I won't say buying my old hybrid was a "mistake", but it was definitely an uninformed purchase. I just paid attention to what was popular back then, marched down to my local LBS, and said I wanted a hybrid. I suppose the LBS staff could have taken the initiative to ask how I planned to ride, etc. but I was pretty determined that I wanted a bike that could "do a little of everything". Back then, hybrids were more of the modified MTB style than they they are today.

Well, the bike could do a bit of everything, but not much of each exceedingly well. I went in thinking compromise, and that's what I got. I'm not a bike guru, but judging from what I see these days as hybrids in the LBS, I'd say hybrids have definitely evolved into a truer and better performing all purpose bikes.

If I had some advice to a new bicyclist, I'd suggest he or she leverage friends who are really knowledgeable about bikes and have some different styles of bikes: talk to them and to try out their bikes. Cyclists LOVE to talk about bikes... especially THEIR bikes. If you can, hop on them and take them for a spin - even if the size is a bit off, it will give you a feel. Go to a reputable LBS and try out different bike styles: road, hybrid, commuter, urban, etc. Rather than spending a lot of money on a single, all purpose bike, it might be worth getting two, less expensive bikes - say a road bike for those times you want to just go, and more robust commuter bike for daily rides to work.