Ten Ways To Deal With Difficult People (And Even Work Well With Them)

Updated: Oct 2

Have you ever had to work or get along with someone difficult? Maybe it's a boss, a coworker, a classmate, or a family member. Recently, I was chatting with a friend who is facing a difficult boss and team members. I also happen to be dealing with some difficult students this semester. We are both reading The Daily Stoic, and we catch up once a month to discuss our learnings and practice, so this month, we discussed the topic of difficult people.


We had a great conversation, and I continued to reflect on this topic afterwards. Below, I summarize ten ways to work well with difficult people:

  1. Focus on what you can control

  2. Focus on the greater good

  3. See it as necessary training

  4. Reduce expectations

  5. View it as normal

  6. Cultivate gratitude

  7. Find the good

  8. Practice empathy and kindness

  9. Do the opposite in positive

  10. Believe in yourself and practice

(You can click on the list item to jump to that section)


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1: Focus On What You Can Control

If I had to summarize the core essence of Stoicism, it would be this: Focus on what you can control (your own thoughts and actions), and let go of the rest (other people and outside circumstances).

On March 19 of The Daily Stoic, Epictetus said,

"For there are two rules to keep at the readythat there is nothing good or bad outside my own reasoned choice, and that we shouldn't try to lead events but to follow them."

In other words, whether something is good or bad depends on our own thinking, and our own thinking is within our control. We also should not focus on external events, which are outside our control, but on our reactions to them, which are in our control.

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To be clear, we can make plans (in our control), but when we implement them, things will often not go according to plan (outside our control). When this happens, we should "follow" the situation at hand by reacting in the best way possible (in our control) as opposed to being stubborn about our previous plan and becoming unhappy about unexpected obstacles.


A great analogy is water in a river flowing against a rock. Water yields to the rock, yet it wears away the rock. If we are stubborn like rock, and we fight with another rock, both of us well be harmed. But if we can be soft and flexible like water, then we will find a way around the rock and overcome the rock indirectly.

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When facing a difficult person, if we always think, "That person is at fault, that person has these problems, that person is wrong, this situation is so annoying…" then we are focusing on things outside our control, and we are being hard like rock. No wonder we feel like an unfortunate and helpless victim.

On September 17 of The Daily Stoic, Marcus Aurelius said,

"What if someone despises me? Let them see to it. But I will see to it that I won't be found doing or saying anything contemptible. What if someone hates me? Let them see to that. But I will see to it that I'm kind and good-natured to all, and prepared to show even the haters where they went wrong. Not in a critical way, or to show off my patience, but genuinely and usefully."

In other words, other people behaving unreasonably is their matter. How we behave is our matter. We need to behave properly regardless of how others behave. We can think, "OK, this is the kind of person I have to get along well with. I will not be like that. I will not be dragged down by them, and if possible, I will lift them up."

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To take this train of thought one step further, if we want others to behave better, we have to first role model that behavior. For example, if we want them to be more polite and respect, we have to be polite and respectful to them first. If we want them to be patient and genuinely helpful to us, we have to role model that behavior first. Otherwise, if we tell them to be better behaved, they will think, "Well, you're no better than me, what right do you have to tell me to behave better?"


Notice that the situation is exactly the same, but one way of thinking will lead to hopelessness and conflict, while the Stoic way of thinking will lead to hope and improvement.


Real-Life Practice 1:

To give a personal experience, I work as a high school teacher, and this semester, I got many difficult students who failed many classes in the past and have weak ability. I could complain and fret over being given "bad" students, but I cannot change that situation, so it is pointless and counter-productive to complain. Moreover, complaining makes me a bad teacher, which means I have been dragged down by them.

Instead, I focused on how I need to change myself to adapt to these students. For example, I need to talk to them more than regular students to help them feel like the teacher actually cares about them. I also need to improve my patience and kindness, as well as my teaching abilities to help students with lower ability understand the class content.

I made a list of things I could try this semester to be a better teacher, and I reported this to my principal. She was really happy about it and asked me to share my experience to help other teachers. What initially seemed like a "bad" thing became "good" because I focused on what is in my control.


