When you're born into one of the world's hardest hustling families, you better be prepared to work.
From the moment they're introduced to the slice of Southern California the Kardashian-Jenner clan call home, the brood's youngest offspring get a front row seat to brand management, courtesy of Lovie Kris Jenner and a crash course on just how possible it is to achieve the wildest of dreams.
After all, Aunt Kylie Jenner became a billionaire cosmetics magnate before the age of 22 while Auntie Kendall Jenner took her first step toward supermodel status at 15. Thankfully Kim Kardashian's eldest two already have some options. Four-year-old Saint West has the smoldering eyes on the cover of a magazine thing down and 6-year-old North West has all the makings of a YouTube personality or a stylist depending on which way her desires lead. Which is good considering Kim and husband Kanye West, 42, have no intention of bankrolling their kin forever.
"We talk about it all the time, about not getting too much and just trying to be as grounded and well-rounded as possible," the 39-year-old penned in an essay for Wealthsimple, outlining her strategy for raising unspoiled kids. Even with two well-off parents of her own, Kim still spent her teen years toiling, first at a clothing store and then at dad Robert Kardashian's office. "I always was working. I never asked people for money," she noted, saying she hasn't quite figured out what she'll do with her children. "It's a different time. I don't know if I'm going to do that. I have to discuss that with Kanye."
For now, though, she's content to let her kids live the good life.
Well before marking her second birthday today, Chicago West—now big sister to 8-month-old Psalm West, had already explored the likes of Jackson Hole, Wyo., Miami, the Bahamas and Bali and learned that flying private is really the only way to go. And while she has no cash on hand just yet, she does have a place to store it, thanks to the mini Louis Vuitton that Santa brought.
As for future job options, perhaps veterinary school is in the offing, considering her recent no fears encounter with a snake. Or maybe she'll try the whole makeup mogul thing that seems to run in the family. She's already got a head start, what with posing for Mom's KKW Beauty line at 9-months-old. In the snap, taken by legendary photographer David LaChapelle, Chicago manages to pull focus from Kim's bold pink shadow look, causing the proud mother to caption the frame, "My heavenly baby."
To be sure, hers was a blessed arrival. Having accepted that carrying a third child wasn't medically possibly, thanks to the preeclampsia and retained placenta that led to a doctor arm-deep inside her scraping out her placenta, Kim began exploring the idea of using a gestational carrier in 2017.
"I hated being pregnant," Kim shared in the April issue of Elle. "But as much as I hated it, I still wished I could have done it on my own. The control is hard at the beginning. Once you let that go, it's the best experience. I would recommend surrogacy for anybody."
Ceding control of such a crucial operation was tough for a woman so regimented she irons her children's name into their clothes and deletes the majority of her text message conversations to keep her life as streamlined as possible.
"It is frustrating, like, to not be able to do it on your own," Kim revealed on KUWTK in 2017. "It is a weird dynamic. Like I go to all the doctor's appointments and I try to be really present, but when you're not carrying it yourself it is such a fine balance of how much you're going to be in their lives. Of course I want to know ever last detail that's going on with my baby and that's super frustrating, but I really trust my surrogate and I don't want to be that person that's trying to control her every move."
To that end, the KKW Beauty mogul placed just a handful of restrictions on the woman who became like family to her during the 2017 ordeal. She requested that the gestational carrier use her doctor and deliver in the same L.A. hospital where she had welcomed North and Saint and, if at all possible, fill up mainly on healthy, organic eats.
Though, that last one was more of a suggestion, she admitted to Elle: "I straight-up told her, 'Look, I ate doughnuts every single day. If you want doughnuts and ice cream, go for it. Do whatever you feel. I'm not going to be picky like that. That's just ridiculous.'"
The pair maintained close communications for the full nine months and when the time came for Chicago's arrival, Kim and older sister Kourtney Kardashian were in the delivery room with Kanye in an adjacent area playing Connect 4 with friends.
"Kim witnessed the birth and had first skin-to-skin contact when she was born," a source told E! News at the time. "Kanye was waiting behind a curtain in the room and held her immediately after Kim did."
