Help Wanted Mailbag!

Summary

Podcast Summary: Help Wanted Mailbag! (March 5, 2026)
Podcast: Help Wanted | Hosts: Jason Feifer & Nicole Lapin, Money News Network

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Episode Overview

This episode of Help Wanted is a special “Mailbag” edition, in which Jason Feifer, Editor-in-Chief of Entrepreneur Magazine, and money expert Nicole Lapin tackle real listener questions about work, career transitions, and achieving success. Jason addresses two heartfelt emails: one from a listener struggling with identity after job loss, and another seeking advice on the “best pathway” to career success. The tone is supportive, insightful, and motivational, providing empathic, practical wisdom for anyone feeling stuck or at a crossroads.

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Key Discussion Points & Insights

1. Navigating Identity After a Job Ends

(Main segment: 05:11–09:15)

• Listener Question (Val):
  Val, whose company recently closed after she dedicated her entire career there, wonders: “When my job ends, who am I?” She’s facing grief and uncertainty about her sense of self and future.

• Jason’s Response:

  • Validation of the Struggle:
    “It is okay that this is hard. You devoted a lot of your life to that work, and in doing so, it became a part of you.” (05:44)
  • Grieving and Self-Discovery:
    Jason acknowledges that losing a long-held job is not just a professional blow but also a personal and identity crisis.

    “Now you’re carrying around boxes labeled my identity and my purpose and trying to find somewhere else to put them.” (05:52)

  • Transition Phases:
    • Grieving
    • Asking big questions
    • Experimenting with answers
    • Rediscovery of self
    • Jason emphasizes:
      “It’s helpful to recognize where you are in this process, what phase you’re at, so that you don’t carry the expectations of every phase at once.” (07:02)
  • Advice on Moving Forward:
    The importance of “confronting the unknown,” giving oneself permission not to have all the answers yet.

    “Transitions happen in phases, and those phases go something like this…You don’t need answers in this phase. Answers come later.” (07:15)

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2. The “Best” Pathway to Success: Patience vs. Urgency

(Main segment: 09:20–13:35)

• Listener Question (Junaid):
  Inspired by Jason’s decades-long career journey, Junaid asks if, given the chance to start over, Jason would take Warren Buffett’s slow-and-steady compounding approach or Elon Musk’s pursuit of rapid, high-risk growth.

• Jason’s Career Backstory:

  • He began with humble, sometimes miserable jobs, slowly climbing the ladder.
  • A pivotal moment: After being criticized by a boss early in his career, he realized his “ambitions were larger than [his] abilities.” (10:15)

    “If I was talented enough to work for major newspapers like I wanted…well then frankly, I would be working there. I would have gotten that bigger job, but I wasn’t ready.” (10:32)

• Balancing Patience and Impatience:

  “Growth comes from balancing patience with impatience. We must have the impatience to push ourselves…but we must balance that with patience for learning and self-discovery. Without both, we go nowhere.” (10:53)

• Four Reasons Why Accelerating Success Isn’t Simple:

  1. Success is Relative:

     “No matter how much you accomplish, you will never feel like you’ve made it anyway.” (11:11)

  2. Unclear Destination:

     “You cannot accelerate furiously towards an unknown destination. You must instead give yourself the time and space to discover it.” (11:33)

  3. You Might Not Be Ready:

     “I have seen plenty of young people reach a too large stage too early and it is ugly.” (12:11)

  4. No One-Size-Fits-All Work-Life Balance:

     “I know many people like [Elon Musk] who ceaselessly push themselves to achieve and acquire more, no matter the costs…they are often miserable people.” (12:27)

• Defining Your Own Success:
  Jason’s core message is that there is no “either-or” between Buffett and Musk—success is personal and must align with one’s needs and life.

  “It is not about Warren versus Musk. It is not about choosing whether to be slow…or fast…It is really both, but also neither.” (13:08) “It is not a question of the path we take. It is a question of how we shape that path and how that path shapes us.” (13:18)

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Notable Quotes

• Jason (On Identity After Loss):

  • “You’re going to feel a burden to have answers. Please release yourself from that burden.” (06:41)
  • "Confronting the unknown is the accomplishment." (07:41)

• Jason (On Success and Balance):

  • “Success…requires trade-offs…we must all find the right balance for ourselves.” (12:52)
  • “Success is ours to define at any stage of the journey.” (11:24)

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Important Timestamps

• 05:11 – Introduction to Mailbag and Val’s question: Identity after job loss
• 06:10 – Jason’s empathy and advice for managing grief in transitions
• 09:20 – Junaid’s question: Choosing the fastest path to success
• 10:15 – Jason’s story about his early career setback
• 11:11 – Four reasons why “faster” does not always mean better
• 13:08 – Closing thoughts on personalizing your pathway to success

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Memorable Moments

• Jason encouraging self-compassion:
  “Give yourself the grace and time to ask and wonder and stare into the great open sky until it stops feeling like you’re falling into it.” (07:52)

