I've just finished up school and am now exploring the tech/start-up industry now (a.k.a entrepreneurial endeavor) so my requirements are pretty flexible. I just need something that's versatile, durable and comfortable- and preferably not ugly. I thought the rucksack might fit the description.
The briefcase seems great but I've always had some shoulder problems with messengers and it doesn't seem as grab-and-go as the rucksack. Maybe I'll get a Filson briefcase further down the line.
Should I reconsider pulling the trigger on this?
Well, from what you're looking for, the rucksack is definitely durable and aesthetically pleasing . However, in terms of comfort and versatility I personally would not recommend it. Unless you plan to pack light every time or carry the bag for short amounts of time, the narrow bridle shoulder straps can get quite uncomfortable along with no back support. On a heavy load, I found that the bridle straps begin to dig into your shoulders and it also pains your neck. Also, the two leather buckles can get quite tedious if you need to access your bag frequently (I just left it undone most of the time).
Currently for school I rotate between my Filson 256 and a Deuter backpack (for heavier stuff). The 256 can get heavy as well, but when it does I just carry it by hand.
I think this might be more suitable for you - http://store.archivalclothing.com/products/copy-of-archival-rucksack-gray-waxed