I never ever check bags unless I have gear (skis, climbing gear). My main carry-on is a 21" Rimowa Salsa Air Ultralight (upgrade from the Salsa Air). My second bag is a large tote or cross-body (Valextra Babila, Longchamp Le Pliage, or Bottega Veneta medium Gardena).
The Rimowa holds my clothes and shoes. The personal bag holds toiletries and other things I need during the flight - noise canceling headphones, a pair of socks, shawl, etc... Easy peasy way to travel as I only have to worry about two pieces. I'm off the plane before everyone and through passport control before anyone else.
I usually have to remind the car service that I'm usually through security quickly so I don't have to wait for them. Last time I had a new driver and he said he'd never seen anyone get off the plane and out of the airport so quickly.