Have you ever asked yourself: “Can I really afford to do what I want after corporate?”
If the answer is yes, maybe, or even “I’m not sure yet”—you’re not alone. Take a listen to this conversation with host Natalie Benamou, Founder of HerCsuite® and Lisa Sakai, Founder of One Vision Retirement and Bucket List financial planner. This heartfelt conversation is about how to build your next chapter with clarity and confidence—no matter what that chapter looks like.
Whether you're dreaming of launching a business, joining a board, stepping into a fractional role, or creating a mosaic portfolio life, this conversation will shift how you think about what’s possible—and how to fund it.
💡 3 Mindset + Money Shifts:
✨ Let go of the word 'retirement' and embrace financial freedom.
✨ You don’t need all the answers, you need a plan that fits you.
✨ Build your next chapter around what you truly value.
🔎 What Should You Be Thinking About?
Lisa shared some powerful insights that every woman in transition should consider:
- Not every next move needs to be a business. Starting something new can feel exciting—but also exhausting. Some women need time to recover from burnout before jumping into entrepreneurship. In those cases, board service or fractional consulting might be a better fit.
- Know your "three magic numbers." Lisa walks clients through identifying what they truly need financially: a baseline for freedom, a stretch goal, and a safety buffer. This creates room for both dreaming and practicality.
- Stress-test your vision. Financial plans often assume rosy outcomes. But what if income dips? What if expenses spike? Being ready for volatility can make or break your plan.
- Think liquidity. If your assets are tied up in retirement accounts, accessing them may not be easy—or tax efficient. Portfolio careers require flexible cash flow.
- Check in with your mental readiness. After 20+ years in high-powered roles, many women feel unmoored when they stop working. The shift isn’t just logistical—it’s emotional. Evaluate how will you keep using your superpowers in new ways.
🎯 Lisa and Natalie Are Teaming Up!
We are thrilled to be launching our new HerCsuite® Portfolio Career Program August 27th to help you move into your next chapter with a personalized plan, support, and a network of women doing the same. Whether you’re still figuring it out or ready to leap—we’ll help you make it happen with clarity and confidence.
👉 Get the details here.
🎧 Press play to start imagining—and building—the portfolio life you deserve.
✨ Keep shining your light bright. The world needs you.
👋 Connect with Natalie Benamou
Natalie Benamou is the visionary behind Women Leaders on the Move, a Top 25 Women's Leadership podcast by Feedspot. As the Founder of HerCsuite®, she leads a strategic collective for executive women navigating board service, portfolio careers, entrepreneurship, and leadership in the second half of their professional lives.
About Lisa Sakai
Lisa Sakai is a Financial Consultant who works with clients on Bucket List Acceleration—getting to live the life they want now. As the co-founder of One Vision Retirement, she has helped clients nationwide for over 12 years. Lisa’s guidance turns financial planning into approachable, actionable steps you can take immediately.
🔗 Connect with Lisa on LinkedIn
Website: www.onevisionretire.com
YouTube Channel: @financialfreedomwithlisa
