How To Ask For What You Want

Summary

Help Wanted — "How To Ask For What You Want"

Podcast by Money News Network | Aired: February 5, 2026
Hosts: Jason Feifer (Entrepreneur Magazine) & Nicole Lapin (money expert)

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Episode Overview

This episode of Help Wanted dives into the psychology and practicalities of asking for what you want—whether at work, in personal situations, or everyday interactions. Host Jason Feifer draws from a relatable real-life scenario to unpack why people hesitate to speak up, how this silence actually creates discomfort for everyone, and why clear communication is an act of responsibility and collaboration.

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Key Discussion Points & Insights

The Struggle to Ask for What You Want

• Common scenario: People often hesitate to ask for what they want, both in significant and trivial situations, due to fear of upsetting others, disrupting the status quo, or initiating "hard conversations."
  • Jason Feifer (03:12): “You hesitate to ask for what you want... There are many reasons for this. Maybe you're unsure how the other person will react. Or you don't want to upset them or test them, or the limits or challenge the status quo.”

The Massage Parable: Politeness as Pain

• Story shared: Jason recounts the experience of his friend, Les Carl Saltarelli (co-founder of Midday Squares), who endured pain during a massage rather than speaking up about the pressure.
  • Les explains: "As a startup founder, I'm having hard conversations all day. I just didn't want to have one while trying to relax." (Paraphrased, 03:55)
• Insight: Even those who routinely have tough conversations professionally avoid them in trivial scenarios due to wanting to avoid discomfort—even if it hurts.

The Practitioner’s Point of View

• Interview with Venus Jones, massage therapist at Rescue Spa:
  • Jason asks what it's like for a professional when clients do or don’t speak up.
  • Venus Jones (04:41, read by Jason):
    • “I generally welcome clients’ feedback about pressure. Everyone’s body is different and I see pressure as something we collaborate on... What's more concerning to me is the absence of feedback, because silence doesn't always mean comfort.”
• Core Lesson:
  • Feedback is seen as helpful collaboration, not criticism.
  • Silence actually creates uncertainty for the practitioner and can hinder their ability to do good work.

The Larger Lesson — Collaboration, Not Criticism

• Communication is collaboration:
  • Jason ties Venus’s response to the broader theme—when we speak up, we foster collaboration.
  • Jason Feifer (05:47): “Feedback is collaboration, and…no feedback is concerning.”
  • Silence doesn’t eliminate risk or embarrassment—it creates uncertainty for all.
  • Jason (06:36): “If you stay silent, you are robbing [the other person] of [the reward of competency]. As it turns out, the hard conversation makes things easier on everyone.”

Scaling Outward — Work, Life, and Relationships

• Relationships:
  • When you don’t communicate your needs, your partner senses something is off, creating discomfort.
• Work:
  • Not asking for growth or responsibility may be perceived as lack of investment or ambition.
  • Colleagues and bosses may see silence as lack of desire to collaborate or grow.
  • Jason Feifer (07:29): “These are the costs of silence. When we keep things to ourselves, we don’t eliminate discomfort. We actually create it.”

The Costs of Staying Silent

• Missed connections, misunderstandings, lost opportunities:
  • Silence breeds discomfort, confusion, and mistrust.
  • Not everyone will respond positively, but that’s a filter for the people you want to work and live with.
  • Jason (08:01): “How do you find out which people are worth collaborating with? There’s only one way. You speak up and see how they respond.”
• Responsibility, not selfishness:
  • Asking for what you want sets expectations and builds clear, collaborative relationships.
  • Jason (08:19): “Asking for what you want is not selfish at all. It is responsible.”

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Notable Quotes & Memorable Moments

• On why we hesitate (03:12):
  • Jason Feifer: “You hesitate to ask for what you want. You know the words that you would say, but you don't say them.”
• On the therapist’s view (04:41-04:56):
  • Venus Jones (via Jason): “Everyone’s body is different and I see pressure as something we collaborate on... What’s more concerning to me is the absence of feedback, because silence doesn’t always mean comfort.”
• On silence and discomfort (07:29):
  • Jason Feifer: “When we keep things to ourselves, we don’t eliminate discomfort. We actually create it for ourselves and others.”
• On courageous communication (08:01):
  • Jason Feifer: “How do you find out which people are worth collaborating with? There’s only one way. You speak up and see how they respond.”
• On asking as responsibility (08:19):
  • Jason Feifer: “Asking for what you want is not selfish at all. It is responsible. You are setting expectations, making lines clear, and inviting people into your shared goals.”

