Design Your Dream Life with Natalie Bacon | Dealing With A Challenging Person

Do you struggle with knowing how to deal with a challenging person in your life? The holidays are a time when we’re around more people who, of course, we love, but who challenge us in ways that we might not experience throughout the regular part of the year.

Spending time learning how to manage your mind around people who challenge you is worthwhile. Accepting your default thinking will only increase the separation you feel and make it more challenging to be around them.

In this episode, I’m showing you how to deal with a challenging person in your life and decide on purpose how you want to show up. You don’t need people to change and see things from your point of view to do this work, but learning to manage your thoughts around this will make your whole experience easier.

If you’re a mom, you’re in the right place. This is a space for you to do the inner work and become more mindful. I can help you unbusy your time, reduce anxiety and overwhelm, and live every day a little more soulfully and purpose driven. And, if you want to take this work deeper, doors are open for my Grow You virtual life coaching program. Click here to learn more and join us. 


What You’ll Learn from this Episode:
  • Why the challenging person doesn’t need to change for your experience to be easier.
  • How our brains are trying to make sense of what happens around us.
  • The problem with feeling that other people are wrong and you are right.
  • How to change your thoughts around challenging people.
  • Why there is no right or wrong way to show up.
Listen to the Full Episode:


Show Resources:
Full Episode Transcript:

Welcome to the Design Your Dream Life Podcast where it’s all about designing your life on your terms and now your host, Natalie Bacon.

Hey there. Welcome to the podcast. I hope you are doing well and your season right now, if you are in the midst of the holidays. Getting started with thanksgiving and Christmas and whatever other holidays that you celebrate. I hope it’s going well for you.

That is what prompted me to come up with today’s episode. I want to talk to you about dealing with a challenging person. Because I think the holidays are a time when we’re around more people who we love, of course, but who also challenge us in ways that throughout the regular part of the year we might not experience.

So I’m also going to be holding a class called holidays on purpose. I would love for you to come. It’s this upcoming Monday, November 22nd. It’s a free class. It’s just a small way for you to get a little bit more ahead and feel in control of how you show up and how you experience the holidays.

I’m going to talk about navigating that challenging relationship today, but I want to hear from you and help you specifically in this live class. You’ll be able to ask me questions and get coached on anything with relationships or holidays as you show up to the class.

I’ll also give you some other tools on how to have a more purposeful holiday season like balancing consumerism and the meaning of the season for yourself, your family, the kids, and reducing that feeling of busy with all of the activities and events and the sort of social calendar that can become even more packed during this time of year.

Overall really I just want you to be able to feel your best and have a more purposeful holiday experience this year. So you can learn more, grab your seat over at

Then also on that day, November 22nd, the doors are opening to Grow You. As soon as you join, you will get access to the relationships on purpose class that I taught this month. That is going to help you go deeper with what I’m talking about today. So if you are already in Grow You, make sure you access that curriculum. It’s the work that we’re doing. If you’re not yet in Grow You and you want help navigating your challenging relationships, this is definitely going to be the best time for you to join. You can learn more about Grow You when the doors open at

So that brings me to what I want to teach you today, which is how to deal with a challenging person. So as we go through this content and this episode, I would love it if you had someone in mind. Because I think from a high level when we’re not thinking about someone else, all of this makes sense. Then when we apply it in our lives to a specific person, it’s much harder to apply because, of course, of our brains. This is for the healthiest, most amazing people in the world. They still have this challenge.

So as we go through all of this, I would love it if you had someone in mind who is more challenging for you. In Grow You, most commonly I’m coaching on mother-in-law relationships, sister-in-law relationships, relationships with the biological mother, relationships in the immediate family. So it might be someone else for you.

In this episode I’m going to give you an example of a challenging sister-in-law relationship. If it’s someone else, just swap out sister-in-law for whoever is most challenging for you. It’s important that you just think about it in terms of that one person. Because usually it is just that one person that if they showed up differently, everything would be better, right.

So in this example, let’s assume that you have a sister-in-law who speaks badly about people behind their backs. She often shows up, in fact she always shows up really negatively. She can be loud and kind of overpower and dominate conversations.

You find it really challenging to love her, to show up and be kind to her, to feel really connected to her and be present with her. You often leave family gatherings or whenever you hang out with her you leave that time feeling more drained. It’s not energy giving. It’s energy draining. You feel like you’re not seen by her. It’s just a challenging relationship. That’s the example we’re going to go through in this podcast. That’s the example I want you to have in mind here.

Now what we do, I say we because I’m guilty of this too. All humans do this. We make ourselves right and we make the other person wrong. This is because our brain is trying to always make sense of all of the chaos happening in the world. So there’s just a bunch of facts happening outside of us, and our brain needs to make stories up, so we better understand how to navigate the world.

This is great because it helps us show up in the world in ways where we can sort of expect how our relationships are going to go to a certain extent. It’s really useful. We don’t want to be having to reinterpret every single person and create every single new story from our prefrontal brain every single time we have an interaction. It would just be exhausting. So instead our brain comes up with stories. We store the stories in our memories. We look for evidence to validate that story.

So with the sister-in-law example, it would sound something like okay, I am showing up as my best. I’m trying to be loving and kind. I’m trying to allow other people space to talk. I’m showing interest in them. I’m not talking behind their backs. This is sort of how people should be and how they should show up in a respectful way.

