When Success Doesn’t Feel Like Success Anymore

There’s a version of success we all recognize. The titles.The promotions.The moments where people look at your life and think, she made it. But there’s another version that doesn’t get talked about enough.

The one where you’re showing up, doing everything you’re supposed to do…and quietly carrying things no one can see. That’s what this conversation with Shirell Gross reminded me of.

Shirell has had an incredible career. Global chief counsel. Advising leadership. Sitting at tables where real decisions are made. But what stayed with me wasn’t her title. It was her story. Because while she was building that career… she was also experiencing loss. Real loss. The kind that changes you. And like so many women, she kept going. She went back to work. She stayed strong. She did what needed to be done. And I think a lot of us know what that feels like.

The Part We Don’t Always Say Out Loud

There was a moment in the conversation where we talked about Black maternal health. And I want to sit there for a second… because this isn’t just about one story. Too many Black women have had experiences where they weren’t heard. Where something didn’t feel right… and they had to push to be taken seriously. Shirell made a decision at one point to really advocate for herself. To ask questions. To do the research. To be fully engaged in her care. And that made a difference. That part stayed with me. Because we assume we’ll be taken care of… but the truth is, sometimes we have to be part of the process in a different way.

Pushing Through Isn’t Always Strength

One thing I kept thinking about after we talked was how often we equate strength with pushing through. Just keep going. Don’t fall apart. Handle it. I’ve done that. If I’m being honest, work was a distraction for me during my own hardest seasons. It gave me somewhere to put the energy when I didn’t know what to do with what I was feeling. But that doesn’t mean it was always healthy. Sometimes pushing through is survival. But sometimes… it’s avoidance. And knowing the difference matters.

When Your Definition of Success Changes

Shirell said something that really hit me. She talked about how she’s probably less driven now than she’s ever been, and how that might surprise people. But what she really meant was… her definition of success changed.

It’s not about the next role. It’s not about constantly striving. It’s about peace. That’s a different kind of ambition.

And if you’re in a season where what used to motivate you doesn’t hit the same anymore… you’re not alone.

That might not be a problem. That might be growth.

Stepping Away Takes Courage

At one point, Shirell made the decision to step away from her career. No next job lined up. No clear plan. Just the awareness that something didn’t feel right anymore. That takes courage. Because from the outside, everything probably looked fine. Maybe even great. But internally… she knew she needed something different.

And I think more of us have had that moment than we admit. That quiet knowing.

What I Took From This Conversation

What stayed with me most is this: You can be successful… and still need to stop. You can be strong… and still be grieving. You can have everything “together”… and still feel like something is missing. All of that can exist at the same time. And maybe the real work isn’t trying to fix it immediately… Maybe it’s being honest about it.

Something to Sit With

If you’re reading this, I want to leave you with this: Where in your life are you still pushing through… when you might actually need to pause and pay attention?

Not what looks good. Not what makes sense on paper. But what feels true for you right now.

Listen to the Conversation

If this resonated with you, I’d encourage you to listen to the full podcast discussion, episode 4 or watch the YouTube interview.

Grief, Ambition & Black Maternal Health: Redefining Success After Loss

There’s a lot in this one.

Final Thought

Reinvention doesn’t always start with a big decision. Sometimes it starts with a quiet realization: This version of my life doesn’t fit me the same way anymore. And that’s not failure. That's the awareness needed for you to walk through a new door of opportunity, even if you don't know what's on the other side.

Peace and Blessings,

Dorinda