You know Herman, I was thinking about that time you tried to help our neighbor, Mr. Henderson, move his entire library of vintage encyclopedias on a Tuesday afternoon when you had three major deadlines looming. I remember seeing you through the window, staggering under the weight of a box labeled nineteen sixty to nineteen seventy, looking like a man who had completely lost his sense of self-preservation.
Oh, please, don't remind me. I think my lower back still hasn't forgiven me for the nineteen eighty-four edition of the Britannica. It was the year of the heavy binding, apparently. I remember standing there in his hallway, sweating through my shirt, while he told me a twenty-minute story about how he acquired the letter Q volume in a dusty shop in London. And the whole time, my phone was buzzing in my pocket with notifications from my editor. I felt like I was physically vibrating with anxiety, yet I just kept nodding and saying, of course, Mr. Henderson, I can take another stack to the garage.
It’s funny because you clearly didn't have the time, and you definitely didn't have the physical stamina for it—no offense, Herman, but you’re more of a desk athlete—but you just couldn't say no. It’s a classic case of what we’re diving into today. Today’s prompt comes from a listener named Daniel, and it’s about the heavy, often complicated world of boundary setting and interpersonal relationships. Daniel writes that he struggles enormously with saying no, and when he finally does, he’s hit with this tidal wave of guilt and shame.
Herman Poppleberry here, and yes, that encyclopedia incident is the perfect, albeit painful, example of a boundary failure. Daniel’s prompt really gets to the heart of something many of us struggle with, which is the internal friction between wanting to be helpful and the need to protect our own well-being. It’s not just about saying the word no. That’s the easy part, linguistically. It’s about the psychological weight that comes after you say it. The guilt, the shame, and that nagging feeling that you’ve somehow failed as a friend, a neighbor, or a colleague. Daniel mentioned that he finds it hard to distinguish between healthy relationships and extractive ones, and that is a distinction we really need to unpack.
Exactly. And Daniel mentioned something really specific that I want us to dig into, which is the idea of extractive relationships versus healthy ones. How do you tell the difference when you’re in the thick of it? Because on the surface, helping someone feels like a good thing. It’s virtuous, right? We’re taught from a young age that being a good person means being available. But there’s a line where it stops being a mutual exchange and starts being a drain. How do we spot that line before we’re already three boxes deep in someone’s garage?
That’s a great place to start. In psychology, we often talk about reciprocity as the bedrock of healthy relationships. It’s not a transactional, I did this for you so now you owe me X, kind of thing. It’s more of an emotional and functional balance. In a healthy relationship, there’s an ebb and flow. Sometimes I give more, sometimes you give more, but over time, it levels out. An extractive relationship, however, is characterized by a persistent imbalance. It’s one-sided. One person is the perpetual asker, and the other is the perpetual giver. It’s almost like a parasitic biological relationship where one organism benefits at the expense of the host.
But how do you identify that without feeling like you’re keeping a scoreboard? I think that’s where the guilt comes in for people like Daniel, and frankly, for me too sometimes. If I start measuring what I’m getting back, I feel like I’m being a bad friend. I feel like I’m being calculating or cold.
Well, the scoreboard is the wrong metaphor. Think of it more like an energy audit. A healthy relationship should, generally speaking, leave you feeling energized or at least stable. An extractive relationship leaves you feeling depleted, resentful, or even used. If you find yourself dreading a notification from a certain person because you know it’s going to be another request for a favor, that’s a massive red flag. If your first thought when you see their name on your screen is, oh no, what do they want now, you’re likely in an extractive dynamic. In a healthy relationship, you might be busy, but you don't feel that visceral sense of being hunted.
That’s a really clear distinction. The feeling of dread versus the feeling of connection. But Daniel also touched on why this is so hard for some of us. He mentioned growing up in a stressful home where conflict was common, and how that led to a strategy of avoidance. I think that’s a huge factor that we can't ignore. If your early blueprint for conflict was that it’s dangerous, overwhelming, or leads to abandonment, then saying no feels like lighting a fuse on a bomb.
You’re hitting on something called the fawn response. Most people know the classic stress responses: fight, flight, or freeze. But fawning is a fourth survival strategy that is often overlooked. It’s when you try to appease the other person to avoid conflict or to feel safe. If you grew up in an environment where you had to manage the volatile emotions of the adults around you just to keep the peace, you become an expert at reading people’s needs and putting them before your own. You become a human barometer for other people’s moods. It’s a survival mechanism that outlives its usefulness. As an adult, you’re still using that same software, even though the environment has changed.
So, for someone like Daniel, saying no isn't just a logistical choice about their schedule. It’s an act of perceived rebellion against their own safety system. No wonder it feels like shame. His brain is telling him that if he doesn't comply, he’s in danger.
