Making Peace with Letting Someone Down

June 16, 2024

It’s so easy to think making peace is avoiding conflict or not standing up for yourself because things appear peaceful. But a lot of times, getting to a place of peace requires conflict or boundaries, and it’s really hard to do. How do we make peace with letting someone down?

Today we’re going to cover three main points. Number one, we’re going to talk about the difficulty of letting someone down. Then we’re going to talk about what it looks like when you care too much. And third, we’re going to talk about how to do the work. In other words, how to make peace with letting someone down. 

Why is it so hard to let someone down?

I think first and foremost, it’s because you’re really letting two people down: You’re letting that person down and you’re letting yourself down. I don’t think any of us want to not meet other people’s expectations. And we have this whole dynamic of how we interact with others, how we’re received by them. We may have fear of being abandoned by them if we let them go or of hurting them. I don’t think any of us want to hurt those people who are close to us or be hurt ourselves. So if I let you down, you may then retaliate or do something to me that hurts me in response. I think also just generally the desire to please people—I think there’s kind of a survival instinct to fit in and make other people happy and “keep the peace” which may not actually be keeping peace. It may just be not rocking a boat at the moment.

I think that fear of abandonment thing is really, really huge because I’m just thinking about all the ways that I’ve been abandoned in my life, and it has caused me to say yes to a lot of things that I have no business saying yes to just because I don’t want to let someone down or I’m afraid they won’t keep asking. And I deal with a lot of FOMO. That FOMO piece is huge. Like, I don’t want to miss out on what they’re offering, but knowing I don’t have capacity makes it really difficult too, to take care of myself. We always want to put other people first. I know that’s been my thing. Also, letting someone down is totally within our control. We have the choice to not let someone down. And in a world where everything is so crazy and outside of our control, being able to say, “Okay, I can control this. I can manage someone’s feelings and my codependency, my actions, my yeses, my nos,” for better or worse and sometimes it’s for worse.

I think as a single parent, we already feel like we’ve let so many people down. I know for me, I did. So before we even get into thinking about having to draw a boundary or letting someone down, one of the reasons it’s difficult is because I’ve already felt like I’ve let my kids down. I wasn’t able to keep a marriage together. I feel like I’ve let so many people down already moving into the solo season. I didn’t want to keep doing that. And so then when I’m thinking about the baseline being set as “I’ve let a lot of people down” any one of these issues—abandonment, disappointing people, etc., really become a much more significant kind of presence for me because I already feel like I’ve started at the bottom.

I’ve learned that people being let down causes a lot of drama, and I have no bandwidth or desire for drama which means I try to manage people’s expectations, manage their emotions, and it really is a false sense of control.

But there may be this illusion that, well, if I just keep ____ happy, then I can make him think X, Y, or Z, but I can’t; it’s impossible. And then adding in keeping my kids happy because I don’t want to let them down or tell them they can’t have things or we can’t afford something. And the truth is we may not be able to afford it, but I don’t want to let them down so I continue to just placate or make people happy. 

Let’s talk about what it looks like when we care too much or how do we know when we care too much about letting someone down?

Disappointing others or disappointing someone in particular is not always a bad thing. It can actually be a sign that you care. It could be that you want to finish what you started. You want to stick with your commitments. If you’ve already said yes to someone else, saying no to something else is an opportunity cost. When you say yes to something, you have to say no to something else. And so you have to stick to your commitments. But constantly thinking about and living your life so that you don’t upset and hurt and worry other people is just not truly living. Unfortunately, part of life means that we’re going to be let down. We’re going to let other people down. And so I am learning it over time. I don’t think I’ve been very good at it because of my codependency. But that’s kind of a way that you know you care too much—when you are living in that codependent state and people-pleasing tendencies are running strong. You agree to do things you don’t want to do because you don’t want to rock the boat. You’re paying attention to what everyone else needs to your own detriment. 

I think we get so consumed with managing other people’s feelings that we don’t want them to experience another bit of disappointment. And so the codependency really happened with my daughters during my solo parent season. I didn’t have a whole lot of other relationships that were expecting anything from me. It was just full tilt raising my girls. And I really did struggle with this. And I have to say I wasn’t successful. I gave in too much. I was trying to manage their experience, their feelings.

How has that affected them now? What was the (negative) outcome of you managing their feelings? 

One of the first podcasts that I did was with Sissy Goff, and she introduced me to this phrase of emotional entitlement. Emotional entitlement is where I feel responsible for making someone else happy. And they become emotionally entitled when they think others are responsible for making them happy. They’re not able to sit in loneliness enough. Something must be terribly wrong because no one’s here to manage my feelings. And so relationally, I put a little bit of a deficit in their minds into thinking that as they’re choosing a mate or are in a relationship, the other person is responsible for making them happy. That’s emotional entitlement. And we’ve had to talk about that and work backwards in that a little bit. 

