16 Women Who Out-Earned Their 9-5s in Just One Year

This content was created by Girlboss and Dreamers & Doers.

Leaving behind the stability of a steady paycheck to pursue entrepreneurship is no small move—it’s a declaration that you’re ready to create something bigger than a 9-5. The real challenge usually isn’t the hard work (you’ve got that covered). It’s the lingering question: Will I ever match—or even surpass—my old salary?

The truth? So many entrepreneurs prove that those fears shrink in the face of smart strategies, intentional choices, and the confidence to bet on yourself. In this piece, you’ll hear how they fueled financial growth in year one and the advice they’d give you if you’re hesitant to make the jump for yourself.

Building Your Brand and Visibility

Nicole Leon

Founder of L. Leon Virtual Assistance, a boutique virtual support business for stretched-thin leaders who are ready to delegate with intention.

“Instead of pouring money into ads or fancy tools, I showed up consistently online, shared value, and talked to people like the real human I am. I built trust first—and that trust turned into clients, referrals, and a booked-out roster within my first year. The approach also kept overhead low."

Her #1 tip? “I recommend starting scrappy. Build what you can with what you have and trust that refinement will come with time and experience. You don’t need the final version on day one.”

Lakeya Cherry

CEO and Founder of Lakeya Cherry LLC, a dynamic executive coaching and consulting business that empowers leaders and organizations to maximize their potential.

“In my first year, I leaned heavily on bootstrapping, investing time and energy into promoting my personal brand and sharing my new path widely with my network. I made it clear that I was available for coaching, facilitation, consulting, and speaking opportunities, even while holding a full-time role. To build credibility quickly, I discounted my rates early on to attract clients and gather testimonials.”

Her #1 tip? “Start preparing now. Save to create a financial cushion and experiment with side hustles to test the market and build confidence.”

Sara McCarthy

Founder and Chief Creative Officer of One Eleven Creative Inc., a copy and ideas studio built for brands that hate boring.

“I jumped into LinkedIn to succeed in my first year. Cold DMs every day, no shame—just sharp outreach and a clear point of view. I treated it like digital door-knocking: high volume, high intent, and zero fluff. That consistency brought in my first wave of clients and helped me sharpen my pitch in real-time.”

Her #1 tip? “You'll always have a salary cap when working for someone else. But when you have skin in the game because you work for yourself, the earning potential is limitless.”

Leveraging Relationships and Partnerships

KK Hart

Founder and Expert of Generational Growth, a content and media platform based on her decades of experience as a 10x entrepreneur, strategic investor, and acquirer.

“Rather than building everything from scratch, I focused on identifying and partnering with established brands, creators, and platforms that aligned with our mission. Instead of spending months building an audience from zero, we were able to leverage the trust and reach of our partners.”

Her #1 tip? “Instead of seeing your earning potential as a linear path with a fixed salary, view it as a portfolio of opportunities. Your entrepreneurial leap isn't just about replacing your current income; it's about building an asset that can generate income in multiple ways, including intellectual property, brand equity, and the potential for a future acquisition.”

Amanda Northcutt

Founder and CEO of Level Up Creators, a boutique consulting firm specializing in transforming the businesses of subject matter experts, thought leaders, and creators from launch-dependent to sustainably profitable.

“In my first year, I focused on finding partners who shared my vision and served a similar audience, but in complementary ways. Instead of chasing every opportunity, I built a circle of collaborators where referrals, co-marketing, and shared resources felt natural and mutually beneficial.”

Her #1 tip? “Start by building a business model that isn’t tied solely to your time so your earning potential grows with the value you create, not just the hours you work.”

Nichole Bascue

CEO and Co-Founder of  N² Consulting, the unapologetic brainchild of Indigenous brilliance.

“From day one, I ran N² through a high-value, high-alignment filter, which meant only taking contracts that matched our values and promised transformational results. I turned down work that drained capacity, even if it came with a big check.”

Her #1 tip? “Price yourself at the value of your outcomes—not the hours on your calendar—and stop negotiating against yourself before the client even says a word.”

Laying the Financial Foundation

Stephanie Skryzowski

Founder and CEO of 100 Degrees Consulting, providing financial strategy and bookkeeping services to nonprofits around the globe.

“I focused on monetizing skills I already had. I spent my evenings identifying ideal-fit clients and reaching out with personalized cold emails. By offering services I could deliver confidently and efficiently, I was able to sign several clients quickly and to replace my full-time salary so I could hit the ground running.”

Her #1 tip? “Start by offering services that are rooted in the skills and industry you already know. It's the fastest path to earning income and building confidence.”

Linda Du

Managing Director of Okta Investment GmbH, a Berlin-based private investment firm backing high-impact ventures in renewables, emerging markets, and late-stage tech.

