Need Inspiration To Quit Your Day Job? Read These Powerful Stories

Now more than ever, women have the potential for upward mobility in their careers — just consider the growing rate of female-led companies or the ongoing fight for equal pay. But despite such progress, leaving a structured company behind to start something on your own terms is still scary AF, especially as a woman — and even more so without the safety net of a bimonthly payday. The good news is, it's possible.
Muslim media mogul Amani Al-Khatahtbeh, Insta-famous disability advocate Mama Cax, and Ali Kriegsman and Alana Branston, a New York duo reviving the retail scene in 2017, prove it. Inspired by Cole Haan's #Extraordinaries mission, we tapped these four business-savvy millennials — all of whom courageously left their traditional 9-to-5s — to find out how they turned their side hustles into profitable enterprises. Get to know these inspiring women, the lessons they've learned from venturing out on their own, and their motivational advice for pursuing whatever it is you're destined for, just below.
Amani Al-Khatahtbeh, 25
After years of feeling alienated in her conservative, suburban hometown, Amani Al-Khatahtbeh launched, the first online space dedicated to Muslim women. What started as a blog in Amani's bedroom has now grown to see millions of unique visitors.
Tell us what it was like to grow up as a Muslim woman in a post-9/11 era. Do you remember the first time you realized that Islamophobia was an issue in America?
"Everything changed after 9/11. I was 9 at the time, and I started to experience a very different treatment in society. It was the first time I was called a racial slur. My family endured a lot of abuse in our suburb — our house was egged and water-ballooned. I started hiding the fact that I was Muslim from my classmates because I was so terrified of what they’d think of me."
What was the catalyst for you in accepting your identity?
"The turning point for me was my first visit to the Middle East. I was exposed to this culture and religion that I’d only heard about in the news and learned about from my parents. I was met with hospitality, which opened my eyes to the way things are being misrepresented in Western media. That's when I started wearing the headscarf, because to me it was symbolic of me reclaiming identity — an identity I felt forced to hide from my peers and educators — and a way to say I’m proud to stand with these people."
What are some of the challenges you've encountered launching your own business?
"Muslim women have been systematically excluded from cultivating a presence in the media world, so it has been a challenge getting people to take us seriously and realize that our voices do matter."
What still needs work in the media industry, and how can we close the representation gap?
"The media industry needs to wake up to the fact that representation and visibility are two different things. They're excited to make minorities visible in an outward way, but newsrooms need to be made up of the people we're choosing to make visible — that's the key."
Is there an outfit that makes you feel like your most confident self?
"I have a Steve Jobs-esque uniform — he's my idol. I wear different variations of it: black pants, a denim shirt, and a simple scarf and baseball cap. To me, the cap is rebellious; it’s a reminder that wearing the headscarf doesn’t negate you from wearing anything else. We can rock it."
Ali Kriegsman, 26, & Alana Branston, 30
Once desk mates at a predominantly male tech company, Ali Kriegsman and Alana Branston left their jobs behind to launch Bulletin, an innovative retail space that brings online-only, female-run brands to IRL storefronts. Their instant connection sparked one of the buzziest business ventures in New York — and it doesn't seem to be slowing down anytime soon.
You two have been close for years. What are some of the challenges that come with running a business with a friend?
Ali Kriegsman: "Bulletin wouldn't be what it is today without our closeness, but we're never not working. Even if we go out to dinner, we'll always circle back to the business. It feels like the pure work-free nature of our friendship is a thing of the past."
Was there any fear in quitting your 9-to-5 to launch your own business?
Alana Branston: "Definitely. We wanted to make sure we had enough money to pay the bills, so we were very cautious about when we quit, making sure we had a certain amount of money tucked away. We waited to have some success with the business before taking the plunge."
Is there anything you wish you knew before starting your own business?
AB: "Your original business idea might not work. We started out as a digital magazine, and we didn't have the foresight or experience to know that sometimes your original business idea doesn't work and you need to be prepared to evolve and adjust."
How does Bulletin promote positive female relationships?
AK: "All of the brands that sell with us are run by women, so you get a really special community of female business owners in our stores. And our Bulletin team is fully female, as well."
Who are some extraordinary women you look up to?
AK: "I find Alana to be truly extraordinary. She refuses to take no for an answer. She'll strategize and go back to the drawing board to get what she thinks is right. She's a soft and inspiring leader for the team. I also find my mom extraordinary. She's been through hell and back and has always found a way to make money on her own terms, supporting our family on her own."
AB: "There aren't a lot of female founders to look up to, unfortunately, but women like Sophia Amoruso and Emily Weiss are inspiring for us. Seeing them make it all work in their own way has helped us believe and understand that this is all totally possible."
Mama Cax, 27
Cancer survivor, lifestyle blogger, and disability advocate are just a few phrases that describe Mama Cax. With experience in the nonprofit sector, she now splits her time between finishing her masters in international studies, leading inspirational speaking engagements, and modeling.
You were diagnosed with cancer when you were 15 years old. How did you find the strength and optimism to overcome that?
"Of course I had a great support system in my family. But my personality is curious and wants to explore. I wanted to see so many places around the world; for me, that was my main reason to fight. I wanted to know what the future would look like."
You mentioned that after you lost your leg to bone cancer, you were severely depressed and preoccupied with body image. What inspired you to become an advocate for women with disabilities?
"Once in college, when my leg was being repaired, I missed class for two weeks because I felt ashamed. The length that I had to go to seem or appear normal was time-consuming and weighed down on my emotional well-being. Through Instagram, when I started to share my experience, positive comments helped boost my morale in general. So it was a process. I wanted to not only feel confident in my body but also to use that experience to empower other women to do the same."
How do you handle self-doubt?
"In the wake of rejection, sometimes I would think I'm not good enough. But a friend told me, 'You're not for everyone. Just because you don't fit into their agenda doesn't mean you're not good enough.' So whenever I doubt myself, I remind myself I'm not right for them but maybe I'll be [right] for someone else."
How has your social presence helped redefine the body-positive movement?
"When it comes to body positivity, I bring a different narrative. People tend to think body positivity is just embracing yourself if you're full-figured. But it's much more than that — it's a celebration of bodies that have been marginalized for a long time."
What does being extraordinary mean to you?
"Being extraordinary means not only giving yourself a voice when you’re silent in a lot of spaces, but finding ways to empower others to do the same."
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