Failures Podcast

The Curse of Being a People Pleaser

Failures Media Episode 34

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 1:02:48

In this episode of Failures Podcast, Rich and Justin break down the hidden cost of being a people pleaser.

Saying yes to everyone might look like loyalty, generosity, or being a “good man” — but over time, it can turn into approval addiction. When you can’t say no to family, friends, coworkers, or relationships, you slowly give away your time, identity, energy, and peace.

The guys unpack how people pleasing creates resentment, weak boundaries, conditional love, and missed opportunities in your own life. They also talk about why so many young men struggle with saying no, how this shows up in family dynamics and the workplace, and what it actually takes to reclaim control of your life.

If you’ve ever felt guilty for choosing yourself, this episode is for you.

Failures: The Podcast  2025
We're not gods. We're not gurus.
Just two men in our 30s sharing what we’ve learned the hard way—so you don’t have to.

🎙️ New episodes every week
📲 Follow @FailuresMedia on all platforms
 🧠 Join the movement: https://failuresmedia.com/subscribe

If this episode helped you, share it. That’s how we grow.

SPEAKER_01

Bro, if they punish you for a no, you're not being respected. As an individual, as a person, that is the answer. If you were looking for answers on, like, damn, what is the dynamic between me and said person? What is the relationship we have? How solid are we as friends or as co-workers? Say no to someone and see where that goes. If the answer is punishment, that person does not respect you. If the answer is all right, cool, no problem, that person respects you, right? They respect your ability to say no and draw a line in the sand and have a boundary.

SPEAKER_00

I don't know, Justin. I just can't tell my mom, my co-workers, my girlfriend no. If you can't say no, you don't have a life, straight up. You just have a schedule that other people write for you. And I know this hits because most of us have been there. I know I've been there. Saying yes to everything, thinking that what's loyal looks like me just sacrificing all my time. I'm a good man because I prioritize everyone else. It's a trap. It's a trap. It's not generosity, it's actually more like an addiction. You're addicted to other people's approval. You're addicted to not feeling friction whenever you have to tell someone no. And there's nothing wrong with that. Rich and I have most definitely been there before, but it is something that once you solve in your life, it frees up a lot of valuable things that will pay you back. One most important thing that it frees up is your time. When you stop donating your time to other people who use your time for what the fuck they need to do and not what you need to do, you start finding that you start looking at that free time as a way to solve some of your life problems that you have. And the other thing that it helps with is money, because most of the time when you have trouble saying no to somebody, it's usually money or something associated with money. So today's episode, we're going to zoom in on people pleasers and how this can really affect your life if you don't address it early. And I know a lot of young men that go through this problem. I have a crazy story I want to share later about someone in my family that just went through this. But Rich, off top, I know this is an easy subject to talk about, but does anything come to mind when you hear of this people pleaser disease or people that are addicted to not saying no? Yes.

SPEAKER_01

In my 20s, I was a people pleaser, right? Like, you know, I wanted to be in everyone's good graces. I wanted to be resourceful. I wanted to be liked by my coworkers, my parents, my friends. And I just wanted to be someone that was pleasant to be around. And over time, I started to find that if you're just always living for other people, then you're not living for yourself. And that's when I realized that being a people pleaser wasn't benefiting me in the long run. And the more you focus on people pleasing and people pleasing others, the more you stray away from who you are as a person. So that's sort of what we're here to unpack today.

SPEAKER_00

Rich, you know, what when you say that, the first thing that came to mind is that weird knot that you get in your stomach when somebody you love or care about, or somebody at work, maybe like your boss or a coworker, and you want to be seen as a good person. You want to be seen as someone that's helpful or resourceful. And then not you feel in your stomach when you're you're telling someone no. You know that like you're telling someone no, I'm sorry I can't do that. Even me saying it out loud is like uncomfortable. If you were to ask me a question, literally right now, while we're recording this, hey Justin, can you do XYZ for me? And just saying the two letters no, it feels like a negative thing. Like, what a bad person to say the word no. Where does that resistance come from? I feel like there is like a maybe a scientific reason why we don't say no to the people we love, but there is something powerful about drawing that line and learning the power of those two letters and that one word. No.

SPEAKER_01

Yeah, I mean, listen, I think part of it is empathy, right? You don't want to feel like you're the one letting another person that you care about down. And letting someone down feels negative, feels like you're creating resistance that potentially doesn't need to be there. But you know, ultimately, we're saying that when you do say no, when you have the ability to say no, you are drawing a boundary, right? You you are drawing the line in the sand and saying, hey, I know I'm resourceful, I'm available, I do a lot of things for you, but this time around, this no that I'm giving you is me setting a boundary that I don't want you to cross. And for the few times where I do say yes, and now I'm saying no, I'm saying no for me. I'm choosing me this time versus choosing a yes and being resourceful for everyone else.

SPEAKER_00

Rich, in our show prep, I was able to find an author. I forget his name, but I pulled out an excerpt from like one of his books and I wanted to read it because it triggered a lot of thoughts that I had. And like you said, at 39 years old, it brought me back to a 20-year-old version of myself that was trapped in this identity where, oh, if I help everyone else, I become more valuable. And I and I exist in my family and my friend group as someone that is resourceful. So this is an excerpt that I pulled because I I thought it was dead on our subject today. People pleasing looks like being loyal, but it often functions like approval addiction. It is an addiction when you get into the habit of being valuable to friends and family and loved ones through their approval. But what happens is you trade your time and identity for short-term peace. And this trade compounds into regret math. You miss major career movements, you don't spend time on developing your own skills, going to the gym, finding your own peace. And those weak boundaries are allowing other people to control your life, control your time. So you have to get control of your boundaries before you can get control of your life and your time.