In that moment, any fears Kim had held that she might have trouble bonding with this baby, disappeared. "All of that goes out the door, and instantly she's ours. It was such a good feeling," she would later share with Ellen DeGeneres. As she wrote on her blog, "The connection with our baby came instantly and it's as if she was with us the whole time."
And the fact that she was basically Mom's mini me, with a touch of older brother Saint, didn't hurt. "I think I was so nervous to have a surrogate and to have that connection that God was like, 'I'm going to make her look just like you,'" she opined on the October debut of Ashley Graham's podcast, Pretty Big Deal. As for her unique moniker (like her older siblings, she has no middle name), that was pure Kanye. Though they toyed with naming her after his late mom Donda West, Kim worried that would be a lot to live up to, settling on a tribute to her husband's hometown. "The city is really connected to his memory of his mom," she explained, "and so we went with Chicago."
Of course this little princess, Chi for short, was to hold court some 2,000 miles outside the Windy City, her palace a reflection of Mom and Dad's newfound minimalist taste and love of white.
"I wanted to keep all the décor in neutral colors," Kim wrote on her now-defunct app of the nursery, a blend of functional pieces and just a bit of indulgence. The $4,900 lucite Vetro crib—a hand-me-down from North, also used by Saint—has its place next to a vintage Jean Royère bed, the French designer's pieces, long beloved by Kanye, starting out at $75,000. Daddy's little girl also has the option of resting her head in a $1,900 Jenny Walker basinet or cuddling up with Kim on Monte's $1,495 Italian wool glider.
And custom clothing? Yeah, she's got some, the most surprising pieces arriving courtesy of the Chicago Bulls shortly after her birth. (Though that particular fan affiliation could get awkward when the NBA team is facing off against her bestie True Thompson's dad.)
Should sports not prove to be their thing, Chi, True True and the third member of the family's triplets, 23-month-old Stormi Webster could hit the concert circuit thanks to their dads' connections and there are always slumber parties, play dates and cupcake parties to enjoy.
"All the kids want to hang out. It's just a whole different experience now," Kim told E! News at her KKW Beauty Pop-Up in 2018. "It's so much fun."
With most of the siblings' homes situated in L.A.'s Hidden Hills and Calabasas neighborhoods, there's always someone on hand to babysit (Khloe has said she'd most likely tap Kourtney or Kim because "They already have so many kids. What's one more?") or handle carpool. (While partying with Kourtney at an Oscars bash, Kim revealed she "took one for the team and left early" so she could shuttle all of their kids to school the next morning.)
It's particularly handy should she and Kanye need to jet to Uganda, for instance, or board their own private 747 to Tokyo. "We pick up the slack for each other," Kim explained. "I know that if Kourtney's out of town, then the kids will sleep at my house and we'll plan these fun things where the kids always feel loved. We're always helping each other out." (Take the time everyone in Kim's house came down with the flu and she asked sister Khloe Kardashian to take Chicago back to Cleveland with her.)
A plethora of properties and access to private jets means the world is literally at Chicago's fingertips. But for Kim, there truly is no place like home. Which, is understandable when your main base is a sprawling, eight-bedroom estate. Cuddling with her trio of kids a day after they helped present Kanye with a homemade chocolate-frosted cake for his June birthday in 2018, Kim made it clear she had all she needed.
"Welcome to the good life," she wrote.
And sweet Chi is proving she's also easy to please. Though last year's birthday was an over-the-top Alice in Wonderland-themed bash ("The inside was designed like an outdoor garden with faux grass, red roses and a fun maze for the kids to run through. Outside they had a bounce house and Alice characters to entertain the kids," a source shared with E! News) Chicago's request for this fete were decidedly laid-back.
She'd like a "Minnie Mouse cake!" she proclaimed in a recent video—ideally pink. "That would be so cute," agreed Kim.
Though if Aunt Kourtney wants to come through with another pint-sized neon yellow Mercedes G-Wagon, well, that would be fine too.
(Originally published Jan. 15, 2019, at 3 a.m. PT)