The Most Important Word is Yes

Summary

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Episode Summary: The Most Important Word is Yes

Podcast: Help Wanted
Hosts: Jason Feifer (Entrepreneur Editor-in-Chief), Nicole Lapin (Money Expert)
Release Date: October 9, 2025

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Overview

In this thought-provoking episode of Help Wanted, Jason Feifer shares a personal perspective shift on the power of saying "yes" versus "no." Drawing inspiration from writer Dave Eggers, Jason explores how embracing new opportunities—even those that feel uncomfortable or uncertain—can fuel personal and professional growth. The episode challenges listeners to reflect on their own tendencies to play it safe and invites them to reframe effort and participation as valuable accomplishments in and of themselves.

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Key Discussion Points & Insights

The Culture of "No" vs the Potential of "Yes"

• Jason admits to growing up defining himself by saying no:
  “I grew up saying no. Maybe you relate to this. I defined myself by what I wouldn’t do and who I wouldn’t hang out with. Those kids? Screw them. That music? Hate it. That party? Never.” (03:13)
• Context of the 'sellout' culture of the 1990s and 2000s, where authenticity was policed, and saying yes to mainstream success was seen as a betrayal.
• Jason describes how reading Dave Eggers’ essay challenged this mindset:
  “I thought, my life will not be defined by the things I say no to. It’ll be defined by what I try.” (05:44)

Dave Eggers’ Perspective on Saying Yes

• Eggers’ notable quote (read aloud by Jason):
  “...I really like saying yes. I like new things, projects, plans, getting people together and doing something, trying something, even when it’s corny or stupid. I am not good at saying no, and I do not get along with people who say no... When you die, and it really could be this afternoon, you will not be happy about having said no. You will be kicking your ass about all the no’s.” (04:14)
• The essay castigates a “no” mentality and celebrates open-minded, adventurous living—ultimately arguing that effort and new experiences shape a meaningful life.

Redefining Accomplishment: Effort Matters

• Jason challenges the notion that only achievements count:
  “But these things aren't fully controllable. Achievements are hard and slow. Goals may never be reached. These measurements slow our sense of personal growth. So here's an idea. What if saying yes is treated as an accomplishment by itself?” (06:05)
• Instead, effort—even participation—should be celebrated, much like a "participation trophy." He critiques the common backlash against rewarding effort, calling it “stupid.” (06:36)

Overcoming Fear and Rewarding Curiosity

• Jason relates this challenge to his kids:
  “I have two young boys... they frequently refuse to try new activities because they're convinced they won't like them. I would love to see them try anyway. Effort will open their worlds.” (06:44)
• Admits adults behave the same, often saying no out of habit or fear.
• Encourages listeners to list five things they've said yes to this year, regardless of outcome, and treat those as accomplishments. (07:20)

The Role of "No" and the Value of Selectivity

• Jason nuances the message: “Not everything is a yes. And that's okay. You should not say yes to everything. That's just unrealistic. You should say no to many things, just like I do every day.” (07:59)
• Key distinction: Saying no frees you to say yes to what matters most, but you must use that freedom intentionally.

The Urgency of Now

• Eggers’ wisdom on curiosity and seizing the moment:
  “I say yes because I am curious. I want to see things.” (08:27)
• Jason’s personal anecdote: Overcoming reluctance to drive three hours to see Eggers speak, leading to a lasting memory:
  “You only make memories by saying yes.” (09:14)

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Notable Quotes & Memorable Moments

• Jason Feifer:

  • “My life will not be defined by the things I say no to. It’ll be defined by what I try.” (05:44)
  • “When we celebrate yes, we incentivize saying yes. We create a positive feedback loop for ourselves.” (07:33)

• Dave Eggers (read by Jason):

  • “No is for wimps. No is for pussies. No is to live small and embittered, cherishing the opportunities you missed because they might have sent the wrong message.” (04:57)
  • “What matters is that you do good work. What matters is that you produce things that are true and will stand.” (05:12)
  • “I say yes because I am curious. I want to see things.” (08:27)

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Timestamps for Important Segments

• 03:13 — Jason shares his childhood mindset of saying no
• 04:14 — Dave Eggers’ perspective on saying yes, read aloud
• 06:05 — Jason reframes accomplishment as effort, not just achievement
• 06:44 — Jason discusses encouraging his kids (and adults) to try new things
• 07:20 — Exercise: List five things you said yes to this year
• 07:59 — The necessity and selectivity of saying no
• 08:27 — Eggers’ reflection on curiosity and yes
• 09:14 — Jason’s memory of meeting Eggers and the power of yes

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Conclusion

Jason encourages listeners to:

• Treat effort and the act of saying yes as accomplishments
• Be intentional in deciding what to say yes and no to
• Recognize that memories and personal growth are built on openness and curiosity

This episode provides both practical advice and philosophical inspiration for anyone seeking to break out of their comfort zone and live a more engaged, rewarding life—at work and beyond.

