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Nicole Lapin
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Jason Pfeiffer
This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.
Nicole Lapin
Entrepreneur Magazine, and I'm money expert Nicole Lap. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.
Jason Pfeiffer
And on Thursdays, I give you one way to improve your work and build a career or company you love.
Nicole Lapin
And it starts now.
Jason Pfeiffer
You know what you want, but it doesn't make you happy. Maybe you reached a goal, but it wasn't as satisfying as you expected. Or you're chasing a goal, but it feels perpetually out of reach. Either way, now you feel stuck. Today, I'm going to share the antidote, which I call say yes to More than what you want. It is a way of thinking beyond your immediate goals so you aren't trapped by them. When you do this, when you say yes to more than what you want, you will find more satisfaction, more opportunity, and you become less attached to any one outcome. Frankly, it is the secret to my own happiness. Today I'll show you how to do it. But first, let's look at someone who didn't follow this advice. I met my friend Tim in 2009 when we were both low level magazine editors. He had a dream of working for one specific magazine and every career step that he took was designed to get him there. And you know what? It worked. A few years later, he got his dream job. And then he discovered that it was terrible. The hours were awful, the culture was rotten, the boss was impossible to work with. He was constantly overworked and disappointed. But he stayed for years. This is where I've always wanted to be, he would explain to me, even as it made him miserable. This is the trap of hyper specific goals. The way I see it, Tim followed the classic advice. He identified a goal, then he worked to achieve it. But there's a problem. That advice does not account for variables. Goals may not be achievable, or if you achieve them, they may not be as satisfying as you hoped. In pursuit of goals, we often say yes to a small number of things and no to a lot more. It is time to fix that. You need to say yes to more than what you want. Why? Three reasons. Reason number one, you're accounting for the possibility that you won't always get what you want. Number two, you're spreading out your emotional investment so any single failure or disappointment will feel less devastating. And reason number three, you're giving yourself more chances to succeed. To do all this, we need to dig deeper into what you really want. And here's how to do that. Before you say yes, you must ask why. Let me tell you about something called the why Test. It was created by Emily Hayward, co founder of a branding agency called Red Red Antler. Red Antler is the engine behind Hinge, All Trails, Ramp, Supergoop and more. They do incredible work. And you know what they say on their site is our work isn't done until people can't imagine life without you. So Emily Hayward's job is really to create incredible branding, which means that she must know and understand why any particular brand is meaningful to its customers. And so she created a little exercise to help her and her team accomplish this. And here's how it goes. Exercise is this. Number one, you start by describing a brand's core product. Number two, you ask, why does that core product matter? And then number three, you take whatever the answer was to the question you just asked, why does that matter? And then you ask it again. Well, okay, why does that matter? Then get an answer and do it again. Why does that matter? Until you reach something meaningful. For example, let's say that Red Antler is working on a brand that makes high quality running shoes, right? That's a client of theirs. They've got some high quality running shoe brand that comes to Red Antler and says, help us improve our branding. Make us connect with consumers. Okay, well, Red Antler might ask, number one, why do these shoes matter? The answer is, because runners need reliable, comfortable shoes. Now let's ask it again. Why does it matter that runners need reliable, comfortable shoes? Well, because when runners have the right shoes, they perform better and avoid injuries. Great. Okay, why does that matter? Well, because when runners can focus, they push personal limits and feel unstoppable.
Nicole Lapin
Boom.
Jason Pfeiffer
Okay, now that is the start of a powerful personal brand, right? You just got down to the real question of why something matters. Now here's the best part. Although Emily Hayward and Red Antler use this test for branding, you can use it to identify your core motivations. Start by stating a specific goal, whether that's a job, an accomplishment, a career, metric, whatever. Now ask, why does that matter? Why does that matter? Why does that matter? It's like you're digging downward, searching for what really motivates you. Once you find the answer, you can build back up towards specific opportunities. For example, imagine doing this with my friend Tim. He wanted to work at that specific magazine. So I don't know. Let's ask him, hey, Tim, why that magazine? He might have said, because my favorite writers work there. And then you would say, okay, why does that matter? And Tim might say, because it's a symbol of success. And then you might say, why does that matter? And Tim might say, because I want to work at levels that match my ambition. Okay, now we've got somewhere. Tim's goal isn't to work at that magazine. It's to feel rewarded for his talents. Where else can he find that? What else can he say yes to? Now the fun really starts. But here's the thing. Don't wait until you need this exercise. Because here's the thing. Eventually, Tim was laid off and he had to do a lot of soul searching. Took some random jobs, and now he leads a global content team for an incredible brand where he feels challenged in all the right ways. But Tim could have saved himself a lot of trouble and time and searching by asking why earlier and finding other things to say yes to. That's the most important part of all of this. Do not wait to say yes until you're miserable. Saying yes is not a backup plan. It's what you should do constantly, even when you're happy. For example, when I became editor in chief of Entrepreneur magazine, it was the fulfillment of a career long goal. But I immediately asked myself what other opportunities are now available to me. I realized that I'm not motivated by making magazines. I'm motivated by building useful things with my voice and perspective. Magazines are just one way of doing that. So what else could I say yes to? I started exploring speaking, making this podcast, writing a newsletter, starting new companies. This made me less afraid of failure and less attached to the outcome of any one project. If Entrepreneur disappears tomorrow, for example, I'll be sad. But I have other avenues to pursue. That feels like freedom. Not everyone has this kind of flexibility, of course. But that's okay. Saying yes doesn't require side hustles. Saying yes just means thinking bigger, challenging your sense of self and your goals. Saying yes just means chasing curiosities, talking to new people, developing a larger network, exploring new ideas. Saying yes just means saying yes to yourself, that you can do more than you thought and that you might even love it more than you thought was possible. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
Nicole Lapin
Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoie. You want some help? Email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagram Money News and Tik Tok MoneyNews Network for exclusive content and to see our beautiful faces. Maybe a little dance?
