Financial Feminist - 242. How to Be a Great Leader (Without Losing Yourself) with Amanda Litman

Episode Date: June 30, 2025

What if leadership didn’t mean overworking your team, sacrificing your mental health, or pretending to be someone you’re not? In this episode, I’m sitting down with repeat guest, Amanda Litman��founder of Run for Something and author of When We’re in Charge—to talk about how millennials and Gen Z are reshaping leadership from the inside out. We dig into what it takes to lead with empathy, accountability, and boundaries in today’s work culture—and why the old playbook just doesn’t work anymore. From navigating social media and hybrid workplaces to building inclusive, sustainable teams, Amanda offers a refreshingly honest take on how we all can be better leaders, whether you're managing a team or preparing for your first promotion. Amanda’s links: Website: https://www.amandalitman.com/ When We’re in Charge: https://www.amandalitman.com/when-were-in-charge  Run for Something: https://runforsomething.net/  Read transcripts, learn more about our guests and sponsors, and get more resources at https://herfirst100k.com/financial-feminist-show-notes/great-leadership-amanda-litman/ Looking for accountability, live coaching, and deeper financial education? Check out our exclusive community! Join the $100K Club: https://herfirst100k.com/100k-pod Our favorite travel and cash-back credit cards, plus other financial resources: https://herfirst100k.com/tools Not sure where to start on your financial journey? Take our FREE money personality quiz! https://herfirst100k.com/quiz Special thanks to our sponsors: Squarespace Go to www.squarespace.com/FFPOD to save 10% off your first website or domain purchase. Indeed Get a $75 sponsored job credit to get your jobs more visibility at Indeed.com/FFPOD. Rocket Money Stop wasting money on things you don’t use. Cancel your unwanted subscriptions by going to RocketMoney.com/FFPOD. Quince For your next trip, treat yourself to the luxe upgrades you deserve from Quince. Go to Quince.com/FFPOD for free shipping on your order and 365-day returns. Netsuite If your revenues are at least in the seven figures, download the free e-book Navigating Global Trade: 3 Insights for Leaders at NetSuite.com/FFPOD. Saily Get an exclusive 15% discount on Saily eSIM data plans! Go to Saily.com/FFPOD download the Saily app and use code 'FFPOD' at checkout. Masterclass Get 15% off any annual membership at Masterclass.com/FFPOD. Learn more about your ad choices. Visit megaphone.fm/adchoices

We've all had a terrible boss. Here's how to not be one too. Amanda Litman is the co-founder and president of Run for Something, which recruits and supports young diverse leaders running for local office. If you want to run an effective business, you've got to think about how you can build an inclusive environment or your business is not going to succeed. Since 2017, they've launched the careers of thousands of millennials and Gen Z candidates and in the process changed what leadership looks like in America. A good leader knows that if your employees are working 100 hour weeks, that's a failure on every part of the leader, not the employee.

She's the author of two books, one of which we're talking about today, which is When We're In Charge, The Next Generation's Guide to Leadership, which is out now. We're talking today about leadership, but specifically how Gen Z and millennials are changing the game for what the future of leadership can look like, both in organizations and across the world. Millennials and Gen Z are going to get more and more diverse. Our business places are going to be more diverse. The teams that we hire, it is almost hard at this point to hire a non-diverse team, a homogenous team. We get into how to be a good leader, very specifically, as well as how to relate to others but maintain healthy professional boundaries. You can be friendly with the people you manage, but like they can't be your friends. Because also you don't want to fire your friends. As Gen Z and Millennials are rising up in their careers, you're starting to manage

people and you need to know how to manage people well. We're talking about that today. We are so grateful to have Amanda back on the show and this is a must listen if you work in any kind of structural work environment or you're part of a team and an extra must-listen if you were in any type of leadership role. Let's get into it. But first, a word from our sponsors. You know that I know that we love saving you money on this show. So before we get into the rest of the episode, I want to give you all of the deals from our incredible sponsors that allow us to do this show free for you.