I’ve had several situations come up in the last week, where my son Jax and his older brother have had to manage their dad’s feelings. And so thinking about it from the kid’s perspective, where they’re put in a position of managing the parents’ feelings and how unfair that is, and how sad that is for the kids that feel like that’s their responsibility.

I get the sense that [my kids] were aware of a lot of the trauma and the drama surrounding our divorce, and especially the custody battle that went on for so many years. And they saw me depleted. And I can tell now that they don’t want to worry me and they don’t want to overwhelm me and are trying to manage my feelings instead of feeling like we’re in this together. I’ve had to be conscious about making time, especially with my youngest, to slowly let them know it’s okay to lay stuff on me. I might worry, but that’s okay. It’s a natural thing. I want to be in it with them. For a long time, I allowed them to try to manage my feelings because they knew it was a really difficult season. And I feel terrible guilt about that because it wasn’t their job to raise me.

You have to be super tuned into what’s happening with your kids emotionally to catch it so they don’t feel like they have to manage your feelings. But it’s easy for us to pass this along to our kids and them to feel like they have to; they can’t let us down. And I think I’m pretty good at noticing when Jax is withholding or trying to manage my feelings or whatever, and I tell him quite often, “It’s okay for me to be upset right now. It’s okay for me to be sad. It’s okay for me to be whatever.” It’s usually not direct. I’m thinking of times that’s happened and it’s not directed at him, but he notices that I’m stressed out and then he’s like trying to talk me down off a ledge, and it’s like, “Son, that’s not your job. It’s okay for me to be upset. I’m going to be okay, but don’t worry about it. It’s okay. If this is making you feel a certain way, then let’s talk about that, but you don’t have to worry about me not feeling upset.”

Marissa, you’re remarried now, as am I. I know you had betrayal before Bill’s passing, so when you began dating again, did you struggle with not feeling like enough? I found myself questioning myself and not wanting to rock the boat, not wanting to let down the woman I was dating (and eventually married). Did that ever play a role in getting into another relationship?

Absolutely. That second relationship becomes really, really difficult when you’ve got some negative experience, when you have almost a mode of operating where if I do X, the other person on the other side does Y and I get to expect that. What’s been really interesting in my now marriage, is that Matt does not show up like Bill did. And so there were a lot of times where he broke that equation and I’m like, “Wait, you were supposed to get mad too, so I could feel justified, and now I just feel like a big heel” and that caused a lot of self-reflection. And to go back and say, “Well, where was I in my previous marriage?” I didn’t speak up for myself when I should have because I just let things go and didn’t want to rock that boat. You get into really unhealthy relationships, and I think there’s a challenge—where we end up moving through to understand what it is to let people go. I mean, it’s been actually night and day difference with Matt because if I let him down, guess what? He does not change. His affect doesn’t change. He’s just status quo. But letting Bill down would’ve been the end of the world, and it drove everything for me, and it drove the way that I understood my world. And so then when I was dating people other than Matt, I was just constantly afraid that I was never going to be good enough. There was no part of me that thought anything but full-on imposter syndrome in every nook and cranny of my life, whether it was work, parenting, you name it. I expected to walk into a room and be letting people down because I’m here. If I don’t walk into that room, I’m letting them down. I’m not there. I couldn’t win.

I guess that’s why I’m asking because I do think that single parents are carrying this bag of disappointing others, disappointing themselves, disappointing their kids, disappointing God, all of it. I think it permeates almost every area of our interaction with people, and it does bring up the codependent part of us, and I think that’s just natural, and that’s why this is an important thing to talk about. It almost becomes a title. “I am a disappointment because I have disappointed somebody.” I still struggle. Yesterday, I had a conversation with an employee. It went something like this: “So I’m going to give you a raise, and I’m very sorry. I know it’s not enough.” I’m like, “I just gave this guy more money and disqualified it.” I’m like, “That was the worst conversation ever” afterwards.That was really dumb because we don’t know what he was expecting, and I could have totally sold it like a bottle of Coke and been like, “Hey, this is amazing. You love it. Go take it home and chew on how amazing that is. By the way, you get a bonus too. But I didn’t, and I thought, “Why did I just sell a raise as if it was some bad thing, like an apology? ‘By the way, you’re going to have to work Christmas and Easter too.’” It’s this whole story. It’s that baggage—I feel like I walk around with that tag that says, “Hello, my name is Disappointment,” right?

We carry it around and we care too much about it. We don’t just let things lie for what they are, I know it affects me negatively with anxiety, tension. I carry it in my body for sure, and it’s really hard to let go. 

Robert, how do you feel when you let someone down and how do you make peace with it?

