What To Do About That Uncomfortable Conversation You've Been Avoiding

Social entrepreneur, Writer, and Speaker By Andrew Horn
Social entrepreneur, Writer, and Speaker
Andrew Horn is a social entrepreneur, writer, and speaker from Brooklyn. He is the founder and CEO of Tribute.co, which The New Yorker calls "Hallmark 2.0," and of WeJunto.com, a not-so-secret club for the exploration of modern masculinity and personal transformation.
having uncomfortable conversation

A group of 16 men sit in a dimly lit living room on mismatched chairs.

We're in the middle of a men's retreat, and these men all came to this house in upstate New York to redefine masculinity on their own terms and step more deeply into personal integrity. We are about to offer up one of the biggest questions and challenges of the weekend:

Who would you be without the weight of the things you're not sharing? 

What if having the challenging conversation that you are avoiding is precisely the thing that will unlock the strength and motivation you need to become the partner, entrepreneur, or human the world needs?

Over the next two hours, these men will identify the conversations they aren't having and work toward taking the courageous action of sharing all of themselves with the people they love. We ask these men another question to put the exercise in perspective: If they aren't being fully honest, how could they possibly expect full honesty from anyone else?

Here are the two core things I've realized after asking hundreds of people this question about the conversation they aren't having:

  1. When we are not in full integrity, we are incapable of stepping into our full power. We shrink our capacity to serve the people we care about. 
  2. The thing that keeps most people from having this conversation is a made-up story that most times isn't even true. 

Not clear what I mean by "story"?

Here are a few of the stories I often hear…

  • "I can't tell my partner that I have broken one of our core agreements (cheating/porn/money) because they will leave me."
  • "I can't tell my business partner/boss that I need to step down because it will ruin our friendship."
  • "I can't tell my family member that I don't feel like they've been making an effort in our relationship because it will push them away or start a fight."
  • "I can't talk about deep topics and feelings with my friends because it will make them uncomfortable."

At the end of the day, these are all stories. They are predictions of the future, and you simply can't know any of them for certain. This made-up story is what is standing between you and the deep relationships you desire. 

So, let's make this real for you. If you've been avoiding a big, uncomfortable conversation, here are the steps you can take to remove the power of the story you have in your head about how that conversation will go—so that you can move forward, share what you need to share, and step into your full integrity.


Step 1: Identify the big thing you're not sharing with the people you love. Where are you out of integrity? 

Where are you out of integrity? 

Have a Voldemort moment and acknowledge that which hath not been spoken. For you non-Harry Potter fans, Voldemort was the scary villain of the series by J.K. Rowling. Harry and his friends were so frightened of his evil power that they refused to even say his name out loud. What I've found is that many of us feel if we don't say it, it won't exist. We naively hope that whatever is wrong will "go away" if we don't mention it. Wrong. Just the opposite happens. When we "voldemort" something in our life—when we deny it or play ostrich—it just becomes more dominant in its destructive power.

When you think about sharing this thing, what is the story that comes up for you? Ask yourself these questions:

  • How are you assuming people will respond? 
  • What are you telling yourself they will say?
  • What are you worried will happen to the relationship? 

More than likely, these are all negative outcomes, or you probably would have shared the thing already. These negative predictions of the future keep us from sharing ourselves, from stepping fully into integrity. 


Step 2: Strip the story of its power.

To show you that this is just a made-up story, use self-inquiry teacher Byron Katie's powerful framework called The Work.

  1. Is this true?
  2. Can I 100% know this is true? 
  3. How do I act when I accept this as true? (Identify the negative behavior you already feel.)
  4. Who would I be without this story? 
  5. Could the opposite be true? 

And remember this: The story you are believing determines the present you are already living. Whatever you believe is going to happen in the future affects how we feel right now. For example, you have a mountain of work due tomorrow at your job. How do you feel? Most likely stressed. Or you have a seven-day vacation coming up tomorrow. How do you feel right now? Most likely excited.


Step 3: Acknowledge the hard truth. 

We need to be willing to risk the mediocre or undesirable relationships we have to create the relationships we really want. Once you realize this and start taking action on what's real for you without your story, your life will transform in miraculous ways.

According to what's referred to as loss aversion in cognitive psychology, we are psychologically rewarded more for not losing something than we are for gaining something new. We need to act against this biological impulse to create the life and relationships we really want. 

Step 4: Make the conversation easier by repositioning WHY you are having it. 

Here's a framework and some pointers that will make that challenging conversation easier to have: 

It's not about you! It's about us

Rather than hitting people with a firehouse of emotions, guilt, and feelings, position your share as an opportunity to deepen the relationship and empower them to feel like they can be honest as well. Don't use this as a tactic, of course. But this is compassion in action, and when you understand that by sharing honestly, you create space for other people to do the same. It becomes an act of service. 

