Why don’t more people roll their carry-ons like I do?

The only problem with this method is that the briefcase straps can slide off the back of the bag, unceremoniously dropping the bag some distance (depending on the length of the strap). I do this but have a little strap that holds the briefcase shoulder strap sides together in the center of the bag.

I will give the low hanging option a go, for my flight tomorrow in fact. I have put my cabin bag on top and, over the handle using the built in cuff/band and, yes it is top heavy and, I had to re-fix it a couple of times when it swung right around. So even the top loading method isn't without it's frustrations. In response to the couple of commenters re: traveling lighter. Here in Australia Qantas and Virgin carry on bags are restricted to 7kg with one personal item to a total of 10kg. But Jetstar, like Ryan Air, the total carry on limit is 7kg. If your bag itself is 2/3+kg that leaves less than 4/5kg for clothing, toiletries, shoes, digital etc. I can only ask how they can pack enough for a week. I really have tried and have had to either pay for extra weight or lighten my load because my scales at home were calibrated different to the check in counters. I am Not going away on holidays and have to wash every other day in the interest of 'one bag/no checked bag' travel. Or without a handbag which can be anything from 2 to 5kg. So doing the maths you are saying: 7kg limit - 2kg [min] handbag + 2kg cabin bag = I can have only 3kg total for all my possessions for a week/month/year??? I do try to limit my 'just in case' items and have minimised my toiletries and digital but still struggle to do the one bag thing for any trips lasting longer than a week.

I'm a semi-pro photographer and travel constantly with heavy carry-on gear. What you need is this handy little shoulder strap from Think Tank Photo. It has split strap design that allows you to carry an second bag suspended low, as you show above,but securely held to the roll aboard handle. https://www.thinktankphoto.com/collections/camera-straps/products/low-rider-strap Think Tank gear is the bomb, designed to hold much heavier weights than standard carry-on gear, so you can travel with confidence that your laptop won't end up in pieces.

From a super traveller which I am... Very simply, your method has a tendency for 1) the bag to drag on the pavement destroying it 2) the bag to flip around and get caught under the wheel, or just to be a general nuisance 3) If your taller than 5'6 then the strap will be too long to suspend the bag off the ground. Your choice is to keep your bag with an unnaturally short strap or to constantly adjust it when you use it. This is a hassle. 4) many "on the handle" bags have a sleeve to fit over the handle securing it from all of the above problems. having it on the top handle allows you the have a hand on the handle of the bag as well as the handle of the roller board. Also, you have access to your bag (which probably holds things necessary for boarding, phone tickets etc). You can feel it so it does not fall off. Yes it is "heavier", but I'd rather do that than have a destroyed bag or destroyed laptop. You can only use your method if you have a real clip securing the bag in place. Just dropping the shoulder bag strap across the top is a disaster otherwise.

A good suggestion: just don't carry so much stuff with you, travel light! You don't need half your household when travelling. Simple as that. 12-15kg checked in, regardless of the length of your travel and bare necessities as carry on-just in case your 'checked-in' does not make it. My heaviest carry-on is my camera bag, but that's me. It gives me the willy-willies when I see the sh*** some pax carry on board - yes I am talking of the disrespect towards other pax on the plane by hogging half or more of the overhead locker. Remember this next time you fly. Happy travelling