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Timestamps for Important Segments

• 03:12 — The Problem: Why we struggle to ask for what we want
• 03:46 — Les's Story: Real pain from unspoken needs
• 04:41 — Therapist’s Perspective: Venus Jones’s insights on feedback and silence
• 05:47 — Collaboration: Reframing feedback as partnership
• 06:36 — Silent Costs: Misunderstandings and discomfort caused by silence
• 07:29 — Scaling Up: How silence impacts work and relationships
• 08:19 — Responsibility: Framing asking as a responsible, not selfish, act

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Summary Takeaways

• Speaking up about your needs is not rude or inconvenient—it’s essential for true collaboration and healthy relationships.
• Silence, while seemingly polite, can breed discomfort and uncertainty for everyone involved.
• The people worth working with and being with will respond positively to honest, constructive feedback.
• So: Just say it!

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Transcript

[A]

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[B]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer editor in chief of.

[A]

Entrepreneur Magazine and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the and help callers solve their work problems.

[B]

And on Thursdays, I give you one way to improve your work and build a career or company you love.

[A]

And it starts now.

[B]

You hesitate to ask for what you want. You know the words that you would say, but you don't say them. Maybe it's a small request. Maybe it's something big and weighty. There are many reasons for this. Maybe you're unsure how the other person will react. Or you don't want to upset them or test them, or the limits or challenge the status quo. Well, today I will inspire you to speak up and get what you want anyway. And it all starts with a relatable moment where a friend of mine stayed silent and it hurt physically. So here is the story of when politeness becomes pain. My friend Leslie Carl Saltarelli is co founder of the fantastic snack brand Midday Squares. She recently got a massage which started great, super relaxing. And then the massage therapist started to work on her scalp and it hurt. Just way too much pressure. All Les needed to do was ask for less pressure, but she didn't. Instead she laid there silently unmoving in agony throughout the whole thing. I've done this many times. I'm sure you have too. And it is worth wondering why? Why do we do it? Les has her own explanation. She told me, as a startup founder, I'm having hard conversations all day. I just didn't want to have one while trying to relax. And other people might have other explanations. They might be uncomfortable asking for what they want. Or they feel weird demanding a different kind of touch. Or they don't want to insult a person who's trying to make them feel good. But in some way or another, everyone is a little like lesbian. Speaking up feels like a hard conversation. As I talked to Les though, I wondered something I had never considered before. What is this situation like from a massage therapist's point of view? So I decided to ask. There is an amazing spa in Manhattan and Philly called Rescue Spa. My wife went and loved it. Venus Jones is a massage therapist there, so I asked her some questions. I wanted to know what does Venus think when a client asks to change the pressure? And what does she think when a client stays silent? Her answer was eye opening. I'm going to read it in full. Here's what Venus said. She said I generally welcome clients feedback about pressure. Everyone's body is different and I see pressure as something we collaborate on if someone asks me to go deeper or lighter, I take that as helpful information, not criticism. Clear communication helps me meet the body where it is that day. What's more concerning to me is the absence of feedback, because silence doesn't always mean comfort. This was extremely insightful, not just about massages, but about everything. Because here's what Venus is saying. Number one, feedback is collaboration, and number two, no feedback is concerning. So let's break this down. Let's talk about the collaboration we're missing. I really love that word she used, collaboration. When we get a massage, we may think of it as something being done to us, but that is not how the person doing the massage thinks. They think of it as a joint action. They are working with you towards a mutual goal. And this leads to Venus's second point. We often think that if we stay silent, we eliminate the risk of embarrassment or criticism. But actually, the reverse is true. When we give no feedback, we create the discomfort because we introduce uncertainty. The massage therapist never knows if they're doing a good job. Now, could the therapist, you know, ask about the pressure? Yeah, of course. And most do, but they don't want to constantly ask and ruin your experience. Les's therapist, for example, had asked in the very beginning about the pressure before the scalp massage, but then didn't do it again. Your massage therapist is just like you. They wonder and worry if they're doing a good job, and they want to feel the reward of competency. That is human nature. And if you stay silent, you are robbing them of that. So as it turns out, the hard conversation makes things easier on everyone. Now, this applies everywhere. So take it and scale it outward. Are you in a relationship and not saying what you want? Well, a good relationship is collaboration. If you're silent, your partner can probably sense that you're holding something back, which makes them uncomfortable at work. Do you want to move up? Do you want more responsibility? Well, your colleagues want to collaborate with you, and they're looking for signs that you do too. If you're not saying something, they might assume you do not want to collaborate. Maybe they start trusting you less, assuming that you're not invested in the partnership. Or they wonder if you're looking for an out. Maybe they don't see you as someone to grow with. These are the costs of silence. When we keep things to ourselves, we. We don't eliminate discomfort. We actually create it for ourselves and others. Will this be true in every single case? Of course not. I mean, some bosses do not think collaboratively. Some romantic partners don't think collaboratively either. But honestly, I don't want to be around those people anyway. So how do you find out which people are worth collaborating with? There's only one way. You speak up and see how they respond. In this way. Asking for what you want is not selfish at all. It is responsible. You are setting expectations, making lines clear, and inviting people into your shared goals. So you know what? Just say it. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[A]

Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoie. Do 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?

[B]

Oh, I didn't sign up for that.

[A]

All right, well, talk to you soon.