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Hi. first of all, all the best for you trip.
i have already done trip like this so I'd say it is not impossible to go penniless but it is surely very difficult. Try going alone or with just a partner(not a girl preferably) because cars dont give lifts easily, trucks do mostly and they dont give if there are a lot of people. (max two) Carry as least weight as you can because there'll be time when you'd have to wait or walk for hours (i hope it doesn't come true, but still...) Try keeping a taser in case you have to sleep in a jungle or an open area. it might help you in worst cases. Just for self defence.
And at last it would be really life changing experience. you can read my trip below. how i did "Delhi - Leh Under 2250 INR"
https://www.tripoto.com/trip/leh-couldn-t-have-been-597823ff239db
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Okay, I see where you're coming from but please remember that this is India and make sure you take care of your safety first. Carry pepper spray and knives. This is not Europe, so people will definitely try to shank you and take your kidneys away. Honest advice, do not let your guard down and all the best.
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