How To Make Your Side Hustle A Success, According To 17 Millennial Women Who Did Just That

For the third year in a row, Bustle's Upstart Awards are honoring young women who are doing incredible things in the realms of business, STEM, fashion and beauty, the arts, philanthropy, and beyond. Want to be an Upstarts honoree one day? Read on for career tips, insights, and inspiration to help get you there.

If you've dreamed about quitting your day job or pursuing that one side hustle that seems a little idealistic in your mind, you aren't the only one. Sometimes it takes a little courage, a lot of luck, some support, and a clear vision of what you want to encourage you to take a big leap and either leave your current job, or devote a huge amount of your personal time to make it happen.

It's a journey, and just like you, there are many women who dream of taking their side hustle and eventually turning it into something bigger. But that journey doesn't come without setbacks, unexpected hurdles, and a few bruises along the way — the most important thing to remember is that you are capable and smart enough to persevere and make it all happen.

If there's any doubt in your mind as to whether or not you should give your side hustle a chance, maybe all you need is to hear from other women on the same journey. Let these stories from 17 hustlers, entrepreneurs, and leaders shake the dust off that idea you've had in the back of your mind and give you the courage to pursue it.

CreateHerStock
"At the age of 23 I was flying the friendly skies as a full-time flight attendant and while doing so, I also managed a few social media and marketing platforms for well-known restaurants and chefs in Los Angeles, CA. After a few years, I realized my side hustle was expanding and my passion was within social media and public relations. I took a leap of faith and opened my own public relations firm in Los Angeles where my team and I represent many restaurants, chefs, wineries, and breweries throughout the U.S."
"I started my blog, The Million Dollar Mama, in August of 2016. I've always loved writing and I'd been reading various bloggers' online income reports for a while. I'd just given birth to my first child and wanted to find a way to earn some extra cash so I could stay at home with him for at least a year. I decided I'd give blogging a go, hoping I could earn $1,000 a month within a year. I dedicated myself to learning as much as I could about blogging and earning money online and now, 10 months later, I earn more from my blog than I've ever earned working for an employer (I publish my online income reports on my blog)."
"I started coaching public speaking as a side gig in 2012, with a simple online classified ad, and started up a public speaking and communication blog at the same time. As I gained more clients, I decided to test out holding public speaking group classes, which proved to be quite successful. I expanded my work into speaking professionally about public speaking and communication issues, and thanks to writing articles on workplace communication issues I was offered a book deal by Visible Ink Press. My book, 'The Handy Communication Answer Book,' was released this past April, and my speaking has expanded to include both Canada *and* the U.S."
"I'm a stay-at-home mom and look after three little girls ... Just like any young family, we're always looking for ways to save money. I started coupon clipping, which helped us save a lot. But I learned so much about coupons, that I started a coupon blog called www.couponhahama.com to help inform and educate people. And then, the site started making money. So now, I just manage the site. It pulls in about $400-$500 per month."
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"I started offering my web development, marketing strategy, and social media management services to small businesses in 2010. I stayed hyperlocal, focused up, and was able to carve out a niche in my immediate area. My company has since expanded and has allowed me to work with creatives around the country, not just my neighborhood."
"I spent several years working in corporate America and started to experience some pretty intense burnout that was bleeding into my personal life in a very negative way. I made the decision that, instead of jumping on a job-sourcing website and using my same approach for finding something new that would inevitably turn sour six months down the road, I needed to really flip the process upside down. I spent months thinking about how I wanted to *feel* in my career, not just focusing on what tactical things I wanted to do. Months later, I had an evolving side hustle as a Reiki master and life coach and I took the plunge into doing this work full-time a year ago. I've never looked back!"
"I began my side hustle three years ago as a blog to help cheerleading coaches become more competent and confident leaders. After a year, I launched several digital products and resources that I sold to my very engaged audience. That all happened with content marketing online and listening to my audience to create the resources they were telling me they needed. Last year, it became big enough to leave my 9-5 and launch a new business that helps others grow their online businesses with content marketing. Since then I've actually sold the cheerleading business and now pursue this marketing business full-time."
"I couldn't stop thinking about theBOM (The Black Owned Marketplace) — it consumed every waking moment of my being. I became uninspired with my 9-5 and honestly grew upset with my environment knowing I should be working on my passion. I am also indecisive so I was pushed into entrepreneurship as a result of being laid off. I think my ex-bosses knew my mind was no longer on the task at hand and did me a favor by letting me go. I took it as a sign from God saying that I may be more ready than I think I am — if not I better get ready real soon! theBOM is something that is much bigger than me and it gives me a great sense of pride/purpose to work with the dopest Black-owned brands and give them a platform to shine their already amazing products. Your heart will always tell you when it's time to move on."
CreateHerStock
"Until last year I worked full-time and taught classes during the evening to entrepreneurs at We Work and other places. However, a fortuitous run-in with an audience member during a speaking panel turned into a full-time teaching role at the University of Florida where I run a four semester practicum for Masters-level students. This is truly a dream come true and evidence that your next big opportunity may happen when you least expect it."
"I was a museum educator and improviser, and on the side, I was teaching improv classes to non-actors, specifically museum educators and teachers. I wanted to pass along my skills of flexibility and the ability to pivot, so I was renting space at a rehearsal studio, running classes after work, and answering emails about more classes when I got home. People started to hire me to come to them, and after a while non-educators started to sign up for my classes. They started to sell out, and I had to hire a friend to help me keep up.