• Reflections on ambition outpacing ability:
  “My ambitions were larger than my abilities.” (10:17)

• Dismissal of the myth of instant success:
  “You don’t have to learn from your mistakes like I did. You can do it right the first time.” (02:59)

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Summary

In this thoughtful Help Wanted Mailbag episode, Jason Feifer offers actionable empathy and hard-earned wisdom on two universal career challenges: handling identity loss after job upheaval and determining the “best” path to success. Through honest storytelling and clear frameworks, he reassures listeners that both transitions and ambitions must be navigated at one’s own pace—without false urgency or pressure for immediate answers. The message: grant yourself time, set your own definition of achievement, and remember, the path to fulfillment is as personal as it is unpredictable.

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For more, subscribe to Jason’s “One Thing Better” newsletter, or submit your own career question for a future Mailbag episode.

Transcript

[A]

We've had some big wins at my company this year. The kind of wins that mean it's time to expand. Bringing new people onto the team isn't something I take lightly. These people are going to help shape the content that goes out into the world with my brand and my name attached to it. So when I'm hiring, I need to make sure my job listing lands in front of the best possible people. Not just good, the best. Which means this is a job for Indeed Sponsored Jobs. Spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results when you need the right person to cut through the chaos. This is a job for Indeed Sponsored Jobs. And listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed Indeed.com podcast just go to Indeed.com podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com podcast terms and conditions apply. This isn't your job. This is a job for Indeed Sponsored Jobs. Jason, would you like to vent?

[B]

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[A]

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[B]

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[A]

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[B]

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[B]

I started my business as a sole proprietorship and at the time that made sense. I was just trying to get moving. But looking back I realized if I had known what I know now, I probably would have structured it as an S corp at the start. Instead I had to switch later, which was a pain. And you know that is true of many things. There are small decisions that we would have approached differently if only we had known. But you don't have to learn from your mistakes like I did. You can do it right the first time. Under the guidance of today's sponsor, Northwest Registered Agent has been helping small business owners and entrepreneurs launch and grow businesses for nearly 30 years. They are the largest registered agent and LLC service in the US with over 1500 corporate guides who are real people who know your local laws and can help you and your business every step of the way. Northwest gives you access to thousands of free guides, tools and attorney drafted documents to help you run your business with confidence. No upsells, no selling your data. Northwest makes life easy for business owners. They don't just help you form your business, they give you all the free tools that you need after you form like operating agreements, meeting minutes and thousands of guides that explain all the ins and outs of running a business. Don't pay hundreds or thousands of dollars for what you can get from Northwest for free. Visit northwestregisteredagent.com helpwanted free and start using free resources to build something amazing. Get more with Northwest Registered Agent at. Again, here's the website northwestregisteredagent.com helpwanted free. 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]