SPEAKER_01

Bro, the the approval trap is the single thing that can affect your growth beyond any other trap that exists there for a man, right? Because when you're seeking that validation from other people and you don't get it, then you start to feel bad about yourself. You start to feel like, man, I'm not who I thought I was. I can't progress because this person thinks that I can't progress, right? And bro, it just continues to pull you further away from you being able to take actions and decisions for yourself and your own life and ultimately shape your identity, bro. I think ultimately we are all individuals. We all have to make decisions for ourselves. And once we require that validation and that approval from exterior entities, it just hinders your growth, bro, so, so, so much.

SPEAKER_00

The savior identity. I like that. I like the phrasing that you went with there. I mean, we should just get right into it, Rich. There's probably three to four major buckets of people that I originally wanted to say, people that take advantage of this, but I'm going to rephrase that because I want to put a little bit of the accountability on the viewer, the young man that's watching this and wants to regain that balance in his life and learn how to draw boundaries. People are not taking advantage of you. You put yourself in a position to be taken advantage of because you've developed an identity as the savior, as the person that's very helpful. And I want to zoom into two categories where I'll be curious to know where your mind goes, Rich. I find that family is where a lot of this comes from. And it starts young. It could be anyone. You could be the oldest sibling in your family and you take care of all your younger siblings. It could be the relationship you have with your mother, assuming your dad wasn't around. In my situation, is definitely the conundrum that I'm always in with my brother and my father because I'm the youngest. So I always want to seem like I am someone that can help. And I found myself being in a position where this is the best way I could help. So when I kind of point it out that way, Rich, what comes to mind? And why do you think family is so much of an important vertical in this conversation?

SPEAKER_01

Yeah, listen, man, family naturally places labels and identities on you. And it gets to a point where that creates expectations, right? So you always drive grandma to her doctor's appointments, right? And you've been doing that for years, like you become that guy. And the minute you say no, I can't do that, or I can't drive grandma to the doctor's today, you become the villain. You become the bad guy. You're like, but you always do it, right? Like this is what you do, this is what you've always done. And, you know, just like that example, I think there's a lot of things that you become known for, and then you're expected to do. And then unfortunately, when you do get of age where you're ready to draw that boundary, you're villainized and you looked at a bad person because you now you're choosing not to do the thing that you've always done for us. So you're becoming sort of less resourceful in that way. So I think that's where it comes from, the expectations that family has upon you.

SPEAKER_00

And you mentioned it before, Rich. I think for the young man that we're talking to in this episode, in their late teens or early 20s, we've noticed from going in a time machine that is these episodes and trying to enter the headspace of a man in his 20s or someone in their late teens, a lot of this part of your life comes with shaping the identity of who you want to be. And you see yourself as wearing this cape for your family because it allows you to stand there and represent yourself as a man. Like, oh wow, I'm helping my family out. I identify as this person now. And what happens is you kind of get caught in this little loop where if it benefits grandma and it benefits your mom, they're gonna start giving you labels. Like, man, you know what? Rich is the most dependable person in the family. This guy always steps up when people don't want to do anything. You know what was beautiful about Rich? He has a good heart. He's a good-hearted person. He reminds me of my father. He's a good person. You're a good person, Rich. You drove everybody home after Thanksgiving and you got home at 2 a.m. Well, who gives a fuck about you getting home at 2 a.m.? At least you drove everybody home. You're a good person. And I think families do that by mistake. They're not being malicious. They just put identities on you and then you start living in that identity.

SPEAKER_01

And then you know what happens, just when you live in that identity over time when you realize, like, damn, wait a second. I really don't want to be doing this. Or I really hate doing this for my family, even though they expect me to do it.

SPEAKER_00

Well, we need to stop right there. That is a tipping point. That is a pivotal moment in a young man's life when you're like, why do I do this? I fucking hate doing this.

SPEAKER_01

Yeah. And that creates resentment. You mean what with yourself or with other people? With other people, because they've placed these labels upon you, they place these expectations upon you. And then when you have that self-realization that, well, wait a minute, I don't want this label, I don't want this expectation, and I don't want this task or chore. You know, how do how do I remove this from myself and start to think to yourself, like, oh man, I can't. Like they expect me to do this, right? Then you start to create resentment to the people that you love. So yeah, I agree with you. That's that's certainly a tipping point in every young man's life where they just have this self-realization, like, why am I the designated driver in every circumstance, right? Why am I the money giver when there's a a money collection for for any one thing that the family needs? And we're not saying that doing these things for your family is wrong or bad, but we're just saying when you dedicate everything of yourself to others, you continue to stray away more from your self-identity and who you are as a person or who you want to become, right?

SPEAKER_00

Yeah. And I've heard this phrase before, and it's very relevant here is incentives are everything. So the incentives you give is what you get. If you want a gang of pigeons and squirrels around you, just start leaving bread and nuts on the ground at Central Park, and you'll quickly notice that you're being loved by all the birds and the squirrels in Central Park. But if you don't leave bread and nuts on the ground, those animals will never come around you. And I'm saying that to be crass because incentives are everything. If you are the person, when it's someone's birthday or someone graduated, or it's a quincinera, or whatever the fuck is going on in your family, or with your friends, if you become the guy who gives the biggest gift or you give the most money, that now becomes part of your ego. And what happens is when the next party comes around, people realize oh, this guy loves the idea of being the big money giver, the big gift giver. And now you've associated yourself to this action. So this incentive that you've given other people is coming back around with way more momentum every time it comes back around. And I I love that you brought that up, Rich. That's where the resentment comes from. Because you're like, yo, why does everybody keep coming to me asking me for money? Well, if you go back in the time machine, it's probably because you have developed this pride about giving the most money. Now your incentives are drawing back on you. If you don't like bird shit on the floor or squirrels are surrounding you, then stop giving these rewards for something that you don't want. And I know we haven't gotten to actual advice yet, but I do believe that we as young men, well, I'm not a young man anymore, but when we were young men, we wound up suffering in the world that we live in because of a lot of the actions that we took prior. And we don't know how to disconnect them. And I think that's where this becomes a dark hole, Rich, where you can't get out of it because now you've wrapped your identity and you've become a part of this hell that you live in, this curse of being a people pleaser.

