I have a thimble that was my grandmother's, and its worn so smooth on the inside, it's very comfortable. If you can find a thimble that fits snuggly on your finger without being too tight, that will be a start. Mine fits so that I can stop sewing, perhaps look up a pattern, cut more thread or even pet the dog, and the thimble won't come off - I hardly feel it - almost like its a part of my hand. If you can find a thimble like that, it will be easy to just put it on and use that finger to push the needle through. I also have some cheap thimbles that are rough, too loose or pinch. I use them if I am stuck somewhere without anything else, but if that's what I thought a thimble should feel like, I'm sure I would give it up, too. Look for an antique thimble that's " broken in" like mine is, and perhaps you'll give the thimble another chance.