I'm aware that saying "always" can bite me in the backside here, so it may be better to say that I always try to carry certain things on me when I leave the house. This changes a little depending on new things I'm trying and the clothes I'm wearing, but I seemed to have settled on a few "must haves". These go into pockets on my pants (easier when I'm not in my work slacks and I can wear cargo pants or shorts with the extra pockets) or in my coat pockets in the colder months.
Moleskine Ruled Reporter Pocket Notebook - This little notebook is hinged on the top and it is small enough to fit (snugly) in my front pants pocket or (more comfortably) in my side cargo pocket. The pages are ruled and there is a little pocket in the back for holding loose scraps of paper. The hardbound covers are held closed by an elastic band that I also snag a pen under. The pages are acid-free and a pleasure to write in. The last 10 pages are perforated to allow you to tear out notes to share. I keep standard yellow and ruled notecard-sized Post-It notes stuck to the back inside pages to write my "Next Step" to-do lists. Inside I keep my big to-do lists, project ideas, wishlists, etc.
Pilot G2 Pen/
Fisher Space Pen - I use the G2 pens at work and love them. They fit in a shirt pocket fine, but they are a little big for pants pockets. I prefer the Space Pen for my always carry pen. However, I've always owned the plain chrome version which keeps sliding out of my pocket and walking away. I'm going to try to get a matte black version with a clip that I can attach to the Moleskine elastic band. I'm also trying to track down the G2 "mini" pen which might fit better in my pocket. The Space Pen can write in any position, and almost any smooth surface, even underwater. I doubt I'll need to write while swimming, but I might need to write in the rain. (Which means I should also track down some "
Rite in the Rain" paper.)
Leatherman Wave - After watching Les Stroud use this tool in every episode of Survivorman, I asked for one for my birthday. It has not left my belt since. I use it 4-5 times/week at least, often more. It has needlenose pliers, regular pliers, wire cutters, hard-wire cutters, clip-point knife, serrated knife, saw, scissors, wood/metal file, diamond-coated file, large & small bit drivers with double-ended bits (Phillips & standard), large screwdriver, ruler, bottle/can opener, and wire stripper.
Cellphone - currently a Motorola V262 flipphone - In addition to keeping in touch with family, work, and friends, my cell-phone has saved my backside a few times. I shudder to think about what I would have done in the days before cell-phones if my car had broken down on a major highway. In a regional disaster, the texting feature can often be used when the voice network is jammed. I keep emergency numbers programmed in (911, AAA, my local mechanic, and emergency contacts) for rapid access.
All-ett billfold - This thin wallet is made of thin but tough sailcloth. For emergencies, I keep cash, credit cards, a phone card, and a note listing emergency contact numbers.
Palm TX - This lets me keep access to all of my emergency numbers, and I occasionally use it to take temporary notes and for the occasional calculator. I could do without this most of the time if I had to.
iPod 60GB with video - I use this primarily for entertainment purposes. In addition to my entire song library, I keep several TV show episodes on here, including some of the kids' favorites, which has really helped when waiting in line, for restaurant seating, etc.
Timex Ironman watch - Water and shock resistant, it tells the time, has a timer, stopwatch, and alarm, which is all I need of a watch. I like that it is inexpensive so I don't worry about it and can always have it on when I need it.
Keyring with LED flashlight - In addition to my keys, the LED light is good for finding a keyhole in the dark or finding my way on a dark path. It could be used for signaling, but I've never had to do that, thank goodness.
Sunglasses - I have sensitive eyes and so I almost always have these on me (except at night and on very cloudy days)
Splenda - I carry quick-dissolve Splenda sweetener tablets to sweeten the occasional iced/hot tea I may obtain throughout the day.
Purell - I have lots of this at work, but if I am leaving the house on a day off, I carry a small bottle of this hand-sanitizer gel to keep my hands disinfected in a germy world.