Yesterday I shared a guest post from Leo of Zen Habits. His guide to minimalist money was a sort of overview of good financial skills, useful information for those in the first stage of personal finance. But some long-time GRS readers couldn't relate to Leo's post.

Today's post goes in the opposite direction. It's a meditation for those in the third stage of personal finance (or beyond), and it's probably going to seem foreign to those who are still struggling to get debt under control.

The Evolution of Spending

Before I developed smart money skills, I spent without thinking. I accumulated debt because I had no self-control. I bought what I wanted, even when I couldn't afford it.

To repay my debt and build wealth, I learned to be frugal. I was never able to completely discard my tendency to spend, but I curbed it sharply. In fact, I became so frugal that I would debate whether to use two spoonfuls of hot chocolate mix or three when making a cup of cocoa. (And this was just a year ago!)

I'm still frugal. In my day-to-day life, I make choices to save money in every way I know how. I clip coupons, buy store brands, borrow from friends, make do with what I have. I am a proponent of thrift.

At the same time, however, I've reached a point where it's possible to save for some very nice things. I saved for my used Mini Cooper. Kris and I are saving for a trip to France next year. And this weekend we'll receive a shipment of some nice furniture we've saved for.

Because I've made smart choices in other parts of my life, I'm able to spend well on the things that really matter to me.

The Guilt of Wealth

There's no question that I'm happy about my current financial situation. I'm doing well, making smart choices, and enjoying a balance between tomorrow and today. But not everything is perfect. I've found that I feel guilty about some of the things I can now afford to purchase. And I'm not the only one.

I had lunch with a close friend yesterday. Though he was raised dirt poor (way below poverty level), he's worked hard to obtain an education, to build a career, and he now owns a couple of businesses. It was never his aim, but now he finds he's wealthy. He's proud of his accomplishments — but he also feels guilty.

“I look at my extended family, and they're still poor,” my friend told me. “They struggle. And yet I have a nice house a nice car and everything I could possibly want.” A few years ago, my friend purchased an expensive car as a reward to himself for his hard work. He could afford it, but somehow over the past few years, he hasn't enjoyed it as much as he thought he would. He feels embarrassed to drive it. He worries that his kids will grow up to take for granted those things he views as blessings.

This morning, I walked across the street to pick ripe Concord grapes at my neighbor's house. He came out to help. We chatted as we plucked the juicy bunches from the vine. My neighbor has been retired for fifteen years, and through patience and smart investing has built an enormous nest egg.

When my neighbor retired, one of the first things he did was buy a boat. He spends his summers cruising from Seattle, Washington to Juneau, Alaska and back. (He's invited me to spend ten days on his boat with him next year — I can't wait!) My neighbor told me about the first summer he had his boat. One day he anchored in a little cove. Before long, several other boats had anchored in the same spot. He was embarrassed to see that his was by far the biggest boat. “I was worried about what they thought of me,” he said.

A Strange New World

Both my friend and my neighbor are generous. They contribute time and money to their friends, family, and community. They've built wealth through hard work, and can afford the indulgences they allow themselves. Yet they both feel some degree of guilt over the things they have.

Believe it or not, I've begun to experience some of the same feelings. I know I've worked hard to get where I am today, but I've also been incredibly fortunate. I have a great job. I'm doing something I love, which also happens to help other people. I work from home, so can set my own hours. (I spent all yesterday hanging out with friends, but here it is Saturday morning and I'm working.) I've eliminated my debt and am building wealth. As a result, I can allow myself some of the nice things I've always wanted.

So why do I feel guilty? I never felt guilty about the things I had when I was in debt. I felt I deserved them. I don't feel that anymore. Now that my new furniture is on its way, I don't feel happy to have it, or proud that Kris and found ways to save so much money on it. I feel ashamed that I'm able to afford this while my little brother and his family are struggling to stave off bankruptcy.

Yes, I know that his situation is largely a result of his choices, as mine is a result of my choices. But I know there are plenty of people in this world who have worked as hard as I have, but who haven't had the breaks.

Does anyone else experience this? How you handle it? I've decided that the best thing I can do is to continue my frugal lifestyle, allowing myself occasional indulgences as I can afford them. At the same, I'll continue to help as many people as possible improve their financial situation. Maybe if I can help others achieve wealth, I won't feel guilty about my own.