10 Questions Every Woman Should Ask Before She Retires
Because your next chapter deserves more than a financial plan.
Most retirement advice focuses on money—and yes, that matters.
But if you’re a woman approaching retirement, chances are there’s another voice whispering (or shouting) underneath all the spreadsheets:
“What will life feel like when the meetings, deadlines, and caregiving roles fall away?”
It’s not just about preparing your finances.
It’s about preparing yourself.
These ten retirement questions for women are designed to spark self-discovery, clarity, and courage—so you don’t just retire, you reimagine.
✨ Want to go deeper?
I created a free worksheet to guide you through all ten questions. It gives you space to think, dream, and plan. Whether you use it as a journaling tool or bring it to your next coffee date with a fellow retiree-in-the-making, it’s yours.
👉 Click here to download the “10 Questions Worksheet” (no email required)
1. What brings me energy—and what drains it? ⚡️
Start here. Notice how you feel after activities, conversations, or even scrolling sessions. Your energy is a compass—pointing toward the life that wants to emerge next.
2. Who am I when I’m not working or caregiving? 🧭
For decades, you may have been “the director,” “the teacher,” “the caregiver,” or “the one everyone relies on.” But strip away the roles, and who remains?
This is your invitation to meet her again. Not to start over, but to come home.
3. What am I curious about lately? 🔍
Curiosity is often the first breadcrumb on the trail of reinvention.
Amy kept reading articles about sustainable architecture—not because she wanted a new degree, but because it tapped into her long-lost love of design. Now she’s taking a class just for the joy of it.
4. What routines will give shape to my days? 🗓️
Freedom without rhythm can start to feel like floating. You don’t need a rigid schedule—but you do need anchors.
Consider what days you want to protect for solitude, creativity, community, or movement. A gentle rhythm creates meaning and momentum.
5. How do I want to feel in this next chapter? 💖
Peaceful? Energized? Inspired? Free?
List the emotions you crave most. Then reverse-engineer your days around the people, places, and experiences that tend to evoke them. Your emotional GPS matters here.
6. What relationships do I want to nurture—or create? 🌱
Patti realized she missed real conversations. So she reached out to an old friend, joined a book group, and started chatting with her yoga classmates after class. It wasn’t about being busy—it was about feeling connected.
Ask yourself: Who do I miss? Who lights me up? Who might I meet if I showed up somewhere new?
7. What am I ready to leave behind? 🧺
A role that no longer fits. A belief that keeps you small. A habit that doesn’t serve who you’re becoming.
This chapter isn’t just about adding. It’s about releasing what weighs you down.
8. Where do I want to go—literally and figuratively? ✈️
Maybe it’s a long-dreamed-of trip to Tuscany. Maybe it’s finally claiming the front seat in your own life.
Define your destinations—near, far, or deeply internal.
9. What legacy or impact matters to me now? 🌟
Legacy isn’t just about big titles or public recognition. It might be mentoring a younger woman, volunteering in your community, or simply showing up with kindness and courage in everyday life.
Think about the ripple you want to create.
10. What did I love as a girl that I’ve forgotten as a woman? 🎨
Revisit your 9-year-old self. What filled her time? What made her feel alive?
As for me? I adored my Barbie collection. She wasn’t just playing house—she had an airplane, a briefcase, and a convertible. She ran meetings, chased adventures, and charted her own course. That spirit still matters.
Ken? He usually just held her purse while she ran the meeting. 😉
Ready for more clarity?
You don’t have to figure this out alone—and you don’t need to have all the answers.
But you do need a place to begin.
💡 The Retirement Vision Starter Kit is a free guide with 4 powerful, science-backed activities to help you:
Clarify what you want in this next chapter
Let go of old roles that no longer fit
Check in on how you’re really doing across 5 key areas of well-being
Create a vision board for the retirement you actually want
✨ It’s beautiful, easy to use, and designed to help you move from uncertainty to inspiration.
📩 Know someone preparing for retirement?
Share this post—because every woman deserves to enter her next chapter with clarity, confidence, and a touch of boldness.
💭 PS: Want to reflect on these 10 questions at your own pace?
Grab the free worksheet here—it’s simple, printable, and beautifully designed to help you begin.
About Elaine
Elaine Belansky, PhD, is a retirement transition coach who helps women in their 50s and 60s design a bold, fulfilling next chapter. After a 30-year career in public health and education, Elaine now supports women who are navigating the emotional, social, and identity shifts that come with retirement. Her coaching blends science-backed tools, real-life experience, and deep empathy to help women create lives rich in connection, learning, and meaning.
You can learn more at ElaineBelansky.com.
