3 Questions Women Entrepreneurs Should Ask Themselves
Written by Lisa Simone Richards
September has a “fresh start” feeling. Even though it’s not January, many of us treat this season like a second New Year. As female founders, we often jump straight into thinking about what’s next. Personally, I’m already thinking Black Friday, holiday campaigns, Q4 targets and how to squeeze every last goal into the final months of the year.
Something I needed to remind myself as an entrepreneur is that instead of constantly chasing the horizon, it was really important to take a second to celebrate how far I’ve come. Without those moments of reflection, we risk getting stuck in the grind: always chasing, never celebrating. And when I take a second to think about it, the version of myself six months ago would be really excited about where I currently am today, so I get to have a moment and recognize that!
That’s where a September reset for women entrepreneurs comes in.
Before you dive into strategy and planning for the months ahead, take a moment to reflect on your wins so far. Grab a paper and pen to write and reflect on your growth, recognize your resilience, and fuel your confidence for what’s next.
Here are three powerful reflection questions for female founders to guide your September reset:
1. What’s the biggest milestone you’ve achieved in the last 90 days?
Entrepreneurship moves fast, and it’s easy to gloss over the wins in the hustle of daily tasks. Looking back at the past three months helps you recognize progress that deserves to be celebrated, whether it’s securing a new client, joining a community, launching a product, or even taking a bold step you were once hesitant about. This type of reflection for entrepreneurs helps you ground yourself in success before leaping into what’s next.
2. What’s something you know now that you didn’t know one month ago?
Growth doesn’t always show up in sales or metrics. Especially during challenging times, it often shows up in learning. Maybe you figured out a new marketing strategy, overcame a financial challenge, or gained clarity about your business direction. Acknowledging this knowledge reinforces your evolution as a founder and sets the stage for a stronger Q4.
3. What’s something you used to struggle with but now find easier?
We’re always evolving our skillset so take a second to recognize yours! Maybe pitching investors feels less intimidating, or you’ve learned how to set boundaries with clients.
These small shifts compound over time, shaping you into a stronger, more confident entrepreneur. It’s the kind of progress that a fall business reset can highlight—proof that you’re continuously moving forward.
This is your gentle reminder: don’t just measure your success by how far you want to go, that goalpost is often moving. Instead, measure your success by how far you’ve already come.
Before getting into your Q4 strategy, spend just a few minutes with yourself to pause, reset, and celebrate the wins you’ve earned. When you embrace reflection as much as action, you step into the next season of business with more clarity, confidence, and momentum.
If you like these questions, you’ll find even more guided prompts inside the Female Founders Journal — a tool designed to help women entrepreneurs build confidence, celebrate progress (with fun stickers!), and grow with intention every single day.
---
Lisa Simone Richards is the co-founder and CEO of Pearl Spark Pages, a luxury stationery brand designed to help female founders push past imposter syndrome and build confidence through mindful self-reflection. As the host of the Female Founders Journal Club and also the private podcast, The Messy Middle, Lisa creates safe spaces for women entrepreneurs to get real about the ups and downs of business and celebrate their growth.
After years spent helping women-led startups gain visibility, Lisa realized firsthand how much our inner dialogue shapes our journey. Determined to change that narrative, she developed a journaling framework to help founders cultivate confidence, self-trust, and authenticity—the foundation of Pearl Spark Pages. Her mission: empower female founders to embrace their true potential, one page at a time.
Shop the Pearl Spark Pages collection with RevolutionHer >>