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The Messy Middle: How Female Founders Can Successfully Navigate the Toughest Phase of Entrepreneurship
- Rhonda Glynn
- Mar 18
- 5 min read
Updated: Mar 31
“The best way for a start-up to “disrupt” an industry is to be a thesis-driven outsider—someone who hasn’t been jaded by the industry but has a strong opinion for what should change.” - Scott Belsky.
Ever feel like you’re stuck in the chaos of building your business? Welcome to the Messy Middle- the place where dreams meet reality, AND resilience becomes your superpower.
For female founders, this phase can feel even more daunting, BUT it’s also where the magic happens.
But the Messy Middle isn’t just a phase; it’s a test of your vision, resilience, AND ability to adapt. For women entrepreneurs, it’s also an opportunity to rewrite the rules AND build businesses that truly reflect our strength AND creativity.
Excited to discover the secrets to mastering your "messiness"?
Let's get started.
What Is the Messy Middle?
The Messy Middle is the grueling, unpredictable phase of entrepreneurship that comes AFTER the initial launch BUT BEFORE sustainable success. It’s where the excitement of starting something new wears off, AND the reality of building a business sets in.
This phase is filled with trial AND error, setbacks, AND moments of doubt-BUT it’s also where the foundation for long-term success is built.
For female founders, the Messy Middle can feel even more intense. Women often face unique challenges, from balancing societal expectations to navigating industries that may NOT always welcome diversity.
BUT here’s the thing: the Messy Middle is also where women entrepreneurs can shine. It’s where resilience, creativity, AND community become your greatest assets.
“Imagination happens only when your mind has the freedom to run rampant. When you’re always connected and able to find an answer, you stop wondering and wandering.” - Scott Belsky.
Why the Messy Middle Matters for Female Founders
The Messy Middle isn’t just a hurdle to overcome-it’s also a critical phase that shapes the future of your business. For fempreneurs, this presents an opportunity to:
Build resilience: Every setback is a chance to grow stronger AND more adaptable.
Refine your vision: The Messy Middle forces you to clarify what truly matters for your business.
Leverage your unique strengths: Women often bring empathy, collaboration, AND creativity to the table-skills that are invaluable for their journey.
The Data on The Messy Middle
70% of startups fail during the Messy Middle DUE TO lack of adaptability AND resources.
Female-founded startups receive ONLY 2.3% of venture capital funding, making resourcefulness AND resilience even more critical.
90% of successful female founders say the Messy Middle taught them invaluable lessons about leadership AND perseverance.
BUT let’s be real: navigating startup challenges isn’t easy.
That’s why we’re breaking down actionable strategies-designed to help you NOT only survive - BUT thrive during this chaotic yet transformative time.
5 Ways Female Founders Can Successfully Navigate the Messy Middle
1. Embrace Uncertainty (It’s Part of the Process)
The Messy Middle is inherently uncertain. You might NOT know if your product will resonate, if your funding will last, OR if your team will stick it out. BUT here’s the secret: uncertainty is where innovation happens.
Actionable Tip:
Focus on what you can control. Break big goals into smaller, manageable steps.
Celebrate small wins-they’re proof that you’re moving forward, EVEN when it doesn’t feel like it.
2. Build a Support System (You Don’t Have to Go It Alone)
One of the biggest mistakes entrepreneurs make is trying to do everything themselves.
For female founders, building a strong support system is especially important. This includes mentors, advisors, AND a network of fellow entrepreneurs who understand your journey.
Actionable Tip:
Join communities for women in business, like Women Who Startup OR Female Founders Alliance.
Don’t be afraid to ask for help. Vulnerability is a strength, NOT a weakness.
“Look at what your competitors do, and ask yourself a series of questions: “Are their strategy and goals the same as mine?” If their strategy and beliefs are different, and you still have conviction in your own, then you shouldn’t be distracted. Stay the course.” - Scott Belsky.
3. Experiment AND Iterate (Fail Forward)
The Messy Middle is all about experimentation. You’ll try things that don’t work, AND that’s okay.
What matters is how you learn from those experiences AND pivot accordingly.
Actionable Tip:
Adopt a “test AND learn” mindset. Run small experiments to validate ideas BEFORE going all in.
Document your learnings. What worked? What didn’t? Use these insights to refine your strategy.
4. Prioritize Self-Care (You Can’t Pour from an Empty Cup)
As a female founder, you’re often juggling multiple roles-business owner, caregiver, partner, friend. It’s easy to put yourself last, BUT self-care for entrepreneurs isn’t selfish; it’s essential.
Actionable Tip:
Schedule time for yourself, EVEN if it’s just 15 minutes a day.
Delegate tasks that drain your energy, SO you can focus on what truly matters.
5. Leverage Your Unique Strengths (You Bring Something No One Else Can)
Women often bring unique strengths to entrepreneurship, like empathy, collaboration, AND emotional intelligence. These qualities can be successfully utilized during the Messy Middle.
Actionable Tip:
Lean into your strengths. Are you a great communicator? Use that to build strong relationships with your team AND customers.
Don’t try to fit into a mold. Your authenticity is your superpower.
Real-Life Examples of Female Founders Thriving in the Messy Middle
📌Tracy Young: Pivoting to Success
Tracy Young, co-founder of PlanGrid, initially struggled to gain traction in the construction tech industry. During the Messy Middle, she pivoted her strategy, focusing on building a product that truly solved her customers’ pain points. Her adaptability led to PlanGrid’s acquisition by Autodesk for $875 million.
Key Takeaway:
60% of startups that pivot during the Messy Middle go on to achieve sustainable growth.
📌Arlan Hamilton: Building a Support System
Arlan Hamilton, founder of Backstage Capital, launched her venture capital firm while homeless. She leaned on her network of mentors AND advisors to navigate the Messy Middle, eventually building a fund that invests in underrepresented founders.
Key Takeaway:
85% of female founders credit their success to having a strong support system during the toughest phases of their journey.
“It usually takes at least two years before you have any reasonable traction to show that your business might be working, then another few years of driving growth to create something that looks like a moat. Then you can afford to breathe. A little.” - Scott Belsky.
Call to Action
The Messy Middle might feel overwhelming, BUT it’s also where the most growth happens. As a female founder, you have the strength, creativity, AND resilience to NOT only navigate this phase BUT to come out stronger on the other side.
Ready to conquer the Messy Middle?
Share your story in the comments below. What’s been your biggest challenge, AND how are you overcoming it?
Join the conversation on social media using #TheMessyMiddle AND #FemaleFounders.
Download our free guide to thriving in the Messy Middle.
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