The Truth About Growth In Business Is it Sometimes Feels Like Grief
Nov 10, 2025
The Lesson No One Prepares You For
If you’ve been following along with my 10 Lessons from 10 Years of Entrepreneurship series, you already know—most of the biggest lessons don’t come from the shiny, Instagrammable moments. They come from the hard ones. The messy, uncomfortable seasons that force you to grow.
Today’s lesson is one of those.
Lesson Six is this: sometimes growth feels like grief.
And that can be confusing. Because we often talk about growth like it’s all excitement and empowerment and momentum—but no one talks about the heartbreak that can come with it. Sometimes the right decision for your future will also break your heart a little bit.
Leaving a Version of Yourself Behind
When I left my corporate job in 2015, everyone told me how brave I was. I heard things like, “You’re doing what we all wish we could do.” Even my boss said he was jealous. And sure, it was brave—but it also felt like a breakup.
So much of my identity was tied to that career: the fancy title, the luxury car, the steady paycheck, the validation that came with someone else telling me I was doing a good job.
And when I handed back that company car and drove off the lot in something far more practical, I felt the loss deeply. I wasn’t just leaving a job—I was saying goodbye to a version of myself I had worked hard to become.
That’s what no one tells you: when you walk away from something that looks successful on the outside, you’re left to process the quiet doubt that comes with starting over.
The End of One Chapter, the Beginning of Another
Fast forward a few years. I built a gym from the ground up—my first real taste of entrepreneurship. It was my baby until it wasn’t.
Closing it during the pandemic was a strategic decision, but it was also a painful one. Strategy doesn’t cancel emotion. Walking away from that space meant saying goodbye to another version of myself—the one who had poured everything into making that business work.
It was the right move, but it hurt.
That’s when I really learned that growth doesn’t always feel good at first. Sometimes it feels like loss. But looking back, it was the moment I truly started to choose myself—to make decisions not from fear or comfort, but from alignment.
Reinvention and the Grief That Comes With It
If there’s one thing I’ve learned about entrepreneurship, it’s that reinvention is inevitable. Every new chapter—whether it’s leaving a career, closing a business, or redefining your boundaries—comes with a goodbye.
You grieve the routines that no longer work.
You grieve the clients who no longer align.
You grieve the ambitions that once felt big but now feel too small.
And sometimes, you grieve relationships—because not everyone can come with you into your next season. It’s not about cutting people off; it’s about recognizing that not everyone can support your growth.
Grief Is What Happens When Your Heart Catches Up to Your Alignment
Over the years, I’ve learned that grief isn’t a sign of weakness—it’s a sign that you care. It’s your nervous system catching up to your next level.
One of the biggest reframes that’s helped me is this:
You’re not losing something—you’re clearing space.
Grief happens when your heart tries to catch up to your alignment. When you can hold both the sadness of what’s ending and the excitement of what’s next, you move through change with a lot more grace and a lot less judgment.
For every new offer, every pivot, every boundary you set—there’s always a goodbye built in. Goodbye to how things used to be, to what people expected of you, and to the version of yourself who thought she had to do it all alone.
Growth and Grief: Two Sides of the Same Coin
You can be grateful for what was and still ready for what’s next. You can be sad and still excited. You can feel loss and expansion at the same time.
Because growth and grief are two sides of the same coin—one clears space, and the other fills it.
And on the other side of that grief?
Freedom. Clarity. Alignment.
So if you’re in a season of change right now—whether you’re letting go of a client, redefining success, or stepping into a new chapter—remember this: you’re not broken, you’re evolving.
Let yourself feel it. Let yourself grieve it. Because that’s where the next version of you is waiting.
