The Jefferson Fisher Podcast - You Need to Disappoint More People

Episode Date: September 1, 2026

Disappointing people does not make you a bad person. But if you are always trying to manage everyone else's expectations, you will eventually lose sight of your own. In this episode, I break down how to say no without carrying the weight of someone else's reaction, why the feeling after the no is often harder than the no itself, and how to set a boundary without overexplaining, apologizing, or backing down. Order The Next Conversation Workbook: https://www.jeffersonfisher.com/workbook Want a FREE communication tip each week? Click here to join my newsletter. https://www.jeffersonfisher.com/newsletter Thank you to our Sponsors: Gusto: Go to https://gusto.com/jefferson and use code JEFFERSON to get three months free when you run your first payroll. BetterHelp. Click https://betterhelp.com/jeffersonfisher for a discount on your first month of therapy. Like what you hear? Don’t forget to subscribe and leave a 5-star review! Order my new book, The Next Conversation, today! https://www.jeffersonfisher.com/book Suggest a topic or ask a question for me to answer on the show! https://www.jeffersonfisher.com/topic Join my School of Communication. https://www.jeffersonfisher.com/membership Follow me on Instagram https://www.instagram.com/jefferson_fisher Follow me on TikTok https://www.tiktok.com/@justaskjefferson?lang=en Follow me on LinkedIn https://www.linkedin.com/in/jeffersonfisher/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Disappointing people is a skill. If you're going to be a better leader, a better communicator, a better parent, a better anything, you have to learn the skill of disappointing people. It is a skill. Now, some of you, my girl, well, Jefferson, if that's the standard, I am very skilled because I disappoint people all the time. That's not what I mean. I mean the act of knowing that what you're about to say is going to will not meet

their expectation, is going to disappoint that person. It's not the no. It is the feeling you get what's going to come after the no. Welcome to the Jefferson Fisher podcast. If you're listening, I'm going to ask them wherever you're listening. Please find the button where it says subscribe or follow or a thumbs up and click it. It means the world to me and it costs you nothing. Disappointment.

Our world is full of disappointment. But yeah, when it comes to us, when we know we're about to say something to somebody that's going to make them, disappointed, it creates a lot of heartburn, a lot of feelings. There's some people out there, and you might be one of them listening, you go, you know, I really don't like disappointing people. Here's the truth. I don't like it either. I don't like it either. It's, it's, we're going to have to separate some stuff on how to disappoint people, because first, I need you to understand, this is number one, understand the cost if you do not learn the skill of disappointing people. This is what I mean.

First, take the word, disappoint. Disappoint is a noun. It is a feeling. It's a feeling of what? Not meeting an expectation. That's what it means. It's a feeling, just like happiness, sadness, anger, any of that. It's a feeling, disappoint is the feeling you get when you failed to meet an expectation.

All right. That means if you go about your life, people pleasing, always afraid that you cannot disappoint anybody. What that means is you're going to go through your life, always trying to manage somebody else's expectations, any other expectations, other than your own. So there's two different things I want you to see when it comes to disappointment.

There is the no, meaning turning somebody down, and then there's the feeling afterwards, the feeling afterwards. When you are going, I'm going to have to tell them no. I'm going to have to say no to that dinner reservation. I'm going to say no to that proposal. I'm going to have to turn somebody down when they're asking me to do some extra work or something that's really not my responsibility, but I'm afraid.

I want them to like me. And man, if I say this, they're not going to like me. Man, all I really want deep down is just to be liked. If that is the standard where it's not so much the decline, the no, the hard pass button, it's the what comes after. that's the difference. I want you to understand, if you're listening to me,

you go Jefferson, I feel like I really struggle disappointing people. You don't struggle with no. You struggle with the feeling of what happens after the no. You're struggling with the feeling of what's going to happen to you inside.

That makes you feel awkward and it's squeamish and nauseous of going, oh my, they're not going to like me. Things are going to go terrible. They're not going to be my friend anymore. I'm going to have to have this. I'm going to deal with this. I'm going to deal with that.

And all this is what they call the parade of Terribles where you invent it all in your head because you're not wanting to handle the feeling that comes after the no. This is where I want you to lean in real close. If you're listening to me, just turn it up just for a second, right? Just because you tell somebody no

and they're having that disappointment, it is not your responsibility to resolve someone else's emotions. It is not your responsibility to resolve somebody else's emotion, especially disappointment. I'm going to say it again. It is not your responsibility

to resolve someone else's disappointment. You handle your feelings, let them handle their feelings. So when I talk about this number one of the mindset of how you approach disappointment, like how do we practically learn the skill of disappointment? It's first understanding what it is. You're really not afraid to say no, you know that you want to say no, you know you want to decline it.

