I am a very frequent traveler... at least compared to many. I assume you will be flying?
I agree with raaawr, get the full size carry on and pack lighter. Also... if it is a full flight, small regional jet, or you just don't want more hassle... you can plane side check the bag for free and they will send it straight on to your destination just like a checked bag... but without the fee.
Rolling you clothes, rather than traditional folding, will keep more of your clothing from getting wrinkled. Wear comfy clothes on a plane... try shoes without laces, no belt, and no jewelry is best and fastest.
Wear one headphone at the airport with music playing softly. If someone tries to swipe your phone from you pocket/ bag it will disconnect the jack and you will know immediately.