Private-Plane Parenting: ‘Child Support’ for the 1%

Among the wealthy, helicopter parenting is insufficient. Instead, one must pilot the child’s every move, need, whim and future goal.

Among the wealthy, helicopter parenting is insufficient. Instead, one must pilot the child’s every move, need, whim and future goal.
Among the wealthy, helicopter parenting is insufficient. Instead, one must pilot the child’s every move, need, whim and future goal.

“Richard, Media Maestro is on the phone!”

My assistant Carol looked wide-eyed as she pointed to the landline, the sun streaming in my newish Tribeca office.

“Really? Put him through!” I was eager to hear what one of the busiest business execs on the planet wanted to discuss with me. Perhaps a new account for my ad agency NSG/SWAT, peut-être? I looked out from my perch with the bird’s eye view of the new World Trade Center.

“Hi, Richard. Great seeing you the other night at the Alfred V. Moneybagses’. I enjoyed our conversation thoroughly,” he said in a clipped, accented tone. He was referencing the posh Lily Pond Lane cocktail party, which kicked off the summer season at the rambling, shingled-style cottage (a.k.a. mansion). The faded chintz, wicker and an old money patina proved a bit incongruous as the media, entertainment and tech elite rubbed cashmere shoulders in the sun-dappled porch that overflowed into the gardens.

“As did I,” I concurred. “You mentioned you and your lovely bride Pashmina will be in Italy this summer. I look forward to seeing you both if you are in and around Capri.”

“You must come on the boat [actually a ship]. It was kind of you to take the time to hear about Blaze [his son, not real name] who, as I mentioned, wants to become a commercial director.”

“It’s great that he has the creative gene,” I offered, trying to recollect the passing mention of his son at the party.

“I wanted to set up an appointment with Blaze to chat with you and then come by and see you.”

“It would be my pleasure.”

“Blaze has finals but has availability for a call next Tuesday at 12:15 or he can speak to you at 1:50. He is so busy right now.”

I motioned for Carol to bring me my calendar.I would love to see and talk with Blaze, but, alas, it seems I am in a client meeting presenting a new campaign at that time.” I replied, searching for another opening.

“Is it an important client?” he said in a deadpan tone.

“Well, they just pay the bills.” I laughed, assuming he understood absurdity of the question.

“Just joking.” He paused. “Let me see…” I heard typing on a keyboard. “It seems…Blaze also has…no his cross training is that time…hmmm.” He paused again dramatically. “Oh, I think he has an avail at 2:30 on Thursday. Gladys, can you double check with Blaze that he has the time to talk with Richard at 2:30 on Thursday? Great.” A minute of uncomfortable silence ensued.

“Yes, Blaze can chat with you then,” he said in a take-it-or-leave-it tone.

“I look forward to it,” I replied, trying to be genial.

“You will love Blaze. He’s a genius, and it will be good for you to know him.

I was fairly speechless at this point but managed, “I’m sure it will be.”

“By the way, regarding Capri. I will have the copter come and get you and Dana for lunch at the Splendido in Portofino.”

“That’s very kind of you…and I do love La Terrazza—it was my father’s favorite restaurant—but I am a bit of a landlubber. Although, say hello to the spaghetti a la Elizabeth Taylor for me when you are there.”

“Then we’ll come to see you at La Fontelina. They have the best branzino with potato crust. Let me know what you can do for Blaze,” he said as he hung up on me.

“Ciao,” I said into the receiver, but he’d already hung up.


The mainstream media has made a great deal out of the term “helicopter parenting,” which refers to the now common practice of hovering over and cosseting one’s child. However, helicopter parenting is not nearly enough for some 1-percenters. In these rarefied circles, merely hovering is insufficient: No, one must pilot the child’s every move, need, whim and future goal. Call it Extreme (G5) Private Plane Parenting, where the world’s richest and most powerful routinely fly to their child’s aid, setting their course and direction, utilizing the same skills that made themselves successful socially and in business. Parents now personally take the time to “G5” their children’s appointments, internships, and have been known to negotiate and strong-arm raises and promotions with their children’s bosses. They also have become personal travel agents for Junior and their friends, footing the bill for their dream five-star vacations well post-college. Such G5-ing renders the children prisoners to privilege and alternately gives the world’s most successful class a new title they can add to their illustrious resumes: Child Assistants! While G5 parents may genuinely think they are helping their progeny, a leading therapist summed it up: “They’re cutting their children off at the knees—and then they’ll never be able to walk alone.”

That said, who needs to walk when you can fly—private—with your very own CEO/child assistant?

‘Blaze has finals but has availability for a call next Tuesday at 12:15 or he can speak to you at 1:50. He is so busy right now.’