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No, bad leadership gets bad outcomes. I think bad leadership makes people miserable. I've been thinking a lot as I work through this book and talk about this book right now about why it matters in particular in this moment to have leaders who are compassionate and empathetic and boundaried. And I think so much of it is like, what would be possible if work didn't suck?

Like, what would that free up for you in your life if your job, which was important and meaningful and well compensated and had good benefits, but didn't drain you of the will to live, that you could leave at the end of the day? How would that make you a better partner, a better parent, a better citizen, a better friend? What kind of space could that open up in your life?

So bad leadership means you can't do any of that and good leadership means so much more than that. I think when we say, you know, bad leadership, it's easy, especially for, you know, you and I in the conversations we've had previously on the show to go immediately national, global, to talk about Donald Trump, to talk about all of that. How do we think about how bad leadership or good leadership can affect us

in politics and on a more national or global scale? You know, I think about this with the politicians we've got now who are modeling such bad behavior. Like, how much must it suck right now to work for Trump or Elon or any of these dudes? And they're almost all dudes. Like, how miserable must it be to go to work every day with, like, careening goals and priorities with, like, someone who so clearly doesn't care if you have a life outside of work, who so clearly doesn't want to be transparent and open and honest and vulnerable with you.

I think that trickles down. Like we feel that in our day-to-day life. Like the pressure and the tension, the way that like our shoulders are bunched up and it's like hard to relax. Yes, it's the atrocities that they are doing, but it's also the sense that there is no stability, no structure, no clarity. I think that is one of the things, one of the many things that makes this moment so exhausting, is that we don't have clear visionary leaders at the top who can give us a sense of comfort that we know where we are going and that, yeah, there's going to be road bumps, but at least we have a plan to get there. you know? Yeah. Well, and in writing this new book, what was the catalyst for you when we think about like current leadership or business books? Like what did you think was missing from the shelves of Barnes and Noble?

So I think a lot about the last eight years I've had running run for something, which I started with my co founder back in 2017. And before that, I was managing teams for a couple years. I've been managing teams for over a decade at this point, I'm 35 years old. And I have read, I don't know, 60 or 70 leadership books in depth of all kinds. And I think much like you with, you know, financial information, so much of it is written by old white dudes, people who have social safety nets or wives or partners at home who can provide for them or care for their home life, a lot of military people, and so little that seemed grounded in the actual lived experience of being a leader, especially in being a leader right now. Like if you go to the Amazon bestseller list of

leadership books, it takes you to I think number 10 maybe, it depends on the day, to find a woman. It's usually Dr. Brene Brown, God bless. And you don't see another one until 20 and almost none of them are under the age of 35 or 40. Like it's just so many folks who don't actually have the lived experience of managing a team, of being online in this moment, of having to navigate the demands of millennials and Gen Z in the workplace. From my experience, I wanted more of that, but I was also facing challenges that I think very few leaders,

at least in the years past, had to deal with. How do you take maternity leave if you're the boss? How do you post on Instagram if your employees follow you there? How do you think about showing up in the workplace with executive presence when the workplace is Slack or Signal or Zoom rooms? It's like very different ways of thinking about the role of a leader than people had to do even five or ten years ago. I think what anybody listening starts to understand the moment they have managerial responsibility at work is they think shit, I don't know how to do this. Like, I know how to hopefully be a nice person. I know how to work really, really hard at my job. But I do not know how to lead a team. Or I do not know how to get

the best out of other people. Is that what you were seeing with a lot of the interviews you did? Because you did over 100 interviews for this book, and I was one of those interviewees. Thank you for that. But like, was that what you were seeing? There's this moment where it's like, no one's teaching me how to lead properly. It is such a challenge, especially in industries where there aren't like formal apprenticeship models where you get like promoted because you're good at the work, you're not good at leading, they're not good at managing. And there isn't that much resources spent

doing management training or leadership training. And the management training that does exist feels very divorced from the reality of actually leading. And like doesn't actually get at how it feels to lead, which is what I tried to really talk through so much in the book of like the isolation, the loneliness, the vulnerability, the challenges of putting yourself out there. It is so hard.

