Podcast Summary: Help Wanted

Episode: How to Leave Something, Even If You Still Sorta Like It
Date: February 19, 2026
Hosts: Jason Feifer (Entrepreneur editor-in-chief), Nicole Lapin (Money Expert)
Produced by: Money News Network

Episode Overview

Main theme:
This episode dives into the difficulty of leaving a job, relationship, project, or commitment—even when you still enjoy some parts of it. Host Jason Feifer explores how to identify when it’s time to move on, even if you’re reluctant to lose certain perks or comforts, by distinguishing between "forward benefits" and "dead end benefits."

Key Discussion Points and Insights

1. The Challenge of Letting Go—Even When Things Aren’t All Bad

• Many people struggle to leave situations that still offer some form of enjoyment, comfort, or status.
• Jason frames the central dilemma: “You are ready to go, but you struggle to leave a small part behind which is pleasurable and meaningful, just hard to let go of.” [04:24]
• The show isn’t just about jobs; this logic applies to relationships, projects, industries, and more.

2. Jason’s Personal Example: “Drunk Party Jason”

• Jason shares a story from his late 20s:
  • Moved to NYC as a junior editor at Men’s Health magazine, new to the city and often lonely in the evenings.
  • As an editor, he received invitations to glamorous events, which helped him make friends and feel part of the scene.
  • These parties became the “foundation of my social life and they made me feel cool and important.” [05:01]
• Over time, Jason outgrew his job at Men’s Health—the work became boring, and growth opportunities were limited, but he hesitated to leave because he loved the events and social perks.

3. “Forward Benefit” vs. “Dead End Benefit”

• Benefit: Anything pleasurable or valuable gained from a situation (pay, status, lifestyle, access, etc.).
• Every benefit has an associated sacrifice or trade-off.
• Forward Benefit:
  • “A benefit that drives you towards your goals. It moves you forward.” [06:24]
  • Example: Jason’s social life was advanced by attending industry parties when he was new in NYC.
• Dead End Benefit:
  • “A benefit that might be enjoyable, but that leads you nowhere new.” [08:22]
  • Example: Years later, the parties supplied comfort and nostalgia but no longer moved Jason toward new professional or personal goals.

4. The Decision Point—Is the Sacrifice Still Worth the Benefit?

• Jason describes being offered a better job at Fast Company, a move that aligned with his new goals (career growth, higher pay).
• He felt real loss at potentially leaving behind the parties—demonstrating the power of lingering benefits.
• He realized:
  • “When I needed to build a social life, the parties helped me do that. … But a few years later, I had a social life … and it was time to really, truly focus on my career. And that meant the parties, they were just parties now.” [07:23]

5. Growth Means Outgrowing Even Good Things

• Even positive benefits can become obsolete as your circumstances and goals change.
• Sometimes, after you move on, you realize you didn’t lose as much as you feared—or you outgrow the old benefits anyway.
• “Even if you never lose them, you can outgrow them.” [09:38]
• When letting go of a current benefit, remember: change is not just about loss—it can also be about making space for new gains.

6. Takeaway Advice

• “A benefit should help you reach your goals. A benefit should not hold you back from goals.” [10:27]
• When you quit something—even something you love—you open yourself to new opportunities that may align better with your evolving ambitions.
• There are always new benefits to be found as you grow, change, and make intentional choices.

Notable Quotes & Memorable Moments

• On clinging to "dead end benefits":
  • “Change isn’t just about loss. … Change creates gain too, even if it’s harder to see at first.” – Jason Feifer [09:50]
• Advice for listeners considering a change:
  • “The benefits that you enjoy today are not the only benefits you will ever have.” – Jason Feifer [10:50]
• Defining the big lesson:
  • “If you are intentional about your choices, then those new benefits will provide what you need now and tomorrow—not just what you needed yesterday.” – Jason Feifer [11:13]

Important Segment Timestamps

• 04:24: Intro to the episode’s central dilemma: why it’s hard to leave something you still like
• 05:01: Jason’s story of "Drunk Party Jason" and the lure of social benefits in a new city
• 06:20–07:23: Explanation of “benefit,” “forward benefit,” and “dead end benefit”
• 08:22: Realization that certain perks become obsolete as you grow
• 09:38: The idea that you can eventually outgrow old benefits
• 10:27: Final takeaway—move towards what now serves your evolving goals

Tone and Language

• Warm, self-aware, and practical, blending storytelling with actionable advice.
• Jason is candid and approachable, sharing personal stories while drawing out broader lessons relevant to listeners at all career stages.
• The episode avoids jargon, instead focusing on relatable examples and direct language.

Summary for New Listeners

This episode of Help Wanted illustrates why it’s often so difficult to leave behind jobs, projects, or relationships that still offer some “good parts.” Through Jason’s own career fork—choosing between new growth and beloved old perks—listeners learn the importance of distinguishing between benefits that move you forward and those that merely keep you comfortable. The show offers a memorable framework (“forward benefit vs. dead end benefit”) and reassures that letting go creates room for new and better opportunities—if you’re willing to make the leap.