The Cure for Regret

Summary

Help Wanted – “The Cure for Regret”

Podcast by Money News Network
Hosts: Jason Feifer & Nicole Lapin
Date: October 16, 2025

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Episode Overview

In this episode, Jason Feifer, Editor in Chief of Entrepreneur Magazine, dives deep into the all-too-familiar emotion of regret—especially as it relates to decisions at work, career, and business. He offers a psychologically-backed, practical method he calls “Declare It, Then Deflate It” to help listeners address and release their own professional regrets. Through personal stories and expert insight, the episode guides listeners in reframing regret as a universal and ultimately deflatable experience.

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Key Discussion Points & Insights

1. Introduction to Regret

• [03:12] Jason Feifer introduces the theme:
  “You missed an opportunity and you can't stop thinking about it...Whatever it is, you keep wondering if you'd made the right decision, would you be wealthier now? Happier? More successful? This thinking is not healthy.”
• Jason promises a practical solution to moving past regret, based on his own experiences.

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2. Jason’s Personal Story of Regret

• [04:05] Jason recounts a missed opportunity:
  • He declined a chance to be listed on a vastly popular newsletter's recommendation list because moving platforms sounded like too much hassle.
  • The other writer went on to amass over 1 million subscribers; Jason has 75,000.
  • He describes how this decision has haunted him, not just as a matter of lost followers, but lost opportunities.
  • Memorable quote [04:56]:
    “For me, this isn’t about vanity metrics… Newsletters drive significant opportunities, which is why I keep thinking about how much bigger my entire business would be if I'd only said yes to that guy.”

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3. Relating Through Shared Experience

• Jason discloses the regret to a friend, who shares an even bigger one:
  • The friend could have invested in Bitcoin at $250 in 2015, urged by a trusted client, but didn’t—and missed out on millions.
  • Quote [06:09]:
    “Here's the worst for me. A client told me to invest in Bitcoin in 2015. It was about $250 a bitcoin. Don't do the math. It's painful. Yeah, painful. Millions and millions of dollars worth of painful.”
• This helps Jason realize regret is universal and not uniquely his burden.

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4. “Declare It, Then Deflate It”: The Framework

Step 1: Declare It

• Voice your regret to someone else, breaking its isolating power.
• [07:05] Jason explains:
  “Regret is an isolating experience... When you share your regret with others, you discover that you're not alone.”

Step 2: Deflate It

• Seek out alternative “what ifs”—not just the best-case scenario.

• Reference to social psychologist John Petrocelli ([07:43]):

  • The danger is in counterfactual thinking: fixating on one positive alternate outcome and ignoring all other possibilities.
  • Reality: alternative outcomes often would have been neutral or even negative.
  • Jason reimagines his “what if”: Maybe switching platforms wouldn't have paid off, or the recommendation would have been brief, netting “mostly nothing.”
  • About Bitcoin: The friend could have sold early, missing the full upside.

• [08:45] Insightful point:
  “The thing we regret isn't real. It's just one possibility among many. And often it's not even the most likely outcome. The sure thing isn't a sure thing.”

Zooming Out Further

• Consider countless missed opportunities you didn’t even know about—like the unknown lottery numbers, chance elevator encounters, or forgotten ideas.
• [09:30] Jason concludes:
  “We cannot get lost in infinite what ifs. There is no point, no limit. It isn't real or productive. Our lives are the product of everything that came before, not the victim of it.”

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Notable Quotes & Memorable Moments

• Jason Feifer [04:56]:
  “For me, this isn’t about vanity metrics… Newsletters drive significant opportunities, which is why I keep thinking about how much bigger my entire business would be if I'd only said yes to that guy.”

• Jason Feifer [06:09]:
  “Here's the worst for me. A client told me to invest in Bitcoin in 2015. It was about $250 a bitcoin. Don't do the math. It's painful. Yeah, painful. Millions and millions of dollars worth of painful.”

• Jason Feifer [07:05]:
  “Regret is an isolating experience... When you share your regret with others, you discover that you're not alone.”

• Jason Feifer [08:45]:
  “The thing we regret isn't real. It's just one possibility among many. And often it's not even the most likely outcome. The sure thing isn't a sure thing.”

• Jason Feifer [09:30]:
  “We cannot get lost in infinite what ifs… Our lives are the product of everything that came before, not the victim of it.”

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Timeline of Key Segments

• [03:12] – Episode theme introduction: Regret at work and in business.
• [04:05] – Jason shares personal regret about missing a big newsletter opportunity.
• [06:09] – Friend’s Bitcoin regret story puts things in perspective.
• [07:05] – Step 1 of the framework: “Declare It.”
• [07:43] – Reference to John Petrocelli and counterfactual thinking.
• [08:45] – Step 2: “Deflate It” and the reality of alternate outcomes.
• [09:30] – Final reframing: Endless unknowable outcomes, futility of infinite what ifs, and the importance of moving forward.

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Takeaway

Jason’s “Declare It, Then Deflate It” gives listeners a practical way to process and lighten regret—by sharing it with others and zooming out to consider more realistic, less glamorous alternate outcomes. The power of this approach is in normalizing regret and breaking its emotional grip—reminding us that our lives are shaped by a vast tapestry of choices, not defined by the single ones we didn’t make. The episode ends on an empowering note:
“No regrets. Just make the decision that’s right for you.”

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For more tools, Jason’s newsletter “One Thing Better” is available at onethingbetter.email, offering additional weekly actionable career insights.

Transcript

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[A]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of.