SPEAKER_01

Yeah, you know, just to play devil's advocate, and this this might throw a curveball in the conversation, but I feel like sometimes as a young man, you feel like you're only loved in the condition that you provide something, right? So that people pleasing comes from a place of, like you said earlier, seeking validation, but most importantly, seeking love from the ones that are closest to you. And that's sort of a distinction that you need to be able to mentally separate, where you shouldn't, you first of all, if you feel this way, you shouldn't, right? Because no man should feel that they are loved under the condition that they provide something, whether that be conditional love.

SPEAKER_00

Wow. Conditional love, yeah, yeah. Yeah, yeah, yeah. Please finish the thought. I want to stay on that subject. Love based on a condition, friends based on a condition, co-workers, boss given promotion or given extra things based on a condition. A lot of these things are conditional. That's a great, that's a great observation.

SPEAKER_01

Yeah, and I think part of the people pleasing if we're dissecting the issue that this young man may have is that you feel that you are only loved, cared for, liked under the condition that you provide something of value in exchange. And that could be money, that could be your time, that could be being the designated driver, that could be a lot of different things. So there's a lot about a young man's psyche where they're dissecting life, relationships, interactions, family dynamics, and they have to unpack all of these things and figure out damn, what about these relationships is serving me? What isn't serving me? What is genuine? What isn't genuine? Where am I being taken advantage of? Am I giving too much money to the family? You know, every every Christmas? Like these are all things as a young man that you have to analyze uh for for yourself and for your own benefit.

SPEAKER_00

Rich, just kind of scrubbing through Reddit, looking for different perspectives so we don't get caught in our old man beating up on these young guys who have these life issues. I found a line that I really loved and I wanted to discuss it with you. It was um if you don't pick your life, life will rent you out to everyone else. So if you don't pick the things that are a priority to you and what you're willing to draw a boundary around, you just wind up donating your life out to other people so they can get what they need in their life. And I love that because it it doesn't, it doesn't have that stink of like victim or anger. It's just a simple math problem, honestly. It's really a math on your time and energy.

SPEAKER_01

I like that. And what that reminds me of is that I think everyone subconsciously has this meter of receiving. We all we all want to get things from situations, circumstances, or people. So if you're naturally a giver and all you do is give and you give free and you give happily, I guarantee you people will take and people will receive, right? Because you as a giver make everything easy, right? And I don't think that's by malice. I just think that people enjoy comfort, they enjoy things that are easy. So if you are my friend, and part of the friendship dynamic that we have is that every time something in my house breaks, you are the first person that I call because you're very handy with things around the house, then and you don't charge me for it, then I'm always going to call you, right? And there's no malice behind that. That's just like, bro, you make my life easy. You don't charge me, you come over, you fix the issue, and that is our dynamic as a friendship.

SPEAKER_00

Rich, I'm gonna give our younger viewers a very simple analogy. And I just thought of it, it's a little crashed, but follow me. Let's say you are a young single man in your late teenage years or your early 20s, and you don't have a consistent girlfriend, but you have a few girls that are friends that occasionally you hook up with. Chances are the reason why you're not committed to this girl is because she's not completely at the standard that you want for a full long-term relationship. But let's say this girl is hypothetically a strong six, she's not a 10, she's not a knockout, but you do hang out with her occasionally. The only reason why you hang out with this girl after 1 a.m. most of the time is because she's willing to give you something with no real friction, no real pushback, no real hesitation, you don't gotta take her out for dinner, you don't gotta spend too much money. She comes to your house, she finds her own parking, she don't even wait for you to go get her downstairs. She finds her way up to your apartment. The convenience of having a person like that in your life allows the relationship with that person to go on as long as possible. That is no different than what Rich said, but in a more, you know, crassed kind of way. You'll keep taking from that person as long as they keep giving to you without zero pushback. But the minute, this is where the rub comes, Rich. This is where the curse of being a people pleaser comes in 8k clarity. You know where I'm going with this. When she has the conversation with you at 3 a.m. after you done blown her back out for the second time, she tells you, hey, where is this going? I want this to be a real relationship. I've been telling my friends about you. At that point, she just told you no. She just drew a boundary. And you're about to find out the true nature of your relationship with that person. Because young man listening to this, what are you gonna say?

SPEAKER_01

That's not the right time. I'm changing careers, I might move, I don't want to be settled down.

SPEAKER_00

But what are we really saying here, Rich? I just took what you said and gave it a different angle to make it more relatable. What the person, if you say, I'm sorry, I can't do that for you anymore, and if that person gets upset, or if that person pushes back violently, or if that person shames you, then you know the nature of the relationship. It was only one-sided. I I think sometimes when you push back and you draw boundaries, Rich, you're just finding out the clarity of your relationship. And I I had to give the other example because I think it allows people to see it from a different perspective. Because is that woman a bad person for drawing a boundary?

SPEAKER_01

No, in that moment, she's choosing herself. And there's more to the relationship that she was probably seeking that she wasn't getting. So she's trying to establish a boundary and trying to identify like, where is this relationship going? And listen, we've all been guilty of this. We want all the perks of a relationship, but we don't want the relationship label. Yes.

