39 Reflection questions for women entrepreneurs in 2025
If you’re anything like me, you’re always working full steam ahead until the end of December. There’s a two-week period of no-phone time, and then somehow, we’re back to working at capacity in January.
Each year, I vow that I’ll reflect and plan. But truthfully, that time can be hard to come by when my to-do list is already chock full of tasks the moment my out-of-office message ends.
Not only is reflecting on the last year and planning for the next necessary, it’s also fun when you finally do make the time. Finding joy, pride, and accomplishment is an act of defiance in whatever shape it comes in — whether that’s journaling for yourself, or processing with a friend, or writing a piece for others to read.
As a woman in business, I like reflection questions whose purpose is to create space for me to examine my experiences and go far beyond, “how do you balance your work life and family life?” There will be none of that here because it’s a tired question and it’s all life.
I am very aware that my ability to own a business is revolutionary and not one that every woman has. I invite you to join me in being aware of the same and considering how your experiences as a woman shape your business every day — and how you can be aware of the immense power you have to chip away at oppressive structures this year.
Best wishes for the 2025 that you want to have!
Reflecting on 2024
What were my biggest wins in my business last year? How did I celebrate them?
What were my biggest challenges? How did I work through them?
What did I love to do in my business in 2024? Do I want to do more of that?
What did I hate doing? Do I want to do less of that?
Am I proud of myself? About what, specifically?
Preparing for 2025
What are my top business goals for 2025? How will I track my progress toward my goals?
Do I want to grow my business this year? Scale back? Hold strong?
How do I want to feel in December 2025?
How do I want this year of business to feel overall?
What’s one small business-related change I want to make? What’s one thing that I want to keep the same?
Challenges and opportunities as a woman entrepreneur
Who are the people in my life who celebrate me and my business?
How can I build a strong network of supportive women around me?
How can I advocate for other women entrepreneurs and promote or support their work?
Does my business reflect my values and promote diversity and inclusion?
Who is one person that I see as a mentor that I want to reach out to this year?
How will I effectively communicate my value proposition and negotiate fair compensation for my services?
What are my signs of stress and burnout? Do I have a toolbox in place for how to deal with them?
How can I prioritize self-care and ensure that I am taking care of my mental health?
How will I take care of my physical health this year?
What are my absolute red flags when working with others?
How do I uphold the patriarchy that benefits me, but hurts others? How can I examine that? How can I break it down?
How does feminism and women’s empowerment show up in my business? How do I disrupt the patriarchy?
Who can I ask for help and advice when I need it?
Financial considerations
What am I good at when it comes to finances?
What are my financial goals for my business in 2025?
What are the money-related tasks I’ve been avoiding or haven’t been taught to do?
How can I improve my financial literacy and make informed business decisions? Who can help me?
How can I ensure that my business is financially sustainable this year?
What are the processes I need to work on to save, invest, or better understand my money?
Do any of my investments support others’ oppression? How can I divest?
Will I donate money this year? If so, who do I want my donations to help?
How can I talk with other women entrepreneurs about money? How can I learn from them and share my knowledge?
Personal growth and development
What do I do for fun now? What do I want to do for fun?
When will I take time off?
How will I track my time? Do I want to work more and on what? Do I want to work less?
How can I find more fun, flexibility, and joy in my business?
How can I cultivate a growth mindset and embrace challenges as opportunities for learning and development?
How can I celebrate my successes and acknowledge my accomplishments? Who will I share those achievements with?
