Money Matters: How Much Is Enough?

News flash: those shiny, happy people on the front of the 401(k) brochure? Models. Fakers. Well-paid pretty faces. In their blemishless, flatteringly lit world, money is simply a tool for building a better life, not a keeps-you-up-at-night, ulcer-making foe. Brochure people religiously track their modest expenses on the latest version of Quicken. They budget their spending and wouldn't dream of back-ordering the luxe handbag du jour because it's so darling and they just really, really want it. They don't lease or lay away or run up credit card balances as a substitute for self-esteem or meaningful relationships. Vacations and tuitions and retirements have been planned for, the stock market is easy to understand, salaries yield more than enough to get by, and cash, well, it flows.

We hate those shiny, happy brochure people.

But the truth is, we wouldn't mind being that smart about our own money. So O asked psychologists, financial advisers, social activists, and other big thinkers to weigh in on the question of why it never feels as though we have enough—and to offer answers that can help real-life people stop the money madness.

How to get the most happiness from the money you have:

Daniel Gilbert, professor of psychology at Harvard University and director of the Social Cognition & Emotion Laboratory

"One reason we keep chasing dollars and are oddly disappointed when money doesn't provide happiness is that it once did. It's a little like alcohol. You think if one drink makes you feel good, ten will make you feel better. That turns out not to be true. I think most people spend unwisely. To maximize happiness with the money you have:

You'd invest in small pleasures. That's not what most of us do. We save up for the trip around the world or the Ferrari. But we now know happiness comes from lots of good things happening, not one really good thing. When I first came to Harvard, I would have said that the greatest thing is to be here. But it turns out the greatest thing is that I get to walk to work, twice a day, every day.

You'd also invest in disappearing pleasures—chocolates and vacations versus a car or a washing machine. Most of us like things that we can keep, so a washing machine seems like a better investment than a vacation. That's the wrong way to think. Things that stay around have a tendency to disappoint us after repeated use.

And you'd invest in social pleasures: Good marriages and lots of friends are much better predictors of human happiness than wealth."

Ask yourself, "Is this a need or a want?"

Michelle Singletary, The Color of Money columnist for The Washington Post and author of Spend Well, Live Rich: How to Get What You Want with the Money You Have (Ballantine)

"Enough is never enough because there's all this pressure to buy—so many images [of stuff] come at us from television and radio. We're mere mortals trying to fight the marketing machine. We spend too much on stuff—self-storage space is one of the fastest growth industries.

I challenge people to come up with personal mantras about their money and to practice them every day. When you have a mantra, you can use it to respond immediately to any message that you don't have enough. Here are a few of mine:

1. If it's on your ass, it's not an asset. Spend your money on things that appreciate in value.

2. Ask yourself, Is this a need or a want? It is unbelievable how often we fail to ask that basic question. Nine out of ten times, you'll say it's a want and then put it back.

3. Priorities lead to prosperity. I'm talking about focusing your energy and money on things that really mean something to you. Parents say they want to send their kids to college but then spend that money on toys and clothes and gadgets and shoes. You have to match up your priorities to what you want in life. When you create priorities, you set the stage for how to spend your money. That money is then spoken for."