If thoughts and worries about money have never kept you up at night, you can count yourself among a very lucky few. Even if you have a sizable bank account and don’t need to stress about finances on a day-to-day basis, you have bills to pay and goals to meet. Who doesn’t want to level up financially so they can give their children a better life than they had? Or repay their parents for all their hard work? Or pamper their pets? Each and every one of us is working with our own set of money-related baggage — and even celebrities (no matter how apparently successful they are!) — have financial histories that shape the way they approach work and money today.

To prove it, millennial-focused digital investment service Wealthsimple has partnered up with celebs from all walks of fame for an ongoing series called Money Diaries. Through videos and as-told-to essays, these familiar faces pull back the curtain on how they feel about money and how those feelings affect them now. Here are their confessions.

1. Kylie Jenner: If there’s anyone who doesn’t have to stress about money, it should be a member of the Kardashian-Jenner clan, no? According to Jenner’s Money Diaries piece, that’s not entirely true. While she cops to the occasional splurge — especially on luxury cars — Jenner also says that she uses a lot of cheap drugstore makeup, doesn’t buy jewelry for herself, and tries to focus much of her savings on long-term investments. “One day, I’ll step out of the spotlight, I think, and just live a normal life,” she tells Wealthsimple. “And just because I have money now, doesn’t mean I’ll always have money. It’s not a forever thing. I could lose it at any point.”

2. Aubrey Plaza: “[Money] just makes people feel uncomfortable,” actress Aubrey Plaza says in her Money Diaries video. “There are so many feelings wrapped around money: shame, jealousy, greed — but I think it’s good to talk about. The more you talk about things, the less power things have.” Plaza also admits that, despite the fact that her dad is a “wealth management… personal… whatever,” there’s a lot she doesn’t know about finances. We feel you, girl.

3. Alex Karpovsky: Alex Karpovsky (of Girls fame) gets really real in his video, reminiscing about his years of being “pretty much destitute” in his mid-thirties and about the insecurities about finances that he absorbed from his frugal immigrant parents. “Now that I have a little bit of money — for the time being — I’m convinced that it’s going to run out,” he says.

4. Julia Landauer: As one of the most promising young race car drivers in America, Julia Landauer is working toward a top tier of NASCAR driving that could put her in a position to win millions… but she’s not there yet. In the meantime, she makes additional cash by taking on speaking engagements. “I’ve learned not to be afraid to ask for money,” Landauer says. “I’ve also learned to say no. One group recently asked me to speak but said that they didn’t normally pay. So I politely declined. Then they called back to say that they actually could afford to pay. Sometimes you gotta play hardball.”

5. Rita Ora: The singer recalls a hustler mentality in her immigrant family for as long as she can remember. And when she finally felt like she’d “made it” in the music industry, the first thing she did was express her gratitude for those lessons in hard work by paying off her parents’ car bill. What a gem! While Ora says she values creativity (and her sneaker collection) more than money, she also admits that she hopes she never has to choose between the two. That would be a tough call!

6. Brian Tyree Henry: Brian Tyree Henry — star of FX’s Atlanta — admits that a large part of his drive to become an actor was his desire to spoil his mother… and goes on to share what it feels like to realize that those plans were derailed by her recent passing. “What I never accounted for was that I wouldn’t have her when I got that,” Henry says. “I make all the money, but the person I wanted to spend it on the most is no longer here. I know she’s proud. I think the thing I have to do is be proud of myself.” His confessions left our own wheels turning about what — or who — motivates us to be financially successful and what it will mean to actually get there.

7. Tegan and Sara: “Right now, my goal is to be able to live in a way that is comfortable for me,” says Sara of the twin pop star duo Tegan and Sara. She shares the unique challenges of commanding respect in the music industry as a woman and of the misconceptions about just how much money musicians actually make. A piece of financial advice that sticks out to her (and that convinced her to start splurging on business class in 2010)? “You are going to spend your life touring and traveling. That’s your job! People drive a Honda Accord and then they get excited because they get to buy a Prius. Don’t feel ashamed about wanting to move up! Don’t feel ashamed about the fact that you’ve become more successful and you can afford these things.”

8. Mark Duplass: You might recognize him from The Mindy Project or the director/producer of a number of indie films, but the straight-talking, financially minded guy in this Money Diaries video bears little resemblance to the New Age midwife Brendan DeLaurier. Duplass opens by declaring that he doesn’t worry about money, but goes on to discuss the expenses that come with making a movie. He owns the fact that he lives in a big expensive house, but also cops to driving a less-than-opulent car and flying economy class. “I’m a very traditional, kind of 1940s guy,” he says. “You’ve gotta invest and let it appreciate… and compound it.” (This last part he does in an imitation grandpa voice.)

You can check out more Money Diaries from Wealthsimple here.

Do you relate to any of these celebs? Tweet us @BritandCo!

(Photos via Wealthsimple)