The communication habit you’re missing

Saying hard things to people that matter

Once upon a time Seneca said:

We suffer more in imagination than reality.’ — Seneca

He’s dead on. Especially when it comes to having hard conversations with people that matter in life.

Many people would rather consume themselves with fear than have a hard conversation. Super sensible right?

But why are we so fearful of bringing up tough topics?

It’s because Mr. Tribal Brain is kicking in. He does not want you to stand out as a disagreeable member of your community. That is tantamount to suicide if living with 20 other people in an isolated village 8,000 years ago.

But today that’s no longer a useful biological impulse. Overcoming this evolutionary handicap will make your life better. You’ll be able to say things like:

‘I didn’t like the way you just looked at me, it made me uncomfortable.’

‘I find it hard to justify continuing to invest in our friendship after what has happened.’

‘When you walk out the door without saying ‘bye’ it makes me feel unappreciated and small.’

Those things should be as easy to say as:

‘Bro, wanna go see Wonder Woman’?

‘Can you pass the Sriracha?’

‘Vampire Weekend made me a Horchata lover.’

This post is your first step in getting there. It is going to give you two useful strategies along with three action items to start initiating hard conversations.

Strategy 1: Filter irrational people from your life.

Hard conversations are useless if you’re having them with irrational people who don’t listen. If your conversational counterpoint possesses these traits they will not:

  • Hear or accept your feedback
  • Make any changes as a result of your feedback

Trying to use hard conversations to improve relationships with irrational people is not a good use of time. The better approach is to just filter those people out of your life altogether. They aren’t worth it.

This process of filtering will be easy if you perfect strategy 2.

Strategy 2: Mint a hard conversation habit

Everyone feels the same thing when they aren’t saying what they wish they could. I’d characterize it as the feeling of dissonance.

It’s what wells up in your nerves after you hold feelings inside and don’t let them out.

For me it feels like what my body does while sitting in a dentist chair. I try to stay relaxed while they are pricking away at my ill-flossed gums. But still, I’ll find my legs and toes tensing up constantly. I’ll try to focus on releasing that tension but once I go back to thinking about something else it returns.

The feeling that a hard conversation should happen can feel the same. In those moments we have a choice — to suppress (and thus keep suffering inside our imagination) or say what we need to say (improve our reality).

In order to say more than you suppress you need to learn how to use the dissonance feeling as a trigger for habitual action.

In the short term you’ll need to put on your willpower pants to get this done.

That’s because willpower is the activation energy needed to perform a non-habitual action. But while some amount of willpower is needed you can minimize the amount required by planting cues into your environment that remind your experiencing self what your narrator self wants to do.

An easy way to do that is to create a recurring reminder in an app you see daily that says:

‘Say what I’m feeling the moment I feel it today.’

You’ll whiff a lot at first, but once and a while you’ll be able to pass instructions to your experiencing self to actually say the hard thing in the moment it should be said.

If you’ve followed Strategy 1 and surrounded yourself with rational people you will gain great results.

These results will create a positive feedback loop encouraging you to saymore often. Continued positive experiences with this will change the say / suppress probability curve in a compounding fashion.

With each instance you’ll need less willpower to choose to say. Eventually willpower will be unnecessary and the habit will calcify.

Years later you will find yourself tranquilly sitting on your porch sipping horchata.

Suddenly you will be struck with the memory that you used to totally suck at hard conversations. You’ll be stunned that you blunderbussed your way through life for so long without this skill.

Do these things right now

Instead of clicking on the next tab in your Chrome Centipede, make the last few minutes of reading this stupid article worth it by doing three things:

  1. Make that recurring daily reminder in your app of choice encouraging you to say hard things.
  2. Save this article somewhere and reread it in a week to reinforce the concepts.
  3. Fill out this self-quiz I made based of the ideas in the book Crucial Conversations. It’s a great place to start if you don’t know how to find the right words to start a hard conversation.

Good luck — this stuff is not hard. You just have to actually apply the idea in your life to experience any benefits.


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