The hesitancy that you're feeling, the heartburn that you're feeling, is what comes after, is what comes after, that feeling. And you're afraid of them feeling it. Okay, that's the problem we have. Number two, how do we address this? How do we resolve this? How do we teach these tools of disappointing people in conversation? Instead of managing everybody else's expectations and not living your own life, you feel like I just, all I do is I'm in this paralyzed state of trying to please everybody else because I'm afraid. I haven't learned the skill of disappointing people. How do we practically do that? That's a hard concept to teach, and I'm going to

do my darnest. First thing I want you to understand is who the feelings belong to. Who's responsible for the feelings that will be coming up in the conversation? Whose responsibility are they? Whose responsibility are they? It's very helpful to know, have a bright line indicator of, Here are my feelings. These are their feelings. You don't get to just take both of them. That's not your job. That's not your job. When you have that kind of mindset, what I need you to break down next, okay, is when you say the no, and I'm going to give you phrases, of course I'm going to give you phrases, on things to say to help with that no, help with that feeling of disappointment. It's the silence afterwards. The silence. afterwards. After you tell them no, it is the ability to sit in the quiet and not fill it with trying to adjust, measure, suss out, did you meet or not meet their expectation, and what can you do to make it feel better for them? It is a refined skill of being able to allow them to sit with it. Okay. Them to sit in it. To let them be disappointed. Give that to them.

Let them feel that feeling of disappointment. That's their feeling. Let them have it. Three, well, I'm going to go into by the end of this, is what kind of practical takeaways can we use in everyday situations that's going to help you build up that muscle, that practice? That practice. practice. Think of some of the most confident leaders that are out there. Do you think they have any problem disappointing people? No, do you think they know that they're disappointing people? Of course they do. Of course they do. Because it's inevitable. It's inevitable. You're going to disappoint people. You're going to have to maybe break up with that person. You're going to have to tell the job that you don't want to work there anymore. You're going to have to step away from that friendship.

You're going to have to decline that dinner invitation, whatever it is. There are times when it's going to have to happen. Why? Because you need to be much more interested in meeting your expectations for yourself than you are in trying to meet somebody else's expectations for you. Tell them, Jefferson. When it comes to disappointment, here's some phrases that I want to give you. Cool.

Let's just dive into those. A very easy way to step into these waters, walk into it, is to say it out loud. I know this is going to disappoint you. Use the word disappoint. I know this is disappointing, or I know this is going to disappoint you, or this is probably going to disappoint you. Use the word disappoint.

In it. In it. In the phrase where you're telling them no. Say it's in a text, hey, I know this is disappointing. I can't make it. all right hey i know this is probably going to disappoint you i can't make it i can't go

what you'll find is that when you use that word disappoint other people and their very contrarian view are going to go oh it's totally okay oh no no no no i'm not disappointed at all i'm it's going to be great have you ever got yourself so worked up in a conversation that you go oh my gosh i can't i can't tell them no but i have to and i'm going to say ah so you send them that message or you call them and go, hey, listen, I am so sorry. I have just been so swamped and I've just been so overwhelmed.

And I know it's really, really sad. I just, I can't make it. And the other person goes, oh, it's okay. No problem. You know, like, oh, that's, that was it. Wait, in my head they were going to be crushed. In my head, they were going to be totally just downcast and crumbled on the inside because I couldn't be there and I couldn't make it.

And I just knew in my head if I wasn't going to be there, then the whole thing was going to be ruined. Listen to me, we're not that important. We're not that important. Okay? We cannot be. You cannot be the sun of somebody else's universe. If we put ourselves, if I put myself in thinking

that, oh my gosh, you know, I'm not going to make it. They're just going to be so sad because I'm not there anymore. You know what I'm doing is it's like I'm making myself the main character of the story. Oh, my, they're going to be so sad that I'm not there. Or you know what? Find out they're not. They just, they want to make sure you're included if you can't come. Oh, okay.

That's fine. here's something that my dad taught me really early on in life. I can remember telling my dad something about in school, and I wasn't really sure how to handle it. And it was a conversation where I was needing to tell a friend that I couldn't go to some, like, party they were having. It was like a sleepover party. Take it easy.

It was not anything crazy. Trust me. And I said, oh, but I feel like he's going to be one of my best friends that said, he's gonna be really, like, disappointed. And what my dad told me, I'll never forget, he said, yeah, he'll be disappointed. Yeah, he will. Like that, and that was that.

