This article is created by Girlboss and Dreamers & Doers.
Nobody quits their day job on a whim.
Behind every founder who eventually walked away from their 9-to-5 is a story of working into the early hours of the morning, making tough sacrifices (like pulling 80-hour weeks or saying no to social plans), and believing that, despite it all, what they are building is worth it.
Freedom doesn’t just happen overnight. It comes from showing up, over and over again, long before anyone is paying attention.
Here, ambitious women who have lived this journey firsthand share the concrete steps that got them started, the tools and systems that kept them sane, the mistakes that slowed them down, and the milestones that finally gave them the confidence to go all in.
If you've been dreaming about building something of your own but aren't sure where to start —or how to get from where you are to where you want to be—this is the roadmap you didn't know you needed. Pull up a chair and take notes!
The First Building Blocks of a Successful Side Hustle
“I created a detailed five-month strategic business launch plan and brought on an intern to support me in reaching the launch milestones. I always planned to leave my 9-to-5 (the question was just when to do so), and I think that mindset is crucial. A side hustle will stay a side hustle unless we treat it as a growing business that needs to be viable and sustainable.” — Catarina Rivera, Public Speaker, Consultant, and Content Creator of Blindish Latina LLC
“My first concrete step was treating my enthusiasm seriously by making it part of my day. The way the gym feeds the body, a side gig at the start should feed your soul. Wave away the guilt, whether from not staying an extra hour at work or from being away from your kids. The gig cannot be a second thought. Eventually, your day job starts feeling like the distraction, and quitting becomes the obvious next step.” — Laís de Oliveira, Founder and Author of Hacking Communities and Nest and North
“I stopped treating every idea like a permanent decision and started treating them as timeboxed experiments. I’d give each idea a specific window of time, define success metrics upfront, and either double down or move on based on the results. That structure helped me avoid paralysis, learn faster, and figure out what was actually worth turning into a real business.” — Danielle Letayf, CEO of Badassery
“My first step was a LinkedIn post telling my network about my new business, something like, ‘If you're an executive looking for a Chief of Staff, I'd love to find you your next one.’ I'd been creating content in the Chief of Staff space for a while, so I had a hypothesis that asking my network directly would land. It felt scary to switch from giving content to making an ask, but I was burnt out from nearly a decade in startups and figured if I was going to work this hard, I'd rather do it for myself.” — Clara Ma, CEO and Founder of Ask a Chief of Staff
“While I was still working as an associate at another firm, I spent my evenings coaching other lawyers on how to launch and structure their own practices. This approach allowed me to test my theories on entrepreneur education and business strategy before I ever opened my own doors—and to test my interest in entrepreneurship while the safety of a steady paycheck remained intact.” — Kamilah Jolly, Founder and Managing Attorney of Jolly Esquire PLLC
“The first step wasn't strategic but reactive. I was burnt out from a startup role with a long commute and six days in-office, and my husband and I were starting to think about moving to be closer to his family as we thought about starting our own. During this transition period, I happened to reach out about a part-time freelance gig, which happened to lead to another, then another—and six months in, I realized I'd accidentally built something better than any job I would have taken!” — Megumi Calver, Founder and Marketing Strategist of Media Kamo
Balancing Full-Time Work While Building Momentum
“While working full-time, I was putting in an additional 40+ hours each week building my company on the side, squeezing work in before my job, late at night, and on weekends. It definitely required sacrifices, especially when it came to my social life and downtime, but I was intentional about treating the business like a long-term investment rather than a hobby. Even though the schedule was intense, it was one of the most rewarding seasons of my 20s. I could feel the momentum building in real time!” — Emma Tessler, Founder and CEO of Ninety Five Media
“I was in a high-pressure, high-visibility corporate leadership role while getting my coaching certification, and very quickly realized doing both was exhausting. It wasn’t the 10+ hours a week dedicated to coaching that drained me. My day job left me depleted. When an opportunity came up to move into a less demanding (and less glamorous) lateral role, I took it. It gave me the bandwidth I needed to build my side hustle. Old me wouldn’t have done that because I loved the status and power of calling the shots. But choosing alignment over image gave me the space and energy to build what I truly wanted.” — Coco Duan, CEO of Coco Duan Coaching
“I spent 10 to 20 hours a week on my side hustle, divided between 30-minute sprints throughout the day (often sparked by a passing thought or lunchtime conversation) and late-night hyper-focus sessions (which suit night owls like me). Setting boundaries at work was critical, which meant overcoming the guilt of not being the overdeliverer I love to be. Deleting Slack from my phone sounds small, but it was what made the focus sessions actually flourish.” — Laís de Oliveira, Founder and Author of Hacking Communities and Nest and North
“I built my freelance clientele to the point where I was essentially working two full-time jobs at once—40 hours a week in my corporate role and another 40 hours a week supporting freelance clients on the side. At a certain point, it became clear that I either needed to make the leap or completely burn myself out trying to maintain both.” — Emilie Given, Founder of She's A Given
The Strategies and Software That Made My Side Hustle Possible
“One strategic thing I did to help my side hustle podcast gain traction was tap into female founder networking groups. Within hours of posting in those communities, people began pitching themselves to be guests on my podcast instead of me having to chase guests down. That approach not only helped grow the podcast more quickly, but it also expanded my network and connected me with inspiring female entrepreneurs whose stories continue to motivate me.” — Peri Finkelstein, Founder and CEO of Team Peri Foundation
“I went from being a solo founder stretched impossibly thin to having AI agents that genuinely function as my operating team, handling everything from client ops to legal document drafting to billing. That leverage is what made it possible to deliver a premium service without a massive headcount, and it let me focus my limited hours on the things only I could do.” — Kristina Subbotina, Founder and CEO of Lexsy
