Four Questions to Help Demystify Your Relationship With Money

Jennifer Risher took a job in campus recruiting at Microsoft in 1991. She was 25 and given stock options worth several hundred thousand dollars. While working there, she met her husband, David, who had more stock options than she did. He later left to work for Amazon when it was still just selling books and got even more valuable options there.

In a few years, they were worth tens of millions of dollars and on their way to a comfortable life. When Ms. Risher looks back, was it luck or good decisions that helped her land that Microsoft job?

She poses that question and others in her book, “We Need to Talk: A Memoir About Wealth,” which is out next week. They are an effort to prompt critical thinking about money and the status and power that are accrued from it.

“Wealth doesn’t look anything like what Hollywood is selling us,” Ms. Risher said. “I want to demystify wealth — an experience millions of people have but can’t talk about. There’s a normalcy to it when all your friends are similarly wealthy.”

In a country that is politically, economically and racially divided, Ms. Risher is asking her readers for a level of introspection that can be difficult. The timing of her book could end up making her a target of anti-rich opprobrium, several wealth advisers told me.

But asking tough questions about money is an important exercise in understanding what we have, how we got it and how we feel about it.

Of course, the questions people typically pose about their wealth depend on their perspective. Ms. Risher, for example, grew up white and middle class, with a father who worked in the insurance business and a mother who worked at home when Ms. Risher and her brother were young, before resuming a career as a librarian.

That upbringing set Ms. Risher up to attend a private liberal arts college on the East Coast. It did not set up her to understand the tens of millions of dollars that she and her husband would acquire.

The approaches also differ among academics and advisers whose job it is to prompt families to be introspective about their wealth. I reached out to several this week to get their views on Ms. Risher’s questions and ask them what difficult ones they recommend people ask themselves.

Here are four questions that stood out.

“I think that’s a really important question, particularly if you come into money fast,” said Bradley T. Klontz, associate professor of financial psychology at Creighton University. “If you don’t have a good answer to that, you’re going to sabotage yourself. You’re going to find ways to get rid of it.”

One thing to understand in answering that question is the risk of social comparison. No matter how much money you have, people are wired to compare themselves with others.

“It’s the deep subconscious terror that if we feel we’re going to be separated from our tribe, we’re going to die,” Dr. Klontz said.

It’s also something that can cause people with money to do less than they could, he said. His follow-on question is about what meaning a life of wealth should have.

“Our built-in purpose is to fight for our daily survival,” he said. “What is my purpose when that purpose is taken away?”

Without having intention, the wealthy tend to become disconnected from the variety of people they knew before they became affluent.

“We’re here to make the world a better place, however we’re defining the world,” Dr. Klontz said. “It’s the responsibility and the opportunity.”

What comes to mind when you hear this question says more about you than the question itself. It’s open ended, which makes it great for discussion. But it also forces people to be contemplative.

“People can find surprises about themselves,” said Keith Whitaker, president of Wise Counsel Research, a consultancy on family wealth and philanthropy. “Living well at one point meant success in my career. Or it meant being the best parent I could be. Or living well meant forgiving myself for mistakes or choices that turned out differently.

“All these things don’t have anything to do with money, but money can be a means for happy choices or unhappy choices,” he added. “Knowing what living well means provides the North Star for those choices.”

Dr. Whitaker said that even the most introspective people started by listing the superficial trappings of living well — homes, cars, boats, trips. But when people are allowed to sit with those answers, they often come up with more.

“It’s then that they realize, ‘I don’t just want those things,’” he said. “‘I want those things with good friends, or good relationships with my children and grandchild.’ Or ‘I want those things with a sense of integrity.’”

That’s where these questions can move people to think about their money as more than just a way to buy what they want. It gets people to think about how they want to be involved in their family, their community and the world.

“Many of the families and individuals I work with are really questioning the withdrawal from the world that wealth can buy you,” Dr. Whitaker said. “With the pandemic, people are saying: ‘I don’t want less responsibility. I want more responsibility with wealth.’ But that requires first asking, ‘What do my responsibilities entail?’”

For Michael Liersch, head of advice and growth strategies at Wells Fargo Private Bank, this question is the first of three related ones that he puts to every family he works with. (The others: Do you feel that you have enough? Who should be involved in these conversations?)

Dr. Liersch pointed out the importance of framing the question. Finding the most neutral, open-ended way to ask the question creates a greater likelihood of getting a more productive response.

“You can frame questions in a way that will drive you to or from a certain situation,” he said. “You want to bring people into that conversation, not push them away.”

One thing Dr. Liersch tries to do in these conversations is set the stage to get answers and ideas out there for family members to discuss. But he also tries to show people that answering these questions just once isn’t enough, particularly now, when views on wealth and privilege diverge greatly.

“Research would suggest the more intentional we are with creating our guiding principles, the more likely we are to achieve them,” he said.

This was a question Ms. Risher asked herself as she looked back on major life choices, including living in the same neighborhood as fellow tech workers, sending her children to private school and sharing her wealth with family and friends.

“Even with people who have a lot of wealth, money isn’t connecting us,” she said. “When money is a barrier to those connections, that’s a problem. Our silence around money just makes it more powerful than us. We aren’t able to see reality.”

In her book, she wrote about a friend who later told her that Ms. Risher and her family hadn’t been invited to the circus because the friend was afraid they would want to sit in expensive front-row seats. Ms. Risher said she was shocked at first, but then heartened that the friend could raise the issue with her.

“The fact that she trusted me enough to talk about money made me feel closer to her,” she said. “It also woke me up and showed me how out of touch I could be. If we talk more, it raises awareness of how broken our country is right now.”

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