The Hilary Silver Podcast - 25 Years as a Therapist: This Is What People Regret Most

Episode Date: June 6, 2025

We talk a lot about the regrets people have when they're dying, but what about the regrets we carry every single day? In this episode, Hilary Silver, former therapist and master coach of 25 years, shares the four most common regrets she hears in her work with high-functioning women. These are micro-regrets that quietly erode your confidence, peace, and sense of self. From staying silent when you should’ve spoken up, to ignoring your intuition, to being too critical of your appearance, Hilary unpacks the everyday ways we abandon ourselves, and how to stop.   Episode Highlights: What self-abandonment really looks like (and how it shows up) Why burnout keeps you from showing up as your best self How to stop dismissing your inner voice The sneaky regret most women have about their bodies—and how to stop repeating the cycle   Episode Breakdown: [00:00] Why We Regret What We Do (and Don’t Do)   [01:47] Regret #1: Self-Abandonment in Relationships & Life   [04:36] Regret #2: Not Being Your Best Self   [06:33] Regret #3: Ignoring Your Intuition   [07:46] Regret #4: Being Too Hard on Yourself   [09:33] How to Learn from Regret Without Shame     Regret can either weigh you down or wake you up. This episode is your reminder to choose differently, starting now. ✨ Want more? Sign up for Hilary’s free weekly newsletter, Self-Centered, where she shares mindset shifts and lifestyle favorites: https://hilarysilver.com/newsletter/

I've been counseling and coaching high-functioning men and women for 25 years. That means that I've spent thousands of hours in deeply raw, honest conversations, and I've heard it all—things that people do not dare to share with anyone in their real life—the fears, the insecurities, the shame, and yes, the regrets. We talk a lot about the regrets people have when they're dying, but what I hear every single day are the regrets of the living, micro regrets that they carry every single day, the ones that slowly eat away at their peace, their confidence, and their self-worth. So today I'm sharing the four most common regrets that I hear daily so that you can catch them now in your own life and make any necessary adjustments

to how you're living. Because what we don't want is to get to the end of the line and look back with regret about how we lived our lives. Hi, it's Hillary. Welcome to the Hillary Silver Podcast. Thanks for tuning into the conversation today. If you haven't already, it would mean so much to me. If you'd take a minute to just click that five star rating

on your podcast app, leave a review and subscribe so you never miss one of my episodes. And if you're enjoying this podcast, please consider sharing it with a friend because if you like it, they will probably like it too. So the first and most common regret I hear every day is all the many ways women have abandoned themselves. And there are two big ways that this happens. The first is allowing and tolerating. They tolerated being dismissed by a partner, disrespected by a teacher, criticized by a friend, or misunderstood by an in-law.

Instead of speaking up, you stayed silent. Instead of walking away, you stayed. You let it happen. You exposed yourself to being treated unfairly or worse. It's not saying the thing or not doing the thing, not sticking up for yourself, standing up for yourself, speaking up for yourself to set the record straight, to protect yourself and defend yourself and get your own back. Not because you didn't care, but because you froze. You didn't know what to say

in those moments or you didn't know what to do or how to handle it. Or maybe you didn't feel strong enough to say it or do it. You doubted yourself instead of trusting yourself. And you gave them the benefit of the doubt. You avoided conflict. You made excuses for their behavior, turned the other cheek, or were the bigger person. In these instances, the hardest part isn't what they did. It's what you didn't do for yourself. isn't what they did. It's what you didn't do for yourself. That is the biggest regret. You weren't there for yourself when you needed you the most. That is abandonment of the worst kind because you did it to yourself and it's what makes this the most regrettable. The second way that we self-abandon is when we leave ourselves behind. And what I mean by this is when you care so much

about what other people think, you wanna be liked, accepted, validated, or to belong, that you shape shift, as I call it, which is editing, altering, or filtering yourself to be who you think you need to be to gain approval, to be palatable or agreeable. And in doing that, you abandon your true self. It's like you leave her standing there all alone,

silenced, dismissed, ignored, neglected, not seen or represented. These are daily acts of self abandonment. It's quiet, it's invisible, but the toll is heavy because it adds up. Over time, it costs you the ability to trust yourself. It costs you your identity and your joy, not living in alignment and representing your true self in the world.

