How Do We Deal with Difficult People


This is a topic I have spent a lot of time talking to people about over the past few years. I used to work as a counselor at a small private university. Having difficult conversations with difficult people would come up every year as the holidays approached, especially Thanksgiving and Christmas. The college students struggled with going home to parents and talking about the things that different generations seem to have conflict over – politics, social issues, religion, and things like that.


I am writing this in 2020. Over the past four years, I have noticed that this conversation has expanded beyond the holidays to be a year-round concern for people. It has moved beyond our close family members to include coworkers, bosses, friends, acquaintances, and sometimes even that annoying person behind you in line at Walmart.


Difficult People in a Difficult Society


We have become increasingly divided as a society.

This can be attributed to several things.

The prime culprits seems to be the weaponization of social media, the echo chamber we are all able to live in by cultivating what information we receive, the ability we have to find people who agree with us all the time through different online groups and forums, and, a president who has been especially adept at using this division to further his own agenda.


I am uncomfortable laying the blame on Donald Trump like that, but I do not see a way around it. This is not a matter of Republicans or Democrats or conservatives or liberals, but an aspect of the character of the man himself. He has taken trolling to a new level. He tosses ideas out for public consumption regardless of whether or not they are true. When confronted, he throws his hands up, saying he was just thinking out loud. His most rabid and aggressive supporters have picked up on this kind of behavior and it has spread throughout our society.


Those opposed to Donald Trump play a significant role as well. I recently joined a new social media site that claims to be more about deep thinking and compassion than places like Facebook and Instagram, but I saw the exact same memes, tweets, and unsourced broadsides that I saw everywhere else. They just had a left-leaning agenda. As a society, our entire political discourse has devolved into us driving by and mooning each other out the car window, thinking that we have scored intellectual points in the process.


All of this together has made knowing how to have conversations with difficult people much more necessary. This blog post was born from asking people who followed me what would be most useful for me to write about. The question of how to handle difficult people in difficult situations was an overwhelming number one.


Where We are Headed


Our purpose here is to explore ways to make living in such divisive times more manageable in a general sense, while also exploring concrete tactics to deal with people who do not have any respect for the things we believe.

To begin, we will work to make sure we are not part of the problem by cultivating insight into the things that we do that might make difficult situations worse. After this, we will try understand why people do the things they do and why they behave the way they behave, and we will talk about establishing boundaries to help protect ourselves and the people we love from the most toxic people. To wrap things up, we will look at what it means to walk away from a relationship with someone who has no respect for us or our boundaries.


Dealing with Difficult People: A Disclaimer


I should start with a few statements that establish my overall beliefs about other people. You may or may not agree with them, and that is okay.


We need to choose relationship over being right. That being said, we should not necessarily maintain relationship with everybody in our life. This includes family members and people we have been friends with since we were very young.


Unqualified compassion is a necessary component of life. However, compassion does not mean that we do not have boundaries or that we let people run over us. Compassion and weakness are not the same thing.


Having your feelings hurt is not a significant offense against you, but someone who continually hurts your feelings and shows no real remorse for it should not be in your life.


We have to clean up our side of the street before looking at anyone else’s.


It is essential that we have conversations with people who believe very different things than us.


More than anything, we are all in this together and about 99% of us have more in common than we have to fight about.


Lastly, and this is very important, you can understand where someone is coming from and still not agree with them. There’s this strange thing going on in the cultural narrative right now where we label anybody who disagrees with us as baseless and insane. This makes conversation impossible, and that means that things are only going to get worse for all of us.

Everyone is Doing Their Best with What they Have. Even Difficult People.


There’s another bizarre idea floating around in our heads right now. It is the idea that there are people out there who are knowingly and intentionally doing the wrong thing.

I first encountered this idea growing up in the Christian Church. I was told there was this evil figure, Satan, who hated everything and everyone and only wanted to sow misery and sadness and death and destruction in the world. Even as a child, this didn’t make sense because I did not understand what he was getting out of this. Did it bring him joy to make people unhappy?

This confusion solidified my first year in college when I took a philosophy of religion course. We discussed the idea of a perfect god versus a perfect devil. The idea of a perfect God makes sense because, being the good guy, God could do good for the mere sake of doing good.

The problem with the idea of a perfect devil is that for Satan to do these bad things, he must enjoy them, which means he’s not perfectly evil because he is doing something to bring joy to the world, if only for himself. The idea that someone does evil for the sake of evil doesn’t make a lot of sense, especially when we are talking about humans.


One of my core beliefs is that everyone is doing the best they can with the tools they have available to them. As humans, I do not think we can do something without a motivating factor, and that motivating factor must be one we see as beneficial to us. It may be skewed or disordered, but it makes sense to the person.


