When Retirement Feels Like Disappearance: What Companies Are Getting Wrong
We plan for the exit. We forget the human transition.
I was at a networking event recently when a man pulled me aside.
He wasn’t there to talk about business.
He wanted to talk about someone who had left.
A former colleague had retired a few months earlier. Someone he had worked closely with for years. Someone he liked.
Now, that colleague keeps reaching out.
Calls. Emails. Invitations to lunch.
“He’s a good guy,” the man told me. “But… I don’t really have time. And honestly, I don’t know what to say to him anymore.”
He paused.
“It’s awkward.”
The part no one talks about
We have designed retirement as a clean break.
A tidy exit.
A final day. A farewell cake. A speech. A handshake.
And then… silence.
But for the person leaving, it is anything but tidy.
They have not just left a job.
They have left:
Their identity
Their daily structure
Their community
Their sense of relevance
And what do we give them in return?
A plaque.
And a door.
The invisible loss
Here is what most organizations miss:
The people managing retirement have never experienced it.
They are imagining it.
They assume:
“Wouldn’t it be nice to finally be free?”
But they don’t see what comes next.
The quiet.
The disorientation.
The sudden absence of people who once needed you.
And so retirees reach back.
Not because they are “clingy.”
But because they are trying to stay connected to a world where they once mattered.
And inside the company?
Something equally troubling happens.
The person who left… disappears.
Not gradually.
Immediately.
Their name stops coming up in meetings.
Their stories fade.
Their contributions become past tense—and then forgotten.
It is as if they didn’t transition.
It is as if they vanished.
Almost… as if they died.
No one intends this.
But culture moves on quickly.
And without intention, it leaves people behind.
Retirement is not an event. It is a relationship transition.
If companies want to do this well, they must rethink retirement as something ongoing—not final.
Here are a few ways to begin:
1. Design the “after,” not just the exit
Stay connected intentionally. I love these:
Create alumni circles. Invite retirees back as advisors, mentors, storytellers. Respect their past and let them craft their future.
2. Prepare the team, not just the individual
Help those staying understand what the transition means—and how to stay in relationship in a way that feels natural, not forced. Too many of those I have interviewed don’t know what to say or do for the newly retired person. One woman at a networking event even asked me if she would be welcome at these after she left her job.
3. Normalize continued connection
Make it acceptable to have lunch. To call. To stay human.
Not everything has to end just because employment does.
Give some thought to the conversations that have connected you in the past. Imagine some new ones. Aren’t you curious about what retirement is?
4. Honor identity beyond the role
Help people articulate who they are becoming—not just celebrate who they were. Ask them how they are finding new purpose. It is ok to enter this new territory with them.
A better question
The man at the networking event wasn’t unkind.
He was unprepared.
No one had shown him what this moment requires.
So here is the question organizations should be asking:
What happens to the relationship when someone leaves?
Because retirement is not just a workforce issue.
It is a human one.
And if we don’t design it thoughtfully…
We don’t just lose employees.
We lose people.
Closing CTA:
If this resonates, I explore this deeply in my new book Rethink Retirement—and in the workshops and conversations I’m now hosting for individuals and organizations navigating this transition. Learn more about the Masterclass and Intensive Workshops.
Because leaving well…
may be one of the most important leadership moments we never talk about.