Well, it’s hard, and I don’t think there’s one blanket answer, but it’s just part of life. I’ve started to try to reframe letting someone down as helping them in some way. If I am able to deliver a message of disappointment to my daughters wrapped in “But I’m with you in it,” I’m giving them an opportunity for growth. And so I’ve had to go, “Okay, I am not capable of never letting anyone down.” If I were to come to you, Elizabeth, and say, “Listen, I hate to let you down. I can’t give you a raise that you really wanted, and I really want to give you a raise. But let me give you some ideas about how I think we can supplement,” it turns it into “let me work with you to get to a result” instead of “I can’t tell you what you want to hear right now.” 

I’ve had to reframe things in my life, and I think a lot of that has to do with being a single parent and realizing this season can transform us. I have seen my life change because of not getting what I wanted, and I have also seen my life change because I was so convinced it was the right thing, and it’s very evident now that it wasn’t. And so my faith in God as being the ultimate provider of peace has gone up exponentially. If I can keep that in the back of my mind, it helps me deliver things that I know are not going to be what people want to hear. 

I know for me, I hate the word no. I hate receiving the word no, but more than receiving it, I hate giving it. And so I found myself in the past many years with this tendency to go on this three-hour diatribe of why no is an acceptable response to give because I feel like I have to explain. A couple Sundays ago, I was on a call with some family members and I said something and then really explained things. Well, a week later, my mom called and she’s like, “I was really kind of taken aback by that.” And I said, “What do you mean?” She said, “I think it was because of how long you were explaining things.” And I thought, “There it is. Again, my tendency to just try to keep you happy by explaining it away, but the explanation doesn’t actually help. It just makes you feel like I’m beating you over the head with a stick on that explanation.” So it was kind of eye-opening to me, and sometimes I think we just need to say no and let no be no. And no “I’m sorry.” If they have questions, maybe they’ll ask them, but don’t assume they have questions

I think when I give a no to someone and feel like I need to explain it, the explanation is really more for me than it is for them. It doesn’t necessarily help them. They’ve just heard no, and that’s probably all they’re going to hear. It doesn’t matter. So I’m trying to soften it, but I’m not doing anyone any good. I’m just getting myself into a little bit of a deeper hole, and I’m just realizing I’m trying to satisfy my ego and my pride rather than actually being helpful. Yeah, it’s such a good perspective too, because over here I think I’m being more humble by explaining it, and it might be my pride actually coming out. 

I love the thought that we can’t assume what other people are going to feel as a result of us saying no or letting them down, and it may be no big deal, but we build it up in our heads over and over coming from the fear that we were talking about earlier. We make a lot of assumptions, trying to control outcomes, trying to foresee what hurt and pain might be coming ahead. And we don’t know what the other person’s going to feel, and it’s not our job to feel what they feel. Just feel what you feel. Take ownership of that and allow them to feel what they feel and be okay with it.

My ex really, really, really wants me to have some sort of cordial relationship with his girlfriend. But I’ve told him, “I’m not there. I don’t want to have a relationship with this person. I’ll say, ‘Hello’ but that’s about all you’re getting from me right now.” Every time I try to have a conversation with her, she says something inappropriate. She says something hurtful. She says something that makes me a little crazy and why would I put myself in that situation? The old me would have felt bad, telling myself I’m a bad person, I’m not a good Christian because I’m not being overly kind to this person and going out of my way to make her feel comfortable. And then he and his feelings of being uncomfortable would have so much power over me. “I just don’t want to rock the boat. I want to keep the peace. I want him to feel good,” and I would just cater to him so that he wouldn’t have to feel bad about it. And I’m just like, “No, I’m good. Sorry.” I’ve told him over and over every time this comes up, “It is not my responsibility to make sure that you guys are comfortable. It’s not my responsibility to manage this relationship just because you want me to. I am sorry. It’s unhealthy for me and I’m not going to put myself there. It’s not good for anyone.” Which kind of goes back to trying to explain it, and it’s a tendency for all of us to try to get ahead of the disappointment and kind of frame in your mind, “Okay, I’m going to say no and then here’s my justification that I’m going to attach to it.” Well, I don’t tell him the justification. I made the decision that he doesn’t have to understand why. He’ll come back at me and I’ll say, “I’m sorry, but I don’t owe you anything. I don’t owe either one of you anything at all.” And I leave it at that and he’s upset about it, but you know what? We’re fine. It’s fine.