2: Focus on The Greater Good

Another key idea of Stoicism is to think bigger and farther than just our small selves. On April 4 of The Daily Stoic, Marcus Aurelius said,

"Fight to remain the person that philosophy wished to make you. Revere the Gods, and look after each other. Life is shortthe fruit of this life is a good character and acts for the common good."

In other words, philosophy teaches us to respect those above us and love all around us. Marcus Aurelius was the Emperor of Rome, so only the Gods were above him. But for us common folk, we should respect our parents, teachers, bosses, and leaders. We should also take care of all the people around us, such as our siblings, friends, and colleagues. Life is short, and the most meaningful way to live it is to be a good person and to help the greater good.

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To give an analogy, imagine you are on a boat. The boat has a captain and crew. The captain is the leader, so we should all respect the leader. Otherwise, no decisions can be made, nothing can get done, and the boat will get nowhere. If the boat doesn't go anywhere for a long time, everyone starves and dies. Of course, if the leader has faults, we should advise the leader, but do so in a respectful way, with the purpose of helping the whole crew.


We also need to take care of all the people around us. If a crew member has a problem and we don't help them, the whole boat might be in danger. But if we help anyone on the boat do their job better, then we help everyone on the boat be safe, including ourselves.

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Life is the same. We shouldn't only focus on ourselves and think, "Their problem is their problem. As long as I'm fine, I don't care." If a boat member is struggling with their job, you might be unimpacted for a day or two, but after a while, the whole boat will have a problem, and then everyone sinks. Therefore, we should nurture our heart to be bigger and kinder, to want the best for not just ourselves but also all the people around us.


Real Life Practice 2:

With the group of "difficult" students that I have, I could be selfish and think, "The responsibility to pass my course is fully on them. If they don't try, then they fail. I don't care. I get my pay cheque regardless."

But we are all interconnected. If we make the people around us suffer, we will suffer too. If I have this kind of uncaring attitude towards them, I will not be happy at work. That means every day, I have to wake up dreading going to work. Making my students suffer is making me suffer. But if I desire to help my students, and I try lots of different ways to do so, then I feel like my days are very meaningful, and I look forward to class with the same group of "difficult" students.

When I got good results with these students, they naturally told their counselors and spread a good name for me behind my back. I've experienced that helping others definitely benefits ourselves, so long as we are sincere and patient in our kindness.


3: See It As Necessary Training

Stoicism is very pragmatic and down-to-earth. It recognizes that we will all face difficulties in life, and the time to train for difficulties is in the good times. On March 20 of The Daily Stoic, Seneca said,

"I may wish to be free from torture, but if the time comes for me to endure it, I'll wish to bear it courageously with bravery and honor. Wouldn't I prefer not to fall into war? But if war does befall me, I'll wish to carry nobly the wounds, starvation, and other necessities of war. Neither am I so crazy as to desire illness, but if I must suffer illness, I'll wish to do nothing rash or dishonorable. The point is not to wish for these adversities, but for the virtue that makes adversities bearable."

We can be pretty certain that we will encounter more difficult people in the future, and the stakes may be higher in the future. Therefore, we can view the difficult person in front of us as a gift. They are giving us necessary training for our future success.


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Real Life Practice 3:

For my friend, we talked about how she is still fairly young, so it is great that she faced this challenge early in her life. In the future, it is totally likely that she might become a leader and have to work with difficult team members. Or perhaps she will have a big-ticket client worth billions of dollars, and that client sends a representative who is difficult to work with. If at that time, she lacks the virtues to work well with a difficult person, that could cost her company billions of dollars, which would ruin her career. From a personal perspective, maybe our future spouse might have difficult family members that we need to get along with.

So learning to work well with this difficult manager and group of colleagues is actually very necessary training for her life. The question then, is not how to change them, but how to train ourselves to be able to work well with them. When she saw these difficulties as necessary training, she became more hopeful and happy.


4: Reduce Expectations

I used to think that I would be happy if only I could just get what I wanted. Later, I learned from Stoicism and Buddhism this belief was the root of my suffering. On July 3 of The Daily Stoic, Epictetus said,

"The task of a philosopher: we should bring our will into harmony with whatever happens, so that nothing happens against our will and nothing that we wish for fails to happen."

In other words, Happiness = Expectations - Reality. To increase happiness, we can either change reality or change our expectations. Guess which one is easier and 100% within our control?

