When I began interviewing people for Rethink Retirement: It’s not the end but the beginning of what’s next, I wanted to understand what really happens when people leave careers, companies, and professional identities behind.
The people I met came from many different parts of life.
Some were men who had built and sold their companies. Others were women entrepreneurs and small business owners who had done the same. Some had retired after long corporate careers. Several had been fired, downsized, or pushed out—and found themselves confronting retirement far earlier than they had expected.
Their stories helped me see that retirement is not simply a financial event or a date on the calendar. It is a profound life transition.
But the more people I interview, the more convinced I become that there is no single retirement story.
There are different retirement pathways, and each one deserves to be understood on its own terms.
When a woman sells the business she built
Recently, I have been interviewing women entrepreneurs who have sold—or are preparing to sell—their businesses.
I am fascinated by their stories.
For many of these women, the business was never simply a job. It was something they imagined, created, nurtured, and fought to sustain. It shaped their daily lives, their relationships, their sense of purpose, and often their identity.
Selling it may bring financial freedom and a genuine sense of accomplishment. But it can also leave an unexpected emptiness.
Who am I when I am no longer the person everyone calls?
What happens when the decisions, problems, and people that filled my days suddenly belong to someone else?
How do I replace the excitement of building something?
And perhaps most importantly: What do I want to build next?
I would like to interview more of these women. I am also thinking seriously about creating a retreat where women who have sold their businesses can come together—not simply to discuss what they left, but to imagine what they might create next.
When a woman leaves corporate life
A second group I want to understand more deeply is women leaving corporate careers.
I did not have enough of their stories in my original research, and the women I am interviewing now are helping me see how distinctive this transition can be.
Many spent decades learning how to succeed inside complex organizations. They developed expertise, earned authority, led teams, mentored others, and learned to manage demanding schedules. Their days were filled with meetings, decisions, relationships, and responsibilities.
Then that structure disappears.
Some women welcome the freedom. Others discover that freedom without a new sense of direction can feel surprisingly disorienting.
They are asking questions about visibility, relevance, relationships, money, caregiving, and what ambition should look like now. They may want to continue contributing, but not at the same pace or under the same conditions. They do not necessarily want another corporate position. They also do not want to become invisible.
Their challenge is not simply to retire. It is to redesign a life.
And what about men leaving corporate careers?
I also want to interview more men who have left corporate life.
We carry many stereotypes about men and retirement. We assume they will play golf, travel, consult, serve on boards, or finally relax. We sometimes assume that losing a title or professional identity is especially difficult for them.
But assumptions are not research.
How do men actually experience the loss of their corporate role? What happens to the friendships that were embedded in their work? How do they create new routines? Where do they find community? How do they talk with their spouses or partners about the life they will now share differently?
And what does purpose mean when achievement is no longer measured by promotions, revenue, status, or organizational influence?
I want to hear their real stories, not simply repeat the familiar stereotypes.
The questions beneath all these pathways
Although these groups may experience retirement differently, I continue to explore several themes in every conversation:
Identity: Who am I now that I am no longer defined by my previous role?
Daily life: How do I create structure and rhythm when my calendar is finally my own?
Purpose: What gives me a reason to care about tomorrow?
Community: Where do I find friendship, connection, and belonging?
Time: How does my relationship with time change when it is no longer organized around work?
Time has become increasingly important in my interviews. Retirement appears to give us more of it, yet many people are unsure how to use it. Some fill every hour. Some drift. Some feel pressure to make this stage productive, while others are learning that a meaningful life does not always need to look busy.
I would like to hear your story
This next phase of my research is about listening more closely to people traveling along these different retirement pathways.
I am especially interested in speaking with:
• Women entrepreneurs and business owners who have sold or are preparing to sell their companies
• Women who have recently left—or are preparing to leave—corporate careers
• Men who have transitioned out of corporate leadership and are creating their next chapter
If you see yourself in one of these groups, I would love to interview you. If someone comes to mind as you read this, I hope you will share this invitation with them.
These are confidential, thoughtful conversations—not surveys and not sales calls. I want to understand what people are actually experiencing: what surprised them, what they lost, what they discovered, and what they wish they had understood before the transition began.
Retirement is often discussed as though everyone crosses the same finish line.
They do not.
We arrive from different places. We carry different identities with us. And we need different ways to imagine what comes next.
The best way to understand those differences is to listen.
Reach me at info@simonassociates.net.