Because Sadhguru constantly grabs your attention with his contradictions.
Let me explain. But first a micro-dose of Evolutionary Psychology:
When humans evolved in to a separate species in the prairies in Africa we also acquired a new skill - ability to judge a person or a situation. It helped save lives - the rumbling leaves could be a squirrel but it could as well a rattle snake. Millions of years later, we now live in concrete jungles but rumbling leaves still kindle our attention. These also got us pre-conceived notions about things around us. When we hold them individually its called a stereotype and when it's in the collective psyche they are called archetypes.
Now when you think of a Guru, what comes to your mind? Someone like this, who will bore you to death with his teachings and wisdom (random picture from Internet; no malice intended).
And when you think of a comedian, who comes to mind? Perhaps Russel Peters, who will make you laugh until you cry but has no wisdom to share.
Sadhguru is both but neither at the same time.
When you watch Sadhguru on TV or in real life, your mind is constantly trying to judge and stereotype him. But Sadhguru slips away from your stereotypes like ice slipping on a tray. When you expect a wise answer, he gives a witty one and when you expect a witty answer, he gives a wise one. Don't believe me, watch the rapid fire round with Karan Johar.
So in the end, when you watch Sadhguru you may have gained a little bit of wisdom by actually laughing through it. How common is that?
And these contradictions spill over to real life too. One day you see him riding a bullock cart and the next day he is flying a helicopter. One day he is talking with a scientists at MIT and the next day he is playing with kids in a village in Tamilnadu. All the while your mind is going crazy trying to fit him in to a large enough box.
Osho was another teacher who would confuse the hell out of you. When you listen to him talk about Krishna, you would think he is Krishna. When he talks about Sufism, he sounds like a Sufi. And Osho contradicted himself all the time. When talking about Jesus Osho would say Jesus was the greatest master and when talking about Buddha, he would praise Buddha as the greatest master. When asked why he always contradicted himself, Osho would say "What I am saying in the present moment is the truth. What I told before may not be true and I don't know what I am going to say in the future".
This is how a true master should be. If you want to feel good then go to a therapist or give your mom a call. Don't go to your master to prop up your ego. If any thing, a master will keep you in your toes and destroy your ego. Zen stories are full of ruthless masters who acted like thugs.
And remember that you too can master the art of contradictions.
For every character trait you have there is a default complementary character associated with it. If you are smart, for example, your default nature is to be confident and perhaps arrogant. Instead, if you become deliberately and consciously modest then you have used the art of contradiction to your advantage. Or if you are really really wealthy your default complementary character is to splurge the money. Instead, if you live frugally and spend it on charity then you are in the rare breed of people like Warren Buffet.
To conclude, here is a picture which is worth a thousand or so words.
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