This is important because if we think we are dealing with irrational, insane people, there is no way we will ever be able to have a conversation with them. Conversations with people who believe differently than us are critical if we are ever going to grow as people and get out of this mess. Look for the reasons someone believes what they believe.


Everyone’s Beliefs Make Sense to Them


If an idea does not make sense to someone, they will not believe it. This doesn’t mean that what they believe is right or true, only that it makes sense to them according to the life they live and the things they see around them. This is especially problematic in our current situation where we don’t have a news media as much as we have talking heads with an agenda posing as news anchors.


There’s the added complication of social media and its debilitating effect on our cultural narrative. We no longer value expertise or objectivity but instead give credibility to something because it is clever or because it made us laugh.

When you think of things like character limits or an image-based presentation such as that of Instagram, we see a situation where people say very little of substance, but present it as the truth. Even worse is the fact that we can cultivate our feeds and the news we consume to only give us things we agree with, so we are getting shallow little bites of things that do not even challenge the pre-existing ideas that make sense to us. Understand that we are all oppressed by this system.


The Exploitation of Difficult People


It may be useful to substitute the word “scared” for “difficult”. On both sides of the political spectrum, the people I see being the most outrageous, aggressive, and obtuse seem to be very scared.

On the right, you have people who fear government tyranny through gun control, socialism, and the slow wearing away of values and ideals that they believe have served us very well for centuries.

On the left, you have people who fear government tyranny through militias, fascism, and the slow wearing away of social and political freedoms that they believe have steered us very well for centuries.


These people are very vocal about these fears, but they couch them in anger and sarcasm because fear is a vulnerable feeling, and we don’t like to express it. There are plenty of people in our public consciousness who are exploiting these fears and making scared people turn into difficult people.

Because of the echo chamber we’ve created, these people feel validated in their beliefs and are becoming more scared and, therefore, more difficult. It is an unfortunate trend, and I am not sure it will end anytime soon because it has worked out very well for the people who have taken advantage of it.


Why All the Sympathy for the Difficult People?


Here’s my deal: I don’t have a desire to see people get owned or humiliated. I don’t want to see one side lose. I know it might feel good for a moment, but it’s not helpful in any real way.

This isn’t necessarily out of altruism. We are all on the same bus, and we all die if it goes off a cliff. It is crucial that we take the time to understand where other people are coming from to have better conversations with them and help steer them in a more productive direction.


Anger and defensiveness are pretty much automatic conversation enders, but if we can get down to the things that a person fears, we might be able to actually help them, and enough of this can change the society we are living in.

The cool thing about fear Is that it cannot be present unless there is also something they love very much: maybe they love freedom, maybe they love their family, maybe they love their job, maybe they love this country, maybe they love the LGBTQIA community, maybe they love animals, or they love the planet. It is good to love things, but love can flip over to fear very quickly, especially when a charismatic, influential person tells them the things they love are under threat.


Everyone is suffering, and people express this suffering in different ways. It is hard to express suffering constructively in the first place, but it is even harder when you have a thousand different kinds of media working together to turn the suffering into anger and divisiveness.

Cut people some slack. Their response might surprise you.


Insight: Are You One of the Difficult People?


I look for one thing when somebody shows up in my office looking to improve their life: insight, or the ability to look at themselves, their beliefs, and their own behavior with some degree of objectivity. The degree to which this is present is the degree to which they have the capacity to change. We cannot change without the presence of insight.


We must examine where our own opinions come from and take a minute to look at how attached to them we are. One of the uncomfortable truths of life is that our opinions are much more subjective than we think they are. We all like to believe that our opinions are based on fact and long bouts of sifting and sorting through information to arrive at what we believe.

When it comes down to it though, we tend to favor the things that are familiar to us. In fact, hearing a particular perspective tends to shift our opinion towards that perspective. This is why we love such shitty songs. We hear them over and over on the radio, they become familiar and seem like they must be good because everyone must love them enough for them to be on the radio.

Ask yourself why you believe what you believe. What made you choose your position out of the many thousands of positions available on just about every topic?


Ask yourself what it would take to change your opinion on something. If the answer is nothing, then you might be as dogmatic and rigid as the people who are driving you crazy.


Cognitive Biases and Difficult People


I did a short series on Instagram about cognitive biases because we all have them, and they influence the way that we see the world. For instance, the Dunning Kruger effect tends to make the least capable people very confident in the things that they do, while the IKEA effect makes us love things we have created more than we would if somebody else had built them for us.


One of the more dangerous cognitive biases is called Fundamental Attribution. We tend to see other people’s poor behavior and poor choices as evidence of their flawed character while giving ourselves context for our bad behavior.

