Help Wanted – “The Cure for Regret”

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

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.

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.

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.”

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.

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.”

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.”

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.

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.”

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