Episode Summary: "What 75,000 People Regret"

Help Wanted – Money News Network
Hosts: Jason Feifer, Nicole Lapin
Date: October 23, 2025

Overview

This episode of Help Wanted is a thought-provoking exploration into the universal experience of regret, with Entrepreneur Magazine editor-in-chief Jason Feifer sharing responses from a survey of his 75,000 newsletter subscribers. The episode dives into the regrets people harbor about missed opportunities and choices, with the goal of making listeners feel less alone and reframing how we view our past "mistakes." Jason organizes myriad responses into five themes, reflecting on each to offer practical insight and comfort to listeners facing their own regrets.

Key Themes & Discussion Points

1. Giving Up on a Winning Idea

(Start: 04:10)

• Many respondents regret abandoning promising ideas that others later succeeded with:

  • Jason: “I had an idea for an outdoor product... A couple years passed and I saw that same concept being pitched to the sharks [on Shark Tank]... now that product is sold on Amazon and I regret not developing it sooner.” (04:27)
  • Patrice: “Years ago I started a restaurant review site as a hobby... I stopped reviewing restaurants... another company launched the same concept and was acquired by millions.” (04:55)

• Host Reflection:

  • Jason shares his own “Truman Show” regret, never developing a story idea before the film released.
  • Quote: “If you have a similar regret… this is insanely common... It’s called multiple discovery across time.” (05:39)

• Takeaway:

  • Brilliant ideas often arise independently and simultaneously across different people ("multiple discovery"). Success is more about execution than originality of thought.

2. Contradictory Regrets

(Start: 06:30)

• Regrets often cancel out—people can regret opposite choices on the same path:

  • Justin: “I graduated college in 2023... took a risk to attend NYU for my Masters... have yet to secure a job in my desired field. I feel behind.” (06:50)
  • Chris: “...professors encouraged me to go on to grad school... I opted to stay at my job and not go... I have regretted it ever since.” (07:19)

• Host Reflection:

  • “Justin regrets going to grad school. Chris regrets not going to grad school... No decision is obvious. No path is predictively correct.” (07:38)

• Takeaway:

  • For every regret about one choice, someone else regrets the opposite. The "right" path can only be known in hindsight.

3. The Missing Money Opportunities

(Start: 08:09)

• Common regrets are missed chances for wealth:

  • CC: “I was CEO of a startup and had the opportunity to make a strategic investment... it is now worth $22 billion.” (08:20)
  • Natalie: “I passed up on Apple stock in 2004 because I thought a dollar a share was too much.” (08:36)
  • Ben: “Could have bought a 3-bedroom flat in Chelsea [NYC] for $800,000... would have sold that ten years later for $2.5 million.” (08:44)

• Host Reflection:

  • Jason suggests evaluating decisions by whether they were rational given information at the time:
    • “If the answer is yes, then I can’t fault myself... There was no way to predict success.” (09:13)
    • “All life is a form of gambling. We can’t regret having played and lost.” (09:52)

• Takeaway:

  • Prudent risk-taking is necessary, but hindsight bias should not cloud how we view smart decisions that didn’t work out.

4. The “What If” Stories

(Start: 10:01)

• Sliding-door moments where a different choice might have changed everything:

  • Jim: “A billionaire friend offered to help me start a business of my own... I didn’t accept. My partner later betrayed me and it nearly left our family in ruin.” (10:18)
  • S: “My professor offered me a university lecturer gig... I said no because I wanted to attend art school overseas... I feel stunted compared to my peers.” (10:48)
  • Bill: “Was recruited by Coach K to attend West Point, I declined... could have been on his first graduating class [at Duke].” (11:11)
  • Copper: “Turned down a fantastic job opportunity in Italy because my husband wouldn’t relocate. We divorced a few years later... Never got over it.” (11:34)

• Host Reflection:

  • Jason stresses that we tend to imagine alternate paths only working out perfectly:
    • “What ifs are actually just us imagining the best case scenario... The best case scenario is... a small percentage chance of what could have actually happened.” (12:40)
    • “Imagine finishing the sentence ‘what if’ in a more positive way. What if I dodged that bullet? What if I learned something critical?” (13:05)

• Takeaway:

  • Our imagined alternatives are rarely as perfect or certain as we think; reality is always messier.

5. I Wasted So Much Time

(Start: 13:37)

• Regret around time spent in the wrong place or not seizing life:

  • “I stayed at the same job for ten years because I thought they would recognize... and reward me for it.” (13:44)
  • Ajay: “I missed out on so much free learning at my previous job. If I had been just more forward and asked for opportunities... I would have been more experienced now.” (13:57)
  • Jane: “I missed out on being light-hearted and partying when I was the age where you would start those experiences.” (14:15)

• Host Reflection:

  • Jason admits: “That was me too. I was insecure in high school... just never let loose when everyone else did… No matter what you regret, your time hasn’t passed. Your time is now.” (14:22, 14:58)
  • He quotes a guest from another podcast: “There’s only one purpose to the past and that’s to bring you and me right here and now.” (15:38)

• Takeaway:

  • It’s never too late to live differently; regrets about lost time can inspire positive change today.

6. A Regret With a Twist: Seeing "What If" Play Out

(Start: 16:03)

• A respondent, KGJ, declined to audition as an extra for the movie "A League of Their Own":

  • “...years later I told a colleague... they had a friend who did attend those auditions, and that person ended up being Madonna’s bitch for a year. Those were her words. So did I want that too, or did I dodge a bullet? Who knows? But it makes me laugh and remember how much I love my life, regrets and all.” (16:49)

• Host Reflection:

  • “You got to see the path your life could have taken, and it was just as complex and unpredictable as the life you actually got to live... Big moments can mean nothing. Small moments can change our lives... The best that we can do is carry forward with gusto, making the most of our time and living as if there’s nothing to regret.” (17:13)

• Takeaway:

  • Sometimes seeing the reality behind a “missed opportunity” reveals it wasn’t the golden path we imagined.

Notable Quotes & Memorable Moments

• On the universality of regret:

  • “Regret is isolating. It makes us feel uniquely foolish and short sighted. But when we tell someone our regret, we discover that we’re not alone because everyone feels behind in some way.” (03:26)

• On multiple discoveries:

  • “Ideas are great, but they are not unique. Even the law recognizes this. You can’t patent an idea. You can only protect your unique execution of that idea.” (05:56)

• On decision-making:

  • “Whatever you regret doing, someone else regrets not doing it... In the future, the wrong decision might turn out to be the right one anyway.” (07:38)

• On rationality and risk:

  • “All life is a form of gambling. We can’t regret having played and lost.” (09:52)

• On reframing the past:

  • “There’s only one purpose to the past and that’s to bring you and me right here and now.” (15:38)

• On moving forward:

  • “The best that we can do is we can carry forward with gusto, making the most of our time and living as if there’s nothing to regret.” (17:22)

Timestamps for Key Segments

• Regret as universal experience: 03:02–04:10
• Giving Up on a Winning Idea: 04:10–06:30
• Contradictory Regrets: 06:30–08:09
• Missing Money: 08:09–10:01
• The “What If” Stories: 10:01–13:37
• Wasted Time: 13:37–16:03
• A Regret With an Ending: 16:03–17:41

Closing Tone & Message

The episode ends with empathy, humor, and reassurance. By exposing the inner doubts of so many, the show dismantles the myth of the perfect, mistake-free path. Regret is reframed as not only common, but also surmountable; our next move, not our last mistake, defines us.

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