“I set up a flexible investment structure with separate experimental strategies, one focused on renewables and one on emerging markets. This allowed me to pursue long-term wealth growth while paying myself and my team members a salary.”

Her #1 tip? “It's never too late to learn to invest. Start small and experiment, and soon your side hustle could give you the financial freedom to pursue other projects.”

Eman Abdur-Rahman

Founder of Your Virtual Keeper, an accounting firm that supports mission-driven service providers in understanding and incorporating financials into their businesses.

“In my first year, I kept a dedicated business journal to track every client acquisition idea, service offering, and pricing concept, working on each idea before pivoting. I also took on projects through lead-generating platforms like Thumbtack, Bark, and a financial advisor marketplace. While the goal wasn’t immediate profit, these high-volume opportunities allowed me to refine my pricing, onboarding process, and communication skills. Many of those early projects also led to referrals.”

Her #1 tip? “Start by focusing on getting clients in the door, even if the work isn’t perfectly priced at first.”

Alejandra Santos

CEO of Into The Next, helping business owners scale lean and exit smart by turning operational chaos and financial uncertainty into clarity, efficiency, and long-term value.

“Accelerating financial growth always comes down to two things: increasing your average order value and extending customer lifetime value. You can do this through cross-selling, upselling, or introducing subscription or continuity models.”

Her #1 tip? “Build up some savings, secure a few initial clients or customers, make sure your basic needs are covered, then reinvest every dollar back into the business.”

Going All in on AI

Demi Oloyede

Founder of Limpiar Inc., an AI-powered property operations platform helping multi-site commercial brands automate facility services, manage maintenance and small assets, and capture real-time data for scheduling, quality control, and compliance.

“In my first year, I focused on delivering a core service before building out the full technology platform. This allowed me to deeply understand the market, gather real customer insights, and generate revenue immediately. I also pre-sold the product before it existed, securing commitments that funded our early build.”

Her #1 tip? "Don’t wait for the perfect launch. Sell the vision, deliver value fast, and let your customers guide what you build next. The fastest way to replace your salary is to focus on solving a real problem and to get paid for it quickly.”       

Kelly Hubbell

Founder and CEO of Sage Haus, helping busy parents reclaim time by building their village.

“The boldest decision that accelerated my business growth was going all in and leaving my corporate job to dedicate myself fully to Sage Haus. Up until that point, I was treating it as a side hustle, which prevented me from fully investing in my vision.” 

Her #1 tip? “Invest in the support systems that will free up your mental energy and time. Delegate what doesn't need to be done by you so you can focus on what only you can do.”

Jessie Sanchez

Creative Mastermind of Happy Brand Company, a small but mighty creative strategy and design studio specializing in thoughtful design for impactful brands.

“I grew my client base for three years while still working a full-time salaried job. After 5 p.m., I would work on projects and connect with prospective clients on LinkedIn.”

Her #1 tip? “Put yourself out there. It may seem scary at first, but it's so rewarding. There are great directories that support budding business owners. I recommend IFundWomen, Freelancing Females, ilovecreatives, and Dreamers & Doers. There's nothing better than advice from business leaders who have been exactly where you are and have flourished.”

Audrina Blackburn

Co-Founder of Summit Chasers Network, the growth partner for founders, delivering high-impact strategy and execution through expert-led growth sprints, immersive retreats, and full-funnel marketing and AI integrations.

“In our first year, we focused on delivering high-impact growth sprints for founders. During these sprints, we condensed months of strategy, marketing optimization, and AI automation into one intensive week. By providing fast, tangible wins, we built a reputation for speed and results, which led to repeat engagements and strong referrals.”

Her #1 tip? “It’s easy to worry about what your business can earn, but you are the ceiling. If you keep growing your skills, expanding your vision, and pushing yourself to lead at a higher level, your business will grow right alongside you.”

Investing in Yourself Pays Off

Luzy King

Founder of Say Hola Wealth, a financial wellness company and media platform that helps first-generation professionals heal from financial trauma, build wealth, and become powerful investors without guilt or burnout.

“In my first year of business, I hired my first mentor. Her support gave me the clarity and confidence to take aligned action. That investment helped me build a business rooted in purpose and power.”

Her #1 tip? If you want to get on this path, start yesterday. Don’t let the fear of earning less hold you back. Your value multiplies when you decide what it's worth.”

Catherine Valega

Owner of Green Bee Advisory, supporting high-achieving women in their wealth and tax-management needs.

“During my first year, I produced a lot of original content, mostly via blogs. Today, I would say that the focus should be on videos, but the idea is the same.”

Her #1 tip? “Focus on what makes you, you. Don't try to perfect your model before launching. Just go.”

All individuals featured in this article are members of Dreamers & Doers, a highly curated community of extraordinary women entrepreneurs and leaders amplified through high-impact PR, authentic connections, and trajectory-shifting resources.