
Loading summary
A
Welcome to do this not that, the podcast for marketers. We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode. We also keep it short, like this intro. Let's check it out. We are back for do this not that podcast, presented by Marigold. And normally I come on here and I say, hey, stick this in your subject line or do this on a social media post and you'll see all this amazing stuff happen. But I wanted to share something that really has stuck with me, and it's this concept of regret is worse than failure. You know, I've been writing this book which has made me think about all these big life lessons I've learned, and I feel total imposter syndrome. I feel like a clown doing it, but it's really got me thinking in all sorts of different directions about moments in my life that have really been a big deal for me. And probably the biggest moment in my life that happened was how I met my wife. And then also how that translated to. To impacting how I think about work and business and everything else. And hopefully, you know, after you hear this nonsense, you'll be like, you know what? Regret is worse than failure. And you can incorporate that into everything that you're thinking about. Maybe you do that already, but I'm so intentional about it now because it really has transformed things. So what does that even mean? What am I talking about? So here's the story you didn't ask for. Here's how I wound up meeting my wife. So I've been married to Allie for 22 years. She's the most incredible human being on earth, a billion times smarter than me. She's a dermatologist. She's the most amazing human I. We have two great kids. One's a freshman in college, one's a senior in high school. Greatest human beings alive. But it all almost didn't happen. So here's exactly how it went down. So we both went. Me and Ali both went to University of Florida, and I was a year ahead of her. So she was a freshman, I was a sophomore, and we met when she was a freshman. And I just thought she was like the most beautiful, amazing human being. And we hit it off right out of the gate. But we hit off right out of the gate. Neither one of us wanted to have a serious thing in college. We were like, it's college. Went to the University of Florida. Let's go and, you know, enjoy life. And we would hang out in college here and there and we were always in each other's circles and stuff, but we were both pretty much fixed on not wanting a serious thing in college. But she was like, front and center of my brain always. Okay, so fast forward. We graduate and we kind of lose touch. And a couple years passed by. It's like two or three years passed by, but the whole time we lost touch. I. And I'm not just saying this now that I'm married. It's true. I thought about her all the time. I was, I wonder what she's doing, what's going on? And, you know, back then, it wasn't as simple as you go on Instagram and you see what they're up to. You know, you would hear little stories here and there, but you wouldn't really have a clue. And we weren't really in touch and then. But I would always think about her. So we live in South Florida. I knew she still lived in South Florida. And one night I was out in Miami and I was out with a bunch of my buddies, and I was sitting outside at this kind of like, restaurant, bar area, thing, whatever. And then on the opposite side of the street, she couldn't see me. I saw Ali holding hands with this guy and looking really happy and walking along. And I had heard before I saw them that she was in a relationship. And that bummed me out when I heard that. And then I saw them and she looked really happy, and they were walking along, holding hands, whatever, and she never saw me. She didn't even know that I had taught her until years later. And in that moment, I was so upset with myself. Massive regret had set in. I said to myself, holy, oh, my goodness, I let it slip by. I let the person that was my person slip by. And I'm screwed, because now she's happy, you know, and we're at that age where you're like, I don't know, 25ish or whatever, and you're like, that's it. She's going to marry that dude and that's going to be that. And I let the opportunity pass me by years ago in college. Then after college, listen, I know there's no Instagram where I could just DM'd or whatever, but if I. If I had made some effort, I could have found her. Okay, I just was terrible. I sucked and I didn't do anything. And the. The level of regret that set in with me was astronomical. I was. I was beside myself. I was just so upset. After that night, she. Nobody else realized my friends didn't know what was going on. They didn't know. I was upset. She never knew what was going on because she didn't see me. And she was with that guy. She didn't care. Okay, fine. Fast forward. I don't know. A couple months later, I'm out at this bar in Fort Lauderdale, and who do I see up at the bar area? The bar area is packed, but who do I see? I see Ally's there, and she's not. I'd heard that she. Then, um. I didn't know if she was still with that guy was going on. I heard. There was, like. I had heard different things, but