My optometrist taught me my air bubble popping technique and it has a pretty high success rate.
Simply put a finger on the skin underneath your eye (you know, the bit where you can feel the edge of your eye sockect) and push up. Completely pain free, easy, and it will shift the contact just a little bit and pop any bubble. I do this and the contacts tend to only fall out when I’m too slow doing this.
Scrub your hands with soap THOROUGHLY before putting one in no matter how clean your hands or the contact is. Even if your contact’s completely sterile when you get it out of the solution it can become dirty enough to cause you pain just form the acids and dirt of your fingers.
Put in your contacts in very good light (I use direct sunlight) and look at the contact with your glasses on (I wear them at night and in the morning anyway) - this way you can actually see if they have dirt on them pretty easily. If there’s a little dirt, squirt cleaning solution over the thing, just enough to wash it off. If there’s a LOT of dirt, empty your contact case, pour completely new cleaning solution in and dunk it in there for about a minute, while you do your other eye.
You’d be surprised how much difference it makes to the whole pain thing.
One more tip just for free:
If while wearing the contacts you start blinking a LOT more, your eyes are trying out and the contacts will probably fall out within an hour. To combat this, just get saline or cleaning solution, go to a mirror, stand in front of it, and use it like an eyedrop. This will keep you going for hours, and all you have to do is carry a small bottle with you.