Podcast Summary

Help Wanted – “How To Know What’s Worth Your Time”

Release Date: January 29, 2026
Host: Jason Feifer (Entrepreneur Editor in Chief)
Co-Host: Nicole Lapin (Money Expert, intro/outro only)

Episode Overview

In this solo episode, Jason Feifer tackles a universal issue for ambitious professionals: how to stop feeling overwhelmed by commitments and make smarter choices with your time. He introduces a practical framework for evaluating what’s truly worth your energy, illustrated through real-world examples and insights from leaders. The theme centers around creating boundaries for ambition and focusing on what truly matters to advance your goals.

Key Discussion Points & Insights

1. Why We Say Yes Too Often — and Its Consequences

Jason identifies the common cycle: Enthusiasm and ambition lead people to overcommit, resulting in overwhelm and fatigue.
- “You’re ambitious, you’re enthusiastic, you don’t know how to say no. Then you get overcommitted and overwhelmed.” (00:36)

2. The Counterintuitive Rule: Say No to Something Old Before Saying Yes to Something New

Jason shares a core principle: Before accepting a new responsibility, purposefully end or step back from an existing one.
- “Before you say yes to something new, you should say no to something old.” (00:50)

3. The Story of Saying No: Samantha’s Career Decision

Jason recounts a story from John Goodman’s book Unhinged Habits about Samantha, a talent agent who turns down a lucrative promotion to preserve her work-life balance.
- “Ambition isn’t wrong, but chaotic ambition without boundaries is a fire that burns your life to ash while you stand there holding the match.” — Samantha via John Goodman (02:13)
Memorable reflection: Jason lauds this as his favorite line from Goodman's book, underlining the dangers of unbounded ambition.

4. Organizational Wisdom: Amazon VP’s Commitment Filtering

Jason references Mary Beth Westmoreland, Amazon VP of Technology:
- When starting new projects, her team always eliminates an old one.
- “We ask our teams, what’s the most important thing that we need to spend time on to make the biggest impact? Sometimes that means we’re going to stop doing things that are not making the most difference.” — Mary Beth Westmoreland (03:00)
Jason suggests applying this practice on a personal, not just organizational, level.

5. A Personal Framework: Three Questions to Determine What’s Worth Your Time

Jason shares a three-question strategy to clarify priorities:

1. What’s not making the most difference?

Example: Jason realized his online community’s operations took time but didn’t deliver on his current life or career goals.

2. What would happen if I stopped doing that thing?

He emphasizes looking beyond the discomfort of endings to the lasting benefits gained.
- “Endings are not just about one moment. They are about all the moments afterward.” (05:23)
Jason felt relieved when imagining his life post-community.

3. What purpose did it serve?

Assess whether a commitment has already fulfilled its role in your life.
- “Everything serves some function. It taught us, trained us, expanded us... The purpose had been fulfilled.” (06:15)

6. The Encouragement to Move On

A former community member’s note affirmed the value of letting go:
- “As a business owner, you’ve shown me that it’s okay to try something new and that it doesn’t have to be forever. It’s okay for that thing to evolve or not. And ending one thing doesn’t mean the end of all things.” (07:05)
Jason repeats Goodman’s caution: Boundaries allow ambition to serve you, not destroy you.

7. The Ultimate Permission: Prioritize Yourself

The core message: Allow yourself to start and stop projects. You aren’t obligated to continue everything indefinitely.
- “The only project you really need to keep going is yourself. So say yes to that. Everything else is up for discussion.” (08:04)

Notable Quotes & Memorable Moments

On Boundless Ambition:
“Ambition isn’t wrong, but chaotic ambition without boundaries is a fire that burns your life to ash while you stand there holding the match.”
— Samantha via John Goodman, quoted by Jason Feifer (02:13, 07:48)
On Making Decisions:
“Before you say yes to something new, you should say no to something old.”
— Jason Feifer (00:50)
On the Benefit of Endings:
“Endings are not just about one moment. They are about all the moments afterward.”
— Jason Feifer (05:23)
On Permission to Move On:
“Ending one thing doesn’t mean the end of all things.”
— Jason reads from a former member’s message (07:05)

Timestamps for Important Segments

00:36 — Problem: Overcommitment and overwhelm explained
00:50 — Key Principle: Say no to something before yes to something else
02:13 — Story & quote from Unhinged Habits (Samantha’s career decision)
03:00 — Amazon VP’s approach to project selection
04:45 — Jason introduces the three-question framework
05:23 — Reflection on the aftermath of endings
07:05 — Letter from former community member about closure
08:04 — Final takeaway: Only keep “the project of yourself” going

Episode Takeaway

This episode empowers listeners to be intentional with their commitments by regularly evaluating old and new projects against clear personal goals. Jason reminds us that giving ourselves permission to move on is not just acceptable, but necessary for focused ambition and a fulfilling life. Boundaries, not busyness, lead to true progress.

Transcript

A (0:06)

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

B (0:12)

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

A (0:20)

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

B (0:25)

And it starts now.