she was at the bar, and she was talking with this other guy. And I was like, oh. And I said to myself, okay, I don't care. I don't care what's going on. I'm going up. I'm talking to her. I am not letting this opportunity pass by me. I need to tell her how I feel. So I waited, waited, waited, because I don't want to be a jerk. And the guy went to. I guess he went to the bathroom, and he walked away. And the second he walked away, I walked over her, and I said, hey. And she's like, whoa, Jay, what's going on? I said, listen. I go, I know this is out of left field. I said, but I really, really regret us not spending time together, getting to know each other after college. I would love to get your phone number. I want to take you out for dinner. Will you give me your number? And she looked at me. She goes, I'm on a date. I broke up with this other guy, and now it's like my first date since. Whatever. I'm on a date with this guy. He's in the bathroom. I said, okay, great. I go, I'm not moving. I'm not leaving this spot until you give me your number. Please give me your number. And honestly, if I was her, I would have thought I was a weirdo, because I definitely came off a little bit over the top. She. I don't know. She goes, oh. She's like. She could tell, though, in my eyes that I was not kidding. And so she grabbed a pen from the bartender, she wrote down her number, and she shoved in my hand. And then she said, now get out of here. And I did, because I was like, that's it. I just wanted her number. Fine. I left. Now, that night, I got home, and I'm like, I wonder if she even gave me her real number, because I wouldn't have given me my real number. Because I came off really weird. So. But. And everyone's like, you got to wait. You can't call her. You wait a few days. I said, screw that. The next morning, I remember the very next morning, it was early. I just didn't care. I'm like, this is it. No more regret. I'm all over this. And I called her up, and first the phone rang. I'm like, oh, my God, the phone's ringing. I was so happy because I thought it was a fake number. And then she picked up, and it was her. And I was like, oh, my God. She gave me a real number. And that was it. We went out. We have been together ever since. And what that did for me was made me always realize that regret was so much worse than failure. In every business opportunity, you don't ever want to have that feeling where you're somewhere and you say to yourself, oh, I should have introduced myself to so and so, or that was my chance to do that. You don't need to be brave your entire life. You don't need to have courage to do stuff at every moment. You need to be brave for, like, 10 seconds. In that moment, you say, I could do this for 10 seconds. Whatever it is, go up to that person. Ask the difficult question. Do the thing that's uncomfortable. Because when you do the thing that's uncomfortable, one of two things will happen in your life, in your career, in your business, in whatever. Either it's going to work out and you're going to get the opportunity. You're going to meet the person, things are going to head in the right direction, or it's going to be an epic fail. The person's going to blow you off. The opportunity is not going to come your way. You're going to get rejected. But you know what? You're not going to sit there in the land of what ifs? For the rest of your life, which is a horrible place to exist. What if I had asked that person the thing? What if I had reached out to that person? What if I had tried? What? What if I had asked Allie out on a date and she said, yes, what if? That is torture. It is a torture chamber. To live in the land of what ifs. So I know this episode was random. I get it. And you're pro. I'll probably get the most worst reviews I've ever gotten on an episode because, hey, where are the tips? I want to know what to put in my subject line. I get that. But, you know, this. This whole podcast thing, creating content, it's a journey. And you were on one too. When you're creating content, you're trying to figure out, you know, what, what is it that's meaningful to put out into the universe? And this was meaningful, you know, to me. And so this idea of regret being worse than failure, I hope that somewhere in your brain it sticks in there. And you're probably already doing it. You probably could have taught me this lesson much earlier on in my life, but you all are awesome. Thanks for checking this out. And then back to horrible reality TV and all the other garbage next week and check you later. You did it. You made it to the end. But wait, the party is not over. Listen, I want to keep hanging out. Subscribe to this podcast and if it wasn't the worst podcast you've ever listened to, give it a five star review. Why not? But you know what? I want to do even more with you. Go to guru mediahub.com and we can partner there. You can find out about all of our free events, all of our stuff. And if you're epically bored, go to jschwedelson.com and we could stay connected. You could find my newsletter and everything else I got going on. Thanks for being here and hope you subscribe.
