When Regret Becomes Wisdom: Healing, Growth & Why the Ride Was Worth the Fall

Have you ever laid awake at night wondering what would have happened if you had made a different choice?

In this deeply personal episode of Life's a Blog, Trina Stewart explores the regrets that shape our lives and the lessons they leave behind. From relationships and marriage to missed opportunities, intuition, grief, addiction, family, and second chances, Trina shares her own experiences with regret and how she learned to transform shame into wisdom.

Inspired by Brené Brown's quote, "Regret is a tough but fair teacher," this episode examines why regret isn't something to fear, but something to learn from.

Trina reflects on:
 • Staying too long in unhealthy situations
 • Ignoring intuition and red flags
 • Trying to save people who didn't want saving
 • Moving too quickly into another relationship
 • Choosing yourself later in life
 • The regrets we carry after loss and grief
 • How to stop asking "Why?" and start moving forward

The episode also explores Cody Johnson's powerful song The Fall and the message that "the ride was worth the fall," reminding us that even our most painful experiences contribute to who we become.

If you're healing from betrayal trauma, divorce, heartbreak, grief, addiction in the family, or simply reflecting on the choices that shaped your life, this conversation will remind you that regret doesn't have to define you.

It can teach you.

Because at the end of your life, the person you became will meet the person you could have become.

Transcript

Recorded On Mute And Laughing

SPEAKER_02 0:01

So I did it again. Recorded a full podcast on mute. Story of my life. But no regrets. I'll do it again. So, this is a funny thing because I want to talk about something that every single one of us carries, whether we admit it or not. And that's regret. Not just a little regrets. I'm

Regret As A Fair Teacher

SPEAKER_02 0:25

talking about the ones that visit us when we're going to bed at night and trying to get to sleep, or wakes us up at two o'clock in the morning. The ones that surface when we're driving alone. The ones attached to relationships, marriages, friendships, parenting, careers, and dreams. The ones where we look back and think, if only, if only I had left sooner, if only I had spoken up, if only I had trusted my God, if only I had taken the chance, if only I would have kept in touch. I came across a quote recently from Brene Brown that stopped me. Regret is tough, but fair teacher. To live with that regret is to believe you have nothing to learn, no amends to make, no opportunity to be braver with your life. And for years I thought regret was something to avoid, something to be ashamed of, something that proved I'd failed, but now I see it differently. I think regret is proof that we've grown. And I feel like through this whole journey that I've been going a lot through the last eight months, I've been looking at my regrets and realize I can let them go. Because when you look back at your life and see mistakes, it means you've learned something. The person you are today sees things differently than the person you were then. And thank goodness for that. Because if we never evolved, we'd keep making the same mistakes over and over again. And I think today's topic about regret is not about punishment, not as not about shame, but as a teacher. And hopefully I can help you look at your regrets and learn from them. And we'll realize that some of our regrets were actually our greatest lessons. I'm really convinced that every one of us carries a list, a little secret list of the things we wish we would have done differently. I know I do. Some are small, some are life changing, and some still sting. One in particular. Others have softened over time, and what I've learned is that regret has a funny way of changing shape. At first it feels like guilt, then it feels like sadness. Then eventually, if we're lucky, it becomes wisdom. A lot of the times we're stuck in the guilt mode because other people continuously make us feel guilty for the things we've done. Or often people use remorse. And then you feel guilty because you're stuck in sadness. And then once you realize the regrets that you have and the lessons that you've learned, it becomes wisdom, and the challenge is getting there. Because regret loves to keep us stuck in the past. It whispers very quietly, you should have known better. You should have seen it. You should have done more. You should have done less. You should have fixed it. You should have left, or you should have stayed. If we're not careful, we spend years arguing with decisions that can never be changed. So here are a few of mine, and maybe some of them will resonate with you and make you think about things that you regret. One was I was 19 years old. I had just got out of C Shop or I was graduating from C Shop, and I got accepted into the University of New Brunswick.

