It's really good to have a floor pump with a pressure gauge dial and a little "wing" stand that you put your feet/foot on to steady- keep that pump in your garage or wherever you keep your bike. That's the pump you'll mostly use to pump up before you ride. It shouldn't be that difficult to pump the pressure up on it.
The smaller portable pump is the one you take with you for flats- that's the one that it can be a bit harder to get the pressure up by pumping with your hand. It may not have a gauge. It can be compact, might telescope, or you can attach it to under your top tube, or along your frame parallel to your water bottle cage.