Fast forward five years ... and I run The Engaging Educator, www.theengagingeducator.com, a woman-owned and operated professional development organization that teaches presentation, communication, and social skills through improv-based continuing education to over 25,000 people since 2012. We're working with kids on the autism spectrum all the way to senior VPs at companies like Viacom and Time Warner. Along with group classes, we offer individual coaching for everything from empathy training to interview prep. I just turned 35 last week, and couldn't be happier with my side hustle-turned-full-time business!"
"Senior year in college I started doing friends' tax returns on the side, to earn a little extra money. I started working with musicians exclusively, after meeting a keyboardist at an airport and working with him. The side hustle brought in more money every year, until three years ago in 2014, I quit the corporate tax job and now provide money mentorship to music creators full-time through my company, Growth Group."
"Believe it or not, I started a publishing company on the side while I worked full-time in a totally different industry. I have always had a passion for writing, coupled with having an entrepreneurial spirit, so I started my business by publishing my own book. My original plan was to start working with other authors after five years of publishing my own books, but after a year of starting my company I had people requesting to work with me. Three years after running my business on the side, I gave up my full-time job and turned my side hustle into a full-time gig."
Annie Spratt/Unsplash
"Talk about hustling ... I was pursuing a career as a crystal healer (of all things!) while going to school full time and working part time at a new age shop. It was one of the busiest times in my life and I remember getting to a crossroads where I decided to take a leap of faith, drop out of school, and pursue my career as an energy worker full time. Lucky for me, a partnership opportunity at the new age shop opened up around the same time, so I was able to grow both businesses together. Eventually, with some hard work and tons of self-education, I became full owner of the new age shop and grew my practice into a multiple six-figure healing arts school where I teach other women to create their own amazing careers."
"I always knew that I wanted to work for myself, but I also wanted to be smart about how I could grow a business as a sole-proprietor — so I was strategic in the products I chose to design and sell. I got my start in existing niche marketplaces with robust audiences — like Etsy and Shapeways — and focused on designing jewelry using specialized manufacturing techniques with a tech bent, like 3D printing and laser cutting. 3D printing was a total game-changer for me; because I make all my jewelry pieces to-order, I can offer a ton of material options, test designs and ideas in real time with my actual customers, and provide bespoke services without breaking the bank. It took a few iterations and product cycles to find the right flow — and I'm constantly making adjustments — but that element of experimentation and always aiming to be better is what allows me to make this my career."
"In less than a year, I realized how little recognition people of color and people with illness or disabilities received in the travel and wellness world. And while my remote marketing consulting work paid the bills, it was my blog that quickly started resonating with people, and in turn growing faster than any project I'd previously pursued. [...] Don't be afraid to fail but, most of all, don't be afraid of your potential for greatness. And don't be afraid to negotiate payment just as a man would."
"My side hustle is my photography business. I picked up a camera three years ago, captured moments for fun, ended up not totally failing at it, and three year later, I have my own small business. It is worth it to keep pursuing your talents because you never know where that small opportunity can take you. I love what I do and it has opened other doors, even combining my marketing degree with my photography passion which has allowed me to get the best of both worlds."
"After graduating college I immediately dove into a rollercoaster of a career in PR and marketing, always bouncing between in-house and agency. The first six months were usually very exciting with new team members and projects, but eventually, the honeymoon phase would wear out and I would be itching for a change. After questioning whether I was even in the right field, I finally came to the realization that I actually loved the work I was doing, so much that I would even take on passion projects on the side; I just didn't enjoy working for someone else.

I had been saving the extra income I was making with my side projects so that I had enough of a cushion to afford a leap into the world of freelance. Once I took the plunge, I let everyone know what I was doing and was surprised to see how willing they were to help me succeed. If I had known beforehand that there was a supportive community of self-employed millennial women helping other women looking to do the same, I would have taken the leap much sooner."

So get inspired to take the leap, relaunch that project that needed a little more attention, or place your bets on your talents and abilities. These 17 women rewrote the rules about their journey, but there is no playbook that guarantees success. That all depends on how hard you're willing to work for it.