And that was like the theme through so many of the conversations. I know it's something you and I talked about, something I talked about with folks from across a bunch of different sectors of that. This is hard and it feels hard because maybe I'm bad at it, when actually that's not the reason. It's hard because it is structurally set up for you to fail and you've got to overcome that. That I think was one of the themes I heard from so many of the people I talked to, folks from business,

from tech, from the law, from medicine. I talked to people who run day camps, I talked to faith leaders, same stuff, different spaces, same stuff. Yeah. So maybe let's split the challenges in two. Can we first talk about the challenges of leading in the world we're in today? So social media is the perfect example of this. It's constantly changing. DEI, protecting DEI, all of these things are changing so rapidly. So can you walk me through a couple of those challenges, how they're showing up for leaders

right now more broadly before we talk about why uniquely Gen Z and millennials are experiencing these? Yeah. So social media is a good one to start with. A lot of the branding, like the books I would read beforehand would assume that you had built a personal brand without ever being online before. They'd be like, start a Facebook page, go to LinkedIn and update your personal website. I was like, my dudes, I've been on Facebook since I was 15. I've had an email address since I was six. I have been thinking

about personal brand building since I had to set up an AIM message to attract my crush in high school. Like, what are we talking about here? And I think especially leaders right now are acutely aware that every Zoom could be recorded. Every email could be screenshot. Every private Google Doc could be going viral in a Reddit thread that you don't know anything about. The transparency that people demand out of companies, the way that they can leave a Yelp review

or a Google review on a business, they are doing the same thing, but they're employers. So you got to be so intentional about how you show up in all of these spaces and to make sure that the story of you that you're telling on Slack, on Zoom, on your personal Instagram account is unified. And that is a challenge that the leaders before us didn't have to deal with. You mentioned DEI, and this is, sadly, I think one of my hottest takes in 2025. Segregation is bad. DEI is good. Crazy that that's a hot take, but it is.

I know, it is. I mean, I think it's really important to say it straight up. Diverse and equitable teams are good for business. They're also a moral good. They're also a believed reality. Millennials and Gen Z are going to get more and more diverse. Our business places are going to be more diverse. The teams that we hire, like, it is almost hard at this point to hire a non-diverse team, a homogenous team, because that's just not how populations

work anymore. So if you want to run an effective business, you've got to think about how you can build an inclusive environment or your business is not going to succeed. And we're seeing this, like, there's a reason that Nike's like best performing ads of the last six months have been about women's sports, like black women in basketball directed by Malia Obama, like so inspiring, so beautiful and so lucrative for them. We're seeing targets numbers go down as they abandon DEI and Costco's numbers go up. It matters to do this and it

matters to do it right. And I think that is often the challenge that leaders today are facing is that what is the right way to run a diverse and equitable environment? So when we're thinking about leadership for millennials and Gen Z, can you talk me through the things that set those two generations apart in leadership, but also the unique challenges they might have? Yeah, I think for millennials and Gen Z in particular, it's thinking about how the institutions that we used to imagine to exist

for us are no longer there. We have seen financial crises, the pandemic, the elections, like layoffs after layoffs after layoffs. There is not the same kind of safety net for your career that I think our parents or grandparents could have relied on, at least in the grand scheme of things. Obviously, all generations are not on a monolith, like the generalization's here. But generally speaking, we know that our work cannot love us back. So that really changes your relationship to it. And as a leader, it changes your relationship

to your team and the kind of environment you want to build for them. I don't want to work 100-hour weeks. I don't want my team to work 100 hour weeks. I want to have a life outside of work. I want my ambitions to be for my job, yes, but also for so much more than my job. I want a life bigger than my job and I want my identity bigger than my job. So how do I set that up? How do I build that? How do I operationalize that so that that's possible? I think one