“My existing relationships were my most useful tool. Old bosses became first clients and agency colleagues followed me out the door, which is how I walked into an 11-day billable week before I owned a business card.” — Natanya Wachtel, Founder, Chief Architect, Angel and Host of The New Solutions Network
“If you looked at my daily tech stack, Canva would easily be at the top—I’ve leaned heavily into it and other AI design tools to completely elevate our social media output.” — Marissa Pick, Founder of Marissa Pick Consulting LLC
Avoiding the Most Common Mistakes
“One of my biggest early mistakes was believing that being a ‘good’ business owner meant being constantly available, instantly responsive, and willing to do everything myself. In reality, it just made the business harder and more emotionally exhausting than it needed to be. Over time, I learned that healthy boundaries, systems, and support are actually what allow a business to grow sustainably. Ironically, the business became stronger once I stopped trying to prove my value through burnout.” — Emilie Given, Founder of She's A Given
“My biggest mistake was not going all-in sooner. For years, I treated my consulting like a side quest instead of a business, and that really slowed my progress. I wish I had been brave enough to call myself an entrepreneur earlier on instead of thinking that I needed to have a full-time job to be successful.” — Joy Batra, Founder, Podcast Host, and Fractional General Counsel of Quartz Consulting
“Early on, I fell into the trap of taking on too many different types of projects. When you first launch a business, it’s natural to want to say yes to everything. It took some time to figure out what truly energized me, what didn’t, and what made the most sense to outsource. Today, I’m much more intentional. I’ve gotten comfortable saying no, and I’ve built a trusted network of professionals to whom I can seamlessly refer projects when they aren't the right fit or don't align with my current capacity.” — Marissa Pick, Founder of Marissa Pick Consulting LLC
“The surprisingly challenging part is that there's no boss telling you to show up, so the same flexibility that lets you build the life you want will also let you avoid the hard conversations. Learning to manage yourself is the actual founder skill.” — Megumi Calver, Founder and Marketing Strategist of Media Kamo
“Everyone I talked to told me to soften what I was talking about when it came to creating trauma-informed cultures in the workplace—and I mean everyone! But it felt like the wrong choice, so I stuck to it and am so grateful. My work would not be where it is without sticking to my initial spark and passion.” — Stephanie Lemek, Founder and CEO of The Wounded Workforce
Knowing When to Go All-In on Your Business
“I gave myself one year and a number. Once I had enough saved to feel stable, I left. But honestly, what pushed me out the door wasn't just the money. It was the realization that I was working just as hard—if not harder—outside of my job than inside it, and the work outside felt like mine. Leaving was scary and relieving at the same time.” — Nicole Leon, Founder of L Leon Virtual Assistance LLC
“I consistently built up my freelance career over many years, so the leap was softened. I was juggling planning a wedding, increasing freelance, and working full-time. The stress was building, and I knew one of them had to go, so I quit my full-time job. It was hard, because I loved my boss and the work, but because of that leap, life has been way more flexible, allowing for an eight-year adventure of traveling the world and working remotely.” — Jessie Sanchez, Graphic Designer and Creative Mastermind of Happy Brand Company
“I left my 9-to-5 without burning anything down. I told my boss the truth and built the step-down plan with her instead of behind her back. The minute the side work was paying me more than the day job was paying me to play small, the decision had already made itself. I just had to catch up to it.” — Natanya Wachtel, Founder, Chief Architect, Angel, and Host of The New Solutions Network
“Honestly, I never fully felt comfortable leaving my 9-to-5. I planned my exit about a year and a half in advance based on savings, coaching certification milestones, and logistics, but the leap still felt scary when the time came. When you’ve spent your whole life equating safety with financial security, entrepreneurship will feel uncomfortable no matter how prepared you are. At some point, I realized the discomfort wasn’t a sign to stop; it was part of the growth.” — Coco Duan, CEO of Coco Duan Coaching
Building Your New Schedule as a Business Owner
“I'm a mom now, and thankfully, my days are flexible enough to accommodate the realities of raising two little girls. I never have to ask for time off when they're sick, I can always prioritize family time, and somehow I've become even more efficient with the hours in my day. My priorities have never been clearer, and my work allows me to honor them.” — Lexie Smith, Founder and CEO of GROWTH MODE Agency
“My days are much more intuitive, and led by energy and creativity levels versus having to be ‘on’ for eight hours just because that's the unspoken requirement. The most rewarding thing has been actually being able to utilize my talents and gifts and see the reward in our business's growth, opportunity, and sales.” — Natalie De Vincenzi, Founder and CEO of You Are Enough Co.
“I probably work more as an entrepreneur than I did in a full-time job, but it's also been more fulfilling to set my own goals and work on projects that genuinely excite me!” — Joy Batra, Founder, Podcast Host, and Fractional General Counsel of Quartz Consulting
“One of the greatest ROIs of running my own business? Reclaiming my time. I used to spend up to three hours a day on a round-trip commute into the city. Getting those hours back has completely transformed how I show up for both my clients and my family. Now, I have the flexibility to get my work done at the highest level while being fully present at home. Nearly eight years later, I know without a doubt it was the right call.” — Marissa Pick, Founder of Marissa Pick Consulting LLC
“The biggest yet most challenging shift is that I no longer tie my worth to productivity. In corporate, hustling harder was rewarded. As an entrepreneur, I’ve learned that less is more—more strategic, sustainable, and effective.” — Coco Duan, CEO of Coco Duan Coaching
All individuals featured in this article are members of Dreamers & Doers, a highly curated community and PR Hype Machine™ amplifying extraordinary women entrepreneurs and leaders through authentic connections, credibility-boosting visibility, and opportunities that accelerate big dreams.