Because sister-in-law doesn’t follow those rules, she’s the one who needs to change. She is sort of the bad person here. I’m the one who’s showing up in the right way, and she’s showing up in the wrong way.

Then we end up talking about sister-in-law to other people. Like maybe our spouse or our mom or our friends. We’re looking for more evidence that she’s the one who is difficult, and we want to make that a fact. Basically we’re right. She’s wrong. She really just needs to change. This is so normal. It’s happening not because there’s something wrong with you. It’s happening because you have a human brain.

It happens for myself as well. I think that I’m always trying to show up as my best, and there are certain ways that it’s better and more effective to show up as. If everyone else just showed up in that way, things would be better. So if I’m thinking of a challenging person in my life, my default thinking is going to go to, “Gosh if they just showed up differently, this would be better for me, for everyone, for them. They’re definitely showing up in the way that’s wrong.” That’s the default thinking.

The problem with this way of thinking, with making the other person wrong and us right, is that it’s a little bit of black and white thinking. People and relationships are much more complicated than this. Again, our brains want to simplify people and relationships and create a really simple story to make it easier for us to navigate the world.

This is fine when it is the person who is checking you out at the store and they’re a little bit rude to you. You just want to think they’re rude. You never want to do thought work on it again.

What we want to use our mental energy on is with those relationships that are important to us. So your sister-in-law is someone who is going to be a part of your life for a very long time. So spending time learning how to manage your mind around sister-in-law is worthwhile. Accepting the default thinking is only going to increase separation from her and make it more challenging for you to be around her.

So on default, we think that the solution is to tell people what to do and tell them how to act, what not to do, how to think, how to talk, how to parent, how to show up. This is coming from a loving place. It’s well intended, but it’s actually counterproductive. It doesn’t solve the problem.

We tend to think that if sister-in-law could see herself from our point of view that she clearly wouldn’t act how she’s acting. She would see how she’s being inconsiderate, selfish, kind of gossiping, negative. It’s really unattractive to people around her. It’s draining. We think if she understood how we’re seeing her then she’d change. That would be better. She obviously should change.

Unfortunately this never works. It is not the solution. We have to pause and start to notice what’s happening because our brain is trying to be helpful, but it’s actually causing more harm for ourselves than good. Noticing that this is your lower brain and how it’s not the only way to interpret other people, it’s not the only way to navigate challenging relationships. It’s not the only way to kind of think about the world is really going to help you have a completely different experience.

So what is the actual solution? If the solution is not to try to change people and get them to see how they’re being so challenging, what can we do? Well, the first thing you want to do is notice what your story is of sister-in-law ahead of time.

For example, if you have the thought, I just want sister-in-law to be loving, nice, and positive. Doesn’t that thought sound so lovely? Yet it is such an awful and even toxic thought. It aims at trying to manipulate and control sister-in-law.

So instead what we don’t have to go to is the extreme opposite like I want sister-in-law to be mean and gossip and rude and overpowering. If you think about two extremes, there’s so many thoughts that are in the middle that could serve us better. Instead what if you came up with the thought, I want sister-in-law to behave exactly how sister-in-law wants to behave. I want her to show up how she wants to show up. I want her to feel how she wants to feel. I want her to say what she wants to say. I’m just going to love her.

So then you get to decide on purpose how you want to show up. So if you think of the movie of sister-in-law, sister-in-law is playing a role. She’s pretty consistent, right. It’s very rarely I coach someone and it’s not predictable how the challenging person is going to show up. The challenging person shows up how they always show up, which we interpret as challenging.

So play out this movie in your mind where the person continues to be exactly who they are. They behave how they want to behave. They talk how they always have talked. They don’t do what they always haven’t done.

Then in that movie change your role. So far you have decided to show up in one way, and it’s created separation from sister-in-law. It has created challenges for you. What if you played around with your role? what if you decided that you were just going to show up with so much love and interest and compassion and you were going to see sister-in-law exactly as she is without trying to change her. 

This means that you drop your agenda for how the other person should behave. It takes reminding yourself that you don’t need people to change and see it your way. This is such challenging work because, again, it’s just all of our lower brains wanting to have a nicer, more pleasant experience. Which sounds so lovely, but it doesn’t work because everyone is different. We’ve all had different experiences. We have different neural pathways. We all want to show up differently.

So there is no one right way or wrong way to show up. Even if we decide to follow social norms and most of the people show up one way most of the time, it doesn’t mean that how sister-in-law is showing up is the wrong way. Even if how she’s showing up is against social norms and most people aren’t showing up how she shows up.

So it’s really falling into this space in the middle where we don’t want sister-in-law to be rude and angry and overpowering. But also, we’re not wanting her to be different than she is. We are just going to stay out of her thoughts and what we think she should or shouldn’t do. We are going to stay in our thoughts and our feelings and decide how we want to show up knowing that sister-in-law is going to continue to be sister-in-law.

That includes maybe some drama from sister-in-law or that includes gossiping or talking badly about other people. We’re just going to assume she’s just going to continue to be her. Now what? Who do we want to be?

This is the most powerful work that you can do as our relationships are central to our lives and to our mental and emotional health. I want to help you with your challenging relationships. So come on over to Grow You. Get the Relationships on Purpose class when the doors open next week. I will coach you inside. Take care.

If you loved this podcast, you’re going to love Grow You. Grow You is my virtual life coaching program where I take everything on the podcast to the next level. I invite you to join our amazing community of women and moms and deepen your own personal development. Head on over to to learn more.  

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