The Day Michael Jackson Sat in the Audience, Eight-Year-Old Ivanka Thought She Ruined the Entire Show

Source: Diary of a CEO | Published: 2026-04-09T07:00:10Z

From learning about her parents' divorce in the newspaper at nine, to shutting down an eight-figure brand for the White House, to watching her father get shot — Ivanka Trump tells the full story of how these moments shaped her for the first time.

These kinds of "far from normal" childhood experiences were a recurring theme in her upbringing. But she says day-to-day life was actually quite grounded—her grandmother cooked every meal, and when she came home from school, her clothes were already washed, folded, and laid out on the bed.

Her grandmother's love came with zero strings attached

Ivanka's grandmother is 99 years old and currently lives with her family. This immigrant from Czechoslovakia expressed love in the simplest ways: cooking, doing laundry, waking her granddaughter up for lunch when she slept in.

Ivanka choked up several times talking about her grandmother. She said what her grandmother taught her was unconditional love—not love based on what you've done or what you have, but on who you are. Her grandmother's health is declining now, but she still sits at the family dinner table every evening, telling Ivanka's children stories about their mother.

"To be able to be with her in her later years, even if it's just a fraction of what she gave me growing up, is an extraordinary privilege."

This intergenerational passing of the torch also shaped Ivanka's later understanding of what it means to be a mother.

Her mother: raised under communism, and no one could tell her how to live

Ivanka's mother, Ivana Trump, was a member of Czechoslovakia's national ski team. After emigrating to the U.S., she became a trailblazing woman in real estate. She showed up at construction sites in five-inch heels, hair impeccably styled, making everything look effortless.

Ivanka says what her mother accomplished in that era was extraordinarily rare—shuttling between boardrooms and building sites while raising three children. She never pretended she could do it all alone. Instead, she surrounded her kids with people she trusted. Both nannies stayed until the day Ivana died; one still works with Ivanka today.

Growing up under a communist regime forged in her mother an attitude of "nobody tells me what to do." Ivanka says that flamboyance was, in a way, a rebound from years of being suppressed. Her mother was even more outspoken than her father—often making young Ivanka wish the ground would swallow her whole.

In 2022, Ivana died from an accidental fall at age 73. Ivanka says her mother spent her final years writing a book about childhood experiences she had never shared with the family. It taught Ivanka something important: ask the questions while you still can—especially with people who tend to keep the past locked away.

At nine years old, she saw a photo of her parents torn down the middle on a newspaper

Her parents had planned to sit the children down that afternoon and tell them about the divorce. But that morning, on her way to school, Ivanka saw the newspaper in a street box. She doesn't remember the headline. She only remembers the photo—her parents' portrait with a tear ripped down the center.

The divorce reportedly drew more media coverage than the O.J. Simpson case. Reporters camped outside her school, shouting tabloid fodder at a nine-year-old. She says that level of aggression wouldn't be tolerated even today.

But she drew something positive from it: she and her siblings forged an unusually deep bond, because they went through it all together.

At 25, in an interview, she said the experience taught her not to trust anyone. She sees that differently now. At an age when she hadn't yet developed her own judgment, withholding trust was a healthy form of self-protection. But as she grew older, she deliberately trained herself to become more trusting—even if it meant occasionally being let down.

Being underestimated is a weapon—provided you've done the work

When Ivanka entered real estate, she faced a double discount: as the child of successful parents, people assumed she'd coast; as a young woman in development, construction, and acquisitions, she was virtually the only one her age in the room.

She turned that underestimation into an advantage. The logic is simple: if the other side underestimates you, they don't prepare. But you have.

"I'd rather be underestimated than overestimated. If you're someone who's prepared and the other side has underestimated you—they haven't prepared. That almost always works against the person who underestimated me."

She extends this principle to negotiation: what truly matters is figuring out what the other party wants. Often, you can give them their highest priority at very little cost to you, and both sides walk away feeling like they won. Silence is a tool, too—people grow uncomfortable in silence and start volunteering information.

An eight-figure business, shut down just like that

Ivanka launched her own jewelry brand at 26, eventually expanding into 11 categories—apparel, shoes, sunglasses, fragrance, and more. Annual revenue hit eight figures. The brand filled a gap in the market: at the time, professional women's workwear was uninspiring and couldn't transition from the office to an evening out.