Precisely. The brain’s limbic system is literally signaling that you are doing something dangerous by upsetting the social harmony. It’s a false alarm, but it feels incredibly real. But here’s the thing we have to realize as adults: avoidance isn't actually a peace strategy. It’s just a debt-building strategy. You’re avoiding a small conflict today in exchange for a massive internal conflict and potential burnout tomorrow.
I love that. Conflict debt. It’s like high-interest credit card debt for your soul. You keep putting off the payment, but the interest is killing you. You think you’re saving the relationship by saying yes, but you’re actually poisoning it with the resentment that builds up. So, let’s talk about how to start paying that debt down. How do we get better at this? Because Daniel mentioned that even when he does say no, the guilt pulls at the edges of his conscience all day. He can't even enjoy the time he saved because he’s ruminating on the rejection.
The first step is what I call the twenty-four hour rule, or even just the five minute pause. A lot of people who struggle with boundaries are reflexive yes-men. The request comes in, the anxiety spikes, and the yes comes out before they’ve even checked their calendar. It’s a verbal tic. By implementing a mandatory pause, you break that neurological loop. You can say, let me check my schedule and get back to you, or I need to see what my capacity looks like for the rest of the week. This isn't a no; it’s a buffer. It gives your prefrontal cortex a chance to catch up with your panicked amygdala.
That gives you the space to actually consult your own needs instead of just reacting to theirs. It’s like a cooling-off period for a contract. But what about the guilt that follows the no? Is there a way to reframe that so it doesn't feel like you’ve committed a crime?
Reframing is essential. You have to realize that a no to someone else is a yes to yourself. If you say yes to helping someone move their encyclopedias, you are saying no to your own work, your own rest, or your time with your family. We often treat our time as an infinite resource, but it’s the most finite thing we have. When you say no, you aren't being mean; you are being honest about your limitations. Think of it this way: would you want a friend to help you move if you knew they were miserable, behind on their work, and resenting every minute of it? Probably not. By saying no, you’re actually being a better friend because you’re preventing that resentment from entering the relationship.
That’s a powerful shift. It’s not a rejection of the person; it’s an acknowledgment of reality. I also think there’s a nuance in how we deliver the no. I’ve heard about the no sandwich. Is that actually effective, or does it just make things more confusing?
It can be effective if it’s done with sincerity, but you have to be careful. The no sandwich is basically: positive statement, the no, and then a pivot or a helpful suggestion. For example, I really appreciate you thinking of me for this project, unfortunately I don't have the bandwidth to take it on right now, but you might want to check with Sarah or look at this resource. The key is to keep it brief. People who feel guilty tend to over-explain. They give a ten minute monologue about why they can't do the thing, which actually invites the other person to start problem-solving your life for you.
Oh, I’ve seen that happen! You say you can't help because you have to pick up the dry cleaners, and they say, oh, I can pick up the dry cleaners for you if you help me with this! And suddenly you’re in a deeper hole than when you started because now you owe them for the dry cleaning too!
Exactly! Over-explaining is a sign of a weak boundary. It signals that your no is up for negotiation if the other person can just solve your excuses. A strong boundary is a state of being, not a negotiation. You don't need to justify your own capacity. I’m not available is a complete sentence. It feels aggressive at first to those of us raised to be people-pleasers, but it’s actually the most respectful thing you can do for both parties. It provides clarity. Clarity is kindness.
Let’s talk about the extractive people for a second. Daniel mentioned that sometimes these requests come packaged in flattery. Oh, you’re so good at computers, could you just spend a few hours fixing this? Or, you’re the only one I trust with this. That’s a tough one because it plays on our ego and our desire to be seen as competent and needed.
Flattery is a classic tool for extraction. It’s a way of making the request feel like a compliment rather than a burden. It’s what psychologists call positive reinforcement for boundary crossing. But here’s the test: does this person only compliment you when they need something? If the only time you hear how brilliant you are is right before a four-hour troubleshooting session, that’s not a friendship. That’s a service contract you didn't sign up for. You have to learn to separate your value as a person from your utility to others. You are not a Swiss Army knife. You are a human being.
That’s a cold hard truth right there. I think for our listeners, and for Daniel, it might be helpful to categorize these requests. There are the true emergencies, where a friend is in crisis and you drop everything. Then there are the conveniences, where someone could do it themselves but it’s easier to ask you. And then there are the chronic extractions.
Right. And most of what we struggle with are the conveniences. We treat someone else’s convenience as our emergency. To get better at this, you have to start small. Practice saying no to low-stakes things. If a coworker asks if you have a minute and you’re in the middle of a deep-focus task, say, I’m in the middle of something right now, can we touch base at four? It’s a small no, but it builds that muscle. You don't start training for a marathon by running twenty-six miles; you start by walking around the block.
