Take People Up on Their Offer

Summary

Help Wanted — "Take People Up on Their Offer"

Podcast: Help Wanted
Hosts: Jason Feifer (Entrepreneur Editor-in-Chief), Nicole Lapin (Money Expert)
Date: October 30, 2025
Episode Purpose:
Jason Feifer solos this Thursday edition to discuss a surprisingly common mistake professionals make: failing to follow up when others offer help or opportunity. He explores why we do this, shares real regrets from listeners, and offers practical strategies to turn offers into career-changing moments.

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Main Theme

Don’t Miss Out — Take People Up on Their Offers
Jason Feifer explores how hesitancy and self-doubt often prevent us from following up when someone extends an offer, and how overcoming this can lead to real growth and unexpected opportunities.

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Key Discussion Points & Insights

1. A Personal Story: Taking Up Jimmy Fallon’s Offer

• [03:23] Jason recounts interviewing Jimmy Fallon for Entrepreneur Magazine. At the end, Jimmy invited him to reach out with any follow-up questions.

• Initially, Jason felt too guilty to take Jimmy up on his offer, but later realized he needed to ask a crucial question.

• Despite his reservations, Jason reached out. Jimmy’s reaction was both surprising and affirming.

  “Are you kidding? I always invite people to follow up and you’re the only person to do it. That tells me you’re thorough. And thorough people are the people I want to talk to.”
  — Jimmy Fallon to Jason Feifer ([04:44])

  Insight:
  What Jason thought would be an imposition actually increased Jimmy’s respect and willingness to engage.

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2. Listener Regrets: The High Cost of Not Following Up

Jason shares two poignant regrets submitted by his readers, illustrating how failing to act on an offer can leave lasting what-ifs.

• Shannon’s Story:
  Shannon always wanted to work with tigers. The owner of a tiger show told her to write a letter explaining her passion, promising, “If it’s compelling, I will bring you on my team.” Shannon never wrote the letter.

  “I regret it every day.”
  — Shannon ([05:35])

• BP’s Story:
  BP, an aspiring clarinetist, was praised by a Grammy-nominated violinist who offered to play together again. BP never reached out, soon gave up on music.

  “Could that have been the big break I was looking for? ... I'll never know.”
  — BP ([06:07])

  Insight:
  Failing to respond to genuine offers can permanently close doors to life-changing opportunities.

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3. Understanding the Root Cause: “I Thought They Were Just Being Nice”

• Many ignore offers because they fear the offer isn’t sincere.

• Experiences with insincere offers teach us to be skeptical and avoid risking disappointment.

  “We have all been burned before ... Politeness masquerades as genuine interest. And this has taught us not to trust offers of help.”
  — Jason Feifer ([06:40])

  Insight:
  The skepticism is so ingrained that we rationalize inaction as protecting ourselves, but it only guarantees lost possibilities.

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4. Reframing “Being Nice”

• Some may occasionally extend a polite but insincere offer; others are waiting for your initiative.
• Jason challenges the narrative that declining to follow up is a form of self-preservation, arguing it’s actually a way of undervaluing yourself.

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5. Two Key Questions Before You Hesitate

Jason offers a practical decision framework.

• Question 1: If they’re lying, what’s the worst that could happen?

  • Most likely: you get ignored, or someone politely declines. The risk is minimal compared to potential gain.

• Question 2: What could boost their enthusiasm for you?

  • People appreciate specificity and initiative. It’s better to propose clear next steps than to ask, “How can you help me?”

  “Take the lead, do the planning, have the ideas and calibrate. Start slow…”
  — Jason Feifer ([08:01])

  Practical Advice:

  • Be specific in your ask.
  • Don’t overburden—start with a small request.

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6. The Math of Following Up: Why It’s Worth the Risk

• Even if 9 out of 10 offers are insincere, all it takes is one “yes” to change the trajectory of your career or life.

  “Isn’t it worth nine ignored emails to get the one connection that could change everything?”
  — Jason Feifer ([08:48])

  Memorable Analogy:

  • Think of following up as a numbers game: the upside far outweighs the potential downsides.

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7. Final Motivation: Assume You’re Worth Their Time

• Jason closes with a mindset shift:

  “We need to stop believing that we’re not worth spending time with … People are genuinely interested in you, and that’s because you are genuinely interested. You are worth their time and their attention and their partnership. So take people up on their offers.”
  — Jason Feifer ([09:23])

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Notable Quotes & Moments

• Jimmy Fallon’s reaction:

  “You’re the only person to do it. That tells me you’re thorough. And thorough people are the people I want to talk to.” ([04:44])

• Listener’s core regret:

  “I regret it every day.” — Shannon ([05:35])

• Powerful insight:

  “Politeness masquerades as genuine interest. And this has taught us not to trust offers of help.” — Jason ([06:40])

• Encouragement to act:

  “Trying is worth it.” — Jason ([07:35])

• Math analogy:

  “If you don’t follow up … you avoid nine embarrassing interactions … and you miss out on something life changing … If you do, you get ignored nine times, but you’ll also make the connection that could change everything.” — Jason ([08:27])

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Key Takeaways

• Don’t rationalize away opportunities out of fear or self-doubt.
• Sincere offers require action and initiative—be specific, make it easy for others to help.
• Even if most offers don’t pan out, the one that does could be career-defining.
• Assume you are worth others’ time and attention—act accordingly.

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[09:23] — Episode Wrap Up

Jason sums it up: You are worth partnering with. Take people up on their offers—you’ll never know what’s possible if you don’t try.

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For Listeners Who Haven’t Tuned In

This episode delivers an honest, relatable examination of a universal work (and life) hangup. Combining Jason’s personal missteps, powerful listener stories, and a step-by-step mindset shift, it provides both empathy and practical advice for anyone hesitating at the next fork in their professional journey. If you’re waiting for a sign to act—this is it.