For instance, you see another customer snap at the kid who’s ringing up their groceries. You assume they’re an asshole, forgetting that you did the exact same thing last week but decided to cut yourself some slack because you didn’t sleep well the night before.

Cognitive biases are not harmful in and of themselves. If you think about the amount of information the brain is expected to take in and process every second, it makes sense that it is going to use some shortcuts to save time and energy. They only become a problem when we allow them to sway our judgment on things too often, or we treat other people poorly because of them.


Cognitive biases steer us toward trusting people who look like us or who think like us. If we have been successful or life has been good to us, we tend think that the status quo is automatically good.

None of these things make you a bad person. These are just things that we all need to recognize about ourselves, especially when dealing with difficult people. It is helpful to remember that they are laboring under the same kind of cognitive biases we are. It is hard to blame somebody for something that they don’t even know is there.


Difficult People, Difficult Emotions


It is strange to me, but this next idea is often unpopular with people: while you are not responsible for the emotions someone else triggers, you are responsible for every single thing that happens after the initial arising.


Let’s break this down.

This isn’t about kids being so soft these days or millennials being snowflakes or anything like that. Everyone is a snowflake about something, we just tell ourselves that our thing really matters and is worth getting bent out of shape over.

Taking responsibility for your emotions is the path to freedom. The most challenging people we deal with have recognized that if you can knock somebody off their emotional center, you have control of them. This is why abusive and manipulative people resort to harsh language and disrespect so quickly. It gives them control of the situation.


It is not any fun to feel anxious or afraid or angry or defensive, and we need to understand that once those things are present in a conversation, that conversation is going off the rails. When they are present in the other person, that person is going off the rails, and we are about to get ourselves caught up in a very unpleasant situation.


Emotions don’t mean all that much in and of themselves though. If you think about it, emotions start off as a simple energy somewhere in the body – fear seems to manifest in the chest, anxiety in the stomach, things like that. When we can learn to allow them to remain as energy, they come and they go pretty quickly.

The problem arises when the mind takes that simple energy and frames it in a way as to turn it into an emotion. This gives the mind something to think about. It thinks about the activating event and keeps that emotion present. Emotions are like stray dogs; they only stick around if you feed them.


Learn to watch your inner response to things that are happening, and as much as possible, stay out of the way of the energy when it arises. This will take one of the primary cards out of the hands of the trolls.


You Don’t Have to Deal with Difficult People


This might be the most frequent exercise I do with clients: I ask them to list the things they have to do. Most of the time, people list things like feed their kids, pay taxes, go to work – the basics of life in an industrialized society.

They start to walk these back to more and more fundamental things once I point out that they don’t have to do any of those things: we feed our kids because we love them or at least don’t want to deal with Child Protective Services. We pay our taxes because we don’t want to go to prison. We go to work so that we have the money to pay our bills.

All of these things are choices. They may be coerced, but they are still choices. If I were to walk outside today and somebody puts a gun to my head and says “your wallet or your life,” I still have a choice in that situation.


This is important because we often feel that we have to do things that we are choosing to do, including maintaining relationships with the difficult people. There is literally nobody on the planet that you have to have a relationship with. Even if you are a prisoner, you don’t have to have a relationship with the guard who tries to talk to you. You can just not respond and leave everything one-sided. That’s not a relationship; that’s someone talking to themselves.


This is important to remember because for every difficult person you deal with, there is a reason you are choosing to do so. When we don’t own this, we start to feel disempowered at best and sorry for ourselves at worst. There’s only one thing we all have to do, and that is die someday. Everything else in between is a choice, and that’s where our power lies.

Strategies for Difficult People


Let’s talk about boundaries. We have different boundaries with different people. Those closest to us, like our spouses, immediate family, and even super close friends, have a different set of boundaries than that one checker at the grocery store who we talk to every time we go shopping but aren’t even sure what their name is. This seems pretty obvious, but it is something that we often don’t put enough time and energy and intentionality into.


There are three types of boundaries: rigid, diffuse, and flexible. Rigid boundaries are like razor wire where nobody gets past. Diffuse boundaries are like a line spray-painted on the ground that anyone can step over. Flexible boundaries tend to adapt to the situation at hand. Flexible boundaries are the healthiest, and they are what we need to aim for.


The crucial thing with here is to understand that your boundaries are your boundaries. Nobody gets to set them for you. This is important for difficult people because one of the first things they will challenge are our boundaries. They will use guilt, manipulation, and appeal to all sorts of things, such as how long you’ve been friends or things they’ve done for you, to nullify and ignore your boundaries.