SPEAKER_00

I've been guilty of this myself many times. But it takes two willing participants, and that's the point we're trying to make about being a people pleaser. It's a curse and a burden to be a people pleaser because you are giving to give, and that's fine. People that give to give is fine. But when you're giving to get back, now you're in a fucked up situation because now you want validation, you want approval, you want people in your family and your friend group to say, oh, you're this type of person. But all you're doing is giving to get back. I have a question that you should ask yourself when. And you're in a position where you're like, damn, I don't know if I want to do this anymore. I'm tired of being a fucking people pleaser. Are you helping this person because you chose to? Or are you helping this person because you're scared to tell them no? That is the question. When you ask yourself that, it brings a lot of clarity. It brings a lot of clarity. You don't want the friction or the tension that comes with saying no. And I have a remedy for that. And I will discuss that a little bit later, Rich. But one of the first phases of saying no is the soft no. I don't know if I could do that. I'm sorry, I can't really commit to that right now, but I'll let you know. I'm sorry, it's just not that easy for me right now. But just to be clear, here's what's going on in my life. If you have the problem next week, hit me up again. Maybe I'll be available. I'm a fan of the hard no. No, I'm good. You're good. But if you're having issues with the friction, you don't enjoy the friction of saying no, the soft no is a great segue into the stern no. The soft no is, man, I don't know if I could do that, but I'll definitely let you know next week. Give me a minute to get back to you on it. You know who's the king of the soft no? Beautiful women. That is true. If a beautiful woman accidentally mashed with you on a dating app or you met her out with your friends and you shoot her that desperation heave text, like, yo, I'm gonna be in your area next week. Let me know if you want to pop out. Uh I know a few good bars. They're gonna hit you with the soft no. Screenshot the soft no and add that to your uh a survival package.

SPEAKER_01

Yeah, the soft no is uh let me check and I'll get back to you. And then you and then you never get back to them.

SPEAKER_00

Don't hit them back. They will never get back to you.

SPEAKER_01

Yeah, that is true. Bro, to me, that is amazing advice. I think I struggled with being a people pleaser and finding how to say no in a sort of like non-confrontational way, a more graceful way that didn't make me the villain. I think what happens with these young guys is you tend to be a little bit extreme in your 20s. And you you tend to think that everything is is extremely bad. Like if I say no, I'm going to lose them. If I don't help, then I'm irrelevant. Great point. And that mental extreme that you put on every relationship and every circumstance is part of what's reverting you back to wanting to be a people pleaser because you're living in fear. You're living in fear of being replaced, fear of losing a friend, a relationship, a partner, a family member. And, you know, it's keeping you in that like people-pleasing mentality.

SPEAKER_00

Yeah, Rich, one thing you had in your notes, and I wanted to bring up was we should discuss the opportunity costs and the trade of your time, energy every time you say yes to something you don't want to do. I think that's important. That might be financial advice at this point because we've discussed this in other episodes how to get your life together in your 30s. You know, I feel like we had a lot of episodes about helping young men get out of the rut that they're in because they don't necessarily have the job they want. They don't have the life they want, they still live with their parents. This is a big issue with young men in their early 20s. They want to get the engine of their life warmed up so they can start moving in the right direction. And that direction is their the best case scenario on their minds of who they can become. And I feel like the further we get into this podcast and this platform, the further we're getting into the nuances that are really the problems that are leading to them not getting that engine warmed up so they can get their life moving forward. And I think this is one of them, Rich. It's such a nuanced topic, but it's an important topic. The opportunity cost of saying yes to everything comes with time and energy that you're taking away from something that you could be doing for yourself. And I want to unpack that a little bit because you had it in your notes that you sent to me. And I thought that was a big, big conversation that we should get into because I think it reframes the guilt you feel for saying no to maybe, you know, a relative or a significant other when you're like, no, I need these two hours to work on myself, or I need these two hours to go to the gym. I need these two hours to finish this course that I've been working on.

SPEAKER_01

Yeah, I think that happens a lot in the workplace. I think sometimes your manager, boss, supervisor would be like, hey, can you stay an extra hour, even though you're a salary employee, right? Like you're not gonna get paid for it. But in your mind, you're like, damn, this looks good if I do say yes, and I do say the extra hour because I could potentially write this in a job review or end of the year review for a promotion. And you start to tell yourself that in the workplace, everything needs to be a yes, because I need to be put on this pedestal of a reliable guy, resourceful guy, guy that when they talk about promotion, he's an automatic yes, right? And unfortunately, sometimes when you are that guy and review time does come and you don't get the promotion, then you start to feel resentment in the workplace because you're like, damn, but I did everything. I said yes to everything, and I did all the overtime, I did all the extra projects, I did all the PowerPoint slides, like why am I being overlooked? And that's part of what we're saying in this, you know, people pleasing theme is that you need to be able to self-reflect on what are the things in your life that are okay to say yes to and where are the things that you're being taken advantage of. And I feel like the workplace is one of the easiest places to be taken advantage of.

SPEAKER_00

My advice to the people pleaser, Mr. Yes Man, if you're Mr. Yes Man, understand this. If everything gets a yes, nothing gets your best. It's a simple phrase, but you should remember it. Rich, I love that you brought up the workplace because reorganizing the fucking backstock for your manager or helping him carry his daughter's 60-year-old birthday party boxes to his G-Wagon and you're staying at work an hour and a half late just to kiss ass, is you being a yes man. There's nothing wrong with doing it as long as you genuinely want to do it. But if you're a yes man, you're gonna live in a world of resentment. That's a fact. I've been there before. I'd be resenting shit when I don't get exactly what I want. Listen, I done took people on luxury dinners in my single days, and I resented the fact that things didn't go my way after the fact. So, did I do that dinner out of courtesy? Did I say yes to everything that came before her politely saying, Oh, I think I'm gonna go home now? Did I do that for me or did I do that because I wanted something? So, Mr. Yes Man, just understand every time you say yes, if it's not coming from you genuinely, you are going to find out in a few weeks whether you genuinely did that or you didn't. Because again, if everything gets a yes, nothing gets your best. So you have to learn the opportunity cost of trading your time and energy for something you could be doing for yourself. And if we're speaking to the same young man that is listening to a podcast that's about getting your life together in your 20s or even in your early 30s, just understand there's only 24 hours in a day. You can't say yes to everything and assume that you're gonna get your life together. You have to focus on getting your life together. It's the greatest priority above everything else. And every time you say yes to somebody else, you're not putting your best into anything else.

SPEAKER_01

I love that. That's amazing advice. And you know what's interesting, just when you sort of do find the ability or you muster up the energy to say no for that first time. We said there's two ways, do the soft approach and then get to the more direct approach. But whatever approach you take, make sure you're intentional about that approach and specific about that approach. What I mean is that if you leave any gaps in your approach to saying no, then people naturally find a way to still persuade you to do something, right? And it's because you feel wishy-washy, right?