of the biggest challenges that millennial and Gen Z leaders have is that we are managing our peers, that millennials and Gen Z have very different demands out of the workplace. They want more transparency, more accountability, more insight into decision making. They want work to provide more for them. You'll think about the big tech companies that would like offer, you like offer laundry services and workout classes and free food in the cafeteria and All of that was really just meant to keep you chained at your desk or at the office to do more Yeah, you think about the flexible work environments that people want all of this is totally reasonable in many ways to want But then the onus becomes on leadership to be so clear about what they can and can't provide I think that's one of the challenges that for millennials and Gen Z, both as leaders

and as members of team, to be so on the level about what is responsibility of the workplace and what is the responsibility of the employee. And as I argue in the book, to be so generous and expansive about what the workplace can do within the constraints of what is meaningful or reasonable for a workplace provider. Things like compensation, healthcare, benefits, clear definitions of success and failure, good team environments, inclusive team environments.

Like we should be as generous of an employer as we can be and also be so boundaried about what is and is not the responsibility of leadership. After the break, we talk about some of the sticky parts about being a leader, including how to create boundaries with coworkers and some of the simple tactics Amanda uses to create a leadership persona, which is one of my favorite takeaways of the episode. Stay tuned.

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And of course, I think it got ripped out of context because if you listen to the whole episode, I actually think she's right where she's like, assuming you're a great place to work and you offer good compensation and you offer good benefits and you offer all of the things, it isn't my job to actually manage your life outside of work. And it shouldn't be my job. I don't know how you felt about that clip too. And if you listen to the whole episode, but it feels kind of like what we're talking about. Yeah, I think like the way that she phrased that was the most artful way of doing so.

But yeah, definitely. The onus is on leadership to create the guardrails so that people can have the latitude to run their lives the way they want to. I think the problem is that so many companies don't. They ask so many questions. They treat people like shit. And the thing that I want to push for is like, it has to start from the top. But if the top is bought in, so much more is possible. So much more is possible. Yeah. Something that I really want to talk about, because anybody who's listening right now, who's in any space of leadership, whether that's just managing one person, whether that's managing a whole team, I think the

peer to peer versus leader to support a subordinate position, like that starts getting really messy. And it's something even I had to learn as someone who employs people around my age, sometimes older or more experienced, that was really difficult because I like and respect all of the people I work with. And I think, you know, we are friends, but at the same time, I am their employer. So how do you find how they manage or how good leaders manage that relationship where, yes, we can be friends

or friendly, but ultimately, there is still a power dynamic here. The number one red flags in the US people are like, my workplace is a family. Family? Not a family. Not a family. Nope, can't fire my family, which sometimes I would like to can't fire my family, which sometimes I would like to, can't fire my family. And I think that is such an excuse to paper over bad behavior for treating people like shit. Absolutely.

And I think the thing you named is that you can be friendly with the people you manage, but they can't be your friends. Because also, you don't want to fire your friends. I think that is one of the things that makes leadership so lonely, is that the folks that maybe you came up with or your colleagues that you're now responsible for, like you have to maintain some kind of emotional distance. And you want to be collegial, you want to be a human, you want to have like honest and authentic relationships with them. So the tension between those two things, like that's the tension of next generation leadership is I want to be friendly, but I can't be their friend. I want to be human. But like, also, I have to make decisions that are about the care for the whole, which sometimes compromises care for the individual.

It's fucking hard. And the thing that I came back to in so many of my conversations is like, how do you network in this moment? How do you build relationships with other leaders outside of your workplace? How do you find a mentor or a thought partner? How do you do it when it's often like the mechanics that people used to network before no longer exist as one of the challenges of remote workplaces, which I think are still net good, but have their own separate limitations. So many people brought up to me group chats, which I think is really fun. I was like, yeah, of course it's a group chat

or a Facebook group. One person who became a partner in a law firm in Chicago was telling me that her number one networking space was a Facebook group called S.Y.R. Moms. And it was where she was in conversation with other moms who were lawyers across the country. And they would refer business to each other. They'd talk about their different practice issues.

