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Nicole Lapin
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Nicole Lapin
Time for most of my life, I've been CEO of my life. I've been the person in charge of my cash flow, my financial goals, my everything. It was just me and my spreadsheet. But then I got married and had joint accounts with my husband and we needed a system that would let us both have insight into our joint financial life. And that solution. Monarch Money Monarch isn't just another financial app. It's a tool that real professionals and experts actually love. It's been named the best budgeting app of 2025 by the Wall and Forbes Best App for Couples. You and your partner have a personal dashboard with budgets, goals and spending all in one place. They don't need to ask you if the power bill has been paid, they can just look it up. When you can both check the budget and the accounts, you can save money. But more than that, you can save yourself from being the brains of the.
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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 Lapin.
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. Build a career or company you love.
Nicole Lapin
And it starts now.
Jason Pfeiffer
Dina Marie, thanks for calling the helpline.
Nicole Lapin
What's your question?
Dina Marie
What I feel happening is even though I've accomplished so much in my career and in my personal life, I hit these moments where that voice inside me says, not quite good enough. Why are you reaching so high? Isn't right here fine. And that can lead into a little bit of imposter syndrome happening. Like, well, am I supposed to be reaching so high? How high is high? And that can slow me down.
Jason Pfeiffer
Dina Marie, is it a feeling like you don't deserve the thing that you're trying to get?
Dina Marie
Yes, that's a piece of it. And that leads me to. It can go down that spiral of why am I reaching so high? Who else is around me that is pushing past this and what are they doing to push past it? And do we all feel this in moments and none of us really talk about it? And there's been so much conversation in the last couple years about our vulnerability and being honest with ourselves and that others may be going through the same type of situation. And that's what led me to reach out to you and ask that question.
Nicole Lapin
Well, short answer, I think yes. Longer answer, I'd love to know specifically what you're grappling with.
Dina Marie
For myself, it is reaching that coo, that top of management level, that's making that break into being a true leader, not just a manager. It's kind of bridged between. I've been in two different roles, but both of them I'm hitting this peak and it's a ceiling that I'm sure I'm putting on myself. And I don't quite know because I've not done it before, that makes me feel inexperienced in that. Although I've achieved so many other things that I've pushed past that are proof that I'm capable of more in many different ways. This leap from manager to leader seems to be that ceiling that I've put over myself. And whether it's in a role that was more direct with a team, not a real heavy corporate structure, or more aligned to where I am right now in a corporate environment. Here I am. I put the same ceiling over myself.
Nicole Lapin
It's interesting that you say manager versus leader.
Jason Pfeiffer
Yeah, I wanted to have you define that. What are the differences?
Dina Marie
Okay. In my mind, the difference is being able to manage roles of a team, manage roles that other individuals are playing into it, versus the leadership role where I see myself, where I am able to receive input, get buy in from the members on the team and help to really lead the organization, or that Mission forward.
Jason Pfeiffer
What I'm hearing is a difference between executing someone else's vision, which is what a manager does. A manager is taking orders from someone above them and then making sure that everyone below them is following those orders. A leader is driving vision from something that is coming from within them. They're relying more on their own instincts, and they have to be inspiring enough for other people to want to follow them. Is that the distinction?
Dina Marie
That's really good, Jason. Yes, that's an excellent way to frame that.
Jason Pfeiffer
So then it feels like if we were to really boil this down, if the thing that you're running up against is that, you know you're a good manager, you know you can execute someone else's vision, and the thing that you're afraid of is, do you have enough personally of what it takes to have other people follow you? Is that it?
Dina Marie
That was quick. Wow, you boiled that right down for me.
Jason Pfeiffer
Well, we like to get to the point here. The show doesn't go on for hours. That makes it feel like we have a very specific thing to focus on, which is what is the thing that's blocking you or that you don't feel. Feel confident enough in saying, I can lead other people, that people should follow me. What's that?