It’s not often I am seated between a drug-addled celebrity in couture and a social swan at a legendary address, but it is apparent that dinner placements have become increasingly less soignée and more sensational. Social Swan came late, and somewhat aflutter, as she placed her Carolyn Rowan mink-and-feather capelet on the Jean Royere chair and proceeded to apologize for her tardiness.

“It’s so difficult when one is overcommitted,” she  declared. After the main course of Dover sole with sea foam (it seems every uptown entrée is now foamed), we succumbed to polite dinner conversation.

“What are your summer plans?” I inquired nonchalantly.

“Don’t you know?” She looked perplexed. “I am moving to Warsaw [not real city] in August.” She shrugged as if we were old friends catching up.

“No, I didn’t.” I raised an eyebrow, as we had just met. “Are you of that descent?”

“Not in the least.”

“Why Warsaw, then?”

“Don’t you know?” She paused and looked at me as if I had three heads. “Wilfredo [not real name]. We got him the most divine flat on Nowy Swiat, so, that’s the s-t-o-r-y,” she said in a sing-song manner.

“The story?” I was having hard time following her train of thought.

“My son, Wilfredo.” Again she looked perplexed. “He’s studying there.” She glanced at her bedazzled iPhone under the table.

“Oh, how nice.”

“And I am moving there so he has technical support.”

“Is he in grammar school?”

“Why would you think that?” She suddenly seemed slightly taken aback.

“Because you’re moving there to be with him.” 

“No, he is a junior in college. What about this are you not understanding?” She suddenly became exasperated, twirling her vintage (and monumental) David Webb Emerald cocktail ring.

“Sorry. We’ve only just met, and I have no idea how old your son is. So you are actually moving there?” I tried to move the conversation along in a positive way.

“Yes, I need to decorate his apartment. I want him to feel comfortable, as it’s only a rental, and I want to make sure he has a brand new mattress, pillows, etc. I can’t abide used anything. It’s not hygienic. Then I need to find the proper markets and set up all his accounts and have the food delivered. It’s a full-time job.”

“Is your husband moving with you as well?”

“What, you don’t know Cristobal [not real name]?”

“No, I don’t believe we’ve had the pleasure”

“That’s so strange. Well, anyhoo, we’re divorced, but Chris did also take a long-term lease at Five-Star Hotel. He’s very good with mapping and making sure Wilfredo’s driver will have the most efficient routes to his classes and to all the clubs.” She toyed with a Parmesan crisp, which she artfully moved to one side of the china.

“Well, Wilfredo is very lucky. When I went off to college, it was rare to see my parents more than four times a year.”

“That wouldn’t work for Wilfredo. Although he is a genius…” She paused.

“Let me guess, he’s super smart but not great at the day-to-day?” I couldn’t help myself. “Such as stocking a kitchen or laundry?”

“You see you do know Wilfredo!”

“No, we have never met.”

“I know he wants to be a director, so maybe you can help him when he graduates. Or give him an internship. I hear you do…something creative? Did I mention he’s a creative genius? He’s won trophies for it, you know.She puffed out her implants.

“Trophies! Really!” I stifled an eye roll. “It would be my pleasure to chat with him.”

“He’s just so busy now in Paris, getting ready for Warsaw. I’ll let you know when he has the time. Anyhoo, Ivor originally tried to steer him to London.”


“You don’t know Ivor? How can that be? My fiancé. Ivor, the rapper/entrepreneur/trainer [not real profession]. You could use Ivor.”

“You’re not suggesting I am out of shape?” I played along.

“No you’re perfect. But Ivor makes you perfect-er.”

At this point I decided to play along. “I’ll give you my card to give to him since I’m obviously preparing for my Ironman.”

“You won’t be s-o-r-r-y! Anyway, Wilfredo told Ivor who told Martine who told me that he thought London was played out.” She plucked a Chanel compact out of her Chanel “strassed” bag.

“I didn’t realize an entire city could be played out.”

“Well, Wilfedo has been on the scene since [Swiss boarding school] and needs to meet some new people since he already knows everyone in London.”

‘Look, he needs to understand that my son, who is a GENIUS, is not going to stick around for that measly salary he’s paying him and working 60 hours a week with two weeks off a year. Who does that?’

“I guess, he will in Warsaw.”

“Really, the things you say. Who is going to meet there? At least in London, he could go to [exclusive private club].”

“Well, you’ll be there to direct him!”

“It’s just that it is such a ‘B’ city. I’m telling you they ship in last season’s couture. No one there could ever tell. The entire city is like a suburban discount mall.”

“But think of all the culture: Chopin, Paderewski… Pierogies.” I laughed cheerfully.

“I just adore Pierogies. So does Wilfredo,” she yawned. “One of the truly great composers.”


“You do what?” Dana asked a well-Vuitton’ed Hamptonite, who was sitting astride her beach chair with her feet in the sand at a certain Bridgehampton beach club.

