The Regret You Keep Making

High-achieving women often spend enormous energy avoiding one kind of regret - regret about doing the wrong thing. But in doing that, we create another kind of regret that costs us far more: the regret of not having been ourselves.

In this episode, Penelope explores:

• The two kinds of regret and why we focus on the wrong one 
• Why the regret of NOT speaking, NOT setting boundaries, and NOT being yourself is more expensive than any other choice
• How to stop using "kindness" as a disguise for self-abandonment 
• The pattern that traps most women in a cycle of regret 
• What changes when you decide that staying silent costs more than speaking the truth?

Key Insights

• Regret isn't the problem; it's information about misalignment
• Fear is usually driving the decision to stay quiet, and naming that fear changes everything
• You're going to regret something. The only question is what.
• The moment you decide to be honest, numbness turns into an active choice, and that feels completely different.

This podcast is part of my deeper work supporting women who are capable, accomplished, and exhausted from overgiving, overcarrying, and losing themselves inside the life they’ve built.

If you’re ready to go deeper, here are a few ways to begin:

Take the Burnout Assessment
Explore my book, Claws Out: Thriving in a World That Wants You Tamed
Book a Reset Session with me and get clear on the deeper reason behind your pressure, confusion, or emotional exhaustion.

Transcript

Penelope Magoulianiti 0:00

I want to ask you something before we even start today. When you look back at the decisions you've made in your relationships, in your work, in your life, do you spend more time regretting what you did or what you didn't do? More time thinking I shouldn't have said yes to that, or I should have had that conversation. I shouldn't have sacrificed that or I should have protected that. Because I think the answer matters and I think most women get it wrong. Most of us think our biggest regrets are about the things we got wrong, the times we overextended, the moments we made the wrong call. But what I found working with hundreds of women is that our deepest regrets aren't usually about what we did. They are about what we didn't do. They are about the boundaries we didn't set, the conversations we didn't have, the parts of ourselves we didn't protect, the times we watched ourselves disappear and didn't stop it. Today I want to talk about that kind of regret. And more importantly, I want to show you how to stop creating it. And it's not something we talk about directly because it feels too close to home. It's the regret you feel when you finally realize that over the years you have abandoned yourself. And abandonment in this situation did not come from a single incident, but in the form of a thousand small decisions. Where you decided that who you were wasn't enough, so you had to change. When you forgot the things that brought you joy because your partner didn't like them, you didn't want him to feel excluded. When you said yes, when you meant no, where you stayed quiet when you wanted to speak, where you shrunk so someone else could feel comfortable, where you convince yourself that being the one who sacrifices is the same as being the one who loves. And now you're looking back at your life, at your relationships, your marriage, your sense of self, and you're not recognizing yourself anymore, wondering how did I let this happen? And the painful answer is one decision at a time. But here's what I also want to tell you before we go deeper. The minute you see this pattern clearly, the minute you understand it, the regret can become something useful instead of something that paralyzes you. That's what we are working towards today. Let me start by making a very clear distinction because I think confusion here is where women get stuck. There are two kinds of regret when it comes to decisions about yourself. The first is the regret of having done something. This is the one we talk about more. You said something you wish you hadn't. You made a choice that didn't work out, you overextended, you overreacted, you revealed something you wanted to keep private. This kind of regret usually comes with thoughts like, I should have known better. Or I can't believe I did that. Or if I just had more self-control, I wouldn't have. You can fill the blanks. This regret is loud. It is in your face. It makes you want to be harder on yourself, more careful, more controlled. The second kind is the regret of not having done something. This is the quieter one, the deeper one, and honestly the most expensive one. This is the regret of not having said what you needed to say, not having set the boundary you knew you needed, not having asked for what you wanted, not having protected your time, your energy, your identity, not having been honest about the cost of what you were giving. This kind of regret usually comes with thoughts like, I wish I had had the courage to, or I kept silent, and now it's costing me. If I had just been brave enough to stand up for myself, this would be different. And here's what's very important to understand: these