The Person I Used to Be

Grief Over Lost Identity and Roles

A few months ago, I wrote a LinkedIn post titled “Hello. It’s me.” It was my first post in six years after leaving my profession. I’ve linked it here because this piece is its longer answer — the thing I was circling without quite knowing how to say it.

Here’s some context about who I was. For whom I was grieving.

After years of being mentored by some of the best in an industry I knew little about, I co-founded a Benefits and Pension advisory firm at 39, helped build it over 23 years into a business that punched above its weight, survived stage 3 cancer at 45, returned to competitive cycling through charity rides, and sold the firm at 64. I was known in my industry — trusted, sought out, the kind of person whose name came up when serious organizations needed serious advice. That identity was so thoroughly mine that I stopped noticing I was wearing it. It fit like a second skin.

When my firm was acquired, I chose to retire after successfully helping integrate and orient my people into the new organization. My former partners gave me a warm send-off with kind words, plenty of hugs, and a wonderful gift. Then I rode the elevator down to the lobby of Bentall One for the last time, carrying a box of personal items from my office. That image of that day has never left me. It’s where the loss became real. By anyone’s measure, I had completed a great career. Why the sad face?

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Within weeks, the phone stopped ringing the way it used to. The problems I’d spent decades learning to solve were now someone else’s. I went from being highly visible — consequential, in demand — to something I hadn’t experienced since before my career began: invisible. Not because anyone had forgotten me, but because the role that made me legible to the world was gone.

I didn’t have words for what I was feeling. It didn’t feel like grief, not exactly. No one had died. But something had ended, something central to who I was, and the world around me didn’t notice or have language for it. Nobody sends flowers when you retire. Nobody holds space for mourning.

Sociologist Helen Rose Ebaugh spent years studying people who had left central roles in their lives, former nuns, retired police officers, and executives. She called what they experienced “role exit”: the process of disengaging from a role so central to your sense of self that leaving it requires you to construct a new self almost from scratch.

What Ebaugh found, and what rang immediately true, was that the people who struggled most were not those who had hated their roles. They were the ones who had loved them. When the role disappears, a version of you goes with it. Not all of you, but enough to feel the absence.

Research from Cleveland State University confirmed a specific finding: those who leave a role involuntarily, through acquisition, restructuring, or forces outside their control, experience significantly more identity distress than those who leave voluntarily. Even when the choice is technically yours, if the circumstances prompting it were not entirely within your control, the loss carries a complicated edge. I chose to go. I did not choose the conditions that made going feel necessary.

There is also a timing to this grief that catches people off guard. The first weeks of retirement often feel like liberation. That initial relief masks a deeper transition. The identity crisis tends to arrive two to six months later, when the novelty has faded, and the absence feels real. I know that timeline well. I lived it.

What made it more complicated was that I’d always had more than one identity alongside my professional one. I was a competitive cyclist, a father, a husband, and a cancer survivor. Surviving stage 3 cancer at 45 had already taught me something about rebuilding identity from the ground up. That experience clarified everything, stripped away the noise, and pointed directly to what mattered.

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The end of the career did something different and, in its own way, harder: it stripped away the structure through which I’d understood myself for more than two decades and left a quieter, more disorienting question in its place.

But identities carry weight relative to one another. For twenty-three years, the professional identity carried the most weight. It organized my days. It was the one others saw first, the one I reached for when I had to explain myself in a new room. When it went quiet, the other identities, real as they were, didn’t immediately fill the space.

The question beneath it all was one I hadn’t had to ask seriously for a very long time: “Who am I, if not this?”

It sounds philosophical until you’re living it. Then it’s just quiet, a little unmooring, and presents in small moments you don’t expect. At a dinner party, when someone asks what you do, you pause a half-second longer than you used to. When you catch yourself describing your career in the present tense, you correct yourself mid-sentence.

Several months after I retired — deep enough that the honeymoon had worn off, early enough that the new self hadn’t yet taken shape — I posted something on LinkedIn. It wasn’t strategic. It wasn’t part of a plan. I felt I’d been invisible long enough and needed to reclaim something.

The post was a self-deprecating one titled “Hello. It’s me.”

