Why Does My Kindness Keep Attracting Chaos?
What I learned about why certain people are drawn to helpers like us
In one of the live Q&A sessions within my Healing Insecure Attachment course, someone asked me something that clearly struck a nerve with others in the group:
“I’m noticing that certain types of people keep finding me, people who need a lot of reassurance, who want constant processing. I genuinely care about them, but I’m exhausted. Is there something wrong with me? Am I attracting chaos because of my kindness?”
If you’ve ever felt this, you know how uncomfortable the question is. You want to be kind. You want to help. But you’re also wondering why your compassion keeps leading to situations that drain you.
The Compassion Trap
In wisdom traditions, there’s an ancient teaching from Tibetan Buddhism about the integration of compassion and equanimity, “the jewel and the lotus.”
You need both. Compassion alone, without the container of wisdom and boundaries, becomes a trap. You end up drained, resentful, and wondering why your kindness keeps backfiring.
Early in my career, I started noticing something that made me uncomfortable.
There were people who were particularly drawn to me and they all seemed to want the same thing. They were looking for that father figure kind of kindness: the steady presence, reassurance, and the validation they’d never received.
And I genuinely wanted to help them. I am a kind person. That’s not false advertising.
But the demands would escalate. No matter how much I gave, it wasn’t enough. They needed more reassurance, more processing, more of my time and energy.
And I realized that I couldn’t deliver what they were really looking for. No one could.
What they needed wasn’t actually me, it was the father they never had. And I’m not their father. I can’t fill that void, no matter how kind I am.
It’s Not Random Who’s Drawn to You
Here’s what I had to accept: It’s not random who’s drawn to you.
Because of your particular qualities, maybe your warmth, your steadiness, your ability to really listen, you attract people with specific attachment wounds.
If you’re naturally compassionate, you might draw people with anxious or disorganized attachment styles. People who are genuinely hungry for what you offer, but whose hunger runs so deep that no friendship, no amount of support, will truly satisfy it.
Your kindness isn’t causing chaos; your kindness is revealing who needs what you have, and sometimes, what they need is more than any friend can provide.
Once I understood this pattern, I had to ask myself a different question.
Not “Why do I keep attracting difficult people?” but rather: “Who is it that’s drawn to me, and can I actually be helpful to them in a sustainable way?”
Here’s permission I had to give myself, and the permission I want to give you: You can’t be helpful to everyone, and that’s perfectly normal.
Some people are genuinely a good fit. Their needs and your capacity align. You give, they receive, they give back. It’s mutual.
And what other people need requires professional support, or a different kind of relationship, or healing work they can only do themselves. You’re simply not the right person to meet those needs.
And recognizing that difference is wisdom.
Being More Careful (Without Closing Your Heart)
So what did I do with this insight?
I became “more careful” with certain types of people coming my way. Not cold or rejecting. Just discerning.
When I sensed that someone was looking for me to fill a parental void, I could recognize it earlier. I could be kind and supportive, and also know my limits. I could refer them to resources better suited to their needs. I could be honest: “I care about you, and I think what you’re looking for requires more than friendship can provide.”
This wasn’t about protecting myself from all neediness. It was about recognizing the difference between needs I could meet and needs I couldn’t.
And that recognition freed me to be more helpful to the people I genuinely could support, because I wasn’t depleted by trying to be everything to everyone.
The Jewel and the Lotus
This brings us back to that ancient teaching. Compassion (the jewel) without equanimity (the lotus that contains it) becomes overwhelming, depleting, unsustainable.
But equanimity without compassion becomes cold, detached, self-protective.
You need both.
You need the warmth that makes you who you are, the kindness that makes you want to help. And you need the wisdom to recognize your limits, to notice patterns, to say, “I care about you, and I also know I’m not the right person to meet this particular need.”
If you’re reading this and thinking, “Yes, this is exactly what’s happening to me,” here’s what you can do:
Notice the pattern. Who keeps showing up? What do they need from you? Is there a type?
Get curious, not judgmental. Your kindness isn’t a flaw. The question is: Can you sustainably meet what they’re asking for?
Ask the real question. Not “How can I help everyone?” but “Who can I genuinely help, and who needs something I can’t provide?”
Remember: Being careful about who you can help isn’t the same as closing your heart. It’s protecting your capacity to be helpful at all.
The Bottom Line
Your kindness isn’t attracting chaos because you’re doing something wrong. It’s attracting certain people because of who you are, and that’s valuable information.
Some of those people will be wonderful matches. You’ll genuinely be able to help them.
Others won’t. And that’s okay.
Your job isn’t to help everyone. Your job is to be sustainably compassionate, which means recognizing the difference between the needs you can meet and the needs that are beyond the scope of friendship.
The jewel and the lotus: compassion and wisdom. You always need both.
If this was helpful, and you want to sign up for my Healing Insecure Attachment course, use code substack10 for 10% off.
The content in this article has been adapted from my spoken word.