When we talk about growing a business, we usually focus on the visible parts — revenue milestones, new hires, expanded reach, better systems. We talk about clarity, structure, strategy.
What we rarely talk about is the loss that comes with it.
Not loss as in failure.
Loss as in identity.
A quiet moment I can’t forget
A few weeks ago, I was sitting with a client I’ve worked with for over a year. She’s built something remarkable — the kind of business that runs not just on skill, but on deep personal care. She’s thoughtful, dedicated, and now… ready to scale.
She came into the session ready to talk about systems. About delegation. About finally letting go of the pieces that have become too heavy to carry alone.
But about halfway through, her energy shifted. She paused, stared down at the notes she’d been scribbling, and said:
“I know this is the right next step… but part of me is scared I’ll lose who I am in the process.”
And just like that, the conversation changed.
The grief that follows success
Strategic growth demands that we let go of parts of ourselves — sometimes parts we’ve outgrown, sometimes parts we’re still deeply attached to. The version of you who did everything. The one who hustled through the night. The one who knew every client by name, every spreadsheet by heart.
Letting go of that person can feel like a kind of death — even if it’s exactly what you wanted.
It’s not failure. It’s transformation.
And like any transformation, it comes with a sense of grief.
She wasn’t doubting the path. She was grieving the version of herself who built the business by force of will and care and sleepless nights.
And somewhere inside, she was wondering: If I stop being that person… do I still deserve this business?
That’s not a tactical question. That’s a story-of-self question.
Why this grief matters
Ignoring it doesn’t make it go away. It just makes it harder to move forward.
When founders feel stuck, it’s not always because they lack clarity or discipline. Sometimes, it’s because they’re grieving a role they loved — even if it was burning them out. Or because they’re scared of stepping into a version of leadership they’ve never seen modeled.
This grief can show up as procrastination. As sudden doubt. As the urge to go back to what feels safe.
And if we misread it, we end up trying to “fix” it with tools and tactics — when what’s really needed is space, reflection, and a new story about who we’re becoming.
How to work with strategic grief
The first step is to recognize it for what it is. Grief doesn’t always look like sadness. It might look like resistance. Or perfectionism. Or endless tinkering with things that don’t really need to be tinkered with.
Here are a few questions I’ve found helpful to ask — both for myself and with clients:
- What version of yourself are you afraid to let go of?
- What roles have you internalized that no longer serve you?
- What would change if you allowed yourself to evolve without guilt?
There’s no quick fix here. But there is a path forward. It starts by naming the grief. By honoring the role your past self played. And by gently stepping into the unknown, not as a crisis — but as a conscious next chapter.
You’re not broken. You’re in transition.
Strategic grief is a sign that you’re not just running a business.
You’re becoming someone new in the process.
That deserves recognition.
That deserves space.
And maybe — just maybe — it deserves to be built into the strategy itself.
Because clarity isn’t just about where you’re going.
It’s about knowing what you’re leaving behind — and choosing to carry forward only what still serves.
