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Yes, habits are hard to break. To give an example from my own life: I used to want to organize trips down to every last detail before leaving home. My wife is more impulsive and spontaneous than me, and as such just wants to take a train or bus someplace and discover what's there. She doesn't want to research the bejeezus out of it first. I'm slowly coming around to this way of thinking. I still research minor things like transportation--and accommodation if it's an overnight trip--as a fall-back, but I leave a lot more of the trip to chance. Pulling myself out of my habit (comfort zone) has opened me up to a new and wonderful experience.
(I like your device progression. Mine was Handspring Visor Deluxe --> Sony Clie SJ-22 --> Palm Tungsten E2 --> Samsung Galaxy S. I haven't bought a tablet or dedicated reading device.)
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