How To Ask For What You Want

Summary

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

Host: Jason Feifer (Entrepreneur Magazine)
Guest/Co-Host: Nicole Lapin (Money Expert)
Date: June 18, 2026

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Episode Overview

This episode tackles the challenge of asking for what you want, especially at work but applicable throughout life. Jason Feifer guides listeners through real-life stories and expert insights, demonstrating why speaking up isn’t just about getting what you want, but about responsible collaboration. The episode focuses on breaking the cycle of silence, exploring its roots, and providing encouragement and reasoning for why voicing your needs benefits everyone involved—at work, in relationships, and beyond.

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Key Discussion Points

The Reluctance to Ask: A Universal Struggle

• Common Hesitation: Jason discusses how many of us hesitate to ask for what we want, whether for fear of being a bother, challenging the status quo, or facing uncomfortable reactions.
• Relatable Example: He shares a story about his friend Leslie Carl Saltarelli, startup founder and co-founder of Midday Squares, who suffered silently through a painful massage because she didn’t want to confront the therapist ([02:01]).

“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?”
— Jason Feifer ([02:15])

• Why We Stay Silent: Jason underscores that hard conversations, even small ones, sometimes feel too daunting—especially when we're seeking respite, like during relaxation ([02:24]).

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Perspectives from the Other Side: The Value of Feedback

• Massage Therapist’s View: Jason interviews Venus Jones of Rescue Spa to find out how it feels when clients do or do not share feedback ([03:22]).
• Key Takeaways from Venus:
  • Welcomes feedback and sees it as collaboration.
  • Says silence is actually more concerning than requests for change.

“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.”
— Venus Jones (read by Jason Feifer, [03:32])

“What's more concerning to me is the absence of feedback. Because silence doesn't always mean comfort.”
— Venus Jones (read by Jason Feifer, [03:45])

• Reframing the Fear: Feedback isn’t criticism—it's information that makes the process work. The massage therapist’s job is easier and more meaningful when working together with the client.

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Silence Creates Discomfort—for Everyone

• Mutual Uncertainty: Staying silent doesn’t eliminate risk or embarrassment; it creates discomfort and uncertainty for both parties ([04:18]).
• Collaboration at the Core: Good relationships—whether professional or personal—are collaborative. When we don’t voice our needs, it can undermine trust and intimacy.

“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.”
— Jason Feifer ([04:43])

• Application Beyond Massages: The lesson holds in all aspects of life:
  • Relationships with partners: Unspoken needs create distance.
  • Workplace settings: Not asking for opportunities or clarity sends misleading signals about engagement or investment in the team ([05:24]).

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The Real Risk: Cost of Silence

• Damaging Assumptions: When we don’t speak up, others may assume disinterest, disengagement, or discomfort even if none exist.
• Good Collaboration Requires Feedback: As Jason says, “These are the costs of silence. When we keep things to ourselves, we don't eliminate discomfort. We actually create it for ourselves and others.” ([06:10])

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Not Every Environment is Collaborative—And That’s Telling

• Reality Check: Not every boss or partner is collaborative, and silence can help reveal who is worth investing in. If feedback is unwelcome, that might be a sign to choose your collaborators more carefully ([06:39]).

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A Call to Action: Just Say It

• Responsible and Necessary: Asking for what you want is framed as responsible—it sets expectations and creates shared goals.
• Encouragement to Speak Up: Jason closes by encouraging listeners to “just say it,” reminding us that voicing needs is good for everyone involved ([07:13]).

“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.”
— Jason Feifer ([07:13])

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Notable Quotes & Memorable Moments

• “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?”
  — Jason Feifer ([02:54])

• “Clear communication helps me meet the body where it is that day...silence doesn't always mean comfort.”
  — Venus Jones (read by Jason, [03:44])

• “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.”
  — Jason Feifer ([05:55])

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Timestamps for Key Segments

• [01:47] — Introduction to the episode's theme: why we avoid asking for what we want
• [02:01] — Leslie’s story: suffering in silence during a painful massage
• [03:22] — Venus Jones’ perspective: the massage therapist welcomes feedback
• [04:43] — Exploration of how silence creates discomfort for both sides
• [05:24] — Applying this lesson to relationships and career contexts
• [06:10] — The real cost of staying silent at work and home
• [06:39] — Not all collaborators are equal; use feedback to find the good ones
• [07:13] — Final takeaway: asking for what you want is responsible and beneficial

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Conclusion

This concise and insightful episode of Help Wanted reminds us that asking for what you want is an act of collaboration, not confrontation. Through personal anecdotes and professional insight, Jason Feifer lays out why feedback—however minor—is essential for healthy relationships at work and beyond. Silence, he argues, not only robs us of comfort but also our collaborators of confidence and clarity. The takeaway: Speak up, set expectations, and invite others into your journey.

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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 helpline 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 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 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 ins a person who's trying to make them feel good. But in some way or another, everyone is a little like Les. 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. 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 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.