Enjoying Difficult People, Including Yourself: Special Holiday Edition!

I know that “enjoying” sounds like a high bar. If someone’s difficult I find often we don’t want anything to do with them we want them out of our hair and out of our lives. What’s amazing to me and impressive, over and over again, when I practice NVC and I practice self-empathy I get insight that’s transformative and I actually enjoy the other person.

So, what makes people difficult?

One thing that often leads to categorizing someone as difficult that I’ve heard over and over again is: when someone might seem to be critical or judgemental, especially when it’s unsolicited. Another thing that I’ve heard from friends: when someone might be stubborn or unwilling to hear someone else’s opinion. If you experience that the other person doesn’t hear you — you’ll tell them something and they’ll disagree, or it seems that they’ve heard you and they do something different than what they agreed to–that can be really difficult. Sometimes they won’t respond to you at all — I’ve heard of this especially in the work setting.  I’m sure we can think of examples.

I invite you to consider:

What do you consider difficult?

Do you have someone in your life that you consider challenging?

I encourage you to notice that and identify what the behavior is.

Empathy for Self and Others: An Exercise in 4 Steps

STEP 1: Think of a really specific thing that you heard someone say or do that was difficult or challenging in your experience. Write down the specific words that were difficult for you.

Example: A friend heard my cell phone ring, and completely unsolicited and out of context (I thought), said “Wow, that’s a ditzy phone ring!”

STEP 2: Notice how you are feeling.

When I am talking about a feeling, what I mean is a response internally that you are having that is free of judgement.

Example: I could say, “Wow, I feel like that was really obnoxious! I feel like I was judged. That was mean!” Those are not actually feelings. My feelings might be: irritated, frustrated, annoyed, and confused. 

STEP 3: Connect with your needs.

Once you’re aware of what you’re feeling, the next step is to notice what needs are. The feelings often bring up the needs. If you’re feeling impatient, maybe you’re wanting patience. If you’re irritated or frustrated, maybe you’re wanting understanding.

Example: My critical mind is thinking “Why did you have to comment on my cell phone?” I’m really trying to understand what’s going on with the other person. I’m needing understanding.

Click here to download a list of feeling words and need words. You can find more resources like this by going to workcollaboratively.com.

In my example about the cell phone ring, I mostly wanted understanding and connection. And when I connected with that, I actually decided to let it go. I realized that, knowing that this person is really into theater, music, and performance, she’s used to just hearing stuff and commenting on it because that’s her world and how she thinks about things. Once I connected to my needs, I could understand what was going on for her. In this instance, it didn’t really appeal to me to say something. I didn’t actually think it would change her behavior in the long run.

In making these choices, I think it also depends on the kind of relationship you have with someone. The next time she says something like that, maybe I will say something and I’ll be more prepared. Something like, “Hey, I just heard you say that’s a ditzy phone ring, and I guess this is obvious but I chose that ring and I’m just wanting to understand why you would say something like that? What was motivating it?”

I find asking a question like that (when you can ask it neutrally) goes along way when dealing with people we might consider to be difficult.

When I practice self-empathy in this situation with this friend, when I connected with, “Oh yeah, this is just the world she moves in, this is how she thinks about things,” it actually allowed me to appreciate other aspects of her personality that I can actually depend on. If she has seen a movie or a play, for example, I can ask her, “What did you think about that?” I know I’m going to get some qualitative insight about that before I decide to see it. So once I could connect with my own needs and also guess what her needs were I also had a shift and was actually able to enjoy what she says and remember it’s not about me in the end it’s about her hearing something and responding to it.


Guess what the other person might be feeling and needing.

You may have noticed, once I practiced self-empathy, I was able to have more curiosity about what was going on for her. I’m guessing when she heard the ring she was maybe irritated or surprised. Maybe she had a need for understanding, or she just wasn’t enjoying it and has a need to enjoy things she hears. By guessing what she’s feeling and needing — probably for understanding and enjoyment — then I can recalibrate a little bit and not take it personally.

To recap:

  • What are your feelings and needs? (Steps 1 – 3)
  • What are the feelings and needs of other people? (Step 4)

“Favorite Difficult People” & Other Helpful Tips

The four steps above are core practices when using Nonviolent Communication. They are really helpful when you’re triggered. I also want to give you some general tips, especially as we move through all the winter holidays right now where a lot of people might be spending time with their families. And families are often where we might some of our favorite difficult people.

There are also some things you can do pro-actively, especially if you are going into a situation where you know you will be seeing one of your “favorite difficult people.”

  1. Simply ask questions. One of the things I find really helpful is to simply ask questions – in a way that’s connected and coming out a place of curiosity.
  2. Set your intention. Before you go into that holiday event or someone you consider difficult: set your intention. Look over the needs list (like this one, or your own) — which might include words like choice, community, understanding, autonomy. What needs are you trying to meet when you see this person? Are you wanting patience? Connection Understanding? To be heard? Go into that encounter focused on your need or needs. Whenever they say something that might be upsetting, you can bring your attention back to that need. It will help inform what you decide to say and do next in the conversation.
  3. Take time out. If you are getting triggered, and you want to practice the four-step exercise that I shared above, I encourage you to take time out. There’s a lot of ways to do that. For example, if you are at a party, it can be as simple as going to use the restroom. You might use that time just to do a little self-empathy before going back out to the conversation. You can also take time out by saying, “You know, we’ve been talking about this for ten or fifteen minutes and I’m wanting a break and to enjoy our time together. I’d like to switch to another topic if you don’t object. We can come back to it the next time we see each other.”
  4. Focus on the present moment. The other thing I find really helpful is focusing on the present moment. In the above example for taking time out, I’m hoping you hear the four steps: observation, feeling, need, and request. These four steps of NVC supports us in staying connected to the present moment.

The Four Steps of Nonviolent Communication:

Observation: What did I see and hear?

Feelings: What am I feeling right now — not then or in the future, but right this moment.

Needs: What needs are coming up right now? What needs does this moment bring to my attention right now?

Request: What’s best going to meet my needs in this moment?

When triggered, I find we tend to globalize. One of my favorite globalizations is when I’m riding my bicycle in New York City and someone does something I consider dangerous. My thought can be, “No one cares about cyclists.” I know cognitively that’s not true. I’ve had plenty of experiences when someone will slow down or pause for me to pass. When globalizing, I like to go into the present moment again. What exactly happened right now ?Whatever that is: someone opened their car door without looking, someone pulled over in front of me, my brother told me he voted for so-and-so, my friend said that’s a ditzy phone ring. My globalizing could be: “She’s always judging things so much.” The globalizing doesn’t help me. The globalizing actually encourages me to further judge the person and get more frustrated. If I can bring it down to a specific thing — this is what the person said — that can really help me to avoid judgement.

I hope you found these tips helpful.


  1. Self-empathy
  2. Empathic guessing for the other
  3. Asking questions
  4. Setting your intention
  5. Taking a break (which can also involve pacing the conversation)
  6. Keeping your focus on the present moment

I wish everyone Happy Holidays, and that you enjoy your favorite difficult people.

5 thoughts on “Enjoying Difficult People, Including Yourself: Special Holiday Edition!

  1. I just listened to your podcasts over the past few weeks. I really enjoyed all the real world examples throughout – from the shower curtain misunderstanding through to self empathy in the co-op queue. I’ve found it so helpful. Thank you!

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