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)

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.

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.”

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.”

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

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!