“Trust me, you’ll do it too.” Marvel Diamond rolled her eyes as she played with her chic Jennifer Miller stack bracelets, all while searching her LV beach bag for her cell phone. She looked at us like we were both certifiable.

“Do what?” I asked as I sprayed the SPF 50 sunscreen over my pale, winterized arms.

“Marvel was saying that she calls her son and daughter every morning to make sure they are up for work,” Dana whispered as she flipped through Page Six .

“Yes.” Marvel smiled brightly. ”It’s my good morning call to both my children. I get to talk with them, and I’m also making sure they don’t oversleep.” She offered up a perkiness I hadn’t seen since Julie, the cruise director on the Love Boat.

“How long has this been going on?” I asked.

“Since college.”

“Hasn’t Treble [her son] ever heard of an alarm clock? Or a cell phone?”

“Of course, but he slept through his classes the first and second year, and we had no choice.”

“No choice?”

“He was really suffering, and the school was getting very annoyed. We couldn’t let him—”

“Sleep through any more classes?”

“Why yes. And the same thing happened when he graduated and got a job.”

“Maybe, he’s just staying out a little too late?” I joked.

“You’ll see.” She wagged a finger at me. “You laugh now, but trust me Dana will do it. If she’s not doing it already.”

Well, yes, we do wake up the kids,” Dana offered.

“You see?”

“The difference is that I have an 11-year-old living at home,” I countered.

“Well, I enjoy my morning call, and they like it, and it’s working because they are getting where they need to be, and I want to make sure they are getting the proper amount of sleep.”

“Do you call them in the evening as well to bid them nighty night?” I have to admit, I enjoyed chiding her.

Actually, I do. And I have the most wonderful conversations with Treble’s girlfriend Sharpei. She fills me in on his diet and weight and how he is doing.”

“Smart girl.”

“Yes, I view her as an ally and my liaison,” she said firmly.

“Les dangereuses liaisons?”

Richard, you are so funny. You’ll see. Dana will do it. In fact, how do you think that I know where to book our Christmas vacations? Treble’s girlfriend tells me where they want to go, and then I book it.”

“What about what you and Bruce [not real name] want to do?” I asked

“We want to be with Treble and his girlfriend. And if they didn’t want to go to St. Barths with us, then they would most likely go with her [cough] family, and we wouldn’t see him. The same thing goes for Gardenia [their daughter]. If she wants to go to Cabo, then we go to Cabo. We do what we have to do, or we wouldn’t get to see her and Shorty.”


“Shorty [pro athlete who is 6-foot-7 and 360 pounds—not real profession]. You know, ‘the Big Shorty.’ Anyway, that would be no fun. You’ll see. When the kids are out of the house, Dana will be calling to see where the kids and their significant others and friends want to go on vacation, and you will do it because once they are gone, you will want to see them.”

“So unless it’s a five-star Luxury Retreats villa vacation and a nightly call, they won’t see you?”

“That’s right, Richard, I am very realistic, and you are married to a very realistic woman, and she will be calling, trust me. Very few other parents foot the bill once the kids are out of college, and do you know what? Very few parents get to spend as much time as we do with their children.”

“That’s a shame.”

“And the food bills, well, don’t ask.” She paused to apply lotion around her diamond Cartier. “But you know what? I am here to tell you, when the family is together for a chef’s dinner or everyone is having the lobster ravioli at the Eden Roc, well, it all makes everything worth it. You’ll see.” She paused and smiled. “Dana will definitely do it.”


“You did what?” I raised an eyebrow and listened to the mogul, Morton B. Acquisition, and his uber-Machiavellian Child Assistant moves. The scene of the crime was his ornate townhouse, where his fourth wife had just hosted a charity event; the cascading strings of Montevani and the carved gold armchairs with red-velvet upholstery set the tone as he invited me into the library for some aged whisky.

‘There was this family that did a science project where they analyzed the hides of animals for temperature in the 4th grade, and it looked like a graduate school final. I said to the mother, “Where did little Aswan come across crocodile skins and bear skins at his age?” She just smiled and said he was “very industrious.”

“I called his boss and told him off!” He beamed.

Wait. You…called your son’s boss?” I could hardly believe my ears.

“He needs to understand who he is dealing with.”


“The family.”

“What is this? The Godfather?”

“Look, he needs to understand that my son, who is a genius, is not going to stick around for that measly salary he’s paying him and working 60 hours a week with two weeks off a year. Who does that?”

“Everyone who is starting out!” I offered. “My first job was as a receptionist, and I worked for free until I made the princely salary of $9,000 a year.”

“Did you also walk two miles barefoot to school every day? What is this, a Depression sob story?” he muttered. “You’re not old enough to know who FDR is. I am!”

I ignored his taunts. “So what did your son’s boss say when you called him?”

“He was thrilled of course.”