How Regret Turns Into Wisdom

SPEAKER_02 3:50

And it was for computer science. And then when I sat down and looked at the loan university papers, I realized that I had to go to my mother and father and get all their personal information. And I knew my parents were private people, and I thought they'll never give that information. And you know what? I never asked. I never asked them because I just decided that no, if I was gonna do this alone, I wasn't gonna ask for their I couldn't do this alone, I wasn't gonna ask for their help. As well, I asked my boyfriend, who would have been my future husband, whether he'd come with me, and the answer was a strong no. So I decided not to go. And I know that if I had gone at that time, that I would be a completely different woman than I am now. Because I think every young lady and young man should leave the home to learn how to grow and fend for themselves at a very early age. I know financials is difficult now, but I truly feel if they leave the nest and they take a room on a couple roommates, or I think it does so much good in maturing them and learning the responsibilities that they have that they need to take on and not allow mom and dad to be their anchor, if you will. So I know I would have been a very different woman, but again, when I look at it and go, oh, I should have done that, I look at it and go, I probably wouldn't have stayed in computer science. In fact, I took word perfect in C Shap, and I looked at my teacher, professor, it was her name was Evelyn Lego, and I looked at her and I said, ma'am, I I don't like math, but I think I'm dropping out of this course, and I may just take a math course because I hate it so much. So I do think that I probably would have not stayed in that career, anyways. So I think the experience would have been helpful, but the cho the course selection would have been awful. And then at 20 years old, I decided that's it. I quit my job at Zellers Restaurant, and I decided I was moving to London, Ontario, from Gaspie,

Crossroads At Nineteen And Twenty

SPEAKER_02 6:10

Quebec, and I was gonna make a life there. My mom was so mad at me. She was furious, and I think she was terrified of emptiness syndrome, to be honest with you. And so I went again on the premise that in three months' time, my boyfriend, who would have been my who was my husband, later in life, would come find a job, and we'd reside in London and build a future together. So I worked at this hotel, cleaning the whole hotel, which I absolutely hated, and I got laid off three months later. And it was around Christmas, and I asked my boyfriend whether he was going to come here and we'd continue. And he said, No, I'm not going because I don't like it there. And I thought, okay, come and get me, let's go back. But I said, if I go back, I need the promise that we're moving to New Brunswick in three months. And he's like, Yeah, let's do that. So that was fine, go back there. Nothing was happening, nothing was happening, nothing was happening. So I said, I'm 20 years old, I have a plan, and my life plan is to get married by 20 because I want to start a family young. And I regret pushing that marriage proposal. Because when I look at it today, he certainly was not ready to get married. But he did, he proposed, and 24 years later, we broke up. But I still feel that I have deep regrets that I pushed that because a lot of the times what happens in the beginning will happen in the end as well. And I feel that by pushing him, it wasn't a wasn't an authentic relationship, it was very much a I should be doing this type of thing for him. And I feel that I pushed him into it, and I regret that. But then I look at it and go, well, had we not gotten married, we wouldn't have had two children, couple homes, and a decent life. You know, for a lot of the years we were happy, we were safe, we were settled. Towards the end, the safety wasn't there, the happiness wasn't there. But at the end of the day, you gotta look at that regret and go, you know what? It is what it is, and this is what happened. Another whiz is what I have written on my arm. Trust your gut. I ignored my intuition probably since I was a little girl. I've always known right or wrong. I've always tried to live a moral life, and a lot of the times my intuition is screaming at me. Not that I'm psychic or anything like that, but my intuition often screams at me. And throughout my life, I've had that happen so often. And my intuition from 2017 to the end of 2018 was screaming at me so loud. I can remember sitting in the summer in Gasby with my sister-in-law, and I asked, I said, I don't know if he loves me, and I started crying. And I got back, phoned my husband because he was in at our home. I was in Quebec, and I said, I need to know, are we in this together? Or does it just feel like you don't love me? He's like, No, no, no, we're gonna be together forever. Sure enough, a few months later our life blew up apart. So a lot of these things have happened to me in the last eight years, my intuition, and I've been so much stronger in listening to it. Maybe not with relationships, but I'm getting smarter. But my intuition is on top now. And if I wasn't trusting my intuition, I would have probably given up this magazine ten times already. But my intuition keeps telling me to keep going, and I'm gonna keep going. And when it comes to a new relationship, if that ever arrives on my doorstep, that intuition, those red flags, it's gonna be screaming at me, and this time I will listen.

SPEAKER_01 10:37

My third one is trying to save someone who didn't want saving.

SPEAKER_02 10:41

For the longest time after my marriage, I kept a really close eye on actions, and I would report them when I saw things didn't add up. If two plus two didn't equal four, there was an issue. And I would call it out. I would call it out to my ex-husband. He'd always respond to life is better than now that I'm gone, and I would retaliate and say, But I know you're up to something, and I know it's not good, and I don't want you to die. And one big regret I have, and it falls under this, trying to save someone who didn't want saving, was that I wanted to report the ongoings at the business that he worked at. And I regret that today. I regret that wholeheartedly. And why I didn't do it was because everybody was going to be very angry with me because he would have lost his job. But maybe if I would have reported

Pushing Marriage And Ignoring Red Flags

SPEAKER_02 11:40

stuff, maybe he would have lost his job and maybe he would have saved his life. That's the way I would go to bed and think about this. But now when I think about it, I think, you know, I could have reported him. Things could have went haywire, I could have gotten killed maybe, and he probably wouldn't have looked at me again for the rest of his life, which he didn't really, anyways. So to report him, it could have gone two different ways. It was a a Y in the road. And again, much like my brother, no matter what I did, when he stood at the bottom of that Y, he ultimately would have had to make the choice of what direction he was gonna go.

