After a long search, I feel like I finally have a really good road pump. Lezyne makes amazing pumps. I have a version of
this pump and I love it. What I like the most about it is that there is a flexible hose the comes out of the center of the pump and screws onto your valve so that when you're at the side of the road, pumping like crazy, no matter how much you wiggle the valve connection holds and doesn't leak air. Also the pumps get up to 100 psi pretty easily. It's easily small enough to fit in a jersey pocket. I have one that is small enought to fit into my seat bag.