It’s like weightlifting for your personality. You don't start with the three hundred pound deadlift of telling your overbearing relative you aren't coming for Christmas. You start with the five pound dumbbell of not answering a non-urgent text immediately. Or saying no to a second helping of food you don't want.
I love that analogy. And eventually, you realize that the world doesn't end when you set a boundary. In fact, something interesting happens. People who are healthy and worth having in your life will actually respect you more. They know where they stand with you. They know that when you do say yes, you actually mean it and you won't be resenting them the whole time. It creates a foundation of trust. They don't have to wonder if you’re secretly mad at them for asking.
That’s a huge point. Resentment is the poison of relationships. If you say yes when you want to say no, you’re essentially lying to the other person. You’re presenting a version of yourself that is willing and happy, while internally you’re building up a wall of bitterness. That’s not a real connection; it’s a performance. And performances are exhausting.
It’s emotional dishonesty. Boundaries are actually an act of intimacy because they define where you end and the other person begins. Without them, you just become a blurry, resentful mess. You’re essentially saying, I care about this relationship enough to tell you the truth about my limits.
So, for someone like Daniel who feels that deep sense of shame, how does he sit with that feeling? Because the tips are great, but the feeling is visceral. It’s in the pit of the stomach. It’s that cold, prickly feeling that you’ve done something wrong.
You have to treat the shame like a weather system. It’s going to pass. When you say no and that wave of guilt hits, don't try to fix it by changing your answer. That’s the most important part. Don't backtrack. Just acknowledge it. Say to yourself, okay, I’m feeling guilty right now because I’m breaking a lifelong pattern of fawning. This is what growth feels like. It feels uncomfortable. It feels like I’m doing something wrong, but I’m actually just doing something new. If you can sit with that discomfort for twenty minutes without backtracking, the intensity will start to fade. Your nervous system needs to learn that the perceived threat isn't real.
It’s almost like exposure therapy. You expose yourself to the guilt of saying no until your nervous system realizes that you aren't actually in danger. You’re still safe, the sky hasn't fallen, and you actually have an afternoon to yourself. And the more you do it, the shorter that wave of guilt becomes.
Exactly. And over time, you start to see the benefits. You have more energy for the people who actually matter. You have more focus for your work. You stop being the volunteer in everyone else’s life and start being the lead character in your own. You realize that your time is your life, and when you give it away to things you don't value, you’re giving away pieces of your life.
I want to touch on the professional side of this too. In a work environment, especially in tech or creative fields, the lines can get very blurry. There’s this culture of being a team player, which is often code for having no boundaries. By February twenty-six, we’ve seen so many shifts in work culture, but the pressure to be always on is still there. How do you navigate that without being seen as the person who isn't pulling their weight?
This is where specificity and data come in. If your boss asks you to take on a new project and you’re already at capacity, don't just say I’m too busy. That sounds like a complaint or a lack of organization. Instead, use a collaborative approach. You can say, I’d love to help with this. Right now, I’m prioritizing project A and project B. If I take this on, one of those will have to move to the back burner to ensure the quality remains high. Which one would you like me to deprioritize? This is what we call the priority trade-off.
That puts the responsibility of prioritization back on the leader. You’re not saying no to the work; you’re saying yes to the reality of time and resources. It’s a very professional way to set a boundary. You’re essentially saying, I can do anything, but I can't do everything.
It also demonstrates that you care about the quality of your work. You’re saying, I want to do a great job on what I’m already doing, and adding more will compromise that. Most good managers will actually appreciate that level of clarity and foresight. It’s the people who say yes to everything and then deliver mediocre results or miss deadlines who actually hurt the team. They become the bottleneck because they’re over-committed and under-delivering.
That’s such a good point. The yes-man is often the least reliable person in an organization. By saying no, you’re actually protecting the organization’s productivity and your own professional reputation. It’s a paradox. The more you say no to the wrong things, the more impact you have on the right things.
It’s a paradox that applies to all areas of life. Efficiency is often about what you don't do.
Let’s circle back to the extractive relationships in our personal lives. What do you do when you’ve already established a pattern of being the giver, and you want to change it? That transition can be really rocky because the other person is used to you always saying yes. They’ve built their life around your lack of boundaries.
It will be rocky. There’s something in systems theory called change back behavior. When you change your role in a relationship system, the other person will often subconsciously try to push you back into your old role. They might use guilt, they might act hurt, or they might even get angry. They might say things like, you’ve changed, or you used to be so helpful. It’s not necessarily because they’re evil; it’s because you’ve changed the rules of the game and they liked the old rules better. They were winning under the old rules.