I didn’t fully understand what I was doing at the time. Looking back, I think it was the first deliberate act of constructing a new identity after the old one had dissolved. Not announcing a product and not promoting a service. Just saying: I’m still here. I still have something to say. I can still serve. I’m not finished.

That post marked the beginning of The Long Ride, although I didn’t know it at the time. This writing, this whole second chapter, I’m still building. It began not with a business plan but with an act of refusal—a refusal to stay invisible. I’ve come to believe that impulse is not vanity. It’s thriving through reconnection.

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There is something psychologists call “continuity theory”, the idea that people navigate aging most successfully when they can draw a thread from who they were to who they are becoming. Not by pretending nothing has changed, but by recognizing that the core of you — your values, your instincts, the things that made you good at what you did — doesn’t disappear when the role does. It transfers.

The skills I spent three decades building — listening carefully, distilling complexity into clarity, earning trust slowly and losing it quickly if I wasn’t careful- are the same skills I bring to this phase of my life. The stakes are different, but the instincts are the same.

The competitive cyclist who rode at sunrise to be sharp for a morning meeting is still the person who trains hard at 69 because discipline is the point, not just fitness. Consistency is the measure, not just health span.

That reframe took time. Most people in the middle of this kind of transition, post-retirement, post-acquisition, post-whatever-it-was-that-ended, need to hear it said plainly: the loss of a role is real. The grief is real. And you are not required to resolve it before you begin building the next thing. Both can be true at once.

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Here is what I’ve learned, imperfectly at times and still in progress, about navigating the grief for the person you used to be.

Call it what it is. Grief, not just transition.

The culture around retirement — the party, the cake, the “you’ve earned it” — leaves no room for mourning. You can be genuinely glad to be free of the demands and still grieve what you built. Both are true. Name the grief. Give it space.

Let the old identity inform the new one, rather than compete with it.

The skills and instincts on which your professional identity was built don’t retire with the title. They transfer. The question worth asking isn’t “who am I now?” but “what am I taking with me?” That reframe shifts you from loss to continuity.

Resist the invisibility.

Retirement can slip into a numbing quiet if you’re not deliberate about it. You need something that says, “I’m still here.” A social post. A conversation. A project. A course. Something that announces to you as much as to anyone else that the story isn’t over.

Be patient with the gap.

The new identity rarely arrives on schedule. There is often a period — months, sometimes longer — when you are neither who you were nor yet who you’re becoming. That gap is uncomfortable, but it’s not a sign that anything has gone wrong. It’s the space where the next self takes shape.

Let the answer to ‘what do you do?’ morph naturally.

For years, your answer has been a title or a company name. Learning to answer it differently — honestly, without apology, with something that reflects who you are now — is one of the quiet acts of courage this transition demands of you.

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I am still building the answer to the question of who I am now. At 69, studying for my CPT certification with NASM, writing about aging, health, and the emotional interior of a life well-lived. I’m still riding my bike. I am genuinely not finished.

But I am also not the person I was in 2019. That person was real. He built something that mattered. And his absence, the quiet that followed the end of the role, deserved to be mourned before it could be released.

That’s the thing nobody tells you about identity loss. It isn’t that the old self disappears entirely. It’s that it takes up less space as the new self gradually fills in around it. The Founder and Managing Director is still in here somewhere — I hear him in the way I think about problems, listen, and enter a room, even when the room is just a page. He didn’t vanish. He isn’t the whole story anymore.

I imagine some might think me a little self-indulgent at this point in the piece. That’s okay. The person I used to be is the person I am. That’s not a small thing. It’s the whole point.

Next in The Long Losses: “The Clock You Can’t Unhear — Living Fully When the End Is Visible”

Did you feel this shift? The moment you realized you were grieving not a person, but a version of yourself? I’d love to hear about it in the comments.

The Long Ride is still free for all subscribers. I hope to see you here next time.

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Research & sources referenced in this piece

Ebaugh, H.R.F. Becoming an Ex: The Process of Role Exit. University of Chicago Press.

Cleveland State University. Research on involuntary role exit and identity distress. Cited in retirement psychology literature, 2024–2025.

Atchley, R.C. (1999). Continuity theory and the retirement transition. Cited across retirement identity research.