Retail is for schmucks - Step one

I rarely pay retail. I'd like to pay nothing at all, but I rarely pay retail. It's too expensive and in my opinion, too easy to avoid to pay it. Most of the time your best bet is not spending a tremendous time searching for deals, but instead, simply talking with people and managing all your resources. When it comes to my family's resources, the first stop is always rewards points. Whether it's credit card reward points, airline miles, or hotel points, if we need something or are planning a trip, this is where we search first. Making a list of all the points you have and how they can be MOST EFFICIENTLY allocated is a great start to avoiding published prices. However, you want to avoid some pitfalls, in that not all points are worth the same. For example, American Express rewards points are rarely fixed. I always search for the deals where $100 spent = $1 savings, typically. They have an option where you can use points to pay for bills, but most charges are $200-$300 spent = $1 savings...this would not be in your best interest. Instead, you can buy most gift cards for the $100/$1 ration (Amex gift cards are $200/$1 go figure, schmucks) or any travel purchase can be paid 100 to 1.
Airline points are usually all over the place. You best bet is to look for the least popular flights for the trip you are planning. Go on a Thursday and come back on a Saturday, you'll cut the points you have to use in half. Pick the 1 stop flight with an hour layover and cut your point usage by 25% versus the non stop flight. It may cost you an hour of your time but save you $50 worth of points. Making $50/hour for doing nothing sounds okay by me.
Stick with one hotel chain (preferably the largest ones) as often as you can. Loyalty is rewarded usually progressively, meaning the more you stay, the larger the rewards and other perks you get. If it is a chain with many brands, don't stay at the most expensive hotel, they chew up points like a valley girl attacks trident gum. For example, one night at the Intercontinental hotel may be 40,000 points, where as a night at Holiday Inn Express is merely 15,000 AND you get free breakfast at the HDI. Most times when you travel, anyways, you are rarely in the room, so who cares if its a tiny bit smaller or doesn't have marble counter tops.
On the other side of the equation, you want to find the best way to rack those points up as quickly as possible. My first suggestion is always open a credit card or other account that offers a slew of reward points on your first purchase. It is okay to jump around every once in awhile. If you aren't buying a house or car this year, the little ding you take to your credit score won't matter and will be removed over time anyways. So go ahead and cash in on those introductory point offers. However, make sure you get the best bonus you can. The same exact card may have several different point offers depending where you see it. Usually, online is not the best way to find them. Take a second and look at all those offers in the mail, those tend to have much higher starting bonuses. For example, I recently closed on Priority Club card (Holiday Inn chain) in my name and opened one in my wife's name and took in 60,000 points plus a free night stay every year. Since we just married this won't hurt our credit at all and we always tend to stay there anyways out of convenience. I also opened an Amex for 50,000 points which I then cashed in on airline charges to save nearly $500. The Amex offer in the mail was for 25,000 more points that listed online.
Now a lot of times these rewards cards have fees, so always make sure you make enough in savings to offset the yearly cost, and make sure the profit you do net is more than you would with another card. If you are feeling really spry, go ahead and close that card before the yearly fee hits.
Another thing to keep in mind when earning points is where you earn the most for which purchases. One card gives you triple points for airlines, use that one to buy your flights. Your Priority Club card gives you 10 times points on room purchase with the card, use that card for hotel rooms. Organize your purchases to get the biggest point gain, but make sure you are factoring in how much each credit card reward system is really benefitting you in dollars upon redemption. Just because you get more points with one card, doesn't mean that will equate to more dollars in your pockets as savings in the future. With your key purchases typically being gas, restaurants and groceries, make sure you especially have these on lock down.
In the end, your rewards points are valuable savings, turning points and loyalty into actual dollars. Think of them as saving 2% on your groceries or 5% on your restaurant outings. Free flights and hotel rooms over time. A new set of golf clubs. None of them will make you rich, but they will help you spread your hard earned dollars. So spend a little time investigating and invest in avoiding retail.

Check back soon for step two.

Sincerely,

Coco