That was the lesson. He said, yeah, he gets to be disappointed. He gets to be disappointed. Like, that's, his opportunity is gonna happen. Yeah, he's gonna be disappointed. Yep, that's an option. He could be disappointed. That's true.

and that maybe it's not hitting you like it hit me but at that point in my life it was a light bulb that just said wow he get he that's that's for them that's not for me when i choose to guard, protect, and keep myself, my needs out of the discussion, the conversation. And I get so wrapped up about how they're going to feel, and I care so much, so deeply about how they're going to feel about my response that it makes me be less of myself. What I'm really doing, okay, what I'm really doing is saying that the other person is not emotionally resilient enough to handle it. I'm saying in that moment that they don't have the skills, the coping skills,

to deal with my absence, to deal with my decision. They can't handle that of how to deal with me saying no. So I need to also feel their feelings for them. I need to resolve their feelings. I need to make it easier on them. That is not your place. It's not your place.

When you care so much, so afraid of disappointing somebody, I want to talk to the leaders out there, and that really applies to everybody listening right now because you're leading somebody. When you care too much, so much and put so much of your effort into the glass of the other person.

I'm so concerned that I'm going to disappoint them that I'm not telling them the truth. Okay? What you're building is a very toxic mentality that is always going to stunt the other person's growth. You will leave them on crutches

because you are not giving them the nutrition, the extra, the resistance to grow. They have to hear you say no. They have to hear you decline it. Why? Because it's building their resistance. If they're always used to getting what they want, they are going to be a spoiled child that's only now in their 40s and always used to getting their way. Why? Because nobody in their life has ever disappointed them. When you find that you are constantly holding the weight of other people's disappointment.

Okay. It is going, that burden is not going to be felt by them. It's not going to be shared. It is all going to be on you. And you're hearing this right now. I know there are people listening to this. And you're going, Jefferson, that is me. That's me.

I feel like I have so much weight on my shoulders because I just, I can't say the thing that I want to say. I can't tell the truth. I can't be honest because, man, Jefferson, if I were honest, you don't know what would happen. They'd be so upset, they'd be so disappointed, they'd be so, so, so. You are, you are, you are, it's a self-fulfilling prophecy. You're, you're, you're, you're making the decision for them.

You're making the decision for them. Before we keep going, I want to take a moment to tell you about gusto. I have personally been a user of gusto for probably six years. I have been involved in multiple businesses, and I can tell you as a small business owner, payroll is such a headache and a big fear of whether or not, not just if you're going to afford it, can you make it, but it's also everything that comes with it and in between, like taxes, payroll taxes, how to make sure that they're going to be issued at the same time. If you have people that are virtual, people that are out of state, what do you do with making sure that all the paperwork's done and filed and all the forms and all the craziness? And custom makes all of that super simple. All you have to do is create an account and it makes Payroll, easy. You can set the date, the cadence, how much salary, hourly, whatever it is, everything is all in one dashboard and easy. And the best thing about it is, if you have trouble, true trouble, you're like, I have a question that I don't know. You can call and talk to a real

human person quickly on the line and they will easily walk you through. I have called them many times, more than I'm probably willing to admit. All in one solution, payroll, gusto is the only one that I would ever use. Right now, you can go to gusto.com slash Jefferson. and get three months free when you run your first payroll. That's gusto.com slash Jefferson. And now let's keep going. What are some other phrases? Okay.

One thing I really like is, let's say you get invited somewhere or somebody's asking you something. And you begin with the phrase, I've thought about it. I've thought about this and I need. I've thought about this and I need to say no. I need to decline. The other day, all right? We were, my family and I, on a weekend, we had a speaking engagement, and typically I try to bring the whole family on speaking engagements.

And there was somebody who came right to me in the lobby, and they were trying to, you know, some hotels, like try to upsell for some, you know, bigger award point system, something. And I listened for a little bit. And I mean like about four seconds. And I said, I need to stop you right there. I need to decline. Just that right there, as happy and kind as I could be, I need to stop you there. I need to decline.

I need to say no. That phrase, I need confidently with a smile on my face to say, yeah, this is what I need. I need to say no. I always like saying, I've thought about it as well. Hey, I've thought about this. I'm telling the other person, I put thought and effort into this. You see how much better that is than the, hey, look, I just got so much on my plate

and I'm just so stressed and I just really, really this is going to be rough. You can scrap all that. You can use either the word disappoint. I need to disappoint you. I'm going to disappoint you. Then give your no.

