“Hi. Ummm, I love your bag!” the blonde said as we waited in line at My Secret Cafe’ in Town, a popular digital-nomad coffee joint/work space in Chiang Mai, Thailand. “So much character,” she added, running her fingers over the leather. “How many countries has it seen.”

How many countries? God – no clue. Two dozen? Probably more. Five continents, for sure. I bought it because I realized at some point that I was actually a grownup, and I didn’t want to head into meetings around the world with a backpack. I wanted to look like I had a real career, even if most of that career is spent working in coffee shops from Prague to Punta del Este. A messenger bag does that for you – lends an air of professionalism with more than a hint of coolness … exactly the aura of this Satchel & Page Messenger Bag, based on US Postal Service mailbags from the early 1900s.