SPEAKER_00

You're like, uh, you know, it's because your only defense was the first time you said no and you're not ready for that counterpunch. Yeah.

SPEAKER_01

Yeah. So when you do get that counterpunch, but come on, you always do it for me. Now you're negotiating. Yeah, yeah. Now you're negotiating. Do it this one last time and I won't ask you again. And you know what happens? You go back to people pleasing, bro, because you don't want that rejection. You don't want to lose that relationship, you don't want to use that person. So a little bit of actionable advice, but I would say to just be definitive about your approach, right? Whether you're taking the soft approach and then becoming more aggressive with your no's, but be intentional about how you create that boundary and be specific and draw that line in the sand.

SPEAKER_00

Listen, if you can't say no, you're not free, straight up. If you can't say no, you're not free. So negotiating after the no is terrible negotiation skills. Take it from someone that worked his entire life in sales and marketing. The best leverage you have in a negotiation is the ability to walk away. Point, period. That is a little bit of career and salary negotiation advice for you. So if my mother calls me and says, Hey, we are having a family crisis and I need you to sell me a$2,000 in order to help get us out of this family crisis. If I have the money but I don't want to send it, I'm going to say, no, I'm good. Matter of fact, Rich, I actually have a sliding scale for the people pleasers out there. If you're a people pleaser, this is the sliding scale of saying no so you can free yourself of the burden of people coming back to you to ask you to do shit that you don't want to do. Sliding scale number one. This is a big one, Rich. We could end the show after this one. Ready for it? No. No. NO. Just say no and fucking fold your arms and stay quiet. See what the other person says. It's going to feel uncomfortable, but it's gonna be very liberating. Number two, this is the Justin. No, nah, I'm good. Nah, I'm good. Hey, do you wanna go on this trip to Florida with us? The whole family's gonna be there. No, I'm good. Hey, do you wanna chip in on Primita? Uh uh Ingrid's youngest daughter from our father's side of the family who we haven't seen in 15 years. Nah, I'm good. That's number two. Number three, Rich. I got this is my favorite one. This is my favorite one. Absolutely the fuck not. Now that one is a secret weapon. When somebody asks you for some ridiculous shit, like picking up some relative at the airport or your your coworker asking you to do some shit after work, say it with me. Number three, say it with me. Absolutely the fuck not. Rich, does this not feel liberating? It does.

SPEAKER_01

And you you know what that reminds me of? And I hate to villainize the people who do ask for things and you have to make a decision. But in some instances, just this dynamic that you have with people and being able to say yes or no, especially with family, it's a little bit of a control dynamic where it's they are the ones in control. If you're always saying yes to them, they control your time, they control your energy, they control your money. If you're giving them money, they are in control of your life. And that's what we're saying. Gain the ability to say no to reclaim your life and reclaim the control that you have about yourself and your identity and your individuality. I can't stress that one enough, bro, because if you don't have control over your life, you are not an individual and you're not living for yourself.

SPEAKER_00

Listen, we said it before. If you don't pick your life, you're just renting out your life to everyone else. So if you let the people that you love and they love you decide everything for you, it puts you in a tough spot. Another note that you had in our pre-show package, Rich, which I want to discuss because I think it's addressing a little bit of a darker angle, but it is one that comes up every episode. Obviously, we know a huge problem with young men in 2026, and it's been growing year over year for the last 10 years, definitely post-pandemic, is the depression and anxiety that a lot of these young men are suffering from. And we're finding from the research that we did pre-show, this people pleasing and saying yes to everyone is linking to a lot of the tendencies that lead to anxiety and depression. And it just lowers your confidence as a man. I don't have a problem with this anymore. But Rich, can you help me understand why those things are linked?

SPEAKER_01

Yeah, I mean, I think naturally when, like I said earlier, when people place those expectations upon you and you feel that pressure to constantly perform then the label that you've been given, and you don't do that, you start to feel bad about yourself. You start to feel like because those labels have become your purpose, unfortunately, you start to feel like you're not living out that purpose, right? Oh, I'm I'm the guy that always gives money. So my mom sees me as the money guy. But then when you stop giving the money and you're no longer the money guy, you feel like you have no purpose in that relationship, which is why we were saying earlier that unfortunately, sometimes we do things out of the notion that we feel like we need to provide something or we're only loved on the condition that we can provide something. And I think that's part of like the disconnect that causes like the loneliness, the depression, the anxiety, the fear that I can lose this relationship because the dynamic, I'm I'm creating friction in the dynamic of what they've labeled me versus what I think I am.

SPEAKER_00

Man, that's such a good point. You know, we definitely discussed this off air, and I want to package it in a nice little ribbon. The alarm bells in your brain should ring when you hear two separate phrases. One of them is real man. Only a real man does that. You know, I think this is a urban thing, a lower income thing, a Spanish and black thing, a pride thing. I find that in our community, me and you, Rich, there is this abuse of the framing of a real man. Oh, a real man. If you're a real man, you would do this. If you're a real man, you would do that. I call that the real man lie. When people use the phrase real man in order to get something out of you, they are literally manipulating you into using your pride and ego and your fucking caveman brain, your knuckle dragging ass brain, to be like, whoa, well, I'm a real man. I'll do that for you. That is a fucking trick. And if anybody uses the phrase a real man should, just remember that the combination of words and let that be an alarm in your brain and be like, whoa, Justin and Rich told me when this phrase is used, I should be hyper aware of what fucking the rest of the sentence that rattles off this manipulator's tongue.

SPEAKER_01

Yeah, you know what the reflector to that is, bro? You having the ability to set standards for yourself. Because once those standards are identified, created, and they're part of your identity, then you don't get told or asked some ridiculous ass shit. They know you will not do or say yes to, right? So if your family constantly is always hitting you up trying to make last minute plans, but your standard is like, yo, I don't do last minute plans. Don't hit me up for any last minute shit, then they know don't hit Justin up for last minute plans because the answer is always no. Don't hit Rich up for last minute plans because the the answer is always no. But that only comes from you creating those standards that become part of your identity, and then people know what your standards are.

