How to listen when listening is hard

Over the past years I’ve approached strangers on the streets to ask them to draw a beautiful moment. 10.000 people shared their stories. They laughed and cried. And I learned how to listen. The key is to be open for whatever and come as yourself. To be curious for the story of the other person. But listening isn’t always easy. I discovered three main situations which can make it hard to listen.

  1. If the disagreements in view points concern your core beliefs and values.
  2. Being filled with emotions
  3. Judgements

Since my main goal on the street is to be an open listener I developed the following strategies to deal with situations like this. Cherry pick which strategies work for you. I love to hear what works for you and what doesn’t.

Disagreements in core beliefs

‘And with that they turned something good into something evil.’ I’m listening to the man and my spine tingles. What he says directly contradicts some of my core values and the things I believe in. A small part of me wants to walk away. How do I make sure I don’t disconnect?

1. Asking questions

By asking questions I can ensure whether I understand the other person correctly. I can grasp more of his way of seeing the world and learn his story. It makes me focus on his point of view, instead of my own.

2. Find common ground

As humans we like people who are alike. So it helps to find things which you share with this person. In this example, the man I was talking to wanted to know what my opinions on certain matters were. So we found each other in the way we employed curiosity.

3. Avoiding the argument battle

Listening and being there for somebody doesn’t entail an argument competition. It often ensures we entrench ourselves deeper in our points of view and our rightfulness I only express my arguments when I’m explicitly asked for them.

4. An emotional safety net

During the hard conversations I try to leave my emotions out of it. They can come after I finish my conversation. In order to deal with my own emotions it sometimes helps to talk to other people afterwards. People who know me really well and I can say anything to. During one particular tough weekend, I had close friends on a speed dial group in what’s app. After every impactful situation (also the positive ones) I contacted them and they would respond within a couple of hours. Having that connection made me feel safe, gave me perspective and bad jokes when needed. After these short bursts of contact I was able to leave it behind me and be open for the next person.


Have you have heard someone saying: ‘‘Wow. You’re yelling so loud that you took my points really into consideration.’? Mostly is’t because we’re not the best listeners when we’re angry or filled with any emotion basically. Remember that friend that’s so excited you can’t even say a word? In the last strategy I talked about emotions coming up during the conversation. But emotions can also come up even before I speak to somebody.

One morning the news had upset me. Nevertheless I went to the street to talk to people and be kind to people. And listen. So I get in a train. Because I want to contribute to the world I believe in.

And although I speak to quite a few people who draw happily, I ‘m still filled with all these emotions. It blocks me. I don’t feel like walking up to other people. It also hinders me in listening. Because these feelings want me to steer the conversation in a direction. But that distracts from letting the other be and then I fail to make a deeper connection.

I struggle. And I want to have an open heart to be able to listen freely.

As I walk through the streets I wonder how to tackle this. These three things helped me to move forward.

1. Give myself the permission to feel anything

I can’t have an open heart to others if I don’t have one towards myself. So I have to be honest about what I’m feeling. And I’m aloud to feel anything. So if I really don’t want to talk to anybody, that’s okay to.

2. I promise myself I will try until I feel open

This might seem a contradiction with point 1. But it isn’t. I’m still allowed to feel everything, I just have a point on the horizon where I want to end up. Trying doesn’t mean it has the work on the first go. You give yourself the permission not to be perfect. I just don’t want to give up on myself. So I promise myself I won’t stop trying until I can listen openly.

And while I keep on trying I notice it gets easier with each conversation. The last person I speak to on the train home even shares some secrets.

3. Stop and look around

For me it helps to just look around and pay close attention to what I’m seeing. And I noticed the shriek of a bird nearby. It helps me to focus on what’s actually there. Gets me out of my train of thoughts and allows me to be in the moment.


Judgements and expectations can prevent us from hearing what the other one is really saying. Because we filled in bits of information already.

1. Testing my assumptions

One of the assumptions I regular make is whether someone is going to draw. And I force myself to go to people where I think chances are slim they go drawing. Mostly I’m right, but the ones in which I’m not are most often the special ones. The ones who touch me.

Only by asking questions you can make sure your assumptions are correct.

2. Focus on the other other person

‘I just met a man who says tonight is going to be his last night. He wants to commit suicide. I think you are THE person to go and talk to him now.’ These sentences were said to me on the streets of denmark, talking about expectations. Off course, I felt scared. But there was one thing really clear. This guy needed help and it wasn’t about me. So I did what I knew I could: sit down and listen. Focus on him. And he was so courageous to share his stories. About the bad and the good in life.

If you shift the focus truly to the other person, then you’re able to get past the judgements. No matter whether they are about you or the other person.

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