When her father entered the White House in 2017, she shut it all down. The Office of Government Ethics required that her brand stop using her likeness, stop acquiring new customers, and halt international expansion. Rather than let the brand slowly wither, she chose to end it at the top.

She says that when her father asked her and her husband Jared to come to Washington a few weeks after his 2016 victory, she imagined herself 40 years in the future—the version of herself who had turned down her father's request and continued her old life. That image made her uncomfortable.

First lesson from the White House: power, like money, only amplifies who you already are

During her four years in the White House, Ivanka helped double the Child Tax Credit from $1,000 to $2,000, benefiting 40 million American families. She helped secure paid family leave for federal employees, pushed through nine pieces of anti-human-trafficking legislation, and secured $1.3 billion in annual career and technical education funding for 13 million students.

But she says she doesn't have "White House withdrawal"—that addiction to proximity to power that keeps pulling you back. Her reasoning is practical: her eldest daughter is 14, and even if a quarter of their interactions happen through a closed bedroom door, she needs to be present. She knows the countdown to her children leaving home is ticking, and she's unwilling to make them pay the price for her public service again.

One core insight from the White House: those national leaders—whether hereditary monarchs or elected presidents—are ultimately just people. Some have children who won't speak to them. Some had a fight with their spouse that morning. That demystification means she no longer feels nervous in front of anyone.

Eagles don't waste energy fighting crows

Ivanka uses an animal behavior analogy to explain how she handles public attacks: crows are highly intelligent creatures that sometimes attack eagles many times their size, even landing on an eagle's back to peck at it. The eagle doesn't turn and fight. It simply flies higher. Crows aren't built for high altitude—at a certain height, they just fall away on their own.

"You can turn around and fight back—the eagle would probably win. Or you can play by your own rules."

She admits this ability was trained, not innate. When she was younger, she'd be confused—"I didn't even do that, what are you talking about?" Then came the sense of injustice. Eventually she realized that politics is a team sport, and people don't need a reason to attack you. A line from Marcus Aurelius, written in his tent, stuck with her deeply: The soul is dyed the color of its thoughts. If fighting back means losing yourself, the cost is too high.

The day her father was shot, she knew instantly he was fine

In July 2024, Ivanka was poolside in Bedminster, New Jersey, watching in near-real-time as her father was shot at a campaign rally—before he got back up. Two of her children were there. Her first instinct was to turn them away.

She describes something strange: in that instant, she "just knew" her father was okay, knew that wasn't his moment. At one or two in the morning, her father returned from the hospital to Bedminster, and she and Jared were at the door waiting for his car.

Someone tried to publicly assassinate your father—does that make you view the world negatively? Her answer: what does being angry at the world accomplish? It only breeds more negativity. She chose to focus on the outcome—her father is alive, and that's a blessing.

400 million pounds of strawberries rotting in fields, while nearby communities go hungry

In 2023, Ivanka co-founded Planet Harvest with Melissa Ackerman. The project grew out of the "Farmers to Families Food Box" program she created during the pandemic—when restaurants, airlines, and hotels all shut down, farmers had nowhere to send their food, and it rotted in the fields. She built a subsidy mechanism that allowed farmers to route produce through distributors and churches to people in need.

After the pandemic ended, she found the waste problem hadn't gone away. Every year, 400 million pounds of strawberries are left in the fields—not because they're flawed, but because they don't meet cosmetic standards retailers set decades ago: strict specifications for size, shape, and color. Planet Harvest creates demand for these "not pretty enough" but perfectly good products while providing farmers with additional income.

Advice to her daughter: you have to believe in yourself before the world does

Ivanka's eldest daughter, Arabella, wants to be an entrepreneur and investor. Ivanka has three pieces of advice for her:

First, you have to love what you do. At Wharton, she saw plenty of classmates smarter than everyone else who ultimately dropped out because they chose a path that matched their abilities but not their passion. You can't beat someone who's half as smart but works twice as hard.

Second, don't imitate anyone. She cites her friend Naval's observation: When you're copying, you're losing. Be yourself, and no one can compete with you.

Third, you have to believe in yourself before the world believes in you. She now invests in AI and robotics startups, and she frequently sees founders whose confidence far exceeds their résumés. But that's the starting point—if you don't believe in yourself, you'll never take the first step.