When Generosity Meets Taking
Running a business during a slow stretch can make every decision feel existential. A reflection on generosity, boundaries, and the moment kindness is mistaken for weakness.
When Caring Isn’t Enough in Leadership
I’ve always believed that if you care about your people, things will work out.
Give them flexibility. Trust them. Treat them like adults.
For a long time, that worked.
But lately, I’ve been sitting with a harder question:
What happens when caring about someone starts to break the role they’re in?
Supporting Employees Through Hard Times
Someone on my team is going through a lot right now.
A family member is dying. Sleep is off. Energy is gone.
Some days they show up. Some days they can’t.
I don’t question any of it. It’s real.
But the work is real too.
Phones don’t get answered. Things get missed.
And over time, performance starts to slip.
The team feels it.
When Empathy Starts to Erode Standards
My instinct has always been to give more space.
More understanding. More flexibility.
Because I’ve never wanted to be the kind of leader who treats people like replaceable parts.
But there’s a line I’ve been avoiding.
Not because I don’t see it—
but because I don’t want to cross it.
The line where empathy starts to erode standards.
We all go through seasons like this.
Not necessarily clinical depression—but the heaviness.
The stretch where energy disappears.
The fog. The early mornings where your mind is awake but your body isn’t.
It’s part of being human.
Just like happiness is.
The Reality of Workplace Boundaries
And maybe that’s exactly why this is hard.
Because if these seasons are universal…
then the question isn’t whether they happen.
It’s how we carry responsibility when they do.
Because the work doesn’t pause.
And when one person can’t carry it, someone else does.
Quietly at first.
Covering a shift. Picking up a call. Filling in the gaps.
But over time, something else starts to build.
Not frustration with the person—
but with the situation.
The feeling that the standard isn’t the same for everyone—
and that accountability isn’t consistent.
That some people are holding the line…
and others aren’t.
And if you let that go too long, you don’t just lose structure.
You lose trust.
How Leadership Handles Accountability
I don’t like being the one who tells people when they have to work and how they have to show up.
It’s never been how I’ve wanted to lead.
I’ve always believed that if you treat people like adults, they’ll act like it.
But in this case, letting it ride wasn’t leadership—
it was avoidance.
Because I could see where it was going.
If nothing changed, I wasn’t just going to lose one role…
I was going to lose two of my most reliable people—
the ones quietly holding everything together.
Clear Communication in Difficult Conversations
So I had the conversation.
As directly as I could, and as compassionately as I could.
Because I don’t think she wants this either.
I don’t think anyone wants to show up in a way that puts more weight on the people around them.
That’s not who she is.
But intent doesn’t carry the work.
And at some point, reality has to be named out loud.
I’ve written before about The Courage to Say It Out Loud—and this was one of those moments.
She didn’t want to come in and affect the team with her funk.
But her absence was having just as much—if not more—of an impact on the team and morale.
And that’s where leadership gets uncomfortable.
Not in judging someone—
but in holding up a mirror to what’s actually happening.
It’s the kind of communication I’ve tried to describe in Communicate Like You Give a Damn—clear, honest, and human.
With enough care that they feel respected.
And enough honesty that something can actually change.
I still care about my people. That hasn’t changed.
But I’m starting to understand something I didn’t before—
caring isn’t about avoiding hard conversations.
It’s about having them clearly, and at the right time.
Because “enough” isn’t just about understanding people.
It’s about being honest about what the situation actually requires.
“Know what’s enough. Build what matters.”
Related Posts
The Courage to Say It Out Loud
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You’re Not Talking to Everyone. You’re Talking to the Ones Who Are Listening.
When you speak from the heart in a world wired for snark, some people won’t get it. But that doesn’t mean you stop showing up with sincerity. This post is about leading with kindness anyway.
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