SPEAKER_01 12:25

So whether I did anything or not, it was still out of my control, and I have to let go of that regret. Addiction is a beast.

Trying To Save Someone From Addiction

SPEAKER_02 12:37

Addiction is another part of a person that takes control of logic. Addiction is a horrible thing. I've seen it many times. I've seen it with my brother. He sat at the end of the road and wondered which road to take many a times. And the only way there was was re rehabilitation or death. And his ended up being death. So who's to say what my ex-husband would have chosen and how he would have chosen it? It was out of my control no matter what I did. So I've learned now that if anyone wants to save themselves, please don't include me. Well, if they want to save themselves, yes, I'm absolutely there. But don't meet make me be the person to try to save you, because I'm just not. We all have our own responsibility to save ourselves. Another one was moving too quickly into another relationship. And I think this is one of the biggest ones that I've had to come to terms with in the last eight months. Because obviously I have attachment issues. There's no two ways about it. Because when I left my husband, all I wanted to find was love again. And you can't find love at a bottle of a whiskey bottle. You just can't, it's impossible. And especially when the other one's looking for the bottom of the bottle of beer. That is not, it's it's it's it just doesn't work. And you have to learn to sit and grieve and not try to find that replacement. And I'm saying this to anybody that's alone right now in three, four, five, six months, however long it takes you to get over that relationship. It could be a year, it could be two years. Look at my ex, it's 10 years. You gotta get over that relationship before you start a new one because it's unfair. But the thing is with that relationship, I learned a lot of things too. I learned about different types of family abuse that I had never seen before in my life. It made me realize that wow, I'm a really tough human being to never look back. Because, you know, with the sexual abuse that I experienced, the emotional abuse during my breakup, and you know, my children really should have admitted me into some psych war because I really wasn't capable of making any decisions about myself or my future because I was much like Sharon Osborne when Ozzy Osborne cheated on her. I really was bad chick crazy. So I think that relationship allowed me to look at different types of family dynamics and see how disgusted I could actually get with family dynamics. I take that with take that with me from that relationship. Uh he was a really good guy. He had a lot of promise, he could have done a lot of things in life, but he wasn't at the same level as I was. And that's okay, because that was his decision, not mine. It wasn't my my opportunity, it wasn't my it wasn't my position to save him, protect him, stand up for him, even though I did many, many times. Those were his decisions to make. Me moving into a relationship too quickly, big regret, but I learned so much from it. And for that, I appreciate it. Another thing I did, and it's probably because I moved on to a relationship too quick quickly, was spent the last eight years asking why. Why did he do this to me? Why did he do this to our family? Why did he do this to our future? Why did he do this to our retirement? And you know, those are things that I'll never get answers for. And I regret asking why for so long. Because I stopped asking, why not? And during our marriage, I was always the one to go, Ma, why not do this? Like, let's give it a shot. But I stopped asking, why not? And you know, another thing I'm thankful for with my previous partner is encouraged me to get into this business. And I can tell you, in prior to 2018, I probably never would have because fear and doubt and everything like that would have set in alongside a supporting husband that would have set his own fears and doubts. And now I just look forward to all the why nots that I can bring into my life and stop asking why about the past. Because I'll never get those answers, and it's helped me move forward to really embracing what life has in store for me. And another one is not choosing myself sooner. I probably never choose myself. Right from the time I was five years old to now, uh maybe a year ago, I started choosing myself and it's actually started to feel really great. You know, I have a lot of work to do on myself, but now I'm choosing what I want and what I need in life. I've got two grown children, I know they're doing okay, and even if they weren't, they know mom's always there, but mom can't save them anymore because they've got to learn their own things. But the thing I learned about not choosing myself is that I lost a lot of myself. I'm only learning the person that I am now. And I look and I go, 53, overweight, trying to make a go of it, financially struggling, but I don't lose any sleep over any of it. Probably the overweight because it really hurts now, but I'm actually doing a lot of talking about it and seeing doctors, and and I did blood tests, and they all look good. So my liver levels have gone down since I haven't been drinking except on weekends with a couple of friends. My pre-diabetes is almost just at risk, it's just at the lower level, and my cholesterols went down. So there's a lot of things that I can look and go, I'm really trying. I'm trying hard. It's gonna take time. Nothing nothing good happens immediately. So I've actually chose myself, chose my sanity, and chose where I need to be to choose where I need to be in life.