Dina Marie
That's where I think my imposter syndrome comes in. That voice that's in my head that probably started when I was 4, 5, 6, 7, that I wasn't great at sports, I wasn't great in school, I didn't get fantastic grades. But I know I'm a magnetic person and that if there's a group of individuals in a room, I'll find a way to bring them together. So I remind myself that that's probably my superpower and how I'm able to then shift that into leadership of others. And like you said, then taking their ideas as the team and building that into something that I can really help to pull forward and push forward. But with the buy in of everybody on the team, because I believe everything is collaboration.
Nicole Lapin
Sometimes that voice that says, am I okay? Where I'm at is actually an okay voice. Like, I don't hate that voice. I welcome that voice more than some of the, like, entrepreneurial, rah rah hustle culture people suggest, I think that's quite healthy voice, you know. So is it something that really is a goal that you want to go after or should go after?
Dina Marie
Should is the question do I feel like that's what I want to do? Absolutely. I have a calling to it, and that's why I'm always surprised when I put some type of a ceiling over my head or some type of a limitation over myself. It's that internal battle of I feel I'm meant to do this, and yet I keep stopping myself from doing it as well. Nobody else is standing around me telling me there's no way you could ever achieve that. I'm the one questioning it in myself.
Jason Pfeiffer
Well, then I think it's worth engaging with how to get there. Although, Nicole, you make a really important point about sometimes people set these goals that are really someone else's goals and they don't recognize that and spend a lot of time chasing it. You also see it with founders who start a company and think it has to be a billion dollar company. It doesn't have to be a billion dollar company. It can be a company that just feeds your family and that's a great success. But in this case, Dina Marie, it sounds like this is something you want. And getting there doesn't require any kind of terrible sacrifice. It just requires grappling with whatever it is that's holding you back. And it's interesting that when I asked you about it a few minutes ago, about what is holding you back, you went deep. You went like childhood. So you're carrying around something, always starts there, Jason. It does well, and I'm glad that she volunteered it. You're carrying around something for a long time and it's manifesting in all sorts of different ways. And look, Nicole and I are not therapists, so we're not here to engage with it like therapists, but as advisors, shall I say? I think that the most valuable thing that you can do is recognize that which you have. And then instead of framing your thoughts around what you don't have to frame your thoughts around what you do have. Which makes me want to go back to have you double click on this thing that you said a few minutes ago about your superpower. You said you have a superpower. Tell me about it.
Dina Marie
I believe it is my superpower. I have a way of being able to, like I said, come into a room and if there's a 25 individual people having 15 different conversations, I feel compelled to meet people, hear their story, find the common thread and find a way to bring them together. And I make a joke in life that people travel like I love to travel, and they collect souvenirs and I collect relationships and people and it's people that I hold onto and I carry their stories forward and I find ways to connect them to people in the next place. That I am or in my everyday life. And when I say a magnetic personality, it's that I see myself as that connector piece, that piece in the middle that helps people connect and collaborate together.
Jason Pfeiffer
Do you not associate that quality with leadership.
Dina Marie
That is so good? You're right, I do. I think that I have not looked at it in that perspective because clearly then that would be one of the steps that I'm already what I consider to be an expert at.
Nicole Lapin
Do you feel comfortable talking, bringing us a little bit more down to earth and talking about what industry you're in or any specifics around what this role entails?
Dina Marie
Sure. It's actually been in a couple different industries, but I do notice that they all focus around sales and customer service. You can't have one without the other. But I really call it platinum level customer service in my own life and in my own brain, because I strive to do where others would stop short. I want to take it one more step. And so for myself, it might just be a lot of times I ask for that feedback, and I'm open to what that feedback is, because I don't just want to feel like, okay, I delivered the product and now my job's done. I want to actually know that might have felt good for me, but how did that feel for you? Did you get what you wanted? And if not, where could I have improved? Where could the team have improved? What would have been excellent or, you know, an A rating? And I think that that's where I try and take that feedback and again, then turning it into managing and helping the team, whoever I'm collaborating with, see what our next step could have been, and can we integrate that into the next process to make it better from the start?
