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This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of.
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Entrepreneur Magazine, and I'm money expert Nicole Lapin On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.
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And on Thursdays, I give you one way to improve your work and build a career or company you love.
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And it starts now.
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I just asked 75,000 people this question. What big opportunity did you miss that you now regret? And wow, I got a lot of great answers. Today. I'm going to share some of them with you with a very specific purpose. I want you to feel better about whatever you regret. It's part of a tactic that I shared on the podcast last week. So quick recap on that. You can go back and listen or just hear this. Regret if you 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. So that's today's project to share and feel less alone. What I did is I asked my newsletter subscribers. That's the 75,000 number. I have 75,000 newsletter subscribers. I asked them to fill out this form sharing this regret, this thing that they feel like they missed out on. And what came back was so interesting and honest and revealing. And that is what I'm going to share with you today. I'm going to divide them up into five themes, themes of regret. And I'll share a couple examples in each one and then also some thoughts that I have after each one. So let's get into it. Theme number one. The theme of regrets. It is this. Giving up on a winning idea. I heard so many versions of a story that goes like this. I had an amazing idea and someone else succeeded with it. Not that somebody stole it, just that, you know, somebody else did the thing that you had the idea for. Here are two examples. Jason said this. I had an idea for an outdoor product. I started developing it but didn't get far. A couple years passed and I was watching Shark Tank and I saw that same concept being pitched to the sharks. I couldn't believe it. Now that product is sold on Amazon and I regret not developing it sooner or getting it to market. I feel like I missed out on millions. And now here's Patrice who says years ago I started a restaurant review site as a hobby. It got tons of visits, but I had no idea I could make a living off of it. My day job was busy so I stopped reviewing restaurants. Fast forward and another company launched the same concept and was acquired by millions. I still die a little inside anytime someone brings it up now. Thank you Jason. And Patrice, here is my take on this. I have my own version of this exact thing. When I was in high school, I came up with a story about a man who discovers that everything around him is a TV show. I never did anything with this idea. And then the Truman show came out. If you have a similar regret, then here's what to this is insanely common. There's even a term for it. It's called multiple discovery across time. Multiple independent people tend to develop the same world changing ideas at roughly the same time. Both Isaac Newton and Gottfried Wilhelm Leibniz, I think is how you pronounce that. Independently developed the principles of calculus in the late 1600s. Alexander Graham Bell and Elijah Gray. Again, I think that's how you pronounce that. Filed patents for the telephone on the same day in 1876. Charles Darwin and Alfred Russel Wallace independently conceived of natural selection in the 1850s. And on the list goes forever. Ideas are great, but they are not unique. Even the law recognizes this. It's why you can't patent an idea. You can only protect your unique execution of that idea. So do not beat yourself for this. Even if you pursued your idea, that doesn't mean you would have been the winner. Many others likely had it too. All this means is that you are a smart thinker and that will continue to serve you well. Now here is the next theme of regret. Our contradictory regrets. Here are two people who regret the exact opposite things. Ready? Justin says I graduated college in 2023 with no debt and an opportunity to work a full time job at a mid sized new firm. But the firm's industry did not align with my career goals. So I took a risk to attend NYU for my Master's, taking out a loan to cover my tuition. I have graduated now but have yet to secure a job in my desired field. Meanwhile, everyone from my undergrad is enjoying the start of their professional careers. I feel behind and now here's Chris. Chris says I was an undereducated, socially isolated child and attending college was my first real school experience. I felt thrived there and some professors encouraged me to go on to grad school. I even met with the chair of the department I wanted to be part of. Then I opted to stay at my job and not go to grad school. I have regretted it ever since. Now I'm not even in that job anymore. Oof. All right, now here's my take. Justin regrets going to grad school. Chris regrets not going to grad school. But let's be realistic about what happened here. Justin could have declined grad school, took that unsatisfying job, and today might be employed, but maybe miserable. Chris could have attended grad school but would now be saddled with debt and no job. The lesson here is this. Whatever you regret doing, someone else regrets not doing it. They regret exactly the opposite of the decision that you made. No decision is obvious. No path is predictively correct. You couldn't have known what was right, and in the future, the wrong decision might turn out to be the right one anyway. Now here's number three. Theme Number three the Missing Money There were so many regrets about money. Here's just a sampling. CC says I was CEO of a startup and had the opportunity to make a strategic investment into a company with three employees. It is now worth $22 billion. Natalie says I passed up on Apple stock in 2004 because I thought a dollar a share was too much. Ben says I could have bought a 3 bedroom 1500 square foot flat in Chelsea, New York City for 800,000 dol. I passed because the area was a little beaten down. Would have sold that 10 years later for $2.5 million. Now here's my take. When I regret something, I try holding myself to this standard. Did I make a rational decision based on the information I had at the time? If the answer is yes, then I can't fault myself. In the examples above, every decision was rational. There was no way to predict success. Should you sometimes take risks? Should you sometimes do the irrational thing? Yes and yes. But you can't do it all the time or you will invest in nonsense and run out of money. All life is a form of gambling. We can't regret having played and lost. Now here's theme number four. It's the what if stories. I heard so many sliding doors. Moments when life could have taken a different turn. Here's an example. Jim said this. A friend of mine, a billionaire, discouraged me from investing further in a business partnership I was in because he didn't like my partner. He 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. S says this the year I graduated college, my professor offered me a university lecturer gig in my hometown. He was going on a year long sabbatical and I could fill in. I assumed these opportunities would always come, so I said no because I wanted to attend art school overseas. My parents were mortified. After four more years of study, I finally entered the workforce and feel stunted compared to my peers. And Bill says as a decent high school basketball player. I was recruited by Coach K to attend West