They talk about, you know, the challenges of being a working parent. She was like, the other 85 year old partners at my firm do not understand when I talk about how I got this business from someone on Facebook. Like it's incomprehensible to them. Are there practical ways that we can think about setting boundaries as leaders where we can still show up as the cordial, friendly version of ourselves, but also knowing we sometimes have to bring the hammer down? How do we navigate that? Yeah, I talked about this in the first part of the book about responsible authenticity,

which is how do you be yourself, but be the version of yourself that's actually what your team needs and what your mission or your goals need? Because I think that's often the challenge of leadership is, you know, you get to this point, you're like, I'm great, I'm the boss, but it's actually not about us. It's not about us. It's not about us. It's about our team and what they need. So you got to have real deep self-awareness and introspection.

You need to have your mental health cared for, have your needs outside of work cared for, like build a community around you to care for yourself. Know what it is that your team needs of you. Like what version of you do they need? I think, anything about like managing someone directly. You often ask them like, how do you like to receive feedback? It's not how I do, I like to give it.

It's how do you like to receive it? The same is true with how do you think about how you set up, show this show up in the workplace to best present for them? And then what's the overlap between the two? And I talk a bunch about how to create a leadership persona, which to some people feels like, you know, you're talking about faking it

or like wearing a mask or like, you know, not being yourself. No, I'm talking about being the best version of yourself to accomplish your goals. And the hope is that that leadership persona is as close to possible to who you are as a person. But like a little bit of distance can be good because it allows you that freedom to make the hard decisions. And when you get criticism, which if you are a leader and you are standing for something, someone else is not

going to like it, it gives you a little bit of space to deal with that criticism and take the good faith, like the good faith stuff as feedback and the bad faith stuff as a haters gonna hate. You and I talked about that with the social media section of your book too, where the person that you're hearing on this podcast right now or the person that you see on Instagram is me, but it is not the full me. And I think a lot of people understand that,

but are also shocked by that of like, oh, does that mean she's living a lie or she's inauthentic? And it's like, no, I have to keep a degree of separation for my own safety, for my own mental health. And it sounds like we have to kind of do the same thing as leaders because, yeah, if you show up as the fullest version of yourself, that is potentially a liability.

And it's also, you know, I don't want to ever fire people. That's not true to me, is to make somebody else feel badly. But sometimes I have to do that for the benefit of the whole and the collective. So can we talk about the Beyonce versus the Sasha Fierce of it all? Like, how do you, how do you separate without it feeling inauthentic? You know, I think influencers and people who like have built public personas online are such good examples of the tactics that we can think about. Because if you think about

what does an influencer do, it's inspiring their followers, their community to take an action. Like ideally, it's doing something good or buying something and not cyber bullying other people on the internet. But it's trying to get people to take an action. And that's what leadership is. So if you think about the tactics that someone who has created an online persona has done, it's the visuals, it's the language, it's the audio, the music, the tones, the word choice, it's the way in which they engage with others online. Like, are you in the comments? Are you tagging other people? Are you like resharing and remixing? That vernacular of an influencer's brand building can be applied to the workplace. I think especially for folks who are in flexible

or hybrid work environments where so much of their interaction is over Zoom rooms and Slack chats, it can almost feel parasocial. It's not quite parasocial and there is a two-way relationship here, but I can so clearly carefully curate the relationship that my team has with me, that it's parasocial adjacent. So being really intentional about all of it.

I think that that's the theme of so much of this, is there's not a right way or a wrong way to show up as a professional anymore. That's one of the beauties of so many women and people of color and LGBTQIA folks taking power in this moment, is that we've like blown open the model of what it could look like.