Jason Pfeiffer
Okay. Listening to that and then thinking about what you just said before, in which you described your superpower, but you hadn't really associated it with leadership, makes me wonder. In this corporate structure that you're operating in, you're looking at something. You're looking at somebody and the way that they're operating, and you're saying, that is what a leader is. What is that? What are you seeing? Maybe there's a specific person or the way that they're operating, and you're like, that's leadership. Which is the reason why you're not recognizing the thing that you just said you're really good at as leadership.
Dina Marie
I'm seeing someone who's really strongly focused in a direction and able to pull together different personalities, different regional requirements. Because every place around the nation or the world can Be slightly different, but being able to really get a cohesive focus and then getting other people to be motivated and execute it in actionable steps.
Nicole Lapin
Yeah, but, Dina, you collect people. Like, you don't collect seashells or stamps or whatever. You collect these people.
Jason Pfeiffer
It's so interesting because I feel like what you just described is the thing that happens when you do the thing that you just said you do. Right. Like, that's what, you know, like, Nicole's just jumping on that, because that's exactly right. Like, you do this thing, you collect these people, and you get them to cohere to a vision. What you're describing as leadership is literally just the thing that happens after that.
Dina Marie
Oh, I have not put it together for myself that way.
Jason Pfeiffer
We often don't see process. We just see outcome when we look at other people. And so you see someone who is able to have accomplished something, to have mustered people towards something, to have built something, and you think, ah, well, that's leadership. But that's the outcome of leadership. And it was the process that they went through to get there that really was leadership. And that's a little invisible because it's the thing that happened before. It's the thing that's happening underneath. Also, let's not forget that there are a lot of different ways to get to the same outcome. And so you want to utilize whatever your great strength is. And so maybe actually great leaders that you've seen do something a little bit different from what you would do to get to what would ultimately be. Be the same outcome. But I feel like you are not taking into account what it takes to get to the thing that you're recognizing as leadership. But it turns out, I think, Dina Marie, that what you're doing is walking around in the world with the exact qualities that are required to get to that thing, but not recognizing that they're the thing that you just need to do.
Dina Marie
I would agree with that. Based on. Based on our conversation here. Yes, absolutely.
Nicole Lapin
Yeah. It's the connective tissue. It's like somehow rewiring your brain to be like, okay, Dina, a leader is. And we asked you for a person or some embodiment of it, and you're like, no. A good leader is somebody who puts people together in the right way and motivates them. Cool. Okay. So that's what we would assume is their superpower. What's your superpower, Dina Marie? Well, my superpower is putting people together in the right way. Okay, so, like, by the transitive property of equality, this is girl math for you, you know, then being a good leader is this superpower that you have. Was there something blocking you from seeing that you are what you see in a leader?
Dina Marie
Oh, I'm sure that that's where a bit of my imposter syndrome comes from. Of. Because I've been good at a couple things, really great at a couple things, but I haven't reached what I would call the level of success that I've ever really been going for. I don't recognize that it's okay for me to be a newbie in the process of leadership and that it takes time for me to get there. And so I think for myself, it's just recognizing what I have achieved. It's rare. I don't sit down and write down, here's all the things I've achieved, and here's how great I felt when I did them in that moment. And yet I can look back at. If we have, like, a resume, right, I can look back at my own resume and say, wow, I achieved great things. But have I recognized that those are actually traits of leadership? And based on what Jason was just saying, I hadn't.
Jason Pfeiffer
Stick around. Help Wanted. We'll be right back.
Justin Wine Announcer
Welcome back to Help Wanted.
Jason Pfeiffer
Let's get to it.
Nicole Lapin
Leaders had to start leading at some point. Like, Mark Zuckerberg was in his dorm room making Facebook. Like, he had never connected the world before. In fact, he only wanted to connect his school. And he was like, well, maybe it would be cool if somebody could figure out how to connect the world, because that would be really useful. He didn't realize it was going to be him, and he hadn't had any experience connecting the world before that or leading a team that would ultimately connect the world before he did that. So no one has had leadership experience, like, out of the womb. Nobody collects that before they start doing it. So everybody at some point has that imposter syndrome before they start.