Point. I declined. The next year he left for Duke. I could have been on his first graduating class and a foundational player as he built that epic program for non basketball fans. Coach K is a legendary college coach and his Duke program was dominant for decades. And now Copper says this I turned down a fantastic job opportunity that involved moving to Italy for a minimum of three years and a huge salary increase because my ex husband wouldn't relocate with me. He and I divorced a few years later because he said I outgrew him. I so wish I had said yes. Never got over it. Now here's my take. I get it. How can you not obsess over these paths not taken? But if you have a what if story, then please remember this last week I talked about counterfactual thinking. We regret not taking an action, but then because we imagine the perfect outcome of that action, we beat ourselves up for not living our dream right? We don't do a thing. And then we imagine how the thing could have gone. And then we're just stuck comparing how the thing could have gone to what actually happened in our life. But that is not realistic. So let's start imagining other possible scenarios. Jim's friend could have funded a new business. So Jim imagines that the business would have succeeded, but because frankly, perfect outcomes do not always happen. I mean, let's revisit some of these things. Jim's friend Jim's billionaire friend could have funded a new business. And so Jim is right now imagining that the business would have succeeded and S could have taken that university gig. So S assumes it would have led to a wonderful career. And Bill imagines being on Coach K's Duke team and so on. But Jim's billionaire friend could have funded a crappy business and then accused Jim of wasting his money. S could have taken that job and now feel stuck in their hometown. Bill could have gotten cut from Coach K's team, might not have even made it to Duke. All entirely possible. What ifs are actually just us imagining the best case scenario. And the best case scenario is, I don't know, like a small percentage chance of what could have actually happened. So imagine finishing the sentence what if, in a more positive way. What if I dodged that bullet? What if I learned something critical? What if I'm on the right path? What if indeed. Now here's theme number I wasted so much time. This theme resonates with me personally the most. Here are a couple examples. I stayed at the same job for 10 years because I thought they would recognize how great my work is and reward me for it. Ajay says. I missed out on so much free learning at my previous job. If I had been just more forward and asked for opportunities and kept an open mind, I would have been more experienced now, Jane says I missed out on being light hearted and partying when I was the age where you would start those experiences. Now here's my take Jane. That was me too. I was insecure in high school, then I was in a long term relationship through college and most of my 20s. I just never let loose when everyone else did. So here's what I've learned for myself which I hope you all will take to heart. No matter what you regret, your time hasn't passed. Your time is now. Remember a few weeks ago when I talked about saying yes to more things? That's what I was talking about on the podcast. In some ways, I guess that's how I make up for lost time. But I don't see it that way. I just see it as a way to live the life that I want. Now I travel a ton. I optimize for experience. I'm on a constant quest to meet new people. In my wife, I have found someone equally down for great adventures. The past has served its purpose perfectly. Someone said on a wonderful recent episode of the podcast Heavyweight. That is a great show by the way. You should check it out. But most people are cherry pickers, that person continued. Well, I wish that that would have changed. Or I wish that this were different. No, there's only one purpose to the past and that's to bring you and me right here and now. That's what that person said. I love that quote. True words. And now, after all this, here's my favorite regret of all. First, I just want to say thank you to everyone who sent in regrets. I am so honored that you shared them with me and that you gave me the permission to share them here. I read and thought about every single one, but here's the one that stood out to me the most because it's the only one with a complete ending. Most regrets hang in the air like an unfinished sentence. We never truly know what they could have been, but this woman knows. Here's her regret. KGJ says this I was living with my mom after graduating from college, where I spent four years as a varsity softball starter. One day my mom read in the paper about a local audition for a movie where they were looking for girls who could throw a baseball and suggested that could mean me because it was my mom and I was so busy waiting tables at Applebee's. And maybe a little fear, too. I declined to take a shot at being an extra in what became A League of Their Own. Oh, what could have been. But years later, I told a colleague at work about this and 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. And now here's my take one more time. I love this so much. Kgj. 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 good can become bad and the bad can become good, and it is simply impossible to predict what will actually matter in life. So 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. And by the way, I'd mentioned that this survey was originally conducted through my newsletter. My newsletter 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 by going to One thingbetter email. Again, that's a web address, so just plug it into a browser. One Thing Better email. I read them here every Thursday on Help Wanted, so you don't need to subscribe to the email. But I think you would like it because you get it a few weeks early and you get it in a different form. And there's always a bunch of other stuff that I put in there that doesn't make it to the show. Either way, you know, don't regret your decision. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
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Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoy. You want some help? Email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagramoneynews and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?
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Oh, I didn't sign up for that.
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All right, well, talk to you soon.
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.
(Start: 04:10)
Many respondents regret abandoning promising ideas that others later succeeded with:
Host Reflection:
Takeaway:
(Start: 06:30)
Regrets often cancel out—people can regret opposite choices on the same path:
Host Reflection:
Takeaway:
(Start: 08:09)
Common regrets are missed chances for wealth:
Host Reflection:
Takeaway:
(Start: 10:01)
Sliding-door moments where a different choice might have changed everything:
Host Reflection:
Takeaway:
(Start: 13:37)
Regret around time spent in the wrong place or not seizing life:
Host Reflection:
Takeaway:
(Start: 16:03)
A respondent, KGJ, declined to audition as an extra for the movie "A League of Their Own":
Host Reflection:
Takeaway:
On the universality of regret:
On multiple discoveries:
On decision-making:
On rationality and risk:
On reframing the past:
On moving forward:
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.
Want more?
Jason’s newsletter, One Thing Better, delivers more stories and advice every week. See OneThingBetter.email to subscribe.