When we are conscious about our boundaries, when we set them intentionally, it makes it easier for us to stick to them because we have a reason for saying yes or no to people.

Saying “No”


One of the simplest and most effective strategies when dealing with difficult people is to learn to say no and to do so without qualification and without explanation if need be. We are taught to feel guilty for saying no in our society, which leaves the door wide open for the difficult people. Often, they know that they can bear discomfort more easily than we can, so they’re willing to lean on the awkwardness of a situation to force our hand and get what they want.


One of the main mistakes I see people make in saying no is that they overexplain. The more words we use, the more we give the difficult person to twist and manipulate and turn around on us.

As I mentioned at the beginning, this post emerged from questions people had asked me about how to deal with difficult people during such tumultuous social and political times. When it comes to political discussions, saying no to people might look something like this:


I don’t want to talk about politics with you.


I value our relationship, and every time we talk about this subject it makes me like you less, and I don’t want that to happen.


Can we talk about something else? I don’t enjoy having this discussion with you.


I don’t agree with you, and I know you don’t agree with me, and I am OK with that.

I would rather not talk about this anymore.


As you can see, we don’t have to be unkind to be firm. One of the biggest mistakes many of us make is that we wait until we are angry to draw boundaries. When we try to do this, we are not operating out of the prefrontal cortex, the part of the brain that is responsible for all the best parts of being human, so there is almost no way that it will go well.

As I mentioned above, monitor your emotions. When you start to notice anger, fear, resentment, or defensiveness arise, step away by drawing boundaries. The longer you wait to do it, the longer you train the other person that it is OK to have this discussion with you.

When you wait until you are angry to draw boundaries, you are also giving the other person something to use against you. They will believe that you are just angry at the moment, and they will not take your boundary seriously.

Be kind, but be firm.


Walk Away


I would like you to picture a dartboard. In the center you have the bullseye, and then you have rings moving out from there. Look at your relationships like this. The bullseye is the people who are the closest to you, the people who would always be there for you, and you would always be there for them. This is usually your spouse, your children, maybe your parents, or a few very close friends.


As we move out, the relationships become less close and less familiar: close friends, friends, Coworkers, acquaintances, etc., until we get to the outer ring where the people we know but we don’t really know reside. Think of that clerk we mentioned. You may talk to them, they may know a little bit about your life, but they aren’t anyone who’s ever been in your house.


The final ring is actually off the target. I call this exile, but you can call it whatever you want.

This is reserved for the much more drastic violations of relationship where we have no contact with a person any longer. In general, there’s no way back from exile. If someone’s done something wrong enough to get themselves there, you need to think long and hard before allowing them back into your life.


We all instinctively understand that there are different levels of relationship with different boundaries with different people. Still, I don’t know that we consciously decide where people fall into this. For some reason, when it comes to friends, we don’t move them further out in the circles even when their behavior deserves it.


Now let me be clear: I am not saying that when someone makes a mistake they get bumped. I am saying that we need to reassess our closeness with people when they consistently disrespect us, disrespect our beliefs, or disrespect our boundaries. It’s bizarre that we don’t do this with friends. We do it with people we are dating, but when I mention breaking up with a friend, people look at me like I am crazy.


For some reason, we wait for a drastic event to make these changes. If your best friend slept with your wife, they would both get moved outward on the target, maybe even into exile. It is similar to waiting until we are angry to draw our boundaries; we aren’t using our best brain to do this.

Move people around the rings before things get drastic. It might give you a chance to preserve the relationship. When the cousin you’ve been close to or the friend you talked to two or three times a week recognizes that you’re putting up new boundaries with them, it allows them to address the behavior that caused it. If they choose not to address the behavior, then you know that you’ve moved them correctly.


Difficult People: Wrapping It All Up


We are always going to have difficult people in our lives. There’s nothing we can do about this, and I wonder if it will only worsen due to the nature of our society these days. Social media, biased news, and the ability to cultivate an echo chamber online are all toxic things, and they don’t seem like they’re going anywhere anytime soon.


We can understand where someone is coming from, we can have all the love and compassion in the world for why they believe what they believe, and still draw boundaries with them. Not only is this possible, but it is also important and necessary. Do your best to understand why people believe what they believe, but don’t let this discount the need for boundaries and clear expectations of how you want to be treated.


Be conscious about the role people play in your life, and how much of your time, energy, and mental space they are allowed to have. If someone is not honoring these things, it is time to reevaluate your relationship with them. Do this intentionally and with purpose.


You deserve to have loving, affirming relationships that challenge you to be better. You’re the only one that can make sure this happens in your life, don’t ignore the responsibility.

Want more? I write a lot. I also have a podcast and post videos and mini-blogs on Instagram.

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