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A common travel tip from road warriors is to avoid checked luggage as much as possible. It adds extra time to both ends of your trip, has risks of getting lost and, for most airlines today, additional expenses. The solution is to have just a medium-sized travel bag that you can always carry-on. If you're travelling for an extended period of time that could mean having to pack a lot of stuff, and that needs to be done strategically.
About a year and a half ago, we shared this video that showed you how to pack for nearly a month in a carry-on. Recently, we found this video from Men's Journey. It provides packing tips for those travelling for less than a month, but also who want to use a smaller bag.