To be clear, Stoicism and Buddhism are not saying you cannot have any desires. They are saying you should not be attached to anything, to not cling to anything. If I get it, great. If not, that's okay too.

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Real Life Practice 4:

At the beginning of the semester, I had a pep talk with myself. I want to chat with students daily to understand how their studies and life are going, but I must not become demanding towards them. If they don't fix their bad habits right away, I must not get impatient with them. This is easy to say, but much harder to do in practice.

I told myself, "I want the best for my students, but if they don't respond positively, that's okay, I will keep trying my best. I hope for them to respond positively, but I do not demand them to do so. If I have a demand, then I will become upset when that demand is not met. Then I have failed to be a good Stoic."

When I adjusted my attitude, my communication and interactions with my students became a lot more harmonious despite their "difficult" behavior.


5: View It As Normal

Viewing something as normal helps us to reduce our expectations and demands. On April 6 of The Daily Stoic, Marcus Aurelius said,

"When you first rise in the morning, tell yourself: I will encounter busybodies, ingrates, egomaniacs, liars, the jealous, and cranks. They are all stricken with these afflictions because they don't know the difference between good and evil. Because I have understood the beauty of good and the ugliness of evil, I know that these wrong-doers are still akin to me…and that none of them can do me harm, or implicate me in ugliness--nor can I be angry at my relatives or hate them. For we are made for cooperation."

In other words, this world is not perfect. Not everyone grew up with good moral education or virtuous role models. To encounter difficult people in life is absolutely normal. There is nothing to get upset about.

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Moreover, we need to focus on our own behavior (which is in our control) as opposed to their behavior (which is outside our control). Even if they are rude and disrespectful, we do not have to react in the same way. We can respond with respect and consideration. That is the mark of a truly great person.

Real Life Practice 5:

I work as a teacher, and a retired teacher once told me, "A teacher complaining about bad students is like a doctor complaining that he has to see sick people all day. There is nothing to complain about, this is your job!"

I also remind myself that being able to teach good students is nothing special. Being able to teach the difficult students is what truly makes a great teacher.


6: Cultivate Gratitude

Gratitude is another excellent method to reduce our demands towards outside people and events. When we feel fortunate to have all that we have, we then need to take action to repay gratitude.

On August 29 of The Daily Stoic, Seneca said,

"No person has the power to have everything they want, but it is in their power to not want what they don't have, and to cheerfully put to good use what they do have."

In the example of working with a difficult person, we are suffering because we don't want to have a difficult person in our life. But what if we let go of that attachment? If I don't have a difficult person in my life, great. If I do, that's fine too, I can use it as an opportunity to build my virtues and train myself for future challenges. We can also think about all the good fortune we do have and have to put them to good use in the situation at hand.

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Real Life Practice 6:

With my group of "difficult" students, I've had to remind some of them many times to submit their homework, or be on time for class, or use class learnings on assignments. If I get upset, then that is because I demand them to listen and change right away. The source of my anger is within me.

If instead, I let go of that demand, then when they still act according to their bad habits, I would not get upset. I would think, "If you change, great, that is good for your future. If you don't change, that's fine too, I will use your behavior to keep training my patience, kindness, and wisdom."

I can also think about how fortunate I am to have a job that I enjoy, that supports my family and future goals, that gives me great work-life-balance. If it weren't for these students in front of me, I wouldn't have this job. And if it weren't for Stoicism, I wouldn't have the wisdom to handle difficult people. To repay the gratitude of this job and Stoicism, I need to improve my virtues and abilities to help these students have the best learning experience possible. By thinking this way, I naturally become more positive and productive.


7: Find the Good

As mentioned before, whether something is good or bad depends on how we view it and how we use it. I like the way Napoleon puts it:

"Every problem comes with an equal or greater opportunity."

The key is, can we find the good? If we are weak at this skill, then we need to train ourselves to find the good in every situation, and that training takes place in our daily life and our daily problems. A great way to do this training is to cultivate gratitude. Notice all the good fortune you do have, feel grateful for it, and then try to repay gratitude.

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Real Life Practice 7:

My friend told me how her colleagues often have conflicting ideas. I said, "Well, at least you don't have to worry about groupthink." That is an example of finding the good in a situation. This is not empty positivity. This is a true upside of the situation; we just have to notice it to appreciate it.

