I always thought retirement would feel like a celebration. A party at Avra, a Cartier watch I bought for myself, and a dirty martini before noon—served icy cold and unapologetic, just how I like it. I spent 15 years in the trenches building my last business. Just me, a laptop, and way too many late nights squinting at spreadsheets. I hung out my shingle as an Educational Consultant, taught myself what I didn’t know (which was a lot), and somehow built a brand that reached families all over the world.

But here’s the part I can’t dress up—I loved the work. Not in the vague, “it was fulfilling” way printed in retirement brochures, but in the real high-stakes, heart-on-the-line way. I helped teenagers realize their dreams. I helped anxious parents breathe as I held their hands through the complexities and unfair rules of elite college admissions. I made a difference, and I knew it.

Fifteen years, a global pandemic, the Varsity Blues scandal, and the kind of burnout that makes your bones ache—and I was done. Or so I thought. I turned 60 and decided it was time. Time to sell the business. Time to stop offering emergency essay edits at 11:47 p.m. Time to stop solving crises that weren’t mine to carry.

I pictured myself sleeping in. Reading paperbacks in the afternoon. Learning how to make a decent shakshuka.

But instead of relief, I felt something else creeping in. Guilt. Heavy and quiet, like a fog that followed me around my house.

Meeting Pamela—and Finally Feeling Seen

That’s when I met Pamela Balas on Facebook, in one of those women-over-50 groups where someone is always asking about what not to wear or walking solo across Portugal. Someone had posted, “What are you doing after retirement?” A gob-smacking 5,000 women replied. I read every single comment like it was a lifeline. There were travel plans and Marie Kondo’d closets—but alongside all that, there were grimmer comments. Guilt. Confusion. The kind of grief you don’t post about.

Pamela’s comment stood out. It was smart and honest in a way that made me sit up straighter. I reached out. We talked. And for the first time, I didn’t feel like I was failing retirement—I felt like I was acknowledging my own truth.

You think it’ll feel like freedom. But I kept thinking … what about all the families? All the students? I wasn’t just running a business. I was helping kids land in the right schools, receive financial aid, prep for interviews, find their way. That work pulled at me, even after I walked away. It still does.

Letting Go Isn’t Logistical—It’s Emotional

Pamela felt it too. She spent decades in public education as a teacher, reading specialist, and principal. Her whole professional identity was built on being needed. In charge. Useful. When she retired, she didn’t fall apart. She opened a neighborhood coffee shop and kept moving. But the guilt found her later.

“It wasn’t until we sold the coffee shop, five years after I left my principalship, that I started feeling it,” she told me. “I missed the curriculum conversations. I missed being in it. It caught me off guard.”

At first, she still got calls. People asking for her advice, wanting her opinion. She always helped. But after every call, she’d hang up and feel the nagging ache. That flicker of being on the outside looking in. “I was used to being needed,” she said. “And then—it just stopped.”

Her story mirrored mine. The letting go wasn’t about time—it was about identity. Mine. You don’t just drop off decades of purpose like a bag of clothes at Goodwill. You carry it with you, even though you try damn hard not to.

Why Retirement Guilt Pulls at So Many Women

For so many of us, work isn’t just what we do. It’s who we are. We build our lives around being useful and reliable. We don’t just tolerate the chaos—we sort of worship it. Women especially are wired to be the steady one. The go-to when things start to unravel.

So when the calendar clears, and the phone goes quiet, it doesn’t just feel empty. It feels like a bad dream where no one’s looking for you anymore.

And let’s be honest … retirement guilt isn’t just emotional, it’s cultural. We live in a world that says if you’re not busy, you’re not valuable. If you’re not producing something, you’re wasting potential. That’s what pulls at you—the sense that you’ve become invisible by doing the one thing you were told to look forward to.

Who Feels Retirement Guilt the Most?

Not every profession feels this equally. But here’s where it hits hardest:

Educators. Teachers, professors, administrators—anyone who’s spent a career shaping the next generation. You don’t clock out of that kind of relationship.

Healthcare workers. Doctors, nurses, caregivers—when your job has literally kept people alive, stepping back can feel like betrayal, or worse, irresponsible.

First responders and military. Roles where identity, mission, and responsibility are all tangled together. The exit ramp doesn’t feel clean.

Clergy and social workers. When your purpose is helping others stay upright, who helps when you stop?

Entrepreneurs and small business owners. Especially those of us who built something from nothing. We didn’t just create a job. We created an identity. Letting go of it feels like erasing part of ourselves.

This isn’t just a transition. It’s an existential shift.

Pamela’s Turning Point—and Mine

Pamela felt it in waves. “When I retired, it wasn’t just about leaving the job,” she said. “It was stepping away from a whole network. Students, teachers, parents. Even the regulars at our coffee shop.” The guilt didn’t hit right away. It came later—after the applause stopped. When the inbox stayed empty and her name stopped coming up in meetings. That’s when the hard questions started whispering: Did I leave too soon? Did I give up too much?

Eventually, she found her way forward. But it didn’t happen by accident. It took intention. And it took guts.

What I Know Now (That No One Told Me Then)

These aren’t solutions, but they might help. Here are some of the ideas I clung to when the bottom dropped out.

Reinvention Isn’t a Buzzword. It’s a Lifeline.
You’re not retiring. You’re choosing a new way to be vital. Pamela said it best: “It’s not your job to figure out who replaces you. You will be replaced. The world doesn’t collapse without us—but that doesn’t mean we weren’t essential.” That line gutted me. Because she’s right. We were essential. We still are.

Build a Bridge, Not a Void
Pamela opened a coffee shop—not because she needed a job, but because she still needed a rhythm. It gave her structure, purpose, people. You don’t have to start a business, but ask yourself: What small structure can carry me forward?

Keep Sharing What You Know
Pamela later helped write a curriculum for a women’s shelter. “It wasn’t full time, but it was meaningful,” she said. Consulting, mentoring, volunteering—these aren’t fallback plans. This is legacy work.

Accept the Identity Shift—Then Actively Shape It
Pamela said the hardest part wasn’t the silence. It was losing the feeling of being “the one.” The go-to. The fixer. That loss hits deep. Don’t rush past it. Sit with it. Then ask: If I’m no longer Principal Pamela or Essay Expert Susan … who do I get to become now?

You Don’t Need a Permission Slip
No one is going to grant you the right to rest. Or pivot. Or create space. You have to take it. The guilt won’t vanish overnight. But you can stop feeding it. As Pamela said, “Retirement isn’t giving up. It’s making space for a dream you didn’t have time for before.” That’s not indulgent. That’s radical.

Let What Pulls at You Be Something New

When I started PROVOKED, I thought I needed a sign. Some stamp of approval. A voice outside of me saying, “Go ahead. It’s your turn now.” I did the classic version of retirement—it lasted four years. And for me, that was a good run. But then the pull came back. Not to build what I had before but to build something different. To rebrand my life on my terms, with fresh grit and an intoxicating energy.

Here’s the truth.

You don’t have to earn the right to rest. You already did.

If you’re standing at the edge of what comes next, holding guilt in one hand and freedom in the other—put the guilt down. Let what’s pulling at you be something new. Something beautiful. Something entirely yours.

And if this hits close to home, I’d love to hear your story—or what’s still pulling at you.