There is a predictable progression many of us go through as we make a decision to stop living beyond our means. We get cheap. In fact, some even call us cheapskates--a label that personally I enjoy because it proves that I am not the person I used to be -- a credit-card junkie and a totally whacked out spendthrift.

I quickly adopted a mindset that if cheap was good, then cheaper must be even better. As noble as that thought might seem--and it pains me to admit it--that is not always true. In fact, sometimes the cheapest option ends up costing the most. It is a wise person who can see the big picture--not just the cash outlay on the front end.

Case in point: Our house was in desperate need of paint. Spending thousands of dollars to have it painted made me queasy. So when one of the bids came in much lower than the others, I jumped on it. I figured paint is paint. We would get the house painted and still have money in the bank.

It never looked that great, and we were very disappointed. The contractor failed to mention his price did not include painting under the eaves. And before even two years passed, the paint job failed. The trim cracked and peeled, making our paint look 10 years old, not two. By the time we reached the three-year mark, paint was falling in chunks from the stucco. It was truly pathetic and we lived with that mess far longer than I like to admit. I know now that our cheap paint job cost us far more than if we had gone with the highest bid from the start.

Recently we had the house painted again. But this time we paid attention to more than just the bottom line on the bids. Instead of going for cheap, we were determined to buy the most quality we could afford.

The job took nearly six weeks, five of which were devoted to prep--scrubbing, scraping, filling and sanding--followed by three coats of high-quality paint.

We have every reason to believe this job will last for 15 years. That turns out to be much cheaper in the long run than getting a cheap paint job every three years. And our bonus is that the house looks like a million bucks.

There are other times when buying the most quality you can afford is the cheapest way to go. Buying a mattress, putting on a new roof, dental care, a decent pair of shoes--all of these are places where you are likely to pay less in the long run by opting for the most quality you can afford.

So how do you know whether you should go for the most quality you can afford or the cheapest price you can find? You have to ask yourself this question: How long do I want this item to last?

If the answer is As long as possible, that is a sign that you need to buy the most quality you can afford.

If on the other hand your answer is something like, Until the end of the wedding reception, you do not need quality. You need to shift your thinking to finding the best-looking dress at the cheapest price. Who cares if the quality is so poor it could not make it down the aisle multiple times?

The best way to know for sure if you are making the most cost-effective choice is to do the math. In the same way you are careful to consider the unit pricing of items in the grocery store, learn to compare prices on big purchases like paint job, roofs and mattresses using the per use *or* per year cost of the item *or* service being considered.

Take a mattress, for example. First determine the life expectancy of the model you are considering. Now divide the number of years into the purchase price. Now divide that result by 365, to see how much this mattress will cost per day. Do the same for the cheap option, making sure you adjust the life expectancy accordingly. You will not believe how often the cheap option is really the most expensive.

Knowing when to buy the most quality you can afford, and when to go for the cheapest price you can find, is a learned skill.

The more you practice, the better you will get. And the better you get, the more you will enjoy some finer things in life that really will turn out to be the cheapest way to go, after all.

Check out Mary's recently released revised and expanded edition of The Financially Confident Woman (DPL Press, 2008).


Debt-Proof Living was founded in 1992 by Mary Hunt. What began as a newsletter to encourage and empower people to break free from the bondage of consumer debt has grown into a huge community of ordinary people who have achieved remarkable success in their quest to effectively manage their money and stay out of debt. Today, "Debt-Proof Living" is read by close to 100,000 cheapskates.  Click here to subscribe. Also, you can receive Mary's free daily e-mail "Everyday Cheapskate" by signing up at EverydayCheapskate.com.