Acknowledge your assumption

This is the story you've been telling yourself about how they've been feeling or how they will respond to what you have to share. 

For example. "I've been feeling like you are mad at me about the thing that happened a year ago, and I feel like you're just not interested in being close friends with me anymore or making an effort to hang out. I've been worried that by sharing this I'd make you uncomfortable and drive you even further away."

From there, give the person the opportunity to respond without the weight of that assumption: "With that said, rather than responding to the made-up story in my head, I wanted to give you a chance to respond to what I'm actually feeling/experiencing."

This act empowers the other person. Even if they don't like what you have to say, they will appreciate the fact that you are giving them a chance to interact with what is happening in reality. 

Take ownership of your actions. 

Don't tell someone that you did something because they made you do it. Take ownership for doing what you have done. You can tell people something they did and how that made you feel, but telling someone their actions forced you to do something will immediately put them on the defensive and forces you into the role of victim. 

Say it with me: "I am not a victim. I am responsible and capable of creating the relationships that I desire."

A few other things you can do to position the conversation positively: 

  • Tell them how much you care about them.
  • Tell them you want to create a relationship that is based on honesty and integrity.
  • Tell them you want to create a space where they can be fully honest with you as well.
  • Identify the type of relationship you do want (i.e., I want to go to the next level, I want to be able to talk about feelings, I want to be friends but am not interested in a physical relationship, I want us to support each other but no longer have time to hang out socially).

Write down what you want to say.

Writing the words you want to say shows that you are honoring the conversation and message as an important one.


Step 5: Build up the courage to take this step forward in your life. 

As Brené Brown says, "Choose courage over comfort."

If you are feeling stuck, it's often because you are not dealing with the challenging conversation or thing you are not saying. It is only when we are personally in integrity that we can expect that from the people around us. Are you creating a space for radical integrity in your relationships, or are you settling?

When you demand this level of integrity and actualization from yourself, you will develop the natural confidence to demand it from the people you surround yourself with. 

You are not the sum of what you have done in the past. You are the sum of what you have done, what you do next, and all the things you will do after that.

Is this scary? It sure as shit has been for me! 

You think it was easy to tell my wife that I had watched porn again after establishing an agreement that I wouldn't? Add the pressure that it was only a month before we were about to get married. You think I didn't have a story about how this could crush what was supposed to be one of the most meaningful days of our lives that was a few weeks away? You bet your ass I did. That's why I kept it from her. 

But also, this secret was making me an asshole that I didn't like. Making me less present, making me judgmental, making me not trust her and snap at her in a way that was totally out of character. How much of a hypocrite would I have been to commit to her while not being in full integrity? What precedent would that set for the relationship?

When I told my wife, she was rightfully furious because I had broken a very important agreement of ours. What resulted was two of the hardest, most contentious days we've ever experienced. Sometimes, it still comes up as a thing that hurt her.

But guess what? After those two days, the tension lifted. I felt more powerful; I started feeling more comfortable in bed, giving her more of the presence that she had always wanted romantically. We went into our wedding day stronger than ever. Without the weight of that lie, I was the me I wanted to be in our relationship.


The only way forward in our relationships is through these hard conversations.

The energy of integrity cannot be faked. So if you're feeling stuck, just ask yourself:

What is the hard conversation I'm not having?

Where am I out of integrity?

As for the men who sat on those mismatched chairs in the Catskills, here's what happened to them.

One man sent his dad a message telling him how much he loved him and how proud of him he was. He also shared how it hurt to not feel his dad express love in return. The man took me outside with tears in his eyes and read me a message. His father had responded with an email telling him that he loved him for the first time in their relationship.

One man came clean to his wife on a falsehood that he entered the relationship on, a falsehood that he realized was keeping him from trusting her fully. She received his admission with pain and love, letting him know that she understands why he did it. They stepped into some of the deepest connection they have experienced in their marriage. 

One man wrote a letter to his business partner that he had not spoken with since dissolving the partnership. He acknowledged his faults and invited in a relationship that he wanted them to have. 

These are the conversations that set you free, that move your life forward by "yards and not inches," as one of our men said.

You are not the sum of what you have done in the past. You are the sum of what you have done, what you do next, and all the things you will do after that.

What you do next is completely up to you. You are in control. You have the ability to reclaim your power and come back into integrity whenever you choose. You can take action tomorrow, next week, or...never.

Never is a scary thought. You don't want to get to the end of your life with your truth still inside of you. You don't want to be guessing who you could have been, what your relationships could have been.

Don't get to the end of your life with your truth still inside of you. Have the conversation.

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