I try to live my life according to what I believe God wants me to do, and I know that over and over in the scriptures, it talks about putting others ahead—if someone slaps you, turn the other cheek, etc. But I think there’s another side of understanding the greater good, whether it be for that person you’re disappointing or for yourself, going, “I’m going to have to not turn the other cheek right now out of a sense of love. It’s not giving you what you want. It isn’t helping anybody, including you.” And definitely from my perspective, I’m lowering a boundary. And that’s a really hard thing to do when you are carrying the weight of being a single parent and you feel like you’re carrying all of it on your shoulders. And we are not capable of doing that. We’re not capable of carrying everything on our shoulders, and so loosening up that expectation on ourselves and being free to go, “I have to trust that it’s okay to let someone down.” It’s hard, but I think if you recognize that you’re going into this with this weighted bag of disappointment, maybe it’s a little easier to go, “Okay, now I guess I don’t have to explain this way to everybody.” If we’re talking about how to make peace with letting someone down, it’s having a boundary. Understanding that boundary, especially in the beginning, is going to be uncomfortable, and then being able to sit in that discomfort.

Once you exercise those muscles that have atrophied and get used to people being disappointed and you find out that the world doesn’t come to a screeching halt, do you think it gets easier over time?

Yeah, absolutely. It’s definitely gotten easier to disappoint my ex-husband. If you are not familiar with Dr. Becky Kennedy at “Good Inside,” go look her up. I listened to a podcast recently with her on it, and she was talking about entitlement, but with our kids in particular, she was talking about how to not let entitlement set in. She said, “It’s directly correlated to our kids’ ability to be frustrated and to be uncomfortable. And the more okay we are with letting them be frustrated and uncomfortable, the less entitled they’re going to be.” And I’ve actually been practicing that because if there’s somebody in my life that I do not want to feel uncomfortable or disappointed, it is Jax, my 10-year-old boy. I’ve been practicing it and it has gotten easier for me to understand and to reframe it that this is actually good for him. It’s good for him to feel the frustration of something. What’s going to happen when he gets out into the real world and there’s disappointment after disappointment and discomfort after discomfort, and he’s not prepared for it because I’ve coddled him his whole life? I’m not doing him any favors. So yes, all that to say, it gets easier with time. Practice it. I wouldn’t say practice makes perfect, but practice at least does something. It makes it a little easier over time to deal with. Understanding that you have to deal with your own discomfort in addition to their discomfort and be okay with that and separate yourself from that is key. You have to separate yourself from it. 


  1. We need to recognize that letting someone down is doubly hard because we disappoint someone else and ourselves. We don’t want to get into that feeling of discomfort. 
  2. Not wanting to disappoint others isn’t necessarily a bad thing, but there does come a point when we care too much about letting someone else down
  3. Tolerating disappointing other people is key to making peace with letting someone down. Being willing to go, “I can’t control everything. I am going to just let people down” takes practice, but it gets easier. 

Listener Question: When you became a single parent, what’s an act of kindness you remember someone doing and why was it so impactful?

I think I’ve told this story before, but a youth pastor called me and said, “Hey, listen, I want to pick a weekend—whatever Saturday works for you, and some of the girls in our group are going to take your daughters out and have a good time. Then the rest of our youth group is going to clean your house from top to bottom. And I literally got choked up when he offered it because who has time as a single mom or dad to deep clean your house? And most of us can’t afford housekeepers. So it wasn’t just the cleaning thing, but somebody was looking for a way to not only help, but also to love on my daughters. That’s kind of a big act of kindness, but I think it still crosses over into the small things. Finding a small thing that would help a single parent is so important because it lets you know that you helped them and it helps them know that they’re seen and honored. 

I have several examples. I’ll just quickly go through two of them and then maybe tell a story for the third one. One woman brought over some breakfast that we could eat off of all week. We had people bringing dinners, just food helped. I had another—he was my handyman. He is an older gentleman. If he was in town, he would just text me and say, “Hey, you’re not alone.” Just the sweetest guy. To this day, he is one of my best friends because he is just a good soul, a good heart. The third one, actually, the handyman was at my house. Within three months, my husband had passed away, I lost a friend right after him, and then an employee of mine passed away. And I was on my knees that morning saying, “God, there’s no hope. There’s no hope in life. I can’t do this. I’m just done.” I went to work pretty hopelessly and came back and there was a gift bag. My handyman said somebody had left it on the door. Inside that bag was a book that was 365 Days of Hope. That was the name of it. And on it was a card handwritten that said, “You don’t know us, but we know you’re having a hard time and we wanted to reach out to you.” So to me, that was that. There is hope. I will never know who these people were, but just that little act for them to see me made all the difference for me. 

For about eight years, almost monthly, I was in court dealing with custody stuff from the divorce. I had a friend that was like, “Don’t go to court without me. I want to just be there.” He’s not a lawyer. He didn’t have any big wisdom, but just being with me so I didn’t have to [be alone], because family court can be awful. You’re trying to accuse the other parent of how awful they are. And so him being there, I’ll never forget it. It was beautiful.

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