Curiosity Closes the Lifestyle Gap

Imagine an interior designer named Imani Okafor who meets a new client, Mrs. Hale, to talk about her dining room. Imani has an appointment at a tile showroom across town at noon. As they walk through the house, Mrs. Hale asks, “Have you ever worked with a Nakashima?”

Imani does not know the name, and she does not want to seem out of her depth. “Oh, yes. Lovely work,” she says, and she moves on to paint colors.

In the dining room, Imani suggests replacing the old wooden table with a longer one that seats 12. Mrs. Hale looks at her. “That is the Nakashima,” she says. “My father bought it from George Nakashima himself.” She thanks Imani for her time, and she hires another designer.

Suppose instead that Imani says, “I don’t know that name. Tell me about it.” Mrs. Hale walks her to the dining room and spends 10 minutes on the table. Her father bought it from the woodworker George Nakashima. Imani asks what Mrs. Hale loves most about it. At the end, Mrs. Hale asks Imani to design the room around the table. Imani gets to the showroom 15 minutes late.

Imani knows the same amount both times. In the first version, she claims to know a name she does not, and the table shows Mrs. Hale the truth. In the second, Imani’s question shows Mrs. Hale that Imani will say when she does not know something. So when Imani later says that she knows something, Mrs. Hale can believe her.

Many wealthy clients did not start out wealthy

A professional from an ordinary background can feel the distance between their own life and a client’s. The distance can be smaller than it looks. The research firm Altrata studies people worth more than $30 million. In its 2026 report, four in five of those people in North America made all of their money themselves.

Many of them once lived without that money, too. What you need is to learn the parts of a client’s world that your work touches. You can learn them the way you would learn a new material or a new tool.

A tutor to rich families says being dazzled holds you back

Cleo is a private tutor whose clients include families on the Forbes rich list. Gulf News asked her whether the work was daunting at first. “It wasn’t, because I grew into it,” she said.

At 20, Cleo was telling off company bosses who had not done their homework. The reason, she said, was that they had been playing golf with George W. Bush. Then she named what holds people back in her trade. “If you’re going to be wowed by the lifestyle or crave it, then you’re not going to get to the top in this profession.”

In the course’s view, being dazzled by a client’s lifestyle gets in the way of learning it. A professional who is busy admiring the house is not watching how the house runs.

A travel planner studied the guests at a restaurant before she planned their trips

Jaclyn Sienna India plans trips for ultra-wealthy clients through her company, Sienna Charles. “Growing up, our family was not wealthy at all,” she told The Cut in 2024. At 18, she moved to Philadelphia for art school and took a job at Le Bec-Fin, a five-star restaurant. She stayed five years.

India was drawn to the guests. “I wanted to study them and understand who they were, why they wanted things a certain way,” she said. She also wanted to learn “about the ingredients the chef flew in, the pheasant from Northern France, what wines we were pairing with it.” The job, she said, “opened up my whole world.”

After she graduated, India worked at a travel agency. Then she started her own company, which she based “on the ethos of knowing the client, knowing the product, and providing everything they need.”

India learned how wealthy people like things done by studying them and wanting to know why. The course suggests the same with each client. Notice how they like your work done, and ask why. Each answer teaches you a little more of their world.

An estate manager learned art by asking questions

The household staffing agency My Household Managed tells the story of an estate manager who spent 24 years with one family. To protect his anonymity, the agency calls him Alfred Penny.

Penny started with his employer as a private chef and house manager. The employer grew richer, and the two came to trust each other. Then the employer asked Penny to manage the art collection that the employer had begun to buy. “Unfortunately, my knowledge of art was minimal,” Penny said.

Penny’s answer was to learn. “I was humble, extremely humble. I asked questions; I studied.” In time, he was “handling an art collection worth hundreds of millions: de Kooning, Warhol, Calder.”

So when your work touches a part of a client’s world that you do not know, ask about it. Then study it, as Penny did.

Why nodding along goes wrong

Imagine a specialist realtor named Kofi Mensah who is showing Mr. Porter a house in Boston. Mr. Porter wants a place in town for the winters. Kofi has another showing in 20 minutes. On the front steps, Mr. Porter mentions that his family spends the summer at “our place up-island.” Kofi nods as if he knows, and he locks the door.

A week later, Kofi emails Mr. Porter a new listing. At the end, he writes, “Hope the summer is going well on Nantucket.” Mr. Porter writes back, “Martha’s Vineyard, actually. West Tisbury.” On Martha’s Vineyard, “up-island” means the towns at the western end of the island. Mr. Porter starts checking everything else Kofi has told him, and he asks a second agent to send him listings too.

Suppose instead that Kofi asks on the front steps. “Up-island? Where’s that?” Mr. Porter spends five minutes on the house in West Tisbury, and Kofi is a few minutes late to his next showing. In the fall, Mr. Porter buys his winter place through Kofi.

Kofi’s nod was a claim that he knew, made without a word. In the course’s view, a client who catches one claim like that starts to doubt the rest. A question on the steps costs a minute. A question a week later costs more, because it also admits that the nod was pretend.

Asking a client to explain is not admitting that you do not belong

Asking what something means can feel like admitting that you do not belong in a client’s world. That worry often comes with feeling out of place in a client’s house. This feeling does not mean that you are wrong for the job. It comes before you have done anything for the client.

India and Penny each started outside a wealthy client’s world. India studied the guests, and Penny asked questions.

Research on hiring suggests that being yourself helps when your work is already good. In 2017, four researchers wrote in the Journal of Applied Psychology about two sets of hiring data. They looked at the candidates an employer rated among its top 10%. Among them, those more inclined to present themselves as they are were more likely to get offers.

In a separate study with mock interviews, an expert rater found candidates of that kind more genuine. She also found them less likely to misrepresent themselves, so she was more likely to recommend them for a job.

Those were job candidates, and the step to a client’s house is the course’s own. Here is the step. A client who hired you already thinks your work is good. When you say that you do not know something, the client learns that you are who you seem to be.

How to learn a client’s world without pretending

When a client mentions something you do not know, say so and ask. For example, a home organizer whose client says that the Lalique stays in the cabinet can say, “I don’t know Lalique. Which pieces are they?”
Ask one follow-up question about what the client tells you, such as where it came from or why it matters to them. For example, a coach whose client is going to Davos in January can ask, “What does that week look like for you?”
Afterward, look it up. Write down what you learned on a page under the client’s name, in a notebook or a notes app. For example, an event planner whose client mentions “our box at the Derby” looks up the date that evening. She writes, “Mrs. Avery: Kentucky Derby, first Saturday in May. Book nothing for her that weekend.”
Before your next visit, choose one part of the client’s world that your work touches and that you still do not understand. Examples include a furniture maker, a place, or a school. Ask the client about it, or read one good source on it, such as the maker’s own website.
If you have already nodded along, ask the next time you talk, before you have to guess. For example, a personal trainer can say, “You mentioned the Hampton Classic last week, and I didn’t know it. What is it?”

Next: You will see why watching how a client acts tells you more than any personality test.