The scary part of that is that you sort of have to shape it on your own. And you have to decide how you want to show up as a leader and then be so, so thoughtful about that presence. One thing I wanted to talk to you about is the feeling that so many of us have had of being the only one in the room. And especially when you're the only one in the room as a leader. So you are, I've had this experience of being the only woman in the room, but then also the youngest person in the room, and having a better or, you know, a higher job title than the other people in the room. For folks of color, right, being

one of the only black or brown people in the room. If you're queer, being the only, like, how do we navigate either feeling the imposter syndrome, feeling the, oh, someone is going to, like, it just feels very isolating to be the only one in the room, especially when you're in leadership. So have you found ways in your interviews that people have navigated that? Yeah, being so clear-eyed about how the scam is structural in this regard. You feel like you don't fit in because you don't. And it's not you. That's not a personal failing. I remember talking to one woman who was describing to me her challenges finding a mentor. And

she was a young black woman in Hollywood. And she was like, you know, every mentor I've ever had has been a white dude. And they would give me advice about like, you know, I tried this project and I failed, but then I was able to make a documentary out of the failing. And so I get like, it's fine. She's like, Jim, that doesn't work for me. I don't get to fail the way that you do. She would say, I don't get second chances.

I get one chance. Maybe not even that. If we're lucky. And she said to me, she's like, so I take that advice with a grain of salt, and I'm also so not bullshitting myself about what opportunities are available to me or not available to me because of what I look like and who I am. So many, and I think this is true, especially for people who have been the first or the only,

have been so thoughtful in finding joy and bringing up others with them. Like, the amount of people I talk to who said the thing that they, like, get the most meaning out of in their work is mentorship, especially of women and people of color. How can I make sure that while I may be the only one right now, that's not true forever? What happens if your leadership style is then questioned? Like, if you're the only woman in the room

and your leadership style is questioned by men, did you feel, I imagine you felt like that at some point in your career, but how do you respond in a way that is going to navigate that with grace while also setting boundaries? Oh, this is where confidence is your key, you know, to know that both like confidence in yourself, but also just if you're right, you're right. I remember I've, you know, my co-founder over the years was this incredibly equitable guy,

Ross Mraus, who's one of the most thoughtful feminist men I've ever had the opportunity to work with. We would go into meetings occasionally with men in politics and they would address their conversation entirely to him. And Ross would be so thoughtful about like, oh, Amanda should speak on this, you know, we would share equity there. But it really ingrained on me like, if I want them to listen to me, I have to speak up. I have to own the fact that I am in this room because I deserve to be in this room. I have put in the work, I have proven that what we are doing matters.

And if I don't speak up for myself in this moment, they're not gonna give me another chance to do so. It is exhausting. And that actual exhaustion is what I think in many ways makes next-gen leadership so hard is like, man, they don't have to think about this. They don't. This came up even with members of Congress. I spoke with a number of like millennial women in Congress who would tell me like how much time did I spend in debate prep thinking about my vocal fry or my up speak or like how my

suit would look on camera. The men who I was debating with didn't have to think about this shit. I mean, I think about that even in my work a lot of the way I present myself. I don't love getting all made up. I think for me, it feels like a waste of time. I don't love it. But I know I have to in order to present myself in a way where people will take me more seriously. And that is the experience I think of every single woman is,

I don't want to have to do all of these things and spend all of this time worrying about things or worrying about my presentation, but I have to perform my gender know, my gender in a certain way in order to be taken seriously. And like that's a lot of mental and emotional energy to just before you even have focused on how do I do my job well. I talked to this woman, Tiana Epps Johnson, who runs the Center for Tech and Civic Life. She's like a democracy hero. It's a nonpartisan group that does all kinds of work around election administration.

She has raised, I think, half a billion dollars, maybe, to protect elections. She's an icon. And she told me how she always fund raises wearing big gold hoops. She's a Black woman. She said, I wear big gold hoops, and I put my hair in a headband, put my hair in a knot, and it was off my head.