People email me a lot of questions. I really appreciate it. You know, I make things. I make podcasts and newsletters and they listen and they say hey, I wonder what he would say about this and today I'm going to answer two of those questions. A very help wanted ish kind of thing to do. People have want for help, and here I am. Number one, when my job ends, who am I? And number two, what's the best pathway to success? Here we go. Question number one. When my job ends, who am I? This is a question that comes from Val. Val wrote me this. Val says, I devoted my career to one company. It just closed. I'm now grieving, not just for a job, but for my own sense of identity. I turn 50 next year, and for the first time, I'm sitting down to really ask the hard questions. I what am I good at? Who am I without this position? And yet right now, I feel deeply lost. Do you have any guidance as I navigate this transition? All right, that was Val's question. Here is my answer. Val, I know you know this, but I'm going to say it anyway. It is okay that this is hard. You devoted a lot of your life to that work, and in doing so, it became a part of you. Now you're carrying around boxes labeled my identity and my purpose and trying to find somewhere else to put them. This is why, in time, you will be so thankful for this transition. When we're inside something for a long time, whether it's a company or a relationship, we often stop asking ourselves the questions that you listed. What am I good at? Who am I independent of that? Because we have nice, easy answers available. When, you know, we have some job that we've been at for a long time, we can just define ourselves by our tasks or our roles or. Or our bonds. But the trouble is, everything external is changeable. We cannot fully control the fate of our companies or relationships. So when we export our identities to those things, we give up control over our sense of self. What is the solution to this? It lives inside the sentence that you wrote. For the first time, you wrote, I'm sitting down to really ask the hard questions. We should all be doing that all the time, but we rarely do until prompted. And now you're doing it. You're going to feel a burden to have answers. Please release yourself from that burden. Transitions happen in phases, and those phases go something like this. First there's grieving, then there's asking big questions, Then there's experimenting with answers. And then there is a rediscovery of self. There is. Each phase is distinct. It's helpful to recognize where you are in this process, what phase you're at, so that you don't carry the expectations of Every phase at once. Right now, for example, you are at that second phase, Val. You are asking big questions. You don't need answers in this phase. Answers come later. Asking the questions is the work right now. Confronting the unknown is the accomplishment. So give yourself the grace and time to ask and wonder and stare into the great open sky until it stops feeling like you're falling into it. Answers will come. It won't be easy, but nothing good ever is. All right, and now, thanks again, Val, for sending that question. Here's the second question, which is, what's the best pathway to success? And this comes from someone named Junaid. So Junaid asks me this. I'm inspired by your career journey. Thank you, Junaid. I appreciate that. Okay, keep reading. Like many of us, it took you decades to reach the kind of goals you once imagined. But I'm curious. If you were starting again in the 90s and you didn't want to take decades to reach the same destination, how would you do it? Would you still choose Warren Buffett's slow, steady, and calm path with compounding moves? Or. Or would you lean toward Elon Musk's insane sense of urgency and accelerated execution? All right, it's a great question. It's also a question that is rooted in a knowledge of my career, which I really appreciate. So just to fill in a couple gaps there, in case you don't know, so Junaid writes, if you were starting again in the 90s. Well, I was in high school in the 90s, but I graduated college in 2002. I got a tiny community newspaper job, and I really just started working my way up slowly and steadily. It took a long time, and. And I was frustrated along the way, certainly, but, you know, I did it. I did those slow, slow steps. So here is what I wrote to Junaid. I said, junaid, the pathway to success isn't that simple. So before I answer your question, here is a critical learning moment from my career. It was 2003, and I was one year out of college, and I had huge ambitions to write for the world, world's largest newspapers. But instead, the only job that I could find was at a dumpy little paper in a tiny town. So I worked there, feeling miserable and bitter. One day, my boss wrote me a letter that called me a detriment and a drag on the newsroom. He gave me a couple weeks to turn my attitude around, or I would be fired. I was indignant about this, and I quit. Eventually, I realized my real problem, which wasn't exactly that I had that job it was the my ambitions were larger than my abilities. If I was talented enough to work for major newspapers like I wanted, well then frankly, I would be working there. I would have gotten that bigger job, but I wasn't ready. I didn't have that job because I still had a lot to learn. Here is what I now understand. Growth comes from balancing patience with impatience. We must have the impatience to push ourselves, always believing that there's more ahead. But we must balance that with the patience for learning and self discovery. Without both, we go nowhere. Now, would I have liked to be quote unquote successful faster? Yeah, sure, of course. But that was unrealistic. There are four reasons for that, so let me list them out. Number one, because success is relative. No matter how much you accomplish, you will never feel like you've made it anyway. That's true for me as well as every high achieving person I know. So as we think about the right path to success, we must also remember how fuzzy the destination is. Success is ours to define at any stage of the journey. Here's reason number two. Because I didn't know where I was going, you cannot accelerate furiously towards an unknown destination. You must instead give yourself the time and space to discover it. For example, at the beginning of my career, back when I was at that little newspaper and in fact for many steps afterwards, I had never heard of Entrepreneur Magazine. I. I completely stumbled into this role, then spent years experimenting with ways to embody and maximize it. I succeeded because I searched, not because I ran. Oh, and in case you don't know what this role is, I mean, you know, you may not know who I am anyway. Editor in Chief, Entrepreneur Magazine. That's the role. I've had it for 10 years. Number three reason number three, I didn't have what it takes. Like I said before, I had a lot of frustrated ambitions in 2003, but I also had a lot to learn. I was not ready for the spotlight then and I'm glad I didn't get it. I have seen plenty of young people reach a too large stage too early and it is ugly. And reason number four, I wanted a different balance. Success, or just the pursuit of success, requires trade offs. For example, I have never met Elon Musk, but I know many people like him who ceaselessly push themselves to achieve and acquire more, no matter the costs to themselves or others. And I will tell you, they are often miserable people. Their personal lives are a mess. They are lonely at their core, trying to fill a bottomless hole in themselves. That is not something I want and it is not a cost I am willing to pay. Yes, I devote a lot of myself to work and I still have huge ambitions, but I am also willing to trade less money and quote unquote success for other things in life. We must all find the right balance for ourselves. In short, Junaid, it is not about Warren versus Musk. It's not about choosing whether to be slow like Warren Buffett or fast like Elon Musk. It is really both, but also neither. Mostly it is this. It is not a question of the path we take. It is a question of how we shape that path and how that path shapes us. Now I will say those questions came through my newsletter. My newsletter is called One Thing Better each Week, One way to be more successful and satisfied and build a career or company that you love. I read it here on Help Wanted every Thursday, but you can get it early along with other great stuff that I put in the newsletter by subscribing at One Thing Better Email. Again, that is a web address, so just plug it into a browser. One thing better.com email and if you have a question, just respond to the newsletter and maybe one day I will answer it right here on the show. 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 Lavoy. Do you want some help? Email our [e-mail] for the chance to have some of your questions and answered on the show. And follow us on Instagramoney News and Tik Tokoney News Network 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.