Rethinking Retirement Conversations #1
Mary Lou Mackin: When Retirement Doesn’t Feel the Way You Expected
Summary
That image is an imagined woman betwixt and between her two identities—work and life.
We ask in this post, “what really happens after a successful career ends?” Do we just change our clothes and become a new woman?
In this first conversation in my Rethinking Retirement series, I speak with former publishing executive Mary Lou “M.L.” Mackin about her deeply honest journey through retirement. Like many professionals, she believed she had planned carefully for this transition—only to discover that leaving work brought unexpected questions about identity, purpose, structure, and community.
Her story reminds us that retirement is not simply a financial event. It is a profound life transition that deserves thoughtful reflection and intentional design.
Why I’m Beginning This Conversation Series
While researching and writing my new book Rethink Retirement, I spent time listening to people who were navigating this stage of life. Some had just stepped away from demanding careers. Others were several years into retirement. Many were still trying to figure out what this new chapter meant.
Again and again, I heard the same thing:
Retirement today is not what it used to be.
People are living longer. Many remain healthy, curious, and capable well into their seventies and eighties. Yet the cultural script for retirement has barely changed in decades.
We were taught a simple formula:
Work hard.
Save well.
Retire.
Relax.
But the reality is far more complicated.
Many people discover that when their careers end, they are not just leaving a job—they are leaving a structure, a community, and sometimes a core part of their identity.
So I decided to begin a series of conversations with people who are living this transition in real time.
Mary Lou Mackin is the first of those voices.
When Burnout Leads to Retirement
Mary Lou spent decades in a demanding and intellectually rich career in publishing. Eventually she reached a point many professionals recognize: exhaustion.
At age 62, she decided to retire.
She did everything responsibly.
She spoke with her husband.
She met with her financial advisor.
She carefully planned the transition with her employer and even spent six months training her successor.
She entered retirement with travel plans, social activities, and a long list of things she had postponed during her busy career.
For a while, it felt wonderful.
Then something unexpected happened.
“The curtain came up,” she told me, “and suddenly I was completely lost.”
The Hidden Challenges of Retirement
As Mary Lou and I spoke, her experience revealed four themes that appear repeatedly in my research on retirement transitions.
Identity: Who Am I Without My Career?
Before retiring, Mary Lou believed she did not strongly identify with her career.
But once she stepped away, she realized how deeply her life had been intertwined with work—intellectual engagement, travel, collaboration, and problem solving.
Without those anchors, she felt untethered.
“I lived and breathed my work,” she said. “Who I was without that—I was lost.”
Many professionals discover the same thing.
Our work often shapes more than our income—it shapes our identity.
Structure: Freedom Can Be Harder Than Expected
One of the surprises of retirement is how unsettling unlimited freedom can feel.
Mary Lou described mornings when she had already gone to the gym, had coffee, and suddenly realized there was nothing else planned for the day.
For decades, work had provided rhythm—meetings, deadlines, travel, and responsibilities.
When that structure disappears overnight, many people feel disoriented.
As she reflected later, she had carefully planned how to leave work—but not how to live afterward.
Purpose: Why Do I Matter Now?
Perhaps the most profound question people face after retirement is simple:
Why do I matter now?
Work often gives us a sense of contribution. When it ends, we must rediscover how we want to add value.
For Mary Lou, that sense of purpose slowly began to return when she reconnected with her publishing network. Small freelance projects evolved into new creative collaborations.
Today she enjoys mentoring others and helping people tell their stories in what she calls the “third act” of life.
Community: Rebuilding Connection
Another unexpected challenge is the loss of daily social interaction.
Many professionals discover that their primary community existed at work.
Mary Lou rebuilt connection intentionally—by joining a writing group, starting conversations at her gym, and participating in discussions with other women navigating retirement transitions.
Those small steps gradually created a new network of relationships and support.
A Powerful Lesson from Mary Lou’s Story
Looking back, Mary Lou wishes someone had asked her a different set of questions before she retired.
Not just:
Do you have enough money?
But also:
Who will you become?
How will you structure your days?
Where will you find purpose?
Who will be your community?
Retirement is not simply an exit from work.
It is a transition into a new stage of life that requires reflection, experimentation, and design.
A Question for You
As you think about your own future, consider this question:
Where do you still want to matter?
Because retirement isn’t the end of the story.
It may simply be the beginning of what comes next.
A New Series Begins
This conversation with Mary Lou Mackin is the first in a series of interviews I’ll be sharing here on Substack.
In the weeks ahead, you’ll hear from other remarkable men and women who are navigating this transition in very different ways:
• entrepreneurs launching second careers
• professionals redefining purpose
• people who discovered retirement was not what they expected
• individuals designing entirely new lives after work
Together, these stories will help us rethink one of the most important life transitions of our time.
Stay tuned.
More conversations are coming.
Listen to the Full Podcast Episode
You can listen to the full conversation at On the Brink with Andi Simon, where we explore how individuals and organizations can rethink the future of work, leadership, and life.
If this conversation resonates with you, I explore these themes more deeply in my new book, Rethink Retirement: It’s Not the End—It’s the Beginning of What’s Next.
It’s designed to help you think about identity, structure, purpose, and community as you shape your next chapter.
Learn more about “Rethink Retirement: It’s not the end—It’s the beginning of what’s next.”
Stay tuned. More to come.