Jason Pfeiffer
It's funny, Nicole, you just mentioned Zuckerberg, because I just. I can't remember where I was. Like, two days ago, I walked by a TV and I saw some clip of him speaking in front of Congress, getting grilled by a bunch of old people who don't understand the Internet. And a thought occurred to me, which was, how does he know how to do that? And the answer, of course, is that he grew into it. Nobody knows how to do that. You grow into it. And that means that at some point, like, if we had Zuck here with us, I would bet he would have an answer, and that answer would be that he learned something about himself that's probably actually pretty small, but that was really transferable. He's like, oh, what I learned is that I'm a really quick study and so you just put me in a situation and I'll kind of adapt to it. Or what I learned was how to create the right advisor group and then take them seriously. Or what I learned was, right, like there was just something that he figured out in the early part of his career that he just of kept doing. And that thing just kept being useful to him as his job grew and grew and grew from running this small company to running this large company, to running this world dominating company, to being a guy that gets grilled by Congress. And the thing that you have is the ability to pull people together and learn from them and find some way to cohere them. That's a very scalable skill. That's a skill that's useful in a group of five people and useful in a group of 500 people and useful in a group of 5,000 people. But the most important thing is that you recognize that it's a scalable skill. And that I think is what we're accomplishing today.
Nicole Lapin
And it's really cool that you're so thoughtful about it. I mean, at first I really wanted you to tell me what you do and where you work and what job exactly you want, but you keep going back to this esoteric thing of every industry is sales and customer service. And I'm like, okay, but like, tell me like specifically what you're talking about. Like, what are we? Are we in the, like, food business? Are we in the shipping business? And then I was like, you know what, that is quite leadershipy. Like, yeah, all industries are sales and customer service. I was like thinking about our business and I was like, yep, that's exactly right. And I'm sure food and shipping is like all about, right? Getting more customers and selling stuff and making your customers happy.
Dina Marie
Right?
Nicole Lapin
I think you are really thoughtful in that. You boiled that down across all industries and you are, to Jason's point, basically Zuckerberg, no, you're taking those skills and you're making them transferable. No matter what comes up, no matter what industry you're in or what challenge does come up, you've created some paradigm or some framework for yourself to operate within, as quite a leader would do.
Dina Marie
Thank you for that.
Nicole Lapin
No, thank you for that. It's your words. We're just repeating your words back to you, which is actually a concept in psychology. Although we are not again to Clarify, not psychologists. But this idea of mirroring is really helpful sometimes in the world of psychology because you can hear yourself back to. To yourself, I suppose. And once you hear that, you're like, oh, whoa, whoa, whoa, I don't want to do that. Or like, oh, no, I didn't mean that. It's like, well, you just said that. And at that point, it's helpful to start making change because you're hearing back to yourself exactly what you're saying. And it sounds like Jason and I just mirroring back to you is already starting to turn some wheels for you. What's going on?
Dina Marie
It does help to turn some wheels for me. And I think a piece of it is I need to look at this a little bit deeper. I need to break this down for myself and look at those. When we're talking about thinking of a leader, what specific actions is that leader taking? And then if that were myself facing those situations, what would the actions be that I would take? And that's probably a really good way for me to be able to break this down and start to have it in small, digestible steps that I could take forward. And I really think that it does come from experience. Right. So like you were saying, Zuckerberg never meant for it to be this, and he didn't have experience before he did it. So a piece of it is maybe I keep getting to this place with this ceiling over my head because I haven't seen myself in the moments that I have stepped past it already. And I just need to mirror that back to myself and look for the areas that I have passed this point and recognize that that is a step that I would say that a leader is taking.
Jason Pfeiffer
And when you do that, what happens? Play it out for us at work in whatever vague terms you're going to, where you start to rely more on what you're now recognizing as leadership qualities. You're taking more initiative, you're putting yourself more in opportunities that seem to be available to you should you be able to step up and take them. What happens as a result?
Dina Marie
Oh, I believe that a piece of this is. I am not asking for exactly what it is that I want.
Jason Pfeiffer
A leadership role.