two regrets feel completely different in your body. The regret of doing something is often comes as feeling sharp, immediate, something you can identify and work with. The regret of not doing something, it feels like numbness, like distance, like a slow erosion of something you can't quite name. Now, here's what I notice with almost every woman I work with. We spend enormous energy trying to avoid the first kind of regret, the regret of doing the wrong thing. And in doing that, we create the second kind of regret constantly. We are so careful not to upset anyone, we don't say what we need, we are so focused on making the right decision, we don't make any decision. We are so terrified of disappointing people that we end up disappointing ourselves over and over. And then we look around at our lives, comes a time that you stop and reflect and you look around, and you look around on your relationships, at ourselves, and we feel this deep, quiet egg. Because we've made choices designed to avoid regret, and they've created the deepest regret of all. The regret of not having been honest, not having been brave, not having been ourselves. So, why do we spend so much energy avoiding the first kind of regret when the second one costs us so much more? I think there are a few reasons. First, the regret of doing something is visible. You can point to it, you said something sharp, you made a decision that didn't work out, and there is evidence. There is a moment you can go back and say, that's where I went wrong. The regret now of not doing something is invisible. It's an absence. It's something that didn't happen. An absence is harder to see, harder to grieve, harder to learn from. The second lie we have been taught is safety lies in restrain. It lies in being careful, in not making waves, in thinking before we speak, in considering other people's feelings before we express our own. And yes, thoughtfulness is good, but thoughtfulness taken to the extreme becomes self-abandonment. It becomes a strategy for staying acceptable to other people. And most of us were taught this early by parents who valued obedience, by schools that rewarded compliance, in relationships where our needs were conditional on our agreeableness. So now saying no feels risky. Being honest feels dangerous, protecting ourselves feels selfish, and staying silent feels safe. Third reason, and this is the hardest one. The regret of not doing something keeps us in a comfortable relationship with other people. If I don't speak up, nobody gets angry at me. If I don't set a boundary, nobody has to face the consequences. If I don't say what I need, nobody has to change. If I don't express how I feel, my relationship stays safe. Everything stays smooth. Everything stays functional. Nobody leaves. But the cost is that we leave. We leave ourselves. We stay in the relationship, but we stop showing up as ourselves. We become smaller, quieter, more palatable. And over time the people we love aren't actually in a relationship with us. They are in a relationship with the version of us we've decided is acceptable, which means we are never actually known, never actually met, never actually loved for who we are. We are only loved for how easy we are to be with. And that kind of love comes with a price. The price is your self-respect. Now I want to be very clear about something because I know some of you are hearing this and thinking, are you telling me to just say whatever I want, to be brutal and selfish? No, that's not what I am saying at all. What I'm saying is that there's a massive difference between being thoughtful about how you communicate something true and staying silent about something true because honesty feels risky. There's a difference between being generous with your time and energy and abandoning your own needs to keep someone else comfortable. There is a difference between caring about how other people feel and making their comfort your responsibility. And there is a difference between forgetting who you are and what brings you joy so you don't make other people uncomfortable. The shift happens when you stop using kindness as disguise for self-abandonment. So let me name this pattern that most women fall into, and I want you to notice where you are in this. It starts with a choice point. Something comes up, a conversation you need to have, a boundary you need to set, a truth you need to tell. And in that moment you have a choice. You can say what you actually think and feel, or you can say what you think is acceptable, safe, and unlikely to create conflict. Most women choose the second one, and it doesn't have to do with a lack of courage, but because they've been trained to believe that the second option is the more loving one, the more mature one, the more responsible one. So you swallow what you wanted to say, you soften the boundary, you edit the truth. And when you do that, something happens. You send your nervous system a message. My truth doesn't matter because I don't feel safe enough to express it right now with this person. Your body learns I am not safe being myself here, and your nervous system is brilliant at pattern recognition. So it starts scanning for when