Why Being a “Nice Guy” Isn’t Enough

Let me say this as plainly as possible.

A lot of “nice guys” aren’t actually nice.

They’re transactional.

The Deal Nobody Agreed To

For years, I operated with a quiet assumption: If I’m nice, if I show up, if I do the right thing, then things should work out for me.

People should respond well. Opportunities should come. Relationships should feel fair.

I didn’t say it out loud.

But it was there.

A deal I thought the world had signed.

It hadn’t.

When “Nice” Turns Into Entitlement

This is where the “nice guy” logic breaks.

Because underneath it is often a hidden expectation: I did this so you should do that.

I was respectful so I deserve something in return.

I showed up so I should be chosen.

And when that doesn’t happen?

Frustration. Resentment. Confusion.

Not because something unfair happened.

But because the deal was never real.

The Leadership Version of This

This doesn’t just show up in dating culture.

It shows up in leadership all the time.

Leaders who think: “I’ve been supportive, so my team should perform.” “I’ve been approachable, so people should speak up.” “I’ve created a good environment, so results should follow.”

And when they don’t?

They feel let down.

But support is not a transaction. Trust is not a transaction. Leadership is not a transaction.

The Hard Lesson

One of the most uncomfortable things I had to confront was this: I wasn’t being “nice.”

I was trying to control outcomes without admitting it.

Niceness was the strategy.

Expectation was the goal.

And when reality didn’t match that expectation, I blamed everything except the assumption itself.

What Decency Actually Requires

Decency is different.

It’s not about being pleasant.

It’s about being grounded.

You do the right thing because it’s the right thing. You show up because that’s who you are. You lead because you take responsibility.

No hidden contracts. No silent expectations. No scorekeeping.

The Takeaway

Being a “nice guy” often comes with strings attached.

Being a decent man doesn’t.

And in leadership, that difference shows up fast.

Because people can feel the gap between: someone who is genuinely grounded and someone who is waiting for something in return

even if nothing is ever said out loud.

P.S. A lot of the mistakes in The Big F#cking Book on How to Be a Decent Guy come from this exact pattern, confusing good intentions with clean motives. It took me a long time to realise how often I was expecting something back.