Because she said she once had a mentor who told her that wearing big gold jewelry was tacky and low class. She was like, fuck that. I'm showing up as me, and I'm proving that that doesn't stop me from doing the job done. She has this amazing TED Talk that's worth watching where she's on stage with her Doc Marten boots and her skater dress.

And she's like, I am making the case for defending democracy exactly as who I am. And she was describing the challenge of that is that it requires immense bravery. She was like, I think about, I find the bravery to do that because I am playing a role and playing a character of brave Tiana, who is paving the way for other people to do it this way too.

And if I think about it as role modeling, if I think about it as what I can do to make it easier for others, that gives me the strength to do it. I love that mentality. Well, and it's back to what we were just talking about. I think you're exactly right that one of the best things anybody listening can do as a leader is to create the Sasha Fierce to your Beyonce.

Like, what is the version of you that shows up slightly differently than you might show up in your relationship to your partner, or your friends, or your family, because it requires a different set of skills. It requires a different version of you. It can be you, but it is a different version of you. It's a, one person described to me as my Tuesday self versus my Saturday self. Both are me, but my Tuesday self shows up to the board meeting not ready to mess around

on my Saturday self, is home with my family and my dog and my pillows and having a good time. That doesn't mean I'm not me. That just, yeah, but like, how do you do that authentically? And that wasn't a thing that the bosses we've had in years past had to deal with. Cause they could just show up as the worker bee or the robot boss, which that's not what our employees want and that's not what we want. I think that's the challenge, you know?

I love the idea of the Sasha Fierce you that comes into work. Feel free to let us know in the comments if you're listening on Spotify, if this is something you've tried or have a plan to try. When we come back from a word with our sponsors, we're talking with Amanda about how to be a good employer and also what leadership looks like outside of work, especially for instance,

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quote, talent is a product. Can you talk more about that? Yeah, people are what make the work happen. an interview that you recognize that quote, talent is a product. Can you talk more about that? Yeah, people are what make the work happen. Like if you can hire good people, everything gets easier. And I think about this with the work I do at Run for Something, which is recruiting candidates to run for office. You think about a political campaign, the ads are better, the organizing is better, the message is clearer when the candidate is good, when the person doing the work is good. Anyone who's ever had to hire knows how difficult it is. And when you get it

right, oh, what a relief. And when you get it wrong, oh my God, what a headache. Hiring good people and making it so it's a place they want to stay and do their best jobs, like do their best jobs, do their best possible output, is transformative. And I think we know that retention costs for businesses, it can cost up to three times someone's salary to fill an open role between the lost time of having someone doing the work and the time to recruit and the hiring efforts and then onboarding. It's expensive to be somewhere crappy to work. And that is my reminder to business leaders in this moment, or like, why should I run a good workplace? Like, you know, how can I think about AI or all this crap

that like might make it a shitty place to be? It is bad for business to be a bad place, to be a bad employer. To connect this to leading in families, you touch on this connection between different generations' parenting styles and how that can lend itself to these like alternative leadership styles. You say how quote, the first leader most people encounter in their lives is a parent or guardian. Can

you touch on that connection? Like how does our leadership blend into our parenting and then our parenting into leadership? And how does this affect the leadership ability of future generations? This is so personal for me because I wrote this book, I had a one year old and I was pregnant with my second daughter, which was stupid. But it's like never again, never again in many ways. But my you know, I have a toddler now and an eight month old.

By the time this is over, they're a little bit older. But two little girls. And the experience of managing a toddler's self-regulation. Like at home, we use Daniel Tiger episodes. And you count to four and you roar when you're mad. At work, it's a meeting agenda. It's taking a beat before you speak in a meeting. It's the same kind of self regulation. One, honestly, if I could bring Daniel Tiger

to work, I would because it's pretty compelling. I think those same kind of ways in which millennial parents in particular are trying to break the cycle of our parents. Like I am trying to think about how I show up for my daughters in a way that is so different in many ways than my parents showed up for me. Not that they did it right or wrong, but that, like, I don't ever want to talk to my girls

about their bodies. I don't ever want to scream at them, stop crying. I want them to have, like, emotional literacy. I want them to have comfort with who they are. I want them to feel safe in this home so that they can be themselves. Similarly at work, I want to create an environment where my employees can show up and be their best selves and also know that there are boundaries to what work can provide for them. It is such a different way of understanding the role of parent and the role of boss.

