The vulnerability of starting over at 55


When I got laid off at 55, I expected the anger and financial anxiety.

What I didn’t expect was the grief.

Not the kind you feel when you lose someone you love.

But something just as real and disorienting.

I was grieving the loss of my identity.

The Identity Crisis No One Warned You About

Here’s what nobody tells you: You’re not just leaving a job.

You’re leaving the person you’ve been for decades.

The corner office.

The team that looked to you for direction.

The title that gave you instant credibility.

One day, they’re there.

The next day, they’re gone.

Who am I without all that?

I recently had coffee with my friend Rob.

He’d retired three weeks earlier after 32 years.

Planned everything meticulously.

Negotiated a generous package.

Even helped select his successor.

Yet his eyes kept darting to his silent phone.

He checked his watch every few minutes, as if late for a meeting that no longer existed.

“I’m fine,” he said. “Just adjusting.”

I recognized that look.

I’d seen it in my own mirror.

Rob jumped.

I was pushed.

But the landing?

Remarkably similar.

Why Your Exit Story Doesn’t Matter As Much As You Think

Here’s what I’ve learned from working with professionals in transition: Whether you chose retirement or had it thrust upon you, the emotional journey is strikingly similar.

Both paths lead to:

  • Disorientation without your daily routine
  • Feeling invisible without your title and company affiliation
  • Uncertainty about your value outside the corporate structure
  • Anxiety about your relevance in a rapidly changing world

The only real difference is the story you tell yourself about how you got there.

Welcome to “The Void”

After the retirement party or severance package comes something I call “the void.”

Unstructured days that feel both too empty and too short.

A nagging sense you should be doing something but uncertainty about what.

Restlessness alternating with lethargy.

A growing distance from former colleagues.

I made a classic mistake.

I tried to fill it with frantic activity.

Consulting gigs I didn’t want.

Networking events that drained me.

Anything to avoid the fundamental questions.

Rob made the opposite mistake.

He assumed golf and travel would be fulfilling.

When they weren’t, he had no Plan B. Both were attempts to avoid the necessary work of transformation.

The Counterintuitive Truth About the Void

Here’s what changed everything for me: The void isn’t something to escape.

It’s something to move through mindfully.

What we experience as emptiness is actually the necessary clearing for something new to emerge.

The void is uncomfortable precisely because it’s where transformation happens.

It’s where you shed the old identity before the new one has fully formed.

Think of it like the caterpillar in the chrysalis.

There’s a period where it’s neither caterpillar nor butterfly.

It’s just dissolving.

Reforming.

Becoming.

That’s where you are right now.

And it’s supposed to feel uncomfortable.

The Vulnerability of Starting Over

There’s a particular kind of vulnerability that comes with starting over after decades of established success.

You’ve been the expert.

The authority.

The person with answers.

Now you’re a beginner again.

And that’s deeply uncomfortable.

I remember attending my first digital marketing workshop after deciding to build my coaching business.

I was easily 20 years older than most participants.

When the instructor asked us to pair up, I could see the hesitation in the young professional assigned as my partner.

What could this older guy possibly know about social media?

I felt exposed. Inadequate.

Behind the curve.

But here’s what I’ve learned: Embracing this vulnerability is the only way forward.

These moments aren’t weaknesses.

They’re doorways to new connections, new skills, and new possibilities.

Six Tools for Building Emotional Resilience

The emotional journey of leaving your corporate identity behind requires resilience.

Here are the tools that worked for me:

1. Name the losses specifically

Don’t just say “I miss my job.”

Get specific.

The camaraderie of your team.

The intellectual challenge.

The structure and purpose of your days.

By naming these losses specifically, you can seek healthy ways to meet these same needs in your next chapter.

2. Create transition rituals

Write a letter to your former professional self.

Host a dinner where friends share how they’re transitioning beyond their career.

Plant a tree and nurture it.

These rituals help your psyche process the change in a tangible way.

3. Find transition peers

Connect with others in similar transitions.

These peers provide validation and perspective that even well-meaning family members cannot.

4. Practice self-compassion

Speak to yourself as you would to a respected colleague facing the same challenges.

Your struggle is part of the universal human experience, not a personal failing.

5. Maintain a “wins” journal

During transition, progress often feels invisible.

Keep a daily record of small wins, insights, and moments of joy.

6. Seek professional support when needed

There’s no medal for navigating this transition alone. A coach or therapist who specializes in life transitions can provide invaluable structure and support.

The Question That Changes Everything

Here’s the question that began my transformation: “Who am I when no one is watching?”

Not who I present myself as.

Not what I achieve.

Not what others expect of me.

Just me.

For Rob, this exploration led to a surprising rediscovery of his passion for teaching.

Before his corporate climb, he’d considered becoming a professor.

Now he guest lectures at the local university and mentors young entrepreneurs.

For me, it meant acknowledging that while I loved certain aspects of my corporate role, other parts had slowly drained my spirit.

The constant travel.

The political navigation.

The endless meetings about meetings.

Without those constraints, I could now build a life that aligned with my authentic self, not just my professional persona.

Your Turn

I want you to know something important: Your worth was never contained in your title.

Your contributions extend far beyond your former role.

Your most meaningful work may still lie ahead.

Your identity is evolving, not diminishing.

The person you’re becoming isn’t less than the executive you were.

They’re more.

And the journey to discover them is just beginning.

What about you?

Are you in the void right now?

Struggling with identity shellshock?

Feeling the vulnerability of starting over?

I’d love to hear your story.

Hit reply and tell me what’s on your mind.

I read every response.

And if this resonated with you, take 15 minutes today to write your own answer to that question: “Who am I when no one is watching?”

You might be surprised by what you discover.

To your epic encore,

Ted

P.S. If you found this helpful, you’re not alone in this journey.

Thousands of professionals are navigating this same transition right now.

The ones who thrive are the ones who acknowledge the grief, embrace the void, and have the courage to start over as beginners.

You’ve got this.

Ted Prodromou

Join 60,000+ seasoned professionals who are done with the corporate world. Epic Encore is an almost daily newsletter with inspirational stories from leading experts. Your Epic Encore is about turning your lifetime experiences into the cornerstone of the rest of your life. It represents your audacious leap into entrepreneurship, fueled by the wisdom and tenacity you've garnered in your successful career. This isn't about playing catch-up in business and building a 7-figure business. It's about forging a unique path, using your distinct perspective, seasoned judgment, and invaluable insights that can only come from years of life experience.

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