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]

I grew up saying no. Maybe you relate to this. I defined myself by what I wouldn't do and who I wouldn't hang out with. Those kids? Screw them. That music? Hate it. That party? Never. Then in college, I read an essay that changed my perspective. Dare I say it changed my life. Today, I want to share it with you, and I want to challenge you to think deeply about what you say no to, what you say yes to, and whether you have the balance right. Because it is so easy to say no to new ideas, projects, people, experiences. No is safe and comfortable. But in the right moments, yes is what makes all the difference. So let's rewind to the moment that changed everything. But first, some context you may not know, depending on how old you are. In the 1990s and early 2000s, culture was defined by a big question. Are you a sellout? In other words, have you abandoned your authenticity to make money? Punk bands, street artists, indie filmmakers. When these people started making real money, they their fans would scorn them as sellouts. I was an angsty teenager who believed in this. When a cool band signed a big record deal, I felt like they were abandoning me, that they were saying yes to things that we'd agreed to say no to. I know it sounds crazy, but trust me, this made sense back then. Then Dave Eggers came along. He was an obscure indie writer who became famous in 2000 thanks to his excellent memoir, a heartbreaking work of staggering genius. People accused him of selling out, too. Then he wrote a defiant response. I read it as a teenager, and it shook me to my core. Here is just a little bit of it. It was worth reading the whole thing, but here's just a little bit he writes the thing is, I really like saying yes. I like new things, projects, plans, getting people together and doing something, trying something, even when it's corny or stupid. I am not good at saying no, and I do not get along with people who say no. When you die, and it really could be this afternoon, you will not be happ about having said no. You will be kicking your ass about all the no's. You've said no to that opportunity, or no to that trip to Nova Scotia, or no to that night out, or no to that project, or no to that person who wants to be naked with you but you worry about what your friends will say. No is for wimps. No is for pussies. No is to live small and embittered, cherishing the opportunities you missed because they might have sent the wrong message later, he wrote. What matters is that you do good work. What matters is that you produce things that are true and will stand. I read that essay and again, you should Google it and read the whole thing. I read that essay and I thought, my life will not be defined by the things I say no to. It'll be defined by what I try. We often measure ourselves by our accomplishments. Did we achieve the thing? Did we reach the goal? But these things aren't fully controllable. Achievements are hard and slow. Goals may never be reached. These measurements slow our sense of personal growth. So here's an idea. What if saying yes is treated as an accomplishment by itself? We don't give ourselves enough credit for effort, and I think that's a shame. In fact, culturally, we even demonize celebrating effort. Think of all the people who trash participation trophies because they think it teaches kids that winning doesn't matter. That's stupid. I have two young boys, ages 6 and 10, and they frequently refuse to try new activities because they're convinced they won't like them. I would love to see them try anyway. Effort will open their worlds. Effort is rewardable. And this extends to adults, too. How many times have you said no because you were sure you wouldn't like something? What would have happened if you said yes instead? My guess? Some things would have sucked and others would have been revelatory. Isn't massive good worth a little bad? Try this exercise right now. Make a list of five new things that you said yes to this year. Stuff that required effort. Stuff you were unsure of. No matter how those things turned out, please think of them all as accomplishments. I'll be honest, as I think about this myself, I have fewer examples than I'd like. Yes, I've tried some new things this year. Said yes to activities I was unsure of. Took on some new projects. But now I'm thinking, could there have been more? Am I still playing it too safe? My list now feels like a motivator. It also feels like a reminder to keep adding more to that list because adding more will feel good. Look what we've done here. When we celebrate yes, we incentivize saying yes. We create a positive feedback loop for ourselves. But let's be clear. Not everything is a yes. And that's okay. You should not say yes to everything. That's just unrealistic. You should say no to many things, just like I do every day. If I said yes to every request I got, I would never have time for the things that I truly want to say yes to. That is the critical distinction. Saying no creates the opportunity to say yes. The word no buys you time, but it is up to you to spend that time wisely. Towards the end of Dave Eggers essay, he writes this. He says, I say yes because I am curious. I want to see things. I think about that so often. One day, if I am lucky, I will be 90 years old and it will be harder to see things. I'll be weaker, more tired. I'll need to say no a lot more. That means the time is now, right this very second, to see things. Just like the time at age 22 when Dave Eggers was speaking at a venue three hours from me. I said, nah, that's too far. And then I said yes. And I drove and I saw him speak and I waited on a long line to meet him and I took a very awkward photo and thanked him for the change he provoked in me. I will remember that forever. You only make memories by saying yes. 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 Lavoy. You want some help? Email our [e-mail] for the chance to have some of your questions answered on the show and follow us on Instagram, MoneyNews and TikTok MoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

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