Women Who Make Us Want to be Fearless and Honest: 2018 Edition

Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.

One pretty good way to celebrate women on International Women’s Day? Listen to them. And Our Money Diaries series is all about listening as people tell their own stories with as much honesty as possible.

Stories about failure and success — we’ve said it before and we’ll say it again —are powerful. Today we’re highlighting stories from women who said “yes” to whatever it was that took them down the road to achieving their dreams — yes to an audition, yes to an identity, yes to a dermatology Instagram, to the WNBA, to SNL.

So whatever stage of a life story you’re in — the high or the low or the totally unremarkable — we think it’s worth taking a moment (or, fine, more like five minutes) to read and feel inspired by what’s possible, and give a hat-tip to all those who identify as women today.

And, because as our favorite Internet source put it, “International Women’s Day is a public holiday in some countries and largely ignored elsewhere.”


“I’m at a loss for words sometimes, talking about this. It’s unfortunate that men make more money for the same amount of work, or even less work.”

“Skylar Diggins-Smith Wants to Be Paid Like a Man and Isn't Afraid to Say It”

“I hate being in debt. I always pay my credit card on time. I will go without rather than go into debt. I don’t go into hock over things I can’t pay for. People of my generation always think they’re on the verge of being kicked out onto the street. It’s ridiculous, but it’s a mindset.”

“The Handmaid's Tale” Author: For Women, Money Can Be Power.”

“My mom got injured at a job in like 2010. So she hasn't been working. I'm the breadwinner of the house. And I try to get my little brother not to work. I'm like, 'Focus on school. I'll take care of whatever I can take care of.'”

“Halima Aden: Supermodel, Refugee, Muslim, Warehouse Worker.”

“I looked for jobs that gave me flexibility so that I could go on auditions. But I always had a job. I never wanted to be one of those desperate actors just waiting for their next gig, who might have to take something that they didn’t want to do to pay the rent.”

“Why Wendi McLendon-Covey Was Still Freelancing on the Set of 'Bridesmaids'.”

“I find it meaningful to see someone who’s accumulated more wealth than I could even imagine, and found that it didn’t make him feel happy, satisfied, or content.”

“Director Lauren Greenfield Discovered What Hedge Funders, Porn Stars and Rappers All Have in Common.”

“At one point, my channel was bringing in six figures a month, and that was ridiculous.”

“How Exactly Do You Build a Fortune Popping Pimples on YouTube?”

“Performing at a drag bar is like winning the lottery to work in a sweatshop.”

“The World Wouldn't Make a Place for Angelica Ross. So She Made One for Herself”

“I remember having a breakdown at graduation. I was in a stairwell, in my cap and gown, and I was crying because I was like, I don’t know what’s next, like how am I actually going to do this?”

“Natasha Rothwell Plays an Accountant on ‘Insecure.’ Her Real Life Wasn’t So Excel-Ready.”

“We

“For Sasha Lane, Success Meant Being Able to Send Her Mom Home Again.”

“For me money is literally just the energy to keep doing the things I want to do.”

“Why Design World Legend Tina Roth Eisenberg Would Rather Build Four of Her Own Businesses Than Work for Someone Else.”

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