He Always Thought He Was a Nice Guy
We had stumbled onto something important in our previous session.
My client was a people pleaser.
It explained a lot.
He had always thought of himself as a nice guy. He was helpful, got along with people, and was the kind of person others could rely on. But there was another side to his niceness. He had tremendous difficulty standing up for his own needs.
It was particularly damaging in his marriage.
He rarely asked his wife for anything. He accommodated, adjusted, and went along with just about anything and everything that was asked of him. From his perspective, he was being easygoing. From hers, it felt like she was married to someone who wasn’t really there.
There was something dead about being married to an accommodator.
She wanted a husband with wants, opinions, and a voice—not someone whose personality was nearly absent in order to keep her happy.
Even talking to him could be difficult. Before saying something, he would filter it through one question: Will the person hearing this be displeased? By the time he made sure every word was safe, a simple conversation could become a long, drawn-out affair.
It was a new realization, though, and we hadn’t yet figured out what to do with it. We ended the session with the idea percolating in his head.
Our next appointment was scheduled for Tuesday at 1:00 pm.
At 12:59, I was finishing up a phone call with another client.
“I’m expecting my next client at any moment,” I told the person on the phone. “I’m going to have to hang up as soon as he arrives.”
At 1:08, I suddenly realized that my next client still hadn’t arrived. That was very unlike him. I quickly ended the call and texted him.
He responded immediately.
I’ll be there in a minute.
Sure enough, a minute later he walked through the door.
“I’m surprised you were late,” I said. “That’s not like you.”
“I wasn’t late. I was here at one. Through the door I heard you talking. It sounded like you were with another client, so I walked around the building until you were finished.”

That reminded me that I had forgotten to turn on my sound machine.
“Why didn’t you let me know you were here?”
He looked at me as if the answer were obvious.
“Why would I? You were busy with someone.”
“Okay,” I said. “Let’s jump right into this. Why is my other client more important than you?”
He looked confused.
So I explained, “This was your time, not his.”
“But I’m a nice person. Why should I disturb him?”
“For the first few minutes- fine. That’s common courtesy. But by 1:05, enough is enough. This is your appointment.”
He genuinely seemed at a loss.
“So what should I have done? Knocked? That wouldn’t be nice. I could startle the person inside (he thought that my client was in the room at the time).”
“Do you know anyone who isn’t a people pleaser?”, I asked.
“Sure.”
“Imagine he was standing outside my office just like you were. At 1:05, what would he do?”
Without hesitation, he answered, “He’d probably text you.”
Bingo!
Sometimes we can’t find an answer when we are trapped inside our own way of thinking. But borrow someone else’s brain for thirty seconds, and suddenly the answer comes flooding out.
Then he asked the question that was gnawing at him.
“But I don’t want to stop being this way. Being a people pleaser makes me a nice guy. I get along with everyone. People like me. They rely on me. Why would I want to lose that?”
He understood that the pattern was hurting him. He felt powerless to advocate for himself, and his marriage was floundering because of it. But he was afraid that if he removed the people pleasing part of himself, he would remove the good that comes along with it.
So we spent much of the session discussing what actually separates chesed from people pleasing.
I gave him the example of 11:59 p.m. and 12:01 a.m.
On a clock, they look almost identical. In the stillness of the night, they feel identical too. But they belong to two entirely different days. One is the end of last night; the other is the beginning of the new day.
A genuine tzaddik and a people pleaser can look remarkably similar from the outside.
Both do chesed. Both are mevater. Both notice what other people need. Both may sacrifice their own comfort to make someone else happy.
The difference is choice.
The tzaddik is capable of saying no and chooses to say yes. He gives because he is bighearted and wants to give.
The people pleaser often gives because he cannot tolerate what might happen if he doesn’t. Perhaps he fears someone’s disappointment, anger, or disapproval. Or perhaps he is deeply empathic and cannot bear another person’s pain because he experiences that pain almost as his own.
“But what about Imo anochi b’tzarah?” he asked. Aren’t we supposed to feel another person’s pain?
Of course.
But there too, its the same distinction. There is a huge difference between choosing to enter someone else’s pain because you care about him and being unable to remain emotionally separate from it.
Our goal wasn’t to make him less caring.
It was to give him a choice.
We kept talking about what that might look like—remaining generous without losing his personality in the process, being considerate without surrendering his voice, and learning that another person’s displeasure did not automatically mean he had done something wrong.
The session went quickly. I gave him as much time as I could.
Then there was a knock at the door.
My next client had arrived. Apparently, he had no difficulty letting me know that his appointment time had begun.
I looked at my client and smiled.
“One day, in the not-too-distant future, you’ll be able to do that too.”
I paused.
“Or at least you'll text me that you’re here.”
*Details may have been changed to protect confidentiality and to enhance the story line.



