For decades, retirement was sold to us as the finish line.
Work hard. Save diligently. Power through. Then one day, you stop.
But what happens when you get there — and realize you’re not done dreaming?
More and more women are discovering that retirement isn’t an ending at all. It’s a transition. A recalibration. A moment where the noise quiets just enough for a new question to emerge:
How do I want to live now?
On a recent episode of Living Ageless and Bold, I had a powerful conversation with Lisa J. Haynes, a former corporate CFO who managed billions of dollars before reinventing her own life as a certified retirement coach. What she shared reframed everything I thought I knew about retirement — and it’s a perspective every woman deserves to hear.
The Myth of “Done”
Many women arrive at retirement exhausted.
They’ve spent years caring for families, building careers, managing households, supporting spouses, and putting their own dreams on pause. When work finally slows down, there’s relief — but often, there’s also confusion.
No one really prepares us for the emotional side of retirement.
Who am I without my title
How do I structure my days
Why do I feel restless when I should feel grateful
Is it okay to want more
Lisa says this is one of the most common moments where women feel unmoored — not because they failed to plan financially, but because they were never encouraged to plan intentionally.
You planned your career. You planned your family. But no one ever taught you how to plan your retirement life.
From Corporate CFO to Retirement Coach
Lisa J. Haynes didn’t stumble into retirement coaching — she lived the transition herself.
As a high-level corporate CFO, she was responsible for enormous financial decisions. She understood risk, strategy, and long-term planning. On paper, she did everything right.
And yet, like so many women, when she stepped away from her corporate role, she realized something essential was missing.
She had planned the money.
She hadn’t planned the meaning.
That realization led her to become a certified retirement coach and to create a framework designed to help people — especially women — build a retirement that feels fulfilling, purposeful, and joyful.
Why Retirement Feels So Different for Women
Women experience retirement differently than men — and the data backs that up.
Women often retire earlier or later due to caregiving responsibilities
Live longer, which means retirement lasts longer
Derive more identity from relationships and contribution
Have careers filled with pauses, pivots, and reinvention
And yet, most retirement planning still centers on numbers.
401(k)s. Withdrawal rates. Social Security strategies.
Important? Absolutely.
Enough? Not even close.
Lisa’s work focuses on what happens after the spreadsheets — the human side of retirement that determines whether this chapter feels empty or expansive.
Introducing the KILLING IT Framework
Lisa’s book and coaching program are built around a framework designed to help women approach retirement holistically.
The core idea is simple but powerful:
Joy doesn’t happen by accident. It happens by design.
Instead of asking how to stop working, Lisa encourages women to ask how they want to live.
That shift alone changes everything.
Identity: Who Are You Now
One of the first challenges women face in retirement is identity loss.
For years, introductions were easy. Titles gave structure. Roles gave validation.
When that disappears, it can feel like you’ve lost your place in the world.
Lisa reminds women that identity doesn’t disappear — it evolves.
Retirement is an invitation to reclaim parts of yourself that were buried under responsibility.
Creativity
Curiosity
Playfulness
Leadership on your own terms
You don’t stop being valuable when you stop being employed.
In many ways, you finally get to be fully yourself.
Structure Without Rigidity
Another surprise for many retirees is too much freedom.
Without structure, days blur together. Motivation wanes. Energy dips.
Lisa emphasizes the importance of creating gentle structure — not rigid schedules, but rhythms that give days shape and meaning.
This might include dedicated mornings for movement or learning, weekly social anchors, creative projects, volunteer commitments, or simply planning ahead.
Always Have Something to Look Forward To
One of the most powerful ideas we discussed was the importance of anticipation.
Joy thrives on having something to look forward to.
It doesn’t have to be big. It can be a trip, a class, a visit with your kids, a project, or even a small plan on the calendar.
Retirement isn’t about filling time.
It’s about creating moments.
Relationships Matter More Than Ever
Work often provides built-in social connection. When it’s gone, isolation can quietly creep in.
Lisa encourages women to intentionally cultivate friendships, community, and shared experiences.
Connection doesn’t magically happen in retirement.
It’s something you build — and it’s worth the effort.
Purpose Doesn’t Retire
One of the biggest myths about retirement is that purpose is tied to productivity.
It’s not.
Purpose comes from contribution.
Lisa works with women who mentor, volunteer, write, create, advocate, start businesses, and discover passions they never had time for before.
You’re not too late.
You’re right on time.
Financial Confidence Enables Freedom
While Lisa’s work goes far beyond money, she never dismisses its importance.
Confidence around finances creates choice.
Choice creates peace.
Peace creates joy.
Money is a tool — not a cage.
Retirement as a Creative Act
What I loved most about my conversation with Lisa is how she reframes retirement as something you create, not something that happens to you.
It’s not passive.
It’s not waiting.
It’s not fading into the background.
It’s authorship.
You get to write this chapter.
Why This Conversation Matters Now
Women are living longer, healthier, more vibrant lives than ever before — yet too many are entering retirement without a roadmap for fulfillment.
That’s changing.
Conversations like this one are part of a larger shift where women reclaim midlife and beyond as a time of expansion, not contraction.
Thinking of Retirement?
If retirement is on your mind, whether it’s next year, five years away, or already here, this is your reminder:
You are not done.
You are not invisible.
You are not meant to sit on the sidelines of your own life.
Your most joyful chapter may be the one you’re just beginning to write.
🎧 Listen to the full conversation with Lisa J. Haynes on Living Ageless and Bold, available wherever you get your podcasts.
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