Dina Marie
Absolutely, yes. And I am finding it interesting as we're having this conversation. It's my ball of yarns kind of unraveling for me, finding that voice within myself because I'm a recovering people pleaser. And so being able to now step forward and ask for what it is that I want. In a world where you're given a promotion. Okay. Great. But what's it look like for me to step forward and ask to be placed where I see myself or where I want to go?
Nicole Lapin
I wonder though, if we can play around with these semantics. It jumped out to both me and Jason when you said manager versus leader. Because I wonder if what you want is an executive role and what you're doing is leading already. Like I would consider you a leader right now. And so what you're really asking for. Right. And I'm terrible with like corporate structures and like manager, director, like senior, blah, blah, blah. Like all of the org charts are weird and stump me, truly. But I'm assuming you're going to have some director type role. Right. Or manager type role. And what you want is a C suite role. So you want as an executive role.
Dina Marie
Right.
Nicole Lapin
You want a COO role.
Dina Marie
I believe so.
Nicole Lapin
But you're managing people now.
Dina Marie
Right? Right. So that's.
Nicole Lapin
And you're leading people now.
Dina Marie
Right. So am I already kind of on my way?
Nicole Lapin
Well, no, I think you're doing it. That's why I wanted to drill down on like, what do you want? Is it the leadership? Can we get you to a place where you're already doing the leadership, but really what you want is a bump in pay or you want something else more tangible. Like if you go in and you say, I want to be a leader, I wouldn't know.
Jason Pfeiffer
People don't know what to do with that.
Dina Marie
Exactly.
Nicole Lapin
I don't know if that's really what you're asking for.
Dina Marie
I think for myself, I don't see that org chart where you're like, oh, I'm a C suite now. Or I think leadership is. I don't think it needs that title in order to be in a place of real leadership. I think that I've been looking at the difference between management of people as more like managing their emotions. And a piece of that can be managing the different personalities that butt up against each other. And I see myself being able to lead in a way that again, creating that cohesive place at work where we can collaborate together and you're able to feel confident enough of what you're doing to drop the emotional baggage that we can carry from home to work and really get on board with a focused goal at work and get people motivated to get on that train together rather than managing all of the other life stuff that comes with it.
Jason Pfeiffer
Dina Marie, I want to propose a hypothesis. I think that in this conversation we've actually been talking about two things. There's what's available and there's what's available next. And what's available is really to be thinking differently about the thing that you already do. What we have identified, which Nicole very correctly pointed out, is that you came in here wanting to be a leader, but the truth is that you're already doing that. You just aren't recognizing it. And once you recognize it, the next thing that you can do is start to more proactively act it and enact it. And that's exciting. That means that the people that you manage, you can now lead, which in some ways is a semantic difference that you have created in your head, but in other ways is really unlocking your own permission to yourself to act bigger, to think bigger, to drive your team in bigger ways. That's what's available right now. And then there's what's available next. What's available next is locked up in that thing that you just said a second ago about what you need to ask for. There's somebody, you have a boss, and that boss can say yes or no to some promotion. And that boss needs to know when, what it is that you want. And I suspect that you haven't made all that clear what you want, because what you've been afraid of is that you don't have the thing that's necessary to get what you want. But we have revealed today that actually you do. Because the thing is that you do know how to be a leader, because it's a thing you're actually already doing. You just kept calling it management. And so now we know that you can do it. So now you need to start more fully doing it and then start acting like the person who deserves the thing that comes next.
Dina Marie
I like the analogy of the thing that comes next. And I think that actually fits the conversation really well.
Nicole Lapin
Well, because it's not us telling you what the definition of leadership is. I actually think mine would be quite different. I think Jason's would probably be quite different. Your definition of leadership is something that you not only are doing, but sounds like you like doing and just collect for funsies, which is great. So, like you're doing something that you love, you're going to continue to do something you love. I don't think you need to ask somebody permission, but if you feel like you need to ask somebody permission to be a leader, like, I don't think on, you know, whatever, monster.com, like somebody's looking for a job that says leader, inquire within. Like, I don't. I've never seen that. It doesn't Mean, it doesn't exist. But if you need to ask somebody's permission to be a leader, like you can ask us. Yeah, you're. You're fucking leader. You are a leader, Dina Marie. You are a leader now. Asking for a raise, asking for a title change, that's like a whole other. But it doesn't even sound like that's what you're asking for. Like you're asking permission to do the thing that you're already doing. And if you want somebody to give you that stamp of approval, you have two people doing that.