And why this is so important to be talking about now, if this pattern of micro self-abandonment continues, it becomes the regret of the dying, which is, I didn't live a life that was true to myself. So you have an opportunity right now to right this wrong. Starting today, it begins by choosing yourself one small moment at a time. The second most common regret I hear daily is, I regret how I showed up. I wasn't my best self. You were short-tempered, dismissive, snappy, judgmental, distracted. You missed the event. You skipped the bedtime story. You said something that you didn't mean. Not because you're a bad person, but because you were running on empty. You were overworked,

overwhelmed, and overscheduled. And you knew that saying yes to one more thing meant saying no to something else that really mattered. But you said yes anyway. So you were trying to be everything to everyone and lost the version of you that you actually want to be. I've been there, exhausted, depleted, trying to hold it all together and continuing to pile it on. And I just have deeply painful regrets for the times that I fell short, mostly around parenting for me personally. My ready for love clients say I regret not being the model for my kids, or for what I exposed my kids to, in my poor choices. It is really hard to live that down.

But here's the truth. You can't give what you don't have. You can't be patient, present, or powerful when your tank is empty. And you can't do better until you know better. This regret is avoidable, but only if you stop glorifying burnout, living to achieve the next thing, overburdening yourself, and avoiding doing your own work.

Instead, start protecting your energy like your life depends on it, because it does. If you want to live, regret free. The third regret I hear every single day gives me chills. I knew, I knew it wasn't right and I did it anyway. Not trusting your intuition is excruciating because you knew at the time

and you didn't listen to yourself. We've all had those moments. You felt it in your gut, in your chest, in your body, and you heard it, that deep inner voice that said, don't go. Something doesn't feel right. Don't make the move. Don't say yes to this. And yet you went forward anyway, throwing caution to the wind because other people expected it, because it was easier to go with the flow because you didn't want to disappoint anyone, because you saw what you wanted to see rather than seeing what was actually right there in front of you. I've had women tell

me that they knew on their wedding day they shouldn't go through with it. Everything was screaming this is a mistake but they didn't want to let their guests down or their family down and they were they just didn't think they could do it. So that feeling was ignored and dismissed and over time we learned we can't trust ourselves again because we saw the warning signs, the red flags and went forward anyway to our own detriment or even to our own peril. So here's the thing, your intuition is not random. If it smells like a fish, it is a fish. This is your inner wisdom. And the more you listen, the stronger it gets.

You can practice paying more attention to yourself and you should because you're smart. And the fourth regret, I think most women have experienced this is being way too hard on yourself for way too long, especially about your appearance. So raise your hand if you've ever looked back at a photo of yourself when you were in high school or in your 20s and you said, I was so pretty then.

Why did I think I was ugly? Or I was so cute. What was I thinking? Why was I thinking I was fat? I was thin. Why was I fat? Or I was pretty. Why did I think I was so ugly? That, that regret is about not appreciating what we had when we had it. Looking back on all the time that we spent hating on ourselves, being hard

on ourselves, when now we see how wrong we were about ourselves way back then. I have definitely experienced this and I have vowed to appreciate what I am now so that when I'm in my 60s and 70s and beyond, I can say I appreciated my youth and my beauty and my appearance and all that I am actually. This is about not wasting time picking on yourself, being your own worst critic and your own worst enemy, rather than being your own best friend. Life is way too short to be so critical of ourselves and hard on ourselves. We must be kind and loving and accepting

of all that we are now, because it all changes so very fast and it can be gone in an instant. And we can avoid having the experience of being 10 years from now, experiencing the same regret if we just knock it off right now. The truth is, no one deserves to be treated that way, least of all by you.

So here's the thing, I don't believe in regret. It's only useful temporarily to be a warning indicator light, to draw your attention to a lesson that you need to learn. You can course correct and make tiny adjustments now so that you don't live a life that's full of regret at the end. Self-forgiveness is critical. You cannot beat yourself up for decisions you made

when you didn't know better or you hadn't healed all the way yet. That will keep you stuck. And the truth is, you did the best that you could at the time. But now you must commit to doing the growth work for yourself now.

And when you can, make amends, take responsibility, apologize, even if it's to yourself. And simply do better going forward. That is the best that we can do. I promise you, your greatest regret can be your greatest catalyst if you look for the lesson and you allow it to guide you going forward. This is how you live a regret-free life. I hope this was helpful. Please share it with someone See you next time.