• Cash — Yes, you have credit cards, and yes, you may even be able to buy things with a click of your smartphone now.  But not everyone can process those payments, so have some cash on hand to tip your taxi driver with, slip to the busboy (who doesn’t always get a share of the actual waiters’ tips), or just to pay for something in a way that’s fast, convenient, and doesn’t cost an establishment that you like the extra credit card fees.
  • I.D. — A state-issued driver’s license or state I.D. card is your gold standard of I.D.  No one’s going to hassle you about those.  If you need a second I.D. specific to your profession — a security card or student I.D., say — have that as well.  But leave behind all the tertiary I.D. cards like your country club membership or Wines of the World discount card unless you know you’re going somewhere that requires them.  Nine days out of ten that’s wasted space.
  • Credit Cards — Two is the maximum here.  Anything else just makes you look like an irritating coupon-clipper as you rummage for just the right one to get your maximum mileage points or whatever.  A debit card and a credit card is a nice combination.  If you’re really dedicated to saving space try and find one of the newer cards that have perfectly flat numbers — just be aware that there are still a few places (especially temporary stands like farmers’ market stalls) where you’ll have to wait for them to copy the information off the card rather than using a hand-held machine to stamp a carbon copy from the texture.
  • Business Cards — Doesn’t matter if you own a business or not.  Have a few cards with a very simple design that just gives your name, phone number, and e-mail address.  You can get these made very cheaply at most copy shops or print shops, and if you’re part of (or own) a business with its own logo and information you can grab a few cards for it as well.  Three or four of your personal cards and three or four more from your employer/business is usually plenty, unless you’re heading to some sort of meet-and-greet where you know you’ll be giving them out.
  • Your Contact Information — It sounds simple, but you’d be amazed how many men don’t think to have their name, address, and phone number somewhere visible when the wallet flips open.  A business card works for this, obviously, as do some forms of I.D., but the point is to give anyone who finds your misplaced wallet a quick and easy way to get in contact with you.  It’s no guarantee that they will, of course…but not having it there is a guarantee that they won’t!
  • Your Most Commonly-Used Discount Cards — If you’re someone who likes “Frequent Buyer” or rewards types of cards, more power to you.  There’s nothing wrong with getting a good deal.  But exercise some restraint.  Carry the one or two that you use all the time and leave the rest at home.  If you only go to the mall once or twice a month (or less, in my case), it’s a significant enough errand that you’re going to think “oh, better grab my mall discount cards.”  Leave them in a drawer the rest of the time.
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