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Dear Retirement Coach,

I’m retired and financially stable, but something feels missing. I thought I’d feel happy and free, but instead I feel restless and a bit lost. Is this normal? And is there someone I should be talking to—like a therapist or a coach—who can help me figure this out?

Sincerely,

Searching for Fulfillment

Dear Searching for Fulfillment,

First, thank you for your honesty. You’ve put into words something I hear often—but that people rarely say out loud. And yes, what you’re experiencing is absolutely normal.

In fact, your question brought me right back to a moment in my own journey.

After retiring from a decades-long career in banking, I expected to feel light and liberated. I had earned this chapter—time for travel, creativity, family, rest. And for a while, I did enjoy the freedom. But then came a quiet shift. I remember standing in my kitchen one morning, coffee in hand, no meetings on the calendar, and thinking, “So… what now?”

That empty space—once so desirable—started to feel unsteady. I wasn’t sad, exactly. I just felt unanchored. And because everything looked fine on the outside, I didn’t know if I was allowed to talk about it.

That’s why your question matters. Because this is the part of retirement no one warns us about.

Retirement Isn’t Just a Milestone—It’s an Identity Shift

We spend decades building careers, solving problems, leading teams, caring for others. That rhythm becomes part of who we are. When it disappears, it can feel like we’ve lost a part of ourselves.

In my coaching practice, I’ve worked with many high-achieving professionals who experience this same emotional disorientation. Their financial plan is solid, their calendar is technically “open,” and yet… something’s missing. Some say they feel invisible. Others feel restless or oddly guilty for not being happier.

Here’s what I often say:

You can feel grateful and still feel lost. Those two things can exist side by side.

Who Can Help—and When to Reach Out

When people ask me if they should speak with someone—a therapist or a coach—I appreciate that they’re taking their inner life seriously. And that’s important.

A therapist may be the right choice if you’re working through grief, anxiety, depression, or deeper emotional wounds. Therapy is a space for healing.
A retirement lifestyle coach focuses on what comes next—how to reimagine your identity, explore what brings you joy, and build a life that feels aligned with who you are now. Coaching is a space for reflection, creativity, and intentional design.

Many people benefit from both at different points. The key is recognizing when you’re in transition—and giving yourself permission to seek support.

A Story That Might Resonate

One client I worked with—let’s call her Carol—was a retired executive who filled her time with admirable things: volunteering, fitness classes, book clubs. From the outside, she was thriving. But when we spoke, she said, “I don’t feel like me anymore. I’m busy, but I’m not fulfilled.”

Through coaching, we explored what had always energized her—and what she had set aside during her working years. She had a passion for mentoring women in business but had never made time for it. Slowly, she began re-engaging with that passion in small, joyful ways.

She also restructured her week—not for productivity, but for purpose. Her calendar didn’t just look different. It felt different.

What You Might Be Looking for (Even If You Can’t Name It Yet)

Many retirees aren’t seeking “more to do.” What they’re really craving is:

Clarity of purpose – a reason to get up that feels meaningful
A redefined identity – understanding who you are beyond your role or title
An intentional rhythm – a week that reflects your energy, values, and joy
Connection – meaningful relationships and conversations
Confidence – optimism about what lies ahead, even as life evolves

You don’t have to solve all of this overnight. But beginning to ask yourself what really matters now is a powerful first step.

You’re Not Behind—You’re Becoming

The discomfort you’re feeling isn’t a sign that you’re doing retirement wrong. It’s a sign that you’re waking up to what you need. That’s growth.

It’s okay to feel unsettled. It’s okay to not have it all figured out. And it’s more than okay to ask for help. Whether you speak with a therapist or a coach—or simply begin journaling and reflecting on your own—you’re allowed to take this seriously.

Retirement is a transition, not a destination. And like any major life transition, it requires grace, curiosity, and time.

So yes, this is normal. And no, you don’t have to navigate it alone.

Warm regards,

Toni Petrillo

Certified Retirement Coach Founder, Retire With Intention

Do you have any questions that you would like to ask Retirement Coach Toni? Just send them in an e-mail to info@boomingencore.com.

Interested in seeing all of Retirement Coach Toni's Advice? Click here

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Antoinette Petrillo is a former financial executive with over 25 years of experience leading teams. Upon retiring, she noticed a lack of support for professionals transitioning to retirement. Motivated by her passion for coaching and helping others lead confidently, Toni founded her own practice focusing on assisting professionals in navigating this significant life transition. You can reach Toni through her website, Retire with Intention.

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