from living up to a self-image. Pleasure-seeking is a truth in itself, and it’s neither good nor bad, but it leads us down a different path.

28/ Be careful of building up any idealized self-image, be it someone who is good at solving problems or wearing an orange robe meditating in total equanimity.

29/ If you create an image of a person who is better and finds pleasure in progress, inevitably, when setbacks occur and pleasure is withdrawn, you’ll realize that your “freedom” was illusory. Freedom cannot be attained if you’re trapped in the game of recording little gains.

30/ It all circles back to: Do you really want to know? Or do you want to keep playing the shell games of pleasure-seeking?

31/ If you’re genuinely interested in doing something, do it for its own sake without any expectation or validation, internal or external. The greatest desire always win. Often, the quickest way to get over something is to do it because suppression leads to regression.

32/ As a teacher, it doesn’t matter if inspiration lasts within others, the real problems arise when there is a desire to inspire others. When you try to inspire someone it’s mostly about achieving significance in your own mind, whereas if you were free you would not care.

33/ Ultimately, understand that the mind loves keeping us entranced in games – it doesn’t matter what game, spiritual or material – as long as the mind has you captured playing a game it’s fine.

34/ When you realize that it is the mind that is generating all the problems, you’ll see that true freedom is freedom from the mind.

35/ No technique of the mind will free you from the mind. Freedom is to be free from the mind, hence, to attain freedom, you have to look beyond the mind.

36/ The simplest, direct way to arriving at truth without lifting a finger is all about exposure. Our mind is like a tuning fork, if we are exposed to truth constantly, over time we will internalize it and resonate at a new frequency.

37/ It’s critical to savagely and surgically arrange one’s environment in a way that is in accordance with where one wants to go. The human body is capable of treating itself as long as you take care of the input. No medication or therapy needed.

38/ Our mind is a powerful tool, but only if you give it free rein to roam instead of restraining it within the confines of your flawed definitions.

39/ Don’t follow prescriptions mindlessly like an automaton. It’s not about watching your thought, it’s about noticing yourself catching your thought. That is enough. Fires burn themselves out eventually as long as you refrain from fuelling it (with your thoughts).

40/ The simple act of understanding with awareness where it’s going, and not watching it like an automaton, is enough to poke a hole in the illusion. Do it enough times and you might tear a hole and see through it.

41/ You know you have found the truth when a problem is solved for good. When you don’t have it anymore. To solve for freedom, always examine the truth no matter how unpopular or un-transmissible it is.

42/ How do we know that the search for truth and understanding isn’t another shell game invented by the mind? Where there is sincerity or seriousness, that in of its own becomes an instrument of examination.

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