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 I enjoy because it proves that I’m not the person I used to be (a credit card junkie and a totally whacked-out spendthrift).

It didn’t take long for me to adopt a mindset that if cheap is good, then cheaper must be even better. As noble as that thought might seem -- and as painful as it is to admit it -- that is not always true.

Sometimes, the cheapest option ends up costing the most. It’s 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’d get the house painted and still have money in the bank.

It never looked that great, and we were very disappointed from the start. 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 in the long run than if we’d gone with the highest bid.

There are other times when buying the highest 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 at the outset.

So, how do you know whether you should go for the most quality you can afford or the cheapest price you can find?

Ask yourself this question: “How long do I want this item to last?”

If the answer is “as long as possible,” that’s a sign that you need to buy the highest quality you can afford.

If your answer is something like “until the end of the wedding reception,” you don’t need quality. You need to focus on finding the bestlooking wedding dress at the cheapest price. Who cares if the quality is so poor it couldn’t make it down the aisle multiple times?

Knowing when to buy the highest 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’ll get at it. And the better you get the more you will enjoy the finer things in life that will turn out to be the cheapest way to go after all.

Would you like more information? Go to EverydayCheapskate.com for links and resources for recommended products and services in this column. Mary invites questions, comments and tips at EverydayCheapskate.com, “Ask Mary.” This column will answer questions of general interest, but letters cannot be answered individually. Mary Hunt is the founder of EverydayCheapskate.com, a lifestyle blog, and the author of the book “Debt-Proof Living.”