When Grace Becomes Complicity: The Quiet Cost of Being “Nice”

What Is (and Isn’t) Grace.

“Maybe I should give her grace,” Mary said. “She’s going through a lot.”

I paused. “Is she ever not going through a lot?”

We’ve all been there. We’ve been told to be empathetic. To extend grace. But to what end? And what does that mean in practice?

If grace always protects the taker and never the one carrying the weight of the relationship, it’s no longer grace.

Grace says, “You (and your troubles) matter. But your behavior still isn’t okay.” Complicity says, “You and your troubles matter more than I and my troubles do. So I’ll stay quiet.”

One creates space for growth and includes boundaries and expectations. The other creates a pattern of one-sidedness.

The Student Who Got It Right.

Years ago, I caught a student cheating. He didn’t lie. Didn’t flinch. Just looked at me and said, “I know. I cheated. I’m sorry.”

It stopped me cold.

He didn’t just admit the truth. He owned it. Immediately.

I gave him another shot—not on the test, but on the habits and fears that landed him there. We worked together for months. Despite a 0% on the test, he finished the class with a C+.

It wasn’t just impressive. It was honest. That mattered.

That’s what grace requires of us who give or receive it. Not perfection. Just ownership.

The Friend Who Took Too Much.

Kelly wasn’t a student. She was a friend, the kind I bent over backwards for. I gave time, advice, connections, and favors I didn’t have time to give.

It didn’t start big. It never does. A little help here, a little gap there. She asked. I said yes.

But over time—over the course of several years—she took more, gave less. 

And when I needed something? Silence. Silence quickly gave way to active disregard. 

When I finally said I was hurt, she deflected. My tone, my timing, and my expectations were the real offense.

The message? Only she was allowed to have expectations. I was not.

On reflection, it seemed no one had ever told her, “You hurt someone. Address it.” Or, “You screwed up. Own it.” Or maybe they had, but entitlement served her better.

She wasn’t unkind. She was simply unpracticed in accountability.

The Non-Profit Leader Who Knew the Script.

It looked different in a professional setting. But not by much.

He checked every box. Smart. Passionate. Spoke fluent nonprofit.

But once we started the work, the diligence documents didn’t arrive. Deadlines slipped with no heads-up. Our grant requirements were reframed as “collaborative conversations.” Even though I’m a lawyer and he isn’t, he explained the law to me.

I chalked it up to greenness and gave space. Clarified. Tried again.

Eventually, I asked him to pause and reflect:

“Take the weekend. See if this is something your organization can and wants to do. Send your reply on Monday. No hard feelings either way.”

Friday morning, he emailed back. No reflection. No documents. Just another attempt to negotiate away the terms.

So I closed the file.

Then came the final note: a polished, polite, just-condescending-enough email to reveal what I’d been ignoring. Sandwiched between praise and thanks were subtle digs: I was the problem. I needed to be more “well-liked.” We (the Foundation) should reflect on how we work with nonprofits.

He never once suggested he needed to be more prepared.

What I Let Happen.

Both Kelly and the nonprofit leader wanted the benefits of a relationship without the responsibility of one.

But they weren’t the problem. I was.

I was soft on expectations. When I shifted—started expecting mutuality, respect, accountability—I crossed a line they weren’t used to, and they pushed back. And why wouldn’t they? It had worked for them. I had signaled early that they could push without consequence.

I told myself I was being nice.

I wasn’t. I was scared. Scared of being called cold. Scared of saying, “This ends here, even if the relationship does too.” Scared of trusting my own boundaries.

But kindness without accountability isn’t kindness. It’s complicity.

How to Spot It.

There are two types of people in this world:

1. People who mess up and own it.

2. People who never mess up. You're the problem.

The second kind isn’t rare. We are all capable of knee-jerk reflexivity. Some are just more practiced.

While they don’t look like villains, there are clues:

• They talk more than they listen.

• They’re charming. Overly complimentary.

• They rarely apologize.

• They rarely follow through.

• Their problems are always bigger than whatever is going on in your life.

They look like they’re doing their best. They usually are, but only for themselves.

How This Applies to the W.W. Reynolds Foundation.

We're not looking for perfection; we're looking for character.

We’re not interested in polish or charm. We back organizations that make real change because what we reward, we replicate.

And if we reward charm over follow-through, we teach the wrong lesson: that accountability is optional. That consistent effort doesn’t matter. That the best talkers win.

We want to support nonprofits that find the kid who stays up late finishing a paper. The teen who clocks in tired but shows up anyway. The student who makes a mistake and tries again.

That’s why we fund programs like Junior Achievement’s Financial Literacy programs. It teaches kids to manage money, solve problems, and make decisions with long-term consequences. It teaches them to carry their own weight.

That’s not just education. That’s accountability. That’s adulthood.

Bottom Line.

Not everyone will like us. But everyone should trust us. After all, grace is powerful.. But it must be earned, one choice at a time.