it's safe to be authentic and when it needs to stay hidden. And more and more often the answer becomes it's safer to stay hidden. So the pattern deepens. Over weeks and months and years, you make thousands of tiny decisions to stay quiet, to stay small, to stay acceptable. And each one of those decisions adds to the resentment, to the distance, to the feeling that you are in a relationship with someone, but you are not actually with them, and they are not actually with you because your real self is not in the room. And then comes the moment of regret. Maybe it's a specific moment, an argument, a moment of disconnection, a moment where you realize your partner doesn't actually know you, or maybe it's just a slow accumulation, a quiet realization that you've been living someone else's version of who you are, and you think, I wish I had been brave enough to be myself. I wish I had set that boundary. I wish I hadn't been so focused on keeping the peace that I lost myself in the process. That's the regret of not doing something, and it's one of the most painful kinds of regret because it's not the decision. It's not one decision, it's a thousand decisions, and each one of them is still affecting your life right now. So here's what I want you to understand. This isn't about play. This isn't about your partner not deserving kindness. This is about you, about whether you are going to continue making decisions designed to avoid regret about doing the wrong thing at the cost of creating regret about not being yourself. So what changes this? First, you have to stop treating the regret as the problem. The regret isn't the problem. The regret is the information. The regret is your system telling you something here is not aligned with who you are. So pay attention. And once you can see it that way, not as the evidence that you are failing, but as the data about the pattern, you get your power back. Second, you have to ask yourself and be honest, what am I most afraid of? Because I promise you, and it comes from experience, the reason you are not setting a boundary or speaking the truth isn't that you lack courage. It's because you are afraid of something. You are afraid what the conversation might reveal. Maybe you are afraid of the conflict, or maybe you're afraid disappointing someone. Maybe it's the honesty that you are afraid, and you are afraid that being in that honest, they might leave, they might leave you. Maybe you're afraid that if you prioritize yourself, people will accuse you of of being selfish. But they want you to name the fear because the minute you name it, it loses some of its power. Third, you have to make a new kind of decision. And the decision you have to make must be not based on regret about doing the wrong thing, but based on what you are willing to live with. Instead of asking what will keep everyone comfortable, ask yourself what can I live with? Can I live with another year of being invisible in this relationship? Can I live with another conversation where I don't say what I actually think? Can I live with continuing to shrink myself to stay acceptable? The answers to those questions are usually no. And that's where the shift happens. When you realize that staying silent costs more than speaking truth costs. When you realize that avoiding one kind of regrets has created another bigger one. That's when you get your choice back. And the minute you decide to be honest, the regret usually doesn't disappear. But what disappears is the numbness. The regret becomes active instead of passive. It becomes something you choose rather than something you carry. And that feels completely different in your body because you are not living with the weight of unsaid things anymore. You are living with the risk of being honest, open, vulnerable, known. And that risk might be scary, but it's also where real love happens. Love to yourself, first and the most important. I want to leave you with this question. This week. Where in your life are you making decisions designed to avoid regret about doing the wrong thing at the cost of creating regret about not being yourself? Sit with that, journal about it. Because I guarantee you, the moment you see that pattern, the moment you understand where you are choosing comfort over truth, something will shift. And when that happens, you get to decide, are you willing to keep making to keep making those same decisions or are you ready to regret something different? Here's what I know. You're going to regret something. The only question is what. There is no need to figure this out alone. A lot of women come to me saying, I know I need to be different. I just don't know how. And that's what a research session is for. In 70 minutes, we get clear about where you're abandoning yourself, what is costing you, and most importantly, what becomes possible when you stop, regret managing, and start living from truth. The link is in the show notes, but between now and then, I am asking you to do one thing. Tell yourself the truth about where you've been choosing comfort over honesty. Because that honesty, that seeing is where everything changes. Thank you so much for being here. I will talk to you next week.