SPEAKER_00

Yeah, I love that, Rich. I absolutely love that because I live that. I love that because I live that. Yeah. And I'm not here to brag or boast about what I am in my late 30s because I'm a grown man. If I don't have my life together by now, no one should listen to what the fuck I gotta say. I have a lot of holes in my life. I have a lot of shortcomings. There are a lot of things that I'm not great at, but I will never get in front of a fucking camera and give advice on those things because I'm working on those things. One thing that I've become a five-time all-pro, all-American Olympian at is drawing the motherfucking line of my life and separating my time and my energy from what people want from me. And I love that you said that, Rich. We could call my mother right now and put her on speakerphone. She'll rattle off three rules that I give her all the time. And one of them is what you just said. That's crazy. And me and you have never discussed that. I tell my mom all the time, you know I don't do that. You know I don't do that. Last minute shit, I don't do that. Because that just assumes that you could just fucking take my time and my energy and do whatever with it. Give me at least two weeks of a heads up and I'll let you know. Now, is that being mean? For sure. For sure. But what is it with being mean? Is it it helps my family understand, oh yeah, nah, he might not come because of XYZ. That's fine. Yeah.

SPEAKER_01

And you know what, just I think it there's more respect for the person who does have standards. Respect like that. And who has created standards for themselves that's tied to their identity than there is for the guy who people pleases and shape shifts, right? Because even though initially that no or that standard or boundary that you created for yourself amongst other people feels like friction, feels like you're difficult to get something out of.

SPEAKER_00

Yeah. One thing that I did write down, and I think it's squared into this conversation, is I think the biggest fear for a young man who has issues with being a people pleaser, his biggest fear is that if he says no to this person, this person's gonna cut him off. Or this person is gonna remove themselves from communicating with them or seeing them as someone that can be a friend or be a good family member or be a real man or be a real brother or a real son, a real, a real son does this. And my response to that is if our relationship is so fragile that if I tell you no, the relationship is gone. I don't think I need that relationship anyway.

SPEAKER_01

Bro, if they punish you for a no, you're not being respected. As an individual, as a person, that is the answer. If you were looking for answers on like, damn, what is the dynamic between me and said person? What is the relationship we have? How solid are we as friends or as co-workers? Say no to someone and see where that goes. If the answer is punishment, that person does not respect you. If the answer is, all right, cool, no problem, that person respects you, right? They respect your ability to say no and draw a line and the sand and have a boundary. But if the answer is anger, resentment towards you, a punishment, like you might lose a relationship, then they don't respect you, bro. That relationship is very fragile, and you should just move on from it.

SPEAKER_00

Quick story related to what you just said. One of the rules that I have with my family is that I don't pick people up at the airport straight up. I don't do it. I don't do it. I don't pick people up at the airport and I don't help people move. I'm very strong on these two. Well, you should probably say why, like you don't like driving.

SPEAKER_01

That's partly why.

SPEAKER_00

I mean, listen, I'm standing on what I said in the intro. I'm good at saying no one looking somebody dead in their eyes and being like, what? No.

SPEAKER_01

Yeah.

SPEAKER_00

I don't drive to the airport, period. You want to know why? There's this really insanely effective app from some of the most smartest fucking founders and tech billionaires in the world that could they created. It's called Waymo, it's called Uber, it's called Lyft, it's called the motherfucking rapido taxi. I shouldn't have to pick you up at the airport just to prove that I love you. This is a conflated thing that Latinos and people that that that come from these places, like, man, you have to pick up your family when they show up. No, I don't. Now, let's say if I enjoyed driving, which Rich, I'm glad you brought that up. I hate being in a car. I don't like driving. But let's say I did enjoy driving, and I actually wanted to be the first person that my family saw when they got out of the airport. If that was something I truly believed, then I would do it. But I've never seen the logic or understood the logic of obligal, I have to go to the airport. Bro, you have you ever been in Newark Airport when it's jam-packed? Have you ever been a JFK when it's jam-packed? Have you ever been to the LAX when it's jam-packed? We're talking about four hours of your day. Bro, don't let the flight be delayed. Because now you're just sitting at the LAX watching fucking season seven of Friends for the 30th time. I draw lines on certain things that personally my mind and my stomach can't comprehend. So the way I would frame this for you, the viewer that has issues with saying no to people. And the reason why I brought it up, Rich, is because I remember driving to the airport one time and I was at a red light on my way to go pick someone up at the JFK, a family member that came from Florida. And my mom tricked me into going picking them up. And I'm in a shitty two-door Camry that the check engine is on, and I and I'm in Manhattan traffic with a little bit of gas, I was in a bad spot. And I remember sitting at a red light thinking, what's in this for me? Why am I doing this? What's in this for me? And I know the analogy or the example or the story of saying me having to go pick up a relative that came from Puerto Rico from Florida. Yeah, maybe somebody watching this gonna be like, Justin's a dick. I don't like this guy. That's fine. It's cool. You don't have to like me. I got a lot of friends. Rich is my best friend. I do a show with him every week. I don't need you to like me. But what I will say is this when you find your body and your stomach disagreeing with what you just said, and someone taking control of your time and your life, the question you have to ask yourself when everything's quiet is what's in this for me? And if you can't do that mathematical equation fast enough to give yourself one ounce of energy to be like, oh, okay, that is something that's in it for me. Then carry on. But if there's nothing in it for you, you've been tricked. You're being manipulated, you're doing shit for someone else, and there's nothing in it for you. And I think this is the only platform where you could say something like that, Rich.