In my situation, although I have some "difficult" students this semester, when I spent some time getting to know them better, I realized that they all have good points. I just had to find them amongst their more noticeable flaws, and then focus on those good points.

For example, one student is very sloppy with his work. Sure, this is bad in the sense that he will get a low grade. But this is also good in the sense that I know the reason for his low grade, and I know what to guide him with. Moreover, he is aware of his problem, so he does not blame his low grade on me

This situation is also good because he knows I am trying to help with it every time I remind him to do his quizzes slower and to double-check his work. Even more, whenever I remind him in front of the class, the whole class gets a useful reminder. And when he did double-check his work and did well on a quiz, I praised him in front of the class, and the whole class was happy for him. Indeed, every problem has an equal opportunity.


8: Practice Empathy and Kindness

When we have a conflict with someone, we usually think thoughts like, "I can't understand this person…She is so unreasonable…He is so inconsiderate."

When we think that their behavior is unreasonable, we become demanding towards them (we demand them to be reasonable). Then we get angry and upset that they are behaving the way we demand them to behave. How can we solve this problem from within our own minds? Stoicism teaches us to cultivate empathy.

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On August 31 of The Daily Stoic, Marcus Aurelius says,

"Whenever you take offense at someone's wrongdoing, immediately turn to your own similar failings…By thinking on this, you'll quickly forget your anger, considering also what compels them--for what else could they do?"

Being empathetic means being able to see things from the other person's point of view. When we see others act unreasonable, we can ask ourselves, "Have we ever acted unreasonably? What was I thinking back then? How did I feel back then? That is how this person is feeling now. We felt the same way in the past, so we shouldn't be judging them now.

We can also ask ourselves, "How would I like to be treated when I am behaving unreasonably?" Obviously, we hope to be treated with kindness, patience, and understanding. So we should treat that person the same way. Hence, Ryan Holiday says,

"How much more tolerant and understanding would you be today if you could see the actions of other people as attempts to do the right thing?"

No one tries to be stupid, difficult or unreasonable. Everyone (including ourselves) thinks they are being reasonable and proper. When we can see what notions of right and wrong compels them and the influences on them, then we will see their behavior as a natural reaction to their circumstances. When we see their behavior as natural and reasonable, we will stop feeling angry and stop demanding them to be different.


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Real Life Practice 8:

This semester, I am teaching online, and one of my students often comes late to class and leaves early without permission. When I call on her in class, she often is not even there. I tried to set up a one-on-one chat with her many times to try to understand her situation better, but she often leaves before I finish class.

In the past, I would get upset and ignore this student. But this semester, I am trying to be more empathetic. Rather than get upset at her, I saw it as training my patience and reminding me to not be demanding. I also decided to wait until I understood her situation before making any judgments about her behavior.

Eventually, I got to chat with her one-on-one. I learned that she has difficulty sleeping, so she takes sleeping pills. But the side effect is that she gets major headaches randomly throughout the day, then all she can do is lie down on her bed. Moreover, her downstairs neighbor randomly comes over and complains that she walks too loudly, so she has been spending a lot of time arguing with her neighbor.

When I understood her situation, my annoyance faded, and I felt compassion for her. If I were in her situation, I would behave in a similar way. Perhaps I would be more respectful to my teacher and communicate with my teacher more, but that's because I understand the importance of respect and communication. She does not, so of course she wouldn't communicate with me.

I then told her that I'm very sorry to hear about all the struggles she is going through, and I don't want to be an additional source of pain in her life. If she cannot do this course now, she can do it in the future at a better time. If she wants to try to pass this course, I will do my best to help her.

When she felt that I cared for her and was not judgmental or demanding towards her, she started trying harder in class. I continued to chat with her frequently and give her encouragement. Thus, empathy and kindness prevented me from being annoyed at this student for a whole semester.


9: Do The Opposite in Positive

Most of our behavior is habitual. When people behave "unreasonably" it is probably also a habit. On June 26 of The Daily Stoic, Epictetus said,

"What assistance can we find in the fighting against habit? Try the opposite!."

This can apply to correcting our bad habits as well as responding to other people's bad habits.

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Here are some examples for correcting our negative habits:

  • If you find yourself complaining, you could force yourself to list some positives about the situation.