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 Nicole Lapin. 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.

[A]

Someone made you a great offer. Maybe they want to help you or they want to connect you with someone, or they want to discuss an opportunity, but you did not follow up. I ask you why not? Today I'm going to show you why this is one of our biggest mistakes and how taking people up on their offers can accelerate your success in ways you never imagined. But first, I'll tell you about the time that I made this mistake with one of the world's most famous comedians. I just shared this story on the Skinny Confidential big podcast, Skinny Confidential. Hello, anybody who listened to Skinny Confidential and then came over to Help Wanted. It's nice to have you here. So, quick recap. A few years ago I interviewed Jimmy Fallon for the COVID of Entrepreneur Magazine. We talked for like, I don't know, an hour and a half or two hours. It was really great. And then at the very end as I'm leaving, he shakes my hand and he says, hey, if you have any follow up questions, you know, you're writing the story and you're just thinking, ah, I wish I had asked Jimmy that. Just don't hesitate to reach out. And I said thank you Jimmy, I really appreciate that. But I'm not gonna do that because you've already been so generous with your time and I don't want to take any more of it. But then I went to write the story and I got towards the end and I realized I really did have a critical follow up question. There's something that would have just been so much better if I could ask Jimmy one question. And I agonized over this because I didn't want to annoy Jimmy. I had already taken so much of his time. I already told him I wouldn't take any more, but it was important and he did offer. So I asked to follow up. He called me about A week later and I began by apologizing. I said, jimmy, I am so sorry to take more of your time. And his response floored me. He said, are you kidding? I always invite people to follow up and you're the only person to do it. They that tells me you're thorough. And thorough people are the people I want to talk to. In other words, I thought asking for his time was bad, but he thought it was good. And I would have never known unless I took him up on his offer. As you might recall, I recently asked people to tell me their regrets. We aired something about that last week on Help Wanted. And many of the regrets were premised on not following up. Like these two regrets that I heard from readers of my newsletter. Shannon told me this. She said she always wanted to work with tigers, and she once met the owner of a tiger show who told her, write me a letter, tell me why you want to work with tigers, and if it's compelling enough, I will bring you on my team and teach you everything I know. Shannon never did it. I regret it every day. She told me. Here's another one. BP was an aspiring clarinetist. She performed one night and a Grammy nominated violinist told her, you are a fabulous player. We should play together again sometime. But BP never reached out and soon gave up on music. Could that have been the big break I was looking for? BP asked me. I'll never know. I have done many versions of this, by the way. I have ignored invitations from famous people, from incredible potential partners, and back when I was single and dating. Ugh, come on, let's not even talk about it. So before we fix this problem, we must address its root cause. Why do we do this to ourselves? BP explained it simply and perfectly. Here's why she didn't reach out to that violinist. She said, I thought she was just being nice. Yes, it is that funny and strange phrase, just being nice. I thought they were just being nice. We have all been burned before, so I get it. Someone said we should do this again, but they never called. Or colleagues said, I'm happy to help, and then ignored when you asked too many times. Politeness masquerades as genuine interest. And this has taught us not to trust offers of help. If we don't follow up, then we won't be disappointed or worse, feel foolish. But why do we call that being nice? That's not nice. When somebody says they're going to do something and they don't want to do it, that's the opposite of nice. That's. I don't know, it's deceptive, confusing. Now, look, I know this is emotionally complicated. Maybe those people wanted to help, but they didn't have the time. Or they didn't want to make things awkward by saying that they didn't want to help. Or they wanted to help a little, but not a lot. Still, the point is, you won't know any of that unless you try. And trying is worth it. So here's how to take people up on their offer. Are you hesitating to follow up with someone right now? Before you chicken out, please ask yourself these two questions. Question number one. If they're lying, what's the worst thing that could happen? Truly, what's the worst that could happen? Could they not respond when you follow up? Could they say they're busy? Could they dial back their offer? Is that really so bad? And now here's question 2. What could boost their enthusiasm for you? Here's what I've learned. Many times, people really are making genuine offers, but they're also expecting some upfront effort from you. For example, someone tells you, I'd be happy to help, you should not reach out and say, so where do we begin? How are you going to help me? You should say instead, based on your expertise, here are three specific things that I would love your feedback on and we're going to get it done in an hour. In other words, take the lead, do the planning, have the ideas and calibrate. Start slow. Maybe someone is happy to help, give you writing advice or whatever, but they don't have time to read your whole novel. Or they'll take a look at your pitch deck, but they can't introduce you to every investor they know. If they're being nice, we must be nice. In return, here's how you should think about it. Some math that could motivate you. Let's say 10 people make you an offer and now let's say nine of them are just being nice and one of them could change your life. What happens if you don't follow up with these people? Well, if you don't follow up with them, then you avoid nine embarrassing interactions, which is great. And you miss out on something life changing that you never even knew. And what happens if you do follow up? Well, you might get ignored nine times, which will sting. That's going to be annoying. But you'll also make the connection that could change everything. Doesn't this math seem worth it? The truth is, the solution to this problem starts with us. We need to stop believing that we're not worth spending time with. Let's start with a different assumption. Here it is. People are genuinely interested in you, and that's because you are genuinely interested. You are worth their time and their attention and their partnership. So take people up on their offers. Otherwise, you'll never know what's on the other side of it. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[B]

Pfeiffer, and me, Nicole Lapman. Our executive producer is Morgan Lavoie. If 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 Instagramoneynews and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

[A]

Oh, I didn't sign up for that.

[B]

All right, well, talk to you soon.