18 Journal Prompts for Women Considering Entrepreneurship
There's a difference between dreaming about being your own boss and actually taking the leap into entrepreneurship. And if you're reading this, chances are you're somewhere in that messy middle—where the corporate world feels too small, but the entrepreneurial path feels too uncertain.
Maybe you've been scrolling through LinkedIn, watching other women build businesses and wondering if you have what it takes. Maybe you have an idea that won't leave you alone, or maybe you just know that working for someone else forever isn't the life you want.
Either way, you're here because something inside you is stirring, and you're trying to figure out if that something is worth following.
Here's what no one tells you about considering entrepreneurship: it's not just a business decision—it's a deeply personal one. It's about understanding not just what you want to build, but who you're willing to become in the process. It's about getting honest about your motivations, your fears, your capacity for uncertainty, and your relationship with failure and success.
These journal prompts aren't designed to give you a yes or no answer about whether you should start a business. Instead, they're meant to help you explore the deeper questions that will inform whatever decision feels right for you. Because the best entrepreneurs aren't the ones without fear—they're the ones who understand their fears and move forward anyway.
So grab your journal, get comfortable with some big questions, and remember: there's no timeline for figuring this out. Your entrepreneurial journey, whether it starts tomorrow or years from now, will be uniquely yours.
18 Journal Prompts for Women Considering Entrepreneurship
1. What problem do I find myself solving over and over again, either for myself or others? What if that could become my business?
2. When I imagine myself in five years, what does my ideal workday look like? Am I working for myself or someone else?
3. What's my honest relationship with money right now? How do I feel about charging people for my services or products?
4. What would I regret more—trying entrepreneurship and failing, or never trying at all?
5. What skills do I have that I take for granted but others consistently ask me about or compliment me on?
6. How do I handle uncertainty and rejection? What would I need to develop to be more resilient in those areas?
7. What's driving my interest in entrepreneurship—freedom, money, impact, creativity, or something else entirely?
8. If I could solve one problem for women like me, what would it be? How would their lives be different?
9. What's my support system like? Who would cheer me on during the hard days, and who might try to talk me out of it?
10. How much financial runway do I have? What would I need to feel secure enough to take the leap?
11. What part of running a business excites me most? What part terrifies me most?
12. If I started a business and it didn't work out, what would I learn about myself in the process? Would that learning be worth it?
13. What success stories inspire me, and why? What do those entrepreneurs have that I want to cultivate in myself?
14. How do I currently spend my free time? Would I be willing to invest that time into building something instead?
15. What would I need to believe about myself to feel confident charging premium prices for my work?
16. If I could start small and test one idea with minimal risk, what would that look like?
17. What would my business give me that my current job doesn't? What would it require me to give up?
18. If I knew I couldn't fail, what kind of business would I start? What does that tell me about what I really want?
How to Use These Prompts
Go deeper, not faster. Rather than rushing through all 18 prompts, spend real time with 2-3 that resonate most. Let yourself explore tangents and follow interesting threads of thought.
Write without censoring. Your initial responses might surprise you. Don't edit or judge your first thoughts—they often contain the most honest insights.
Revisit over time. Your answers to these questions will evolve as you do. Come back to them in a few months and see what's changed.
Look for patterns. After you've worked through several prompts, notice what themes keep appearing. Are you consistently drawn to helping a specific group of people? Do certain fears come up repeatedly?
Share selectively. While it can be helpful to discuss your entrepreneurial thoughts with trusted friends or mentors, be mindful of who you share your most vulnerable reflections with. Not everyone will understand your vision, and that's okay.
What This Process Might Reveal
These prompts might confirm that entrepreneurship is your next step, or they might reveal that you're not ready yet—and both outcomes are valuable. Maybe you'll discover that what you're really craving is more creativity or autonomy in your current role, not necessarily your own business. Or maybe you'll realize you have a specific problem you're passionate about solving, even if you're not sure how to turn it into a business yet.
The goal isn't to talk yourself into or out of entrepreneurship. It's to understand yourself well enough to make a decision that aligns with who you are and what you want your life to look like.
Remember: there's no such thing as the perfect time to start a business, but there is such a thing as knowing yourself well enough to start from a place of clarity rather than confusion. These prompts are designed to help you get there.
Whether you ultimately decide to take the entrepreneurial leap or choose a different path, the self-awareness you'll gain from this process will serve you no matter what you do next. And that's always worth the investment.