  • If you find yourself feeling demotivated, try giving a motivational pep talk to yourself (or even another person who is also feeling the same way).

  • If you start feeling anxious, list out all the reasons why you'll be OK and how you can take preventative measures.

After practicing this for a long time, our habits will naturally change.

Here are some examples for responding to other people's negative habits:

  • If the other person starts complaining, and then they ask you for your opinion, you can respond by listing all the good points about that situation or person (but don't proactively argue with them).

  • If the other person is arrogant and asserts that they are right, you can be humble and say that you do not know everything, but you will double check with an expert.

  • If the other person is very impolite towards you, you can be extra polite towards them.

When we respond to other people's bad behavior with the opposite good behavior, not only do we improve our virtues, but our goodness is even more visible to all those around us.


Real Life Practice 9:

I used to complain a lot in life, and I decided to fix this bad habit by practicing gratitude. Specifically, I write down at least one thing I am grateful for every day in my journal. Over time, I started getting better and better at being grateful. This semester, I often feel grateful for my "difficult" students because it is thanks to them that my teaching abilities are improving.

When a student was complaining to me about how his other teacher gives excessive homework, I put in a good word for the teacher. I told him that all teachers want the best for their students, and I know this teacher really cares about her students. You should communicate with her more and ask her how you can manage your homework better.

Sometimes when I chat with my students, their minds are very agitated, so they talk very fast and explain themselves a lot. At these times, I remind myself to not get carried along by their agitation. Instead, I respond by talking extra slow and maintaining my calm. It is not easy, and I don't always succeed, but when I do succeed, I always feel a great sense of accomplishment.


10: Believe In Yourself and Practice

We covered many great tips in this article, but they are of no use unless you go and practice them. On August 12 of The Daily Stoic, Seneca said,

"Many words have been spoken by Plato, Zeno, Chrysippus, Posidonius, and by a whole host of equally excellent Stoics. I'll tell you how people can prove their words to be their ownby putting into practice what they've been preaching."

When we practice, we may find that these teachings are simple but not always easy. For example, it is easy to say, "If other people behave unreasonably, I won't get upset. I will remain humble and kind." But when the situation actually arises, can you remember to do it, let alone succeed?

Just like riding a bike, the learning process always has failure. We will fall many times until we finally get the hang of it. When we fall, it is important to believe in ourselves and get back up.


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On June 4 of The Daily Stoic, Ryan Holiday said,

"Don't forget, though, that you come from a long, unbroken line of ancestors who survived unimaginable adversity, difficulty, and struggle. It's their genes and their blood that run through your body right now… as their viable offspring, you're capable of what they are capable of. You're meant for this."

If the great humans of the past could work well with difficult people and accomplish greatness, then so can we. Their genes are no different than ours. Their situations were even worse than ours. For example, Epictetus was a slave, and Seneca was exiled. If they can maintain peace of mind in such hard situations, then so can we.


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Real Life Practice 10:

I keep a daily journal where I reflect on my virtues and faults each day. I had a period of time where I felt demoralized by all my faults and problems. Later, I viewed it as normal that I would have lots of faults, and I must not demand myself to fix all of them all at once. That is being too impatient and demanding towards myself. Instead, I should focus on correcting my faults one by one, slowly but steadily.

As I try to interact properly with my group of "difficult" students this semester, I don't always get it right. I have off days too. But I remind myself I definitely have the ability to become great. The key is to never give up and to always try my best.


Conclusion

Working with difficult people is something we will all experience in life. If we are unable to work well with difficult people, we are guaranteed frustration and conflict. But if we can work well with such people, then we will gain inner peace, growth, and success.


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Rather than focusing our attention on other people or outside circumstances, Stoicism teaches us to focus on changing and adapting ourselves. This article looked at ten Stoic ways to excel around difficult people:

  1. Focus on what you can control

  2. Focus on the greater good

  3. See it as necessary training

  4. Reduce expectations

  5. View it as normal

  6. Cultivate gratitude

  7. Find the good

  8. Practice empathy and kindness

  9. Do the opposite in positive

  10. Believe in yourself and practice

While I do not wish for you to encounter difficult people unnecessarily, I do wish for you the ability to flourish around such people should such a situation arise.


 

Weekly Wisdom Newsletter #202


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