“Yes, to get the second round of investment. Fabio [his son] gets a promotion, a VP title, four weeks’ vacation and a corner office. And Mr. Bossman gets his $5 million.”

He paused. “So I know what you are thinking.”

“What am I thinking?” I raised an eyebrow at the painting, which matched the sofa, which also matched the lamps.

“That you wish your father invested $5 million and you had that deal!” He puffed out his chest. “So you didn’t have to answer the phones!”

“Actually, no. I loved working my way up from the bottom, and I can dine out on that my entire life. But you, my friend…I think if you ever came back in an another life, you should come back as your own child.” I smiled.

“Sweet! Right. Let’s forget the Macallan. José, can you bring over a bottle of Dom Perignon rosé?” he shouted to his butler. “We have to celebrate my son’s promotion.”


My dear friend and former client Lily Whitebread joined me for al fresco lunch at Roc on Greenwich, where the menu always prepares one for Capri and Taormina summer idylls. Lily adjusted her Jackie O shades and Seaman Schepps turquoise-and-gold rope earrings as I filled her in on my next article. She had quite a bit to say.

“All one has to do is take a look at the science or history projects and see how much the parents spent or who they hired.” She shook her head in disapproval. “When the scion of Ph.D. parents or Harvard graduates shows up with the Louvre of science projects a city block long, you just know.”

“How is it the schools don’t understand if your father is, let’s say, a famous architect, and the child shows up with an exact replica model of the Parthenon—isn’t it obvious that some Carnegie Mellon associate working on so-and-so Hamptons palace is doing their bidding in his or her spare time? It is a bit ridiculous when my children show up with Popsicle sticks and oak tag, and they walk in with something worthy of the Pritzker Prize,” I agreed.

“I know, Darling. There was this family that did a science project where they analyzed the hides of animals for temperature in the 4th grade, and it looked like a graduate school final. I said to the mother, ‘Where did little Aswan come across crocodile skins and bear skins at his age?’ She just smiled and said he was ‘very industrious.’ ”

“And it goes on as they get older. I know a family where the father said, ‘I’ll backstop your life until 40, and then you’re on your own.’ As if that is a threat!”

“Well, darling, let’s not forget…Life begins at 40.” She toasted me with a glass of Trebbiano and laughed her Kate Hepburn laugh.

We joined our good friends and fellow school parents Monsieur et Madame Consigliere at the ever-popular and chic Polo Bar restaurant, where the staff seemed to hover and anticipate our friends’ every whim, perhaps because they seem to eat there nightly.

“There’s nothing like a hot popover.” I surveyed the delicious roll. I usually pass on the pain, but in this case, it was worth the calories and the pain.

“Look, we’re all guilty,” Consigliere stated. “We can laugh about it, but we all do it. You and Dana do it too.”

“Do what?”

“O.K., so, let’s turn this into a quiz.”

“You mean the G5 Private Plane Parenting Quiz?” I asked.

“Yes. First, you’re telling me that you have never had a driver follow your kids into a club to make sure they are all right.”

“I can’t deny it.”

“And what about parents who get involved in their kids’ fights and take sides?”

“I think we try to stay above the fray on that one. But it’s hard,” I conceded.

“O.K., and how about paying for two reservations on the Jitney in case they miss one?” He stared at me hard on that one.

“Well, if they miss the one on the Luxury Liner, then they have to go on the Jitney.”

“I did that once,” Dana said. “I call it, ‘Hamptons back up.’ ”

“Or ordering Postmates from Philippe as a snack?”

“We all want what’s best for them, and if they are skinny, we can’t help ourselves.”

“To G5 or not to G5? that is the question.” I toasted.

“G5 it!”

“Well, you know what Oscar Wilde once said. There are only two tragedies in life.  One is not getting what one wants…and the other is getting it.” As the waiter came over to the table, Madame Consig extracted her compact from her Hermès skin bag.

“We’ll have three pieces of your delicious chocolate layer cake,” she said sweetly. “Two to stay and one to go. Byron [their son, not real name] loves the chocolate cake from here, and I want to bring him home a snack. You know—finals!”

Should I call an Uber?” I asked. “Or should I call Teterboro as we G5 the snacking?”

We chuckled as we made our way upstairs into the night, with the wrapped cake perilously close to Madame’s Birkin.

“You know, I asked Dr. Yes, my therapist, what the definition of good parenting is,” I said. “And do you he said, ‘Preparing your child to separate.’ ”

“That’s a good one.”

“So while we know you have to grow up and leave home and go off to college”—and here I mimicked talking to my own children—“have a slice of Ralph’s chocolate layer cake before you go!” We emerged into the night.

“Wheels up!” I said.

“Wheels up!” they answered as we air-kissed. 

Private-Plane Parenting: ‘Child Support’ for the 1%