SPEAKER_01 19:27

And my final one

The Mother-In-Law Goodbye That Hurts

SPEAKER_01 19:30

that I'll probably never ever give up regretting.

SPEAKER_02 19:37

Is not having any communication with my mother-in-law since my breakup. My mother-in-law was like a second mother to me. I loved her so much, I don't think I've ever said a bad word about her. Because there's nothing bad to say. I regret our final conversation. It was probably March 2019. I was talking to her and crying, and I said, Look, I I can't talk to you. I'm just gonna keep talking to you, and I'm just gonna say bad things about your son, and I don't want you to hear it. And again, you know, maybe if I would have expressed to her what was going on and what he had done, maybe she could have helped. But I don't think she could have. Again, her, no more than myself, we can't save anybody. They have to decide to save themselves. And there was a few other people that actually knew what was going on. So if they really wanted to bring it to the attention of anybody, they certainly could have. And then I created a toxic environment where it was almost next to impossible to pick up the phone and call her. I created it. Not that I was mean to her, but you know, just my actions made me feel very guilty to ever approach her again, and and I'll always feel sad about that because she truly was my second mother. I loved her dearly, and then she passed away. Actually, she passed away a few months before my father did. When she ended up in the hospital, I sent her flowers. I feel like I should have called her. And that first Mother's Day after we broke up, for so many years I sent my mom and her flowers, and I didn't, and I deeply regret that. I regret not calling her. It almost makes me teary-eyed now. But you know, sometimes regrets we just have to let let go of and realize that sometimes we were the cause of it. And I was. And I feel very bad over it, but there's nothing I can do now, she's gone. But I think up there she knows that I always loved her. And I think that one day if there's a heaven. We'll meet again. And I just it's just one of my biggest regrets. I probably can't really talk about this much more because I'm really upset over it and I just gotta learn to let it go. So the older I get, the more I realize regret isn't really about the past, it's about the lesson. Every regret points towards a value. If you regret staying too long, you've learned the importance of boundaries.

What You've Learned from Regret

SPEAKER_02 22:30

If you regret staying silent, you learn the value of your voice. If you regret giving too much, you've learned self-respect. If you regret settling, you've learned your worth. Regret isn't there to punish us, it's there to educate us. The problem is we spend so much time focusing on the pain that we miss a lesson. And when we miss the lesson, we keep repeating the same patterns. I've seen that time and time and time again, myself included.

The Ride was Worth The Fall - Cody Johnson

SPEAKER_02 23:04

There's a song that I listened to on full blast whenever it comes on the radio. It's a newer song. It's called The Fall by Cody Johnson. And Cody Johnson is one of my favorite singers. If you haven't heard it yet, go give it a listen. Because it captures something absolutely beautiful. Something I think every one of us needs to hear. The idea that the ride was worth the fall. Now think about that for a moment. The ride was worth the fall. Not because the fall didn't hurt, because it absolutely did. Falls always hurt. Heartbreak hurts, loss hurts, failure hurts, betrayal hurts, disappointment hurts. But the song challenges us to look at our lives differently. Instead of asking why did this happen, it ask, was there still value in the journey? And for me, as many hurdles as I've lived, the answer is yes. Absolutely yes. Would I choose every painful thing again? Yeah, probably not. But would I erase everything? No. Because if I erase the pain, I'd erase the lessons. I'd erase the growth. I would erase the woman I became. And there's another quote that really resonated with me.

SPEAKER_01 24:25

At the end of your life, the person you became will meet the person you could have become. The person you became will meet the person you could have become. Wow. Let's just think about that.

SPEAKER_02 24:44

Every decision, every risk, every mistake, every lesson, every regret, the person you became, the person you could have become. All of it contributes to who we become. The question isn't where whether we have regrets, we all do. The question is whether we're still learning, willing to learn from them, whether we're willing to become braver because of them, whether we're able to move on because of them, whether we're willing to stop carrying shame, regret, and start carrying wisdom. And maybe that's what regret is really for. You know, not punishment or self-loathing, not endless replaying of the past. Maybe regret exists to help us become, to help us grow, to help us choose differently moving forward. I've shared some of my regrets with you, and I know I have regrets, and I probably have a million more. Not because the fall didn't hurt, but because I would wouldn't trade the person I became because of it.

SPEAKER_00 26:09

So the best I can give to you tonight is just be gentle with yourself. Ride the wave. It's your journey.

SPEAKER_02 26:22

Learn a lesson, forgive the mistakes, let the regrets go, and keep moving forward. Because the person you're becoming is still waiting to meet you. And I can't wait to meet you when you get there.