Jason Pfeiffer
Oh, I didn't sign up for that.
Nicole Lapin
All right, well, talk to you soon.
Podcast Summary: Help Wanted – "How to Find What You Really Want"
Release Date: May 1, 2025
Host: Money News Network (Jason Feifer & Nicole Lapin)
In the episode titled "How to Find What You Really Want," Jason Feifer and Nicole Lapin delve into the complexities of goal-setting and personal fulfillment in the workplace. They explore why achieving specific goals doesn't always lead to the expected happiness and introduce strategies to uncover deeper motivations.
Jason Feifer introduces the core concept of the episode:
"The antidote, which I call say yes to More than what you want. It is a way of thinking beyond your immediate goals so you aren't trapped by them."
— Jason Feifer [04:15]
This approach encourages individuals to embrace a broader perspective, allowing for greater satisfaction and opportunities by not becoming overly attached to single outcomes.
To illustrate the pitfalls of narrowly defined goals, Jason shares the story of his friend Tim:
"I met my friend Tim in 2009 when we were both low level magazine editors... he got his dream job. And then he discovered that it was terrible."
— Jason Feifer [04:50]
Tim's experience highlights how hyper-specific goals can lead to disappointment when the reality doesn't match expectations, emphasizing the need for flexibility in career aspirations.
Jason Feifer discusses the Why Test, an exercise developed by Emily Hayward of Red Antler, to help individuals and brands identify their true motivations:
"Start by describing a brand's core product... then ask 'why does that matter?' repeatedly until you reach something meaningful."
— Jason Feifer [06:26]
This iterative questioning process helps peel back layers to reveal the fundamental reasons behind one's goals, ensuring that actions align with deeper values.
Applying the Why Test to personal aspirations allows for a clearer understanding of what truly drives an individual. Jason illustrates this with an example involving Tim:
"Tim's goal isn't to work at that magazine. It's to feel rewarded for his talents."
— Jason Feifer [08:10]
By shifting the focus from the specific goal to the underlying desire for recognition and fulfillment, individuals can explore a wider array of opportunities that align with their true motivations.
Adopting the mindset of saying yes to more than just specific goals offers several advantages:
Flexibility in Uncertain Outcomes:
"You're accounting for the possibility that you won't always get what you want."
— Jason Feifer [05:30]
Emotional Resilience:
"You're spreading out your emotional investment so any single failure or disappointment will feel less devastating."
— Jason Feifer [05:35]
Increased Chances of Success:
"You're giving yourself more chances to succeed."
— Jason Feifer [05:40]
These benefits collectively contribute to a more adaptable and fulfilling career trajectory.
Jason shares his own experience of embracing the "say yes to more" philosophy:
"When I became editor in chief of Entrepreneur magazine... I immediately asked myself what other opportunities are now available to me."
— Jason Feifer [08:50]
By expanding his horizons beyond traditional paths, Jason was able to engage in diverse projects like podcasting, writing newsletters, and starting new companies. This approach not only mitigated the fear of failure but also provided a sense of freedom and multiple avenues for personal and professional growth.
The episode concludes with a strong encouragement to adopt the "say yes to more than what you want" mindset:
"Saying yes just means thinking bigger, challenging your sense of self and your goals... exploring new ideas."
— Jason Feifer [09:30]
Nicole Lapin reinforces this message by inviting listeners to reach out for personalized advice, emphasizing the show's commitment to helping individuals navigate their work-related challenges.
Avoid Hyper-Specific Goals:
Focusing too narrowly can lead to dissatisfaction if the outcome doesn't meet expectations.
Use the Why Test:
Continuously ask "why" to uncover deeper motivations behind your goals.
Embrace Flexibility:
Being open to multiple opportunities reduces the emotional impact of setbacks and increases overall satisfaction.
Expand Your Horizons:
Pursuing a variety of interests and projects can lead to a more fulfilling and resilient career.
For more insights and personalized advice, listeners are encouraged to email the helpline at helpwanted@moneynewsnetwork.com and engage with the show’s social media platforms.