So, here’s what ruinous empathy looks like:

1. You pour out your own cup to fill up someone else’s. If you’re anything like me, then you get annoyed that people keep taking you up on your offers to help—because you’re tired from all the helping you keep offering. In a stunning display of skill, you also deeply embody irony at the same time.

2. You are always secretly hoping someone will offer you aid. But on the rare occasions that they do, you get real uncomfortable and guilty. Then you politely turn them down and do all the work yourself. Logic has no sway in these lands.

3. You have opinions and wants and stuff. But those seem to automatically get deleted when you’re with someone else—especially a romantic partner. When someone asks you what you want to eat, you pull the ole Reverse Uno card on them and ask them what they want instead. Nine times out of 10, you go with what they want and you’re not even sure how you keep getting bamboozled.

4. You are everyone’s go-to “therapist.” Minus the whole getting paid thing. You’ve managed to train some friends to rant at you for 30-60 minutes at a time, without pause. Truly impressive. Many of your conversations end because you get tired of doing nothing but listening, but you can’t bring yourself to stop asking them questions.

5. Part of your brain is convinced it has to fix every problem it sees. Like all of them. Even the ones that people just mention in passing. As with the “therapy” gig, this is an unpaid internship that never ends. You have an astonishing amount of hours logged, wish they would stop increasing, but also can’t help yourself.

6. Some part of you is always tired. You’re dimly aware that you need rest, but like…people are depending on you, man. Not replying to texts feels like baby purgatory, and “resting” sometimes oddly feels like letting people down.

7. Your greatest fear is accidentally offending someone on the internet and getting cancelled. This sounds funny on paper but has also made you launch, unlaunch, pivot, and give up on more goals than you can count.

Sh*t. Why is this happening to me?

Well, dawg, you’re externally referenced. Meaning you determine your self-worth based on how others are feeling around you.

In the grand scheme of things this is actually kind of a cool trait.

You’re the guardian of sorts. You make sure folks are safe and healthy.

The problem? You might not know how to turn it off. It’s a bit like having a hose with no shutoff valve. Sooner or later you’re gonna run out of water—and be real soggy and stuff.

It’s not a perfect analogy.

So, if you wanna kick the habit, first you gotta understand the pillars that support it.

Pillar I: You’re afraid to go first

There are a lot of reasons why this might come to pass, but pure and simple…when they ask for volunteers, we’d sooner die than raise our hand.

When someone wants our opinion on something, we want to hear theirs first. Not because we’re all that interested. It’s because we’re scared sh*tless.

The way through? Start getting comfortable looking like a weirdo.

Take small risks.

Erase that sense of shame and embarrassment. Learn to start asking yourself what you desire in this moment. Then do it.

Pillar II: Uncomfortable people make you uncomfortable

Normally this isn’t a big deal.

When things get weird, we all feel it.

The problem with ruinous empathy is that we also feel compelled to fix it. So if someone we know is going through a rough breakup…

>> We ask how they’re doing.
>> They tell us they feel like crap.
>> Then we start to feel like crap.
>> Then we start to try to fix how they’re feeling so that we can feel better.

In a lotta ways, this is like having a toolbox with just a single, tired-ass hammer inside. (Generally fine, if the problem is small.)

A single nail needs nailing?
I gotchu fam.

But if they need a house?

That’s when we get exhausted. Burned out. Overwhelmed.

We spin out trying to fix something that’s bigger than us—something that was never ours to begin with.

One of the best ways I’ve found to address this is to simply join ’em. Complain too.

To regular people, someone grumping about their lives is an invitation to join in and complain about your life too.

Add your crap to the pile. Then sit back and watch it all burn.

The more you can retrain yourself to not try to automatically rescue someone, the more free you can be.

Pillar III: ’Murica

Let’s be real.

We’re part of a culture that glorifies “pullin yersef up by yer bootstraps.”

What’s really funny about all of that is that the entire movement is based on a joke.

“It’s attributed to a late-1800s physics schoolbook that contained the example question “Why can not a man lift himself by pulling up on his bootstraps?

No one can pull themselves up by their bootstraps. It’s physically impossible. That’s the joke.

Now, normally this would just be a silly mistake. But we’ve built our culture around this.

In our struggle to all become extremely bearded, self-sufficient mountain folks who live off the land, we’ve sorta forgotten how to accept help.

This is one of a few things that keeps people stuck in people pleasing. We secretly want and need help. But we’ve been trained our entire lives to look down on people who need help.

So we can’t accept it.

The only thing we can do is dole it out, which is great when we’re doing well (not so great when times are tough).

Our pride on the matter not only keeps us from getting better but also makes us dicks to the people around us (read: having a hard time and accidentally taking it out on someone who happens to be nearby).

The move here is to start small.

Ask for little things.

Start asking yourself what you want, and then following through.

Say yes when someone offers to help with the dishes.

Humble yourself and let some gratitude squeak by through your gritted teeth.

In the end, we’re accepting outside help all the time—whether we realize it or not. Might as well get used to it.

Everything we own was produced by another person, a plant, an animal, a chance tectonic shift of rock underfoot.

One of the greatest gifts you can give yourself is learning to be gracious in receiving as well as giving.

Pillar IV: Sticky emotions

Anger takes longer to subside.

Disagreeing with someone feels like initiating a fight.

The problem here is that your emotions hit harder and last longer than in other people. Typically this is the result of resisting what you feel.

There’s a truly bizarre Japanese show on Netflix called “Documental” where they stuck a bunch of standup comedians in a hotel room for hours. Each one pays $10,000 to get in. Then they try to make one another laugh. If you laugh. You lose. You’re out. If you make it to the end, all the money is yours.

Obviously people can’t laugh, so they hold it in.

By the end, these comedians are sweating, tired, and in literal pain.

You can see it on their faces.

So you have to ask yourself: If holding in laughter is causing these guys physical pain, what is it doing to my body when I stuff down my anger? Or guilt? Or resentment?

What you resist, persists.

And recovering from people pleasing, nice guy syndrome, or ruinous empathy requires learning how to allow your emotions to flow, without hurting other people.

That way if I take on someone else’s discomfort, I know I can release it. If I’m good at it, I know I can clear that discomfort in seconds.

If I’m worried about stepping on someone’s toes or feeling shame about looking dumb, I can feel what I’m feeling and move on with my life in minutes.

In the end, this is about forming a new identity—one that allows you to prioritize yourself instead of defaulting to taking care of others.

>> No more staying silent for an entire conversation while someone else super talks
>> No more trying to emotionally save everyone who’s in distress around you

It means living your life for your own sake, for, maybe, the first time.

It’s the art and science of filling your own cup first.

Then once the smoke has cleared…
Once the crazy spiraling thoughts subside.

Checking to see if there’s anything that you actually need to do in reality.

For that, you’ll need to learn to be a little more selfish.

The goal here is to give yourself a choice in the moment. One that wins over the automatic reaction of “oh crap, I need to fix this.”

The finish line is balance. Having a choice to occupy either end of the spectrum.

I have the ability to help.

I have the ability to trust people to take care of themselves.

And in this moment?

I can choose which one I want, guilt-free.

Journey well.

~

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