Two tricks to help you.
1. Find the knife that really carries well in your pocket. So well that you don't even know it's there. It also helps if it's one you like to look and and just sort of run your fingers over and use as a worry stone.
2. Leave some of the others laying around on your desk or space and just play with them. Don't do serious EDC cutting with them, but have some bits or leather, jute twine, or other stuff to cut purely for the purpose of cutting. It's not really cheating because you aren't using those knives to do chores with. You are simply, no other word for it, playing with them. HOWEVER... If you suddenly reach for a letter to open, STOP! Reach in and pull out that one EDC knife you're carrying and use it. Then go back to play time for knifeheads.
A knife that carries comfortably and almost unnoticeable is important. That doesn't automatically mean smaller knives. Personally I'm the odd man out in that I generally find the standard Barlow pattern does not ride well in my right pocket. It rides down into an angle that jams up with other stuff in my pocket and I can feel it lumped up there. Yet, a long, single blade Granddaddy Barlow like my Remington Musket-1 (bone scaled version) slips in my right front jeans pocket and the shape and size holds it neatly along the seam and it is very comfortable to carry and I don't notice it until I need it. I stopped carrying and even sold some stag scaled Bokers I had because the stag versions were just too heavy and noticeable in the pocket even though the same pattern in bone or Delrin didn't bug me.
In addition to that Gramps Barlow a few patterns that I have found carry neatly for me are: Peanut or similar jack (of course), a slim, Queen single blade jack (I've carried that one for long stretches nearly as much as my EDC and it's first runner up in the always carry category), and the slimline single bladed trapper. In this case a Case Yellow Handle CV.
One that was also surprising to me for easy carry when it didn't look like it would, is the Remington Lumberjack Moose. I don't recall off the top of my head which year, but it was a Bullet Knife one year. For whatever reason, it disappears into my pocket among keys, and other stuff and finds just the right spot to nestle in out of the way.
I'm not going to join you in the challenge, because as noted in a few threads here lately, I've been carrying a Case Smooth Chestnut Bone Mini-Trapper for a year or more. It's just there as "my pocket knife." If I'm doing something, especially if sitting, I might just reach for a knife that's out and close rather than dig in my pocket for convenience sake. The simple fact is I do have to dig because the Mini-Trapper slide right down like that Moose and lines up with my lighter and carabiner and paracord keyring all stuffed in my pocket and disappears from feel. I sometimes have to reach in and bounce things around a bit or finally just pull the whole pile out of my pocket to find it. It carries that well.
A note on the Soddie. First, when getting back into traditional knives the Case CV "Yaller" was the first one I got. I forced a patina and carried it with me. I cut food with it and carried it in my pocket at work and home in the San Antonio area summers and I sweat. I would just wipe it down (wipe the food off of it) after use. Every week or so I'd wipe a dab of mineral oil on it. If I'd sweated even more than usual I would pull it out and just wipe the condensation off of it.
Sadly, the Soddie is also a knife that never rode just right in my pockets. In a belt sheath like the ones you see with Moore Makers it would be ideal.
So yeah, it can be done, having one "pocket" knife that you always carry and use. It's also proper to use other tools when appropriate. It's looked down on to use a wrench as a hammer.
Little would be gained by me saying I'd go along with you, I'm already there. I will be right in there supporting you and encouraging you though. It's worth doing and will build character while getting truly in touch with the tradition of those before you who had and used their pocket knife. That's singular.
Good luck to all that seek to reconnect with the past actions with their choice of traditional pocket knife EDC. Just remind yourself that EDC means EVERY Day Carry, not Every Third Day Carry (E3DC).
and my downward spiral as a knife floozy was powerfully fueled by luscious images of cutlery overindulgence. Someday, I will just need to disappear from this den of cutlery iniquity, to save my soul from helpless reckless consumerism. Then maybe, just maybe, I can go back to being that "one knife guy" again! 