A (0:28)

Hey, before we begin, do you want to be on the podcast on Help Wanted asking Nicole and I for help? If so, we have a way for you to do that. It is in the show notes. Just go look. There is a form for you to fill out. We want to know what your burning question is. And today I'm going to answer. Well, what I'm going to just guess is a burning question of yours, which is, how do I stop feeling so insanely overwhelmed? Because. Because I have said yes to too many things. And if that is your question, well, here is my answer. You take on too much. And why do you take on too much? There are so many reasons. You're ambitious, you're enthusiastic, you don't know how to say no. Then you get over committed and overwhelmed. Well, here is a question that you should ask yourself more. What is actually worth saying yes to? And here is my counterintuitive answer. Before you say yes to something new, you should say no to something old. Today, I'll give you a strategy to filter commitments so that you can feel lighter, freer, and more focused on what actually matters. But first, let's start with a woman who said no to a big opportunity and the golden reason why. So, my good friend John Goodman just wrote a new book. It is called Unhinged Habits, a counterintuitive guide for humans to have more by doing less. It is a fantastic read for anyone feeling overwhelmed and seeking focus. I strongly recommend it. Unhinged Habits. Okay. Anyway, so in the book, John shares the story of a talent agent named Samantha who spent her 20s and early 30s working relentlessly. Long hours, constant travel, endless dinners. Eventually, she rose to run her agency's entire Canadian operation. Then an international leadership role opened up. Everybody expected Samantha to pursue it because obviously she is a rising star. But you know what? She didn't. John asked her why. She said that this job could have provided her with more money, bigger clients, more recognition from the industry and her peers. But it would have come at the cost of more time away from her family and other things she wanted in life. Ten years ago, she told him, I would have taken it without thinking twice. But But I've realized something important. Ambition isn't wrong, but chaotic ambition without boundaries is a fire that burns your life to ash while you stand there holding the match. That, by the way, is my favorite line in John's great book. We must draw the line between ambition and chaotic ambition without boundaries. As I read Samantha's story, I remembered a conversation that I had with Mary Beth Westmoreland, a VP of Technology at Amazon. She told me that when her team starts a new project, they often eliminate an old project at the same time. We ask our teams. This is her. She says, we ask our teams, what's the most important thing that we need to spend time on to make the biggest impact? Sometimes that means we're going to stop doing things that are not making the most difference. Again, quoting directly from her. At a company, of course, you can do this with data and metrics, but imagine applying this standard to yourself. If you're going to start something new, you must stop doing something old. There is a beautiful logic to this. You must decide if something new is more valuable than your current commitments. You must ask, if I say yes to this, is it worth giving up? That you must make your commitments compete for your attention. I challenged myself to think about this and ask, how would I apply Mary Beth's framework to myself? How do I know what is worth saying no to? The answer starts with goals. Mary Beth's language is instructive. So let's go back to it. She says, we're going to stop doing things that are not making the most difference. Okay? So to accomplish that, we must define the most difference for ourselves. What accelerates our goals? What improves our lives the most? Once we know, we can optimize for it with three simple questions. So here's a framework. Question number one is, what's not making the most difference? An example. A few years ago, I was at a crossroads. An exciting new business opportunity arose, but I was maxed out on time. So I asked myself, what do I want right now? And my answer was, interesting. I hadn't really thought about it. I want things that bring me joy, create financial stability. So, you know, I like them and they make me money, leverage my skills without burdening me with operations. Right? I want to be able to walk into things and just be useful and not have a whole bunch of busy work to do now and leave time for friends and family. So that's really helpful. And then with that in mind, I could ask Mary Beth's question, what isn't making a difference towards that goal? The answer back Then felt clear. At the time, I was running an online community. I loved the members, but the operations consumed time and energy. Growth had stalled, and it barely made money. The community definitely, therefore, was not making a difference towards my goals. Now, question two. Question two again, let me just remind you that question one was, what's not making the most difference? Question two is, what would happen if I stopped doing that thing? It is hard to imagine ending things, and here's why. We often think about the act of ending something. You know, the very act of it. Saying goodbye, and then how hard or sad that's going to feel. But endings are not just about one moment. They are about all the moments afterward. When I imagined ending my community, for example, my first reaction was, ugh, I'll disappoint these great people. But then I kept imagining, what would my life be like a week, a month, a year later, once I reclaim all that time and energy? In truth, it felt really good. So, okay, question number one was, what's not making the most difference? Question number two was, what? What would happen if it stopped? And now question three is, what purpose did it serve? Everything serves some function. It taught us, trained us, expanded us. So if you're considering saying goodbye to something, well, then maybe ask this. What purpose did that thing serve for me? And has that purpose already been served for me? The community served many purposes. I learned about community functions. I met great people, I had fun. I. All of this would remain true even if it ended. The purpose had been fulfilled. And now here's the result. After closing my community, one member wrote to me this. As a business owner, you've shown me that it's okay to try something new and that it doesn't have to be forever. It's okay for that thing to evolve or not. And ending one thing doesn't mean the end of all things. That is so right. That was so powerful. I keep thinking back to that line in John's book. Ambition isn't wrong, but chaotic. Ambition without boundaries is a fire that burns your life to ash while you stand there holding the match. The goal here is to create those boundaries, to make sure that our ambition is focused and that it serves our needs. We do not need to say yes to everything or even to most things. We can start things and stop them. Say yes and say no. Start projects and abandon them. The only project you really need to keep going is yourself. So say yes to that. Everything else is up for discussion. So that's today's help wanted. And like I said at the very beginning, if you want to be on a future Help Wanted episode? Not these solo episodes, obviously, but the one where Nicole and I are talking not just to each other, but to a listener, someone who's got a problem that we can help solve. Just look in the show notes in whatever podcast platform you are listening to this in right now, and you will see a link to a Google form. Fill that thing out and maybe we'll be talking to you soon. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.