SPEAKER_01

What you just said, I feel like is the biggest cheat code in this entire episode. And if we're solving for something, it should be this. If you are saying yes to something, say yes to something that aligns with your priorities. I'll give you an example. If you have friends that are like, yo, I want to go to Costco, would you take me there? All right, cool. I need to get a couple things at Costco. Like that aligns with my priorities. I'll take you to Costco. Yeah, what's in it for me? What's in it for me? I get to shop along with you for things that I already needed to buy anyway. I'm just banging it out with a friend, right? Or uh a trip to the laundromat or whatever it is. But find the ability to match your yeses to things that align with your priority. That sort of reclaims your energy, your mind, money, time back into the things that you do want to be doing that don't deviate too much from who you are and your identity.

SPEAKER_00

Rich, there's one part of the show that we didn't get to, and it was a quote that you had mentioned in the pre-show. And I have to bring it up because I feel like we'd be cooking in the pre-show and we don't ever bring it into the actual show. You said this phrase, and I want you to frame it and unpack it for our viewer who is really suffering from the inability to say no and is a people pleaser. They know they're a people pleaser and they're trying to solve for it. You said certain phases of life come with the territory. And I thought that was so powerful, but it wasn't helpful for the first part of the show because that's a different type of problem these guys are dealing with. Is this more of like accepting it and understanding that a lot of these decisions are going to be uncomfortable? What did you mean when you said certain phases of life come with the territory?

SPEAKER_01

Yeah, I mean, listen, I think naturally when you're in your teens, you want to be a good boy. You want to do everything right for your parents, you want to do good in school, you want to be a good friend amongst your friend group. Um, then you go off to college and sort of the same thing. And there's a change that happens post 18 years old, where you start to change as a person, evolve, your views are different, your identity is different, your physique, you look different, you got a deep, your voice cracked, you're, you know, starting to sound more like a man. And you have to make decisions based on what's best for you and what's gonna move you forward. And sometimes that comes with uncomfortable conversations. And you do have to say no to people that you love, you do have to like not agree to certain things, and you have to be comfortable with that friction because you're evolving as a person. Like my son at 14 says yes to everything I ask him to do. I'm fully aware that post-18, 1920, when he's off to college and I ask him for something, and he hits me with a no dad, I can't, like I have to study for a midterm. I'm gonna be heartbroken, but I have to accept that because it comes with the territory of what phase he's in in his life.

SPEAKER_00

Yeah.

SPEAKER_01

So that's that's what I meant by that. Like different phases in your life come with certain territories that you need to adjust accordingly.

SPEAKER_00

Yeah, you have to be okay with saying no. And I love that 200-level course of failures for the people pleaser is the man that's in his late 20s, early 30s, maybe even your 40s. If you really want to take control of your life, your time, your energy, your money, your attention, attention is so important right now. Where you keep your attention, saying no, it's okay. It's okay to say no as long as you feel like you've done everything possible up to that point to help this person. And if it's the seventh time they come back to you with the same bullshit, and eventually you just muster up the courage and just to be like, no, I'm good. I don't want to lend you that money. I don't want to do that thing for you. I don't want to trade my time to solve your problem. No, I can't do it. You phrased it so well, Rich. Certain phases of life come with the territory. And I think as you get older, your time becomes so much more valuable. I'm going to share something that Rich and I were being very valuable on the phone as two friends. It occurred to us that damn, Justin, you're about to be 40. Most men don't live till 60 something. And don't let people of color in on that ratio because diabetes and bullshit deaths decreases the lifespan. What do I look like donating my time to shit that I don't even want to do if I know my time on this earth is limited? This is really what this comes down to. Time is a luxury, energy is a luxury, attention is a luxury. So you saying that certain phases of life come with the territory is fucking chef's kiss, bro. It's chef's kiss because that is what this shit is really about. Accept the fact that you're going to be uncomfortable, but also enjoy the reward that you now have four hours of your day back.

SPEAKER_01

That's such a great point. And you know, in hearing you speak, Jess, I'm just like reflecting on like different moments in my life. And I'm really thinking to myself, like, bro, saying no has never steered me wrong. Every time I told an employer no on the first offer that they've given me that is an employment agreement with a salary, they've always come back with more money. Right? It's almost like they expected the no, and they're like, okay, well, we really want you. So here's what we could do instead, right? Or they don't want to work with somebody who would say yes to the first offer.

SPEAKER_00

Great point. Great point. This guy is the cheap executive. I don't want this guy. Yeah. I want somebody who has a high standard because they believe they deserve that.

SPEAKER_01

Bro, think about you saying to a woman, oh, hey, I'm gonna be an hour late to the day. And you'd be like, you know what? It's all right. We'll figure out another date. In her mind, she's like having to deal with that like rejection of damn, he said no to me. Like I told him I was gonna be an hour late, and he said no to me. And it initially it feels like friction, but guess what? That woman, the next time a date is set up, she'll value your time. She will be on time for that date and not an hour late. Yeah, there's just a lot of different phases where I'm thinking about dating, money, family dynamics where I've said no to things and it's never steered me wrong. No has always been the right answer because in that moment I'm choosing me, and I'm choosing to preserve my time and my energy. All right, Rich, steel man time. Let's do it.

SPEAKER_00

This is where I turn into the Hulk. This is our best shorts have come from me throwing you a steel man and you just fucking just bring the blicky out and you just shoot it down. But this one's actually pretty good because all right, let's hear it. I'll be honest with you. I think an A-type personality, which I think you and I fall into this category, people that are willing to feel uncomfortable for a longer-term gain, is a certain type of person. So I need you to enter the headspace of somebody that does enjoy being a bit more passive and just going with the flow. So empathy. But the steel man argument is this I feel bad for people who think saying no to everyone and hoarding up all their time to themselves as people that are prioritizing themselves. But what they're really doing is they're denying the love and care they could be getting from helping other people out. Being helpful has built my community and has built my career capital. But I've never seen myself as someone that's saying no and benefiting from it. I do feel bad for that person.

