>>43824805With how low your pokemon are, you're going to have to or you're gonna get bodied before you even reach Claire
Don't rely on getting experience from just trainer battles. Fight wild pokemon and genocide the local populous. That's what you should've been doing since New Bark Town. The time flies. And once you're not getting as much exp from the mons on that route go find another route with higher level mons than the previous one
If you're already at Cianwood you can go bacl to Goldenrod and try out the Bug Hunt. I've used that multiple times to just train my strongest. Extremely easier with a Flying or a Fire since you're just roasting bugs
And while you're there you can get a Scyther. It's a win-win
Hell, after you found the Headbutt tutor in Ilex forest you should've gone back to Violet and headbutted a bunch of trees. Or just headbutt trees in general
Also you should have the Good Rod by then I think so fish my guy. Nobody will attack you for killing off all the fish
Also, before you challenge a gym, save at the entrance or after you're killed all the trainers inside but the Leader. If you fight the leader and lose, reset. Then just leave and train up the bois and come back. Instead of having to buy more items after each loss and losing cash money. Your funds are limited early on
One last thing: If you're still having trouble, head back to Goldenrod and play Voltorb Flip