[B]

Entrepreneur Magazine, and I'm money expert Nic Happen. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[A]

And on Thursdays I give you one way to improve your work and build a career or company you love.

[B]

And it starts now.

[A]

You missed an opportunity and you can't stop thinking about it. Maybe it was big and life changing, or small and nagging. Whatever it is, you keep wondering if you'd made the right decision, would you be wealthier now? Happier? More successful? This thinking is not healthy. So today I'm going to show you the most powerful way to let it go. I call it declare it, then deflate it. It's a way to make your regret feel smaller and less consequential by comparing it against all the other things that could have been. But before I explain exactly how it works, I'm going to share a decision that has haunted me for years and how I just started to feel better about it. A few years ago I met a fellow newsletter writer. I also write a newsletter. I'll tell you about that. More later. I met a fellow newsletter writer who'd built an impressive audience. We had talked about ways to support each other and then he made me this really nice offer. He said he would add me to his recommendations list, which is to say whenever someone subscribed to his newsletter, they'd get a pop up recommendation to subscribe to mine. But there was a problem. He was on one newsletter platform and I was on another. To make this work, I would need to switch to his platform and that sounded like a hassle. So I thanked him and passed. Then his popularity exploded. He is now one of the most successful newsletter writers with more than 1 million subscribers. Meanwhile, I have 75,000 subscribers, which I am very proud of and if you are one of them, then thank you very much. But it is a fraction of what he could have gotten. For me, this isn't about vanity metrics by the way Newsletters drive significant opportunities. Which is why I keep thinking about how much bigger my entire business would be if I'd only said yes to that guy. I have kept this story to myself for years because it seems frivolous and silly, like oh, woe is me. But last week, as I texted with a friend who also writes a newsletter, I told him about this whole thing. And and his response really took me back. He said, here's the worst for me. A client told me to invest in Bitcoin in 2015. Oh no, I said. And then he replied it was about $250 a bitcoin. Don't do the math. It's painful. Yeah, painful. Millions and millions of dollars worth of painful. And this client, he told me about it. I know who that client is. Was a very savvy investor, very trustworthy, very tech insidery. It was totally worth taking that person seriously. So when my friend said this, something switched in my brain. You know, I suddenly realized two things. Number one, I am not the only person to miss a big opportunity. And number two, even if I said yes to that newsletter writer, do I really know what would have happened? That's when I came up with a helpful framework for countering this regret. Declare it, then deflate it. Let us break it down here. Step one Declare it. Regret is an isolating experience. It makes us feel uniquely foolish and short sighted and unable to see around corners, as if we fell behind while others sprinted ahead. So we need to counter that. We need to tell someone. When you share your regret with others, you discover that you're not alone. You didn't fall behind in the race, and everyone else fell behind too. We are all behind where we wish to be. But this is just the start, because the next step is even more important. Step 2 Deflate it. When we regret something, we often fall into a trap called counterfactual thinking. It's what happens when you imagine alternate versions of reality and then beat yourself up for not making them real. For example, you might regret missing an opportunity. And now you imagine how much happier or wealthier you could have been. The imagined what if is counterfactual thinking? I have done it. I'm sure you have. And I wanted to know. How do I get this out of my head? That is why I called social psychologist John Petrocelli at Wake Forest University, who studies this stuff. This is going to sound a little funny, he told me, but the trick is to consider additional alternatives, to consider other counterfactuals. We often imagine how things could have Gone perfectly. But of course, there's no guarantee of that. Outcomes will vary, and many outcomes are neutral or negative. For example, I could have switched to that guy's newsletter platform, and then he could have recommended me for a month and moved on. And that would have meant that my move to the platform was a lot of work for mostly nothing. Also, my friend could have invested in Bitcoin at $250, and then when Bitcoin doubled in price to $500, which would have seemed amazing, amazing back then, he could have sold and his earnings would have been modest. Honestly, these outcomes are more realistic. The thing we regret isn't real. It's just one possibility among many. And often it's not even the most likely outcome. The sure thing isn't a sure thing. So here's what we've done so far. Consider, number one, we had a regret that was stuck in our head. And then number two, we shared it with someone. And then number three, we compared it against all other outcomes. And in other words, we kept zooming out, out of our head, out past our friends, out into the world. Now I want to zoom out even further. I want you to imagine all the missed opportunities that you don't even know about. Did you, I don't know, play the winning lottery numbers on the wrong week? Were you on an elevator a foot away from someone who could change your life and you didn't notice? Did you pursue an idea you've long since forgotten about, but that would have made you millions if you just stuck with it? If this sounds stupid, that is the point. We cannot get lost in infinite what ifs. There is no point, no limit. It isn't real or productive. Our lives are the product of everything that came before, not the victim of it. So if you're carrying around a regret, it is time to let it out. Place it in its rightful place somewhere in the middle of an endless spectrum of unknowable outcomes where some are much greater and some are much worse. But none of them should hold you back from the decisions you still have the great privilege to make today and tomorrow and for all the days after. And by the way, I did mention my newsletter earlier, so that came from my newsletter. It is called One thing Better each week. One way to be more successful and satisfied and build a career or company that you love. You can get it at one thingbetter email. That is a web address. Plug it into a browser. One thingbetter email and. And what you'll really get is the newsletter that I read here on Help wanted, but a few weeks early with some other goodies that I include. So stay tuned to Help Wanted for all this great stuff, but also onethingbetter email gets it to you faster. Either way, just make the decision that's right for you. No regrets. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[B]

Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoie. You want some help? Email our helpline@help wantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagramoney News and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

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