The Startup
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The Startup

The 1 Big Mistake You’re Making In All Your Relationships

“A group of four laughing men sits on an edge overlooking a green valley” by Matheus Ferrero on Unsplash

In June I spent 20 hours making two videos and two blog posts that indirectly called out a hater of mine. In hindsight I felt horrible about that.

I get hurt when people tell me I’m a sell out. I feel horrible about that.

I feel horrible if I don’t respond to my students within 24 hours.

Heck, yesterday in Ho Chi Minh I haggled a hand-made box of Mahjong down from $26 to $12 and felt horrible.

The common thread?

I care way too damn much, and you probably do, too.

Caring Will Toss You Into A Vicious Cycle

I think the main thing to remember is we expect people to reciprocate our feelings.

We expect them to do for us what we did for them. At the VERY LEAST we expect them to appreciate what we did. That’s fair, right?

The problem is they don’t. Caring too much is a recipe for disappointment — then when you’re the one to call people out and metaphorically flip tables you’re the bad guy.

Because it looks like you’re angry and out of control.

But you’re only angry because you got hurt.

Then when you calm down and try to “fix it” with them they don’t care enough to do anything about it.

Because, once again, they don’t care as much as you do.

Then you get angry again and even more hurt.

It’s a cycle of fucking craziness — let me tell you.

And you’re stuck in it.

Because you actually give too much of a damn about people.

I’ll argue this..

Don’t stop caring about people. Keep caring. Just, try not to go overboard.

Instead, ruthlessly “delete” the people who actually don’t care about you and focus on the FEW ones that do.

Like, the very few.

I’m talking family members and extremely close friends.

This takes honesty and the willingness to go through a bit of pain to forget about people that are on the fence, but it’ll save you a lot of heartache later on, I think.

Plus you’ll be spending more time with people that actually deserve your time.

Caring Can Really Bite You In Business, Too

The other side to this blog post is the business one.

At Disney I learned that great customer service is basically all you need to run a good business. Like, that’s the only thing you need to differentiate yourself.


Because, in keeping with the theme of this article, most people don’t.

And this gives you an advantage.

Zappos built their entire brand on good customer service. They were sold to Amazon for $1.2 billion a few years back.

They were so focused on customer service that if someone called in to order a pair of shoes that they didn’t have in stock, they’d actually recommend A WHOLE OTHER STORE to buy them from.

That’s caring.

And it can give you an incredibly big advantage in business — but in this case let’s not act like the rosy walkway to business prosperity goes on forever.

People forget what you did for them. They get USED to you being so helpful.

At Disney I had so many people try to pressure me into giving them food for free because they knew we were cast members and couldn’t refuse them.

In my business, I’ve always assumed people have the best intentions. I’ve realized lately that was just me being young and stupid.

Many times I spend 25% of my day straight-up responding to people. I get 15–20 emails per day with questions. If I spent time responding to every one WITH THE THOUGHTFULNESS THAT I WANTED, it would take me hours to do so.

This is not practical, nor is it exactly fair to me.

And I do this for free! I respond to many people for free.

I’m constantly set back on a financial level by people because:

  1. Time is money. Responding to people takes up time, which takes up money.
  2. I spend more time helping random people than I do on helping my actual freakin’ students.

In short, I care too much.

And I’ve suffered financially for it — there’s no doubt about it.

The Remedy To It All?

There’s a way to be both thoughtful and practical. A way to respond to people while not spending 18 hours of your day doing it.

I used to think I needed to be SUPER hands on with my students going through my online course (like, respond to emails 5 minutes after I got them), but then I realized I didn’t need to be so paranoid.

When people get a response from you in 5 minutes, they come to expect that. The foot’s in the door. Now they’ll expect so much of you.

Then they’re dependent on your thoughtfulness, and because you’re so thoughtful and have answered 30 other people, you’re now getting a flood of emails from people at all parts of the day.

And because you enjoy being thoughtful and aren’t responding, you feel terrible (because you aren’t being thoughtful anymore).

It’s a slippery slope. Caring inevitably leads to you getting taken advantage of because other people’s feet will continually nudge that door open more and more and more until you’re running around like Gollum sleep deprived with wide eyes yelling “TATERS PRECIOUS” trying to hold it all together.

And get this..SOMETIMES they’ll ACTUALLY be mad at you for not getting RIGHT back to them!

Caring leads to entitlement on the part of the people you care for. They will feel entitled to your thoughtfulness. Like you owe it to them — it’s human nature.

My remedy?

Don’t care. Stop caring so much. Stop giving people a level of attention that’s straight-up unprecedented (I mean, five minutes to respond to an email? Sheeeeeeesh)

Know your limits. Be thoughtful, but don’t be too thoughtful. This, in a weird way, will help you be OK with not caring so much in the first place.

Because you won’t care about not caring so much.

Care just a little LESS.

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Tom Kuegler

Tom Kuegler

Travel blogger. 29 years old. Currently in Mexico. Get my free 5-day Medium course via email →