Do This, NOT That: Marketing Tips with Jay Schwedelson – Ep. 419
Episode Title: ❤️How I Met My Wife❤️ Regret is Worse Than Failure!⏳ Jay’s SCOOP
Date: September 26, 2025
Host: Jay Schwedelson
Presented By: Marigold
In this heartfelt and unconventional episode, Jay Schwedelson steps away from typical marketing tactics to share a life lesson that profoundly shaped both his personal life and professional approach: regret is worse than failure. Through the personal story of how he met his wife, Allie, Jay explores the impact regret can have and how taking even brief moments of courage can alter trajectories in life and business. Rather than offering a checklist of marketing hacks, Jay aims to inspire listeners to seize their moments and never settle for the "land of what ifs."
Timestamp: 00:20 – 02:10
Jay reflects on writing his book and the imposter syndrome that’s forced him to consider pivotal life moments.
Central theme: Realizing that "regret is worse than failure"—a personal mantra that’s transformed how he makes decisions, especially in moments of opportunity.
“Regret is worse than failure. And you can incorporate that into everything that you’re thinking about.” — Jay (01:08)
Timestamp: 02:11 – 08:37
Jay details his college years at the University of Florida, meeting Allie, and how both didn’t want anything serious at the time.
After graduation, they lose touch for a few years, but Jay frequently thinks about her, living with growing regret.
Spotting Allie happy with another man in Miami triggers deep regret—Jay realizes he let his chance slip by.
“The level of regret that set in with me was astronomical. I was beside myself.” — Jay (07:25)
Timestamp: 08:38 – 13:45
Sometime later, Jay unexpectedly runs into Allie at a bar in Fort Lauderdale. Despite her being on a date, he decides he “can’t let the opportunity pass by” and musters the courage to approach her directly.
With “10 seconds of bravery,” Jay asks for her phone number, despite feeling awkward and intensely vulnerable.
“I am not letting this opportunity pass by me. I need to tell her how I feel.” — Jay (09:31)
Allie, recognizing his sincerity, writes down her number (even as Jay admits to coming off intense).
Timestamp: 13:46 – 15:49
Jay ignores conventional dating “rules”, calls her the very next morning, and is relieved when the number is real.
They reconnect, and from then on, “have been together ever since.”
“No more regret. I’m all over this.” — Jay (14:59)
Timestamp: 15:50 – 17:40
The lesson solidifies: Key opportunities require just a short burst of courage, whether in personal relationships or business.
Jay affirms you don’t need to be brave all the time—just long enough to take the chance.
“You don’t need to be brave your entire life. You need to be brave for, like, 10 seconds.” — Jay (15:50)
Even if things don’t work out, acting spares you lifelong regret and self-torment.
“What if? That is torture. It is a torture chamber to live in the land of what ifs.” — Jay (16:53)
Timestamp: 17:41 – 18:30
On why this story matters to marketers:
“When you do the thing that’s uncomfortable, one of two things will happen... Either it’s going to work out, or it’s going to be an epic fail. But you’re not going to sit there in the land of what ifs.”
— Jay (16:11)
On vulnerability:
“You need to be brave for, like, 10 seconds. In that moment, you say, I could do this for 10 seconds.”
— Jay (15:53)
On the risk of inaction:
“It all almost didn’t happen.”
— Jay (02:27)
In this uniquely personal episode, Jay Schwedelson breaks from format to deliver a universal piece of advice: Don’t let regret define your choices. A short burst of courage is always less painful than “what if.” The lesson connects directly to marketing by encouraging listeners to act strategically and bravely in forging new relationships, pitching ideas, and seizing moments that can change careers—or lives.
Miss the marketing tips? Jay promises a return to marketing “chaos” and tactics in the next episode!