I do not like briefcase and I would rather use my backpack for hike .  i use the messenger bag for work all the time . I have not use it on my bike but it be extremely comfortable . I carry my laptop , PDA , and file with I . there be plenty of pocket . do not overstuff it or else you will have a hard time close it and carry it around .  it have a quality feel and the stitching be very good . the flap be waterproof and have a strap to mount a blinking lead bike light . the laptop holder be pad and have a clip strap to keep it from fall out . the cellphone pocket be a little small . it have a nice key clip but my key jingle a lot when I use it . the outer drink holder work well for pop can and water bottle .  I wish it have a additional hand carry strap but so far I can live without it .