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.

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.

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.

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.

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.

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.

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.

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.

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])

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])

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.

[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.

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.