Or I thought about this. I need to say no. For me, I love to say it's not in the cards. Not in the cards for me right now. I appreciate that. Not in the cards for me right now. It's an easy way of saying, hey, I can only deal the hands that, you know, I can only, I can only play with the hands that I'm dealt, something like that.

And this is, this is, that cards is not my deck. I can't, I can't, I can't, I will not do it. An easy way of also saying no to some of these invitations you get. And I've talked about this before on how to say no. I'm going to quickly summarize it is first you're going to start with the no. In other words, in start of, oh, I'm so sorry. You know, I'd love to, but I can't. Instead of declining like that, you're going to start with the no.

I can't make it. I can't come. Then start with the gratitude. Thank you so much for including me and thinking of me. Then we're going to add in the kindness. I know it's going to be a wonderful time and, you know, tell me, let me know how it goes. Something as simple as that. You're releasing it.

You're releasing it. Let them deal with the feeling of disappointment. Yep. And another thing my dad shared with me when I was a kid was, this phrase, I don't need you to like it. I just need you to understand it. It's a very bad phrase, which it very much holds true to disappointment.

When I was disappointed with him, he said, no, you don't have to like it. You just need to understand it. There are going to be some things. There are going to be some things that you know people are not going to like. And you know what? That's going to happen.

It's for them to hold, them to resolve. All right, I think we've hit the point there. Here's some things that I'm going to give you three. How can we build this over time? How can we pressure this? I'm going to need you to start saying no to little bitty things just to test them out. Waiter comes by.

Wait just comes by. Would you like any thing else? No, I appreciate it. No, thank you. When you find that you're walking down, I don't know, a busy city somewhere and somebody approaches you to sign some petition or something. Instead of just looking down and continue to walk past them, let them speak to you for two seconds, three seconds, to kind of get a gist of what the ask is. And then I need you to say, I appreciate it. I need to say no. I need to decline. Or I'm going to.

I'm going to say no. I'm going to decline. Right. Get in the habit of creating these opportunities for you to exercise that muscle of turning somebody down, of knowing that it's going to disappoint them. For people who are in charge of other people, people managers is what I might call them, you're finding most likely that you are now in a position that your communication really matters, and one of the biggest skills of managing other people

is learning how not to manage their emotions. That means you have to learn the skill. It is a practice of disappointing other people, of allowing them to be disappointed, allowing them to deal and resolve their own feelings and emotions, to be able to say, hey, I know this is going to be disappointing. We're not going to be able to move forward that project at this time. You hear the difference? then saying, hey, man, you know how it's just, you know, layoffs in the market, you know,

and we really got this stuff. And, you know, I'm sorry, we're just not able to do it. You're the difference? When you disappoint somebody well, they're not mad at you for it. They're not mad at you for it. They have to resolve that feeling within themselves. When you see somebody start to react, okay, or maybe you need to say no, and then they come back with something, and they're upset and they're frustrated. This is what I want you to do. instead of fighting it, just validate that feeling. I know it's disappointing. I understand it's disappointing.

Hey, I understand that's disappointing news. I get it. You see how you can validate their disappointment without volunteering to resolve it for them, without volunteering to feel it and deal with it and fix it for them. It is not your responsibility to fix their disappointment. that's the feeling that comes after the no. That is theirs and theirs alone. So if somebody, after you say no to something,

you need to make a decision, and that decision you know is going to not meet their expectations, and instead of managing their expectations, you are going to state it what happens afterwards, okay? I know that's disappointing. I can imagine that's disappointing. I get that that's disappointing. I understand that's disappointing.

validate that feeling don't volunteer to also fix it for them don't start into like well you know i mean what we what we could do is you know i can take more responsive i can you know maybe an hour day i can like no don't you're when you do that you're kicking the crutches out from underneath them you're not letting them grow okay you have to let them grow don't don't continue to leave them on training wheels, when you are always fixated on feeling somebody else's disappointment and resolving it for them, you are continuing to keep their training wheels on. They need to ride. They got to do it on their own. Like my dad said, yeah, they're going to be disappointed. Yep, that's going to happen. Get ready for it. You need to accept it. Say it to yourself ahead of time. Yep, they're going to be

disappointed. So when you test those little limits of saying no to that breester, that waitress, or somebody offering something to you on the street, or needing to decline an invitation to go somewhere, you need to say no. Understand that that is your chance to practice the skill, the skill of disappointing people. Okay, go out henceforth and disappointing everybody. Thank you.