The World Your Client Lives In
When a client mentions school, a second home, or travel, fit your work around it.
Imagine a personal trainer named Nia Brooks who trains Mrs. Ford at her house twice a week. At the end of a session in May, Mrs. Ford mentions that the family goes to the lake house “right after school lets out.” Nia’s next client is across town in 20 minutes. “Lucky you,” Nia says, and she packs up her bands.
In the second week of June, Mrs. Ford texts Nia. The family has left for the lake, and Mrs. Ford will be in touch in September. Nia loses 10 weeks of fees. Over the summer, Mrs. Ford finds a trainer near the lake, and she does not come back in the fall.
Suppose instead that Nia asks one question before she leaves. “When does school let out, and is there room at the lake house to work out?” Mrs. Ford says that school ends in the second week of June. The lake house, she adds, has a porch but no equipment.
That week, Nia sends Mrs. Ford a plan she can follow on the porch, with a call each Monday to check in. Nia also books their first session back for the day after the family returns. Mrs. Ford keeps paying through the summer.
Nia’s work is the same both times. What changes is that she hears “right after school lets out” as a date that moves her work, and not as small talk.
Six parts of life set a wealthy household’s calendar
A client may have some of these six, or all of them:
- School. For a family with children, the school terms set much of the year. Three economists, Raj Chetty, David Deming, and John Friedman, studied admissions to the Ivy-plus colleges. These are the eight Ivy League colleges plus Stanford, MIT, Duke, and the University of Chicago. Brown Alumni Magazine reports what they found. Applicants from nonreligious private high schools were twice as likely to get in as applicants from affluent public high schools. Those private schools are the ones wealthy families favor. With that much riding on school, expect the weeks around exams and college applications to be tense in the house.
- More than one home. The research firm Altrata counts three luxury homes on average for each person worth more than $30 million.
- Staff. A housekeeper, a nanny, or a house manager may be the person who lets you in and books your next visit.
- Giving. A 2025 Bank of America study found that 81% of affluent households gave to charity in 2024. Those who gave did so to five organizations on average, and 79% gave to causes in their local community. Among people worth $30 million or more, almost one in five has a private foundation, Altrata reports. A cause can also come with a seat on a board or a place on a gala committee. In the weeks before a board meeting or a gala, the client may have less time for you.
- Clubs. A golf, tennis, or dining club is often where the client sees friends, and where word about you travels. In golf or tennis season, the client’s regular game can also decide which mornings are free.
- Travel. Trips, and moves from one home to another, can take the client away for weeks at a time.
A professional who has not lived this way can still work around it. When a client mentions one of the six, ask about it, and ask what it means for your work. If the client names a place or a school you do not know, say so and ask.
A tutoring agency’s clients want to use every home they own
In 2013, CNBC reported on tutors who work for wealthy families. Adam Caller founded Tutors International, a tutoring agency in London. Many of his clients, the report said, are “rich families that travel between multiple homes around the world.”
These families, the report said, “don’t want to be tied to one location because of their children’s school.” “They may be based in New York, have a boat in France and a house in Mexico and in South Africa, and they want to use them all,” Caller said.
So these families hire a tutor who goes with them. “With home schooling and a tutor, they can travel wherever they want and still get to be with their children,” Caller said.
When a client has more than one home, ask where the family will be in each month of the year.
A tutor who moves with the families says to be ready at a moment’s notice
Nathaniel Hannan taught high school in Washington, D.C., before he began tutoring the children of wealthy families. When CNBC spoke to him, he was tutoring in Barcelona, Spain. He told CNBC that he had worked in nine countries over the previous seven years.
The work has its downsides. “You have to be very flexible all the time,” Hannan said. “Clients may need anything at a moment’s notice and you have to get it right the first time.”
Most services cannot follow a family from country to country the way Hannan did. So if your work can travel or be done at a distance, plan it for each place the family goes. If it cannot, decide ahead of time what happens to your schedule in the weeks the family is away. Then tell the client before they leave.
What a passing mention can tell you
Clients rarely announce these parts of their lives. They mention them in passing. Here is what a few common remarks can tell you, and what to do next:
| What the client says | What it tells you | What to do |
|---|---|---|
| “We spend the holidays in Aspen.” | Your work will pause or move in late December. | Ask for the dates, and offer a plan for the weeks away. |
| “Send the invoice to David in our office.” | A member of staff or the client’s office handles the bills. | Get David’s email address, and send every invoice to him. |
| “I’m chairing the hospital gala in October.” | The client’s calendar will be full in the weeks before the gala. | Ask for the date, and book fewer or shorter visits in the weeks before it. |
| “It’s exam season for Leo.” | The household is under strain for a few weeks. | Keep your visits short and quiet until the exams end. |
Why ignoring a passing mention goes wrong
Imagine a dog walker named Jess Alder who starts walking the Parks’ two retrievers in March. On the first day, Mrs. Park says, “Talk to Maria about the key.” Maria Lopez is the Parks’ house manager. Jess gets the key from Maria that afternoon.
Jess has Mrs. Park’s number from the first call, and she has six dogs to walk before dark. So when she needs to move a walk, she texts Mrs. Park. “Running late today, OK if I come at 3 instead of 1?” Mrs. Park answers each text, a little later each time.
Mrs. Park has given Maria the job of running the household day to day. That way, Mrs. Park does not have to deal with it. Each text from Jess hands that job back to Mrs. Park. After a month, Mrs. Park asks Maria to find a walker who deals with Maria directly. Jess loses the client.
In the version that works, Jess asks Maria for her number when she picks up the key. From then on, she sends every change of time to Maria. Maria tells Mrs. Park whatever Mrs. Park needs to know, and the Parks book Jess for the summer as well.
Asking about a client’s homes and trips is not prying
Asking a client where they will be in August can feel like prying into a life that is not yours. The worry is fair, because a client’s homes, trips, and children are private.
The question that works asks only what your work needs. Nia asks Mrs. Ford when school lets out and whether there is room to work out at the lake. Mrs. Ford has raised the lake house herself, and both answers go straight into Nia’s plan.
What keeps the question from being nosy is what you do with the answer. A family that lets you see its calendar is trusting you to keep it to yourself. So the dates and places a client tells you go into your calendar and nowhere else.
How to fit your work around a client’s year
- For each of your best clients, write down the six parts of life: school, homes, staff, giving, clubs, and travel. Leave blank what you do not know yet. Keep the list on a page under the client’s name, in a notebook or a notes app.
- When a client mentions one of the six, ask one question about it, such as the date or the person to contact. For example, a private chef whose client mentions a summer on Nantucket can ask, “When do you leave? Would you like the freezer stocked for your first week out there?”
- Put the dates in your calendar, such as the school terms, the moves between homes, the trips, and the gala.
- A month before each date, decide what changes in your work, and offer the change before the client asks. A month is the course’s suggestion, because it gives the client time to answer. For example, an interior designer whose client leaves for Palm Beach on December 18 can write in November, “I’ll have the curtains hung by the 15th, so the painters can work while you’re away.”
- When a client names the person who handles something, deal with that person from then on. For example, a coach whose client says, “Leila does my calendar,” can ask Leila for her email that day. Then he sends every change of time to Leila.
- Keep what you learn about the household to yourself. For example, when another client asks where the family is spending the summer, a specialist realtor can say, “You’d have to ask them.”
Next: You will see what a wealthy client worries about, and how to hear the worry under an ordinary question.