So you have to be prepared for the pushback. It doesn't mean you’re doing it wrong; it actually means your boundary is working. It’s like a physical barrier—you only know it’s there when you bump into it.
Precisely. If they didn't push back, it wouldn't be a boundary. You have to stay consistent. If you cave the first time they get upset, you’ve just taught them that they just need to be a little bit more insistent or a little bit more dramatic to get their way. You’ve actually reinforced their behavior. But if you hold the line with kindness and firmness, eventually the system will recalibrate. They will either learn to respect the new boundary, or they will drift away.
And if they drift away because you stopped being a free resource for them, that tells you everything you need to know about the quality of that relationship. It’s a painful realization, but a necessary one.
It’s a natural pruning process. It’s painful, but it’s healthy for the overall garden of your life. You’re making room for people who actually value you for who you are, not just for what you can do for them. You’re making room for reciprocity.
I think one of the most important things Daniel can do is to start identifying his own values. If you don't know what you’re standing for, you’ll fall for every request that comes your way. If you value your health, then saying no to an extra project that cuts into your sleep becomes a value-based decision rather than a selfish one. It’s about protecting what is sacred to you.
Values are the compass for boundaries. When a request comes in, ask yourself, does this align with my current priorities and values? If the answer is no, then the response is no. It simplifies the decision-making process immensely. Instead of weighing the other person’s feelings against your own, you’re measuring the request against your own internal standards. It takes the personality out of it and makes it about principle.
This has been such a deep dive, Herman. I feel like we’ve covered the psychological roots, the practical scripts, and the long-term benefits. If we had to give Daniel and our listeners a few concrete takeaways to start with this week, what would they be?
First, implement the pause. Before you say yes to anything, take at least five minutes—or twenty-four hours for bigger requests—to check in with yourself. Second, practice the short no. Stop over-explaining. I can't make it work this time is plenty. Third, identify one extractive relationship in your life and set one small, firm boundary this week. Just one. See how it feels. And fourth, remember the fawn response. If you feel that urge to appease, recognize it as an old survival strategy that you no longer need.
And don't forget to sit with the guilt. It’s not a sign that you’re doing something wrong; it’s just the sound of old habits breaking. It’s the noise of growth.
Exactly. It’s growing pains for the soul. It’s the sound of you becoming a more authentic version of yourself.
I think this is a topic we could talk about for hours because it touches every part of our lives, from our phones to our families. But for now, I hope this gives Daniel and everyone else some tools to start reclaiming their time and their energy. It’s a process, and it’s okay to stumble.
It’s a journey, not a destination. I’m still working on it myself. Just ask my back about those encyclopedias. I still have a tendency to want to be the hero, but I’m learning that a hero who is burnt out isn't much use to anyone.
We’ll get you a back brace and a copy of a boundaries book for your next birthday. Maybe a digital one so it doesn't weigh anything.
I’d appreciate that. Seriously. No heavy lifting for a while.
Well, we’ve reached that part of the show where we look toward the future. I think as we move into a world that’s increasingly connected—where everyone is reachable twenty-four seven through a dozen different platforms—this skill of boundary setting is going to become even more critical. It’s not just a nice-to-have; it’s a survival skill for the twenty-first century. We are living in an attention economy, and if you don't set boundaries, your attention will be harvested by everyone else.
Absolutely. With the digital world constantly demanding our attention, if we don't set boundaries with our devices and our networks, we’ll never have a moment of true peace or deep thought. The boundary is the only thing that preserves our humanity in a world of infinite demands. It’s the fence that keeps our inner garden from being trampled.
Well said. And hey, if you’ve been finding these discussions helpful, we’d really appreciate it if you could take a moment to leave a review on your podcast app or Spotify. It’s one of the best ways to help new people find the show and join the conversation. We’re currently at episode six hundred eighty-seven, and we want to keep going for another six hundred more.
It really does make a difference. We read every one of them, and it helps us know what topics are resonating with you all. It’s our own form of reciprocity with you, the listeners.
This has been My Weird Prompts. We’re so glad you joined us for episode six hundred eighty-seven. You can find us on Spotify, Apple Podcasts, and wherever you listen to your favorite shows.
You can also visit our website at my weird prompts dot com for the full archive of our six hundred eighty-seven episodes and to find our contact form. And if you have a topic you want us to explore, send us an email at show at my weird prompts dot com.
We love hearing from you. Thanks to Daniel for the prompt today. It’s a struggle so many of us share, and talking about it is the first step toward changing those old patterns. We’ll be back soon with more explorations into the weird, the technical, and the deeply human.
Until next time, take care of yourselves and your boundaries. Remember, you are allowed to say no.
Goodbye everyone!
Goodbye!