SPEAKER_01

Listen, what I would say to this person is by the way, they're not wrong, right? The poison that we're highlighting is when you've made the people pleasing your identity and it's all you do, that opportunity cost is the time and energy that you're not working on yourself because you're too busy people pleasing others. So, yes, bro, go fucking donate blood, go to the community center and like I'm saying, like you want to be a good person, right?

SPEAKER_00

Like is the most charitable shit that you've never done. That's what you were thinking about. You were just thinking of all the things you would never do. Yeah. You're right, though. This is it for the philanthropists, people that are like, I build my community from giving.

SPEAKER_01

Go to the community drive and like give out food trays to the needy, like do all these things, say yes to all these things that fill up your soul and your body and continue to enhance that empathy that you feel for people and humanity and mankind. That is fantastic. We'll never tell anyone to not be a good person or not be a philanthropist or not be a good human. But what we're saying is when that becomes your identity and all you do is help others, what about you? What about you? Right? And what happens when people say no to you? How do you feel inside?

SPEAKER_00

You you said this earlier, Rich, and this is relevant right now to this person that's saying, Well, I mean, they said being helpful has always built my community and my career capital. The benefit for them was they didn't have community and they built it. They didn't have career capital and they got career capital. This episode is not for you. You actually got something from what you gave. What was the phrase I said earlier? What's in it for me? You found something that you were able to gain from giving. We're talking about the young man or the grown man who is frustrated at home, chewing their fucking wife's ear off on the drive home from visiting their mother or their father, being like, oh, but my sister doesn't ever do anything. This episode is for that guy. That guy that feels very vindictive and angry because he gives, gives, gives, gives, and people don't appreciate him. We are here to tell that guy, hey man, you don't have to give. You chose to give. Or you let people manipulate you or trick you into giving. This episode is for you. There is a big difference between strategic generosity and just fucking plain old generosity. Strategic generosity is what Rich said earlier. Yeah, you want me to give you a ride to Costco? For sure. I got you. You know what? I also need something from Costco. And if you want to throw in on my gas or if you want to buy me something at Costco to do a little even Stevens here, let's do it. This episode is for that guy, Rich. It's not for the person that gen, and by the way, I think the person who said that is a fucking hipster from Brooklyn that wants to go against the grain and be angry about people wanting to stand up for themselves. This is a fucking handicap. Being a people pleaser is a handicap. This guy is on Reddit forum boards writing a seven-paragraph essay about how his grandma makes him feel like shit because he doesn't wait for her outside of church when she's done. He's donating three hours of his time to picking up his grandma at church, and she doesn't give a fuck about his time. That's what this episode is for.

SPEAKER_01

Yeah, for sure. Listen, and everything, like you said earlier, everything is reciprocal, bro. Like the time and energy you give to people should be reciprocated. And it's not a one-to-one. Don't start tallying up all the favors people do for you and then expect all those favors back. That's that's not what we're saying. I can see that, yeah. But what we're saying is that have the cognitive ability to evaluate every single relationship that's in your life and have the ability to determine what is serving you and what isn't serving you. Yeah. What is taking time away from the things that you want to be doing versus the things you don't want to be doing? And is this identity of people pleasing and these external labels that have been placed upon you are eating away at that time and energy that you could be using towards yourself.

SPEAKER_00

And if you want to gain your autonomy back, if you want to gain your agency back, if you want to gain back your courage, like this was fucking the Wizard of Oz. I'm gonna teach you a little trick that I've learned from disagreeing with my family and my parents, my father and my mother. What I like to do is when I push back and I say no, no, I'm good. What's in it for me? Naturally, people that are used to you just saying yes all the time, they're gonna be shocked. Like Rich said, they're gonna negotiate with you. They're gonna come back with a counter. And then you say the same thing over again. No, no, I'm good. No, what's in it for me? I don't understand why I'm doing this. It's gonna sound selfish. You brought up a great point, Rich. Never have I ever fought back from my time and fought on something that I genuinely didn't want to do and felt bad about it after the fact. I usually feel good when I'm like, oh shit, now I have a free three hours. I can go do whatever the fuck I wanted to do for myself. The 300 level exercise here is you gotta bring out a pen and a piece of paper and you gotta show people that love you where they had you fucked up at. Right here. This is where you confused my time for your time. At this moment, right here, is where you had me fucked up. I'm not doing what you wanted me to do. And this is why you're mad at yourself because you expected me to do it. This is a roadmap of where you had me fucked up at. And this is where you turned left and I turned right. And if people can't agree with that, then that's on them. They have to figure it out. But again, I'm saying this with a caveat. You may lose some people for a few months in your life. You may get people to be very angry at you, even in a group chat with the family, they might start another group chat without you. You have to be okay with that. You have to be at peace with that. And that's the sacrifice that comes with this. And that, like you said earlier, Rich, that's the friction and the discomfort that comes with this. But I've never been mad at myself for fighting for more of my time and energy.

SPEAKER_01

I love that you mentioned that caveat at the end because I think that that's what these young guys are in fear of. They're in fear of losing relationships, not being liked, being cut off, being excluded from the family group chat, right? Like building that resistance with the people they love and not being accepted in that family dynamic.

SPEAKER_00

So yeah, you know what the consequence is for Justin being a little removed from the family. You know what the consequence is? Every now and then I can't lie. I'll jump on Instagram or Facebook, and they'll have a whole ass party, and I had no idea what was going on. It'll be a whole last person's reunion. They came home from jail. Not one message was sent my way. So this is the gift and the curse, man. I get a little emotional, I get a little upset, but certain phases of life come with the territory.

SPEAKER_01

God damn it. There you have it. Failures podcast.

SPEAKER_00

Hey, if this episode was beneficial to you, if you enjoyed anything we said here and you think it can help a friend or somebody that also needs this type of guidance, this type of big homie energy, share it, man. That's all we got. Rich and I don't really sell anything here, so the best thing you can do to help us out is share the content.

SPEAKER_01

Yes, sir. You're not people pleasing us by liking or subscribing to this content or episode or our channel. So follow us. Yeah, if you want to be a real man, like and subscribe at Failures Media. We out,