Jason Pfeiffer
You have collected us and you have brought us together. Now it's time to go do it.
Dina Marie
All that's left is the work. I'm going to take a look at all those things that I'm doing and look at the leader that I'm watching very closely. And I'm going to start to bridge some parallels between what I am already doing and the things that I see and think that that leader is doing that makes them so successful in that leadership role and start to give myself permission to recognize that that's me. I'm doing those things and I don't need anybody's permission. But I already have two fantastic cheerleaders that have told me I'm already taking the steps.
Jason Pfeiffer
Add us to your collection.
Nicole Lapin
That's right.
Dina Marie
Oh, I will. Thank you.
Nicole Lapin
And I think you're very analytical. Right. And so I would encourage you to, as you're looking at whoever this leader is and their quote unquote success that you just talked about, like really measuring to metrics, like is the success financial? What are the specific components that you're measuring against?
Dina Marie
That's a really good perspective for what I'm seeing right now in this leader. It is how the immense focus that this person has had has created and grown a team of people that, I mean, everybody's from very different walks of life and yet we're all on a common mission. And I'm impressed. There's pieces that I recognize I still need to learn before I feel I would confidently be able to move those projects forward with the speed and with the accuracy that it's happened. You know, we all have to readjust, but I see this particular leader making more of the right steps in a more efficient way. And that's something that I want to emulate.
Justin Wine Announcer
Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
Nicole Lapin
Pfeiffer and me, Nicole Lapman.
Our executive producer is Morgan Lavoie.
You want some help? Email our helpline@help wantedoneynews.com for the chance to have some of your questions answered.
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Maybe a little dance?
Jason Pfeiffer
Oh, I didn't sign up for that.
Nicole Lapin
All right, well, talk to you soon.
Dina Marie
Sa.
Date: October 7, 2025
Hosts: Jason Pfeiffer (Entrepreneur Magazine Editor-in-Chief), Nicole Lapin (Money Expert)
Caller: Dina Marie
This episode tackles the pervasive issue of imposter syndrome and its impact on career advancement. Dina Marie, a caller, seeks advice on overcoming self-imposed limitations holding her back from breaking through to true leadership roles. Jason and Nicole guide her through reframing her achievements and strengths, ultimately highlighting how the qualities she doubts are actually evidence of leadership. The conversation is honest and practical, blending personal anecdotes with actionable guidance.
"Even though I've accomplished so much...I hit these moments where that voice inside me says, not quite good enough. Why are you reaching so high? Isn't right here fine?" (Dina Marie, 02:44)
"A manager is taking orders from someone above and making sure everyone below them is following... A leader is driving vision from within them." (Jason Pfeiffer, 05:33)
"I collect relationships and people...I hold onto and carry their stories forward and connect them to others." (Dina Marie, 10:15)
"You do this thing, you collect these people, and you get them to cohere to a vision. What you're describing as leadership is literally just the thing that happens after that." (Jason Pfeiffer, 14:02)
"By the transitive property...being a good leader is this superpower you have." (Nicole Lapin, 15:44)
"No one has had leadership experience out of the womb...everybody at some point has that imposter syndrome." (Nicole Lapin, 17:39) "You grow into it." (Jason Pfeiffer, 18:24)
"Is it the leadership? Can we get you to a place where you’re already doing the leadership, but really what you want is a bump in pay or something more tangible?" (Nicole Lapin, 25:35)
"If you need to ask somebody's permission to be a leader, you can ask us. You're a fucking leader." (Nicole Lapin, 29:12)
Final Empowerment:
"You're a fucking leader. You are a leader now." – Nicole Lapin ([29:12])
This episode offers a relatable, energizing guide to reframing imposter syndrome, validating unique strengths, and stepping confidently into leadership—however you define it.