How Would You Change Your Life If You Were Rich?

I’m a theatre lover, so it won’t surprise you that I know the lyrics to “If I Were a Rich Man” from the classic musical Fiddler on the Roof by heart. In the song, Tevye sings about how his life would change if he were, indeed, a rich man. For the peasant Tevye, his dreams are pretty simple.

But have you ever asked yourself how you would change your life if you were rich?

I sat down with Jack and Mary last week and asked this very question. Both recently retired, they’re financially fortunate. They have been very careful with their money, have saved a significant amount and, as icing on the cake, five years ago they received a large family inheritance. Logic would say that they should be able to relax now and simply enjoy the benefits of a well-planned, well-funded retirement. But when it comes to money, logic doesn’t always prevail. Instead of enjoying their assets, they focus on being frugal—to an extreme. And because Jack is even less comfortable spending money than Mary is, it’s a source of tension in their relationship.

To help de-stress the situation, I gave Jack a little homework: I asked him to simply write down what he’d do differently if he felt rich. When I read his answers, I couldn’t help but think of Tevye’s simple dreams. Why? Because while they aren’t the dreams of a fictional peasant, Jack’s dreams are almost as simple., Jack said that if he felt rich, he would eat more sushi, buy more books on his Kindle, and eat out at nice restaurants more often. If he felt really wealthy, he said he would think about replacing his 10-year-old car, fly first-class on an airplane (at least once!), and treat himself to a new camera. Even in his wildest dreams, Jack is anything but a spendthrift!

My good friend Ava is another example of someone who has turned frugality into an art form. Divorced when her children were still small, she was determined to create a financially sound life for herself and her family. She spent as little as possible, saving every penny she could in jars labeled as “lunch money.” Today Ava’s “lunch money” amounts to tens of thousands of dollars. She may not be rich (yet), but she’s well on her way to a very comfortable retirement. The problem? She rarely lets her frugal mindset—or herself—take a luxury vacation. Over the years, I’ve done everything I can to persuade her to use some of her savings to do things that will make her happy today.

Happily, we’ve made great progress. I’ve had more than a few calls lately that burst with excitement: “Lauren, you’ll be so proud of me!” Ava is finally remodeling her home (something we’ve talked about for over a decade!), and she’s now planning to go to a yoga retreat… in Hawaii. I couldn’t be happier for her. She’ll never overspend, but at least she’s allowing herself to enjoy the fruits of her labor—and her “lunch money.”

If you’ve built your life around saving, it can be quite a challenge to suddenly change your mindset, no matter what the numbers tell you. As an advisor, I know that I can’t solve internal problems with external solutions. You can look at all the charts and projections in the world, but that won’t change how you feel on the inside, and that’s what matters most when it comes to financial confidence and peace of mind. So what’s the answer?

Start by recognizing that the process is different for everyone, and that it takes time. Just as it can be difficult for someone who has overspent their entire life to put boundaries on their spending habits, if you’ve never let yourself feel comfortable spending—even when you have the money to spend—it can be difficult to open your wallet without feeling those old pangs of guilt.

The next step is to take a close look at your assets and your budget. Are you under-spending? If so, do you know why? Are you scared of outliving your money? Did your parents teach you that saving was “right” and spending was “wrong”? Perhaps start by journaling about it to get to your essential truth. Ask yourself why you have trouble spending. And if you’re ready to have some fun, ask yourself the Tevye question: How you would change your life if you were rich? Your answers may surprise you!

Of course, finding the level of spending that’s right for you is a balancing act, and very few of us have such unlimited assets that we can completely forget about budgeting. A trusted advisor can help you understand how much money you have today, establish a realistic budget based on your cash flow, and help you start to internalize your boundaries moving forward. It can be a freeing experience, but it has to come from the inside.

My friend Donna is newly widowed, and understanding how to set her spending boundaries is a learning process. She calls me often for help. “Can I buy this?” she asks. My reply is always the same: “I don’t know… tell me, exactly how long are you going to live?” We both laugh, and then we move on to the reality of helping her find her new balance. It will come. Until then, I just keep reminding her that she does have assets. Her real challenge is to gain the confidence and peace of mind to know she’s not overspending, while still being generous to herself. Donna deserves it. Don’t you?