And it was the thing I heard in so many of my conversations, especially from people who already had kids, which was the re-parenting I have to do to myself so that I show up differently for my kids is making me a better leader at work. What are the concrete things, maybe give us two or three, that separate a good leader from a bad leader? A good leader knows that if your employees are working 100 hour weeks, that's a failure on the part of the leader, not the employee. That the employer has a responsibility to set up really strong guardrails for when work

has to happen, how work happens, and what success looks like. And then the employee has the freedom to make the decisions on how they use their time. So that's point number one. A good leader is themselves in the workplace, but not their full self. And they don't ask their employees to bring their full self to work with them either because work is not the right container for your full self. Work is the right container for your work self. And it should be a welcoming container, an inclusive container. Who that work self is should be expansive. But like, you don't need to bring everything to work with you because it's not fair of me to ask you to do that. It's not fair to the workplace to be the container for it. So the third thing that a good leader can do is reasonable transparency. I think this is a challenge, especially in this

moment, because sometimes people are not prepared to take everything you want to show them, but you should be able to give enough information and insights that people can have a certain amount of accessibility into what's going on. They can know how you're making your decisions, even if you can't always let them have input onto those decisions. I think this is one of the tensions that come in with managing Millennials in Shenzhen Sea where people want agency, but they don't want the commensurate accountability. As a leader, I have both of those things. I am both in charge and also I'm responsible for what happens, and if things go wrong, it's on me.

You got to balance those things, and that I think is a sign of a really good leader that knows how much to let people in and how much to show that I'm making decisions based on my values, and you know what those values are. You know who I am as a person. So you can trust me to make these decisions. And I think that trust, when we talk about authenticity, when we talk about being yourself a workplace, all of that is in service of building trust and creating psychological safety, which then allows people to do their best work and get you

good outcomes, brings us full circle. I think that's one of the hardest things I had to learn as a leader is actually that transparency piece because there have been concrete times I can point to where I was like, I was not transparent enough. And then there's other times I can point to where I was like, I was way too transparent. Way too transparent. And I think one of the biggest pieces of advice I can give to leaders, especially if you're leading a company or the CEO, or you're in the, you know, the executive level, is like, you're there to handle executive level problems. And that is your job. It is not the job of somebody who is, you know, working in your team underneath you to stress about executive level problems. So there would be times, you know, working in your team underneath you to stress about executive level

problems. So there would be times, you know, we were having very transparent conversations about revenue. And there's certain people we want to have those conversations with. But there's other people that think they want to know that, but then they have the executive level responsibility for something that is not on them. So I think it's finding, yeah, what feels like the right level of transparency, both in your values, but also realizing that there are certain things that you are responsible as a leader to carry, that the rest of your team does not need to worry about. Like, I'm worried about everybody's livelihood. That is not my responsibility to pawn that off to my employees.

Like that, my responsibility is making sure every day that I, the company is making enough money to support my team. They shouldn't have to stress about that in the same way that I do. And like it is a problem if they are. That means that we have failed as leaders. Like I've been in those shoes. You know some tough years and it is so tempting to want to unload all of that. To be like, no, look, see, these are the XYZ things happening. This is why this is a problem. I can't. You can't. You can't. And like, the impulse to want to be transparent and know that actually it does not serve them. Like it is not a clarity that would be kind to provide.

Now the clarity that is kind to provide is like, here's who I am, here's who I'm thinking about these decisions, here are the constraints in which we're making them. Like here's how this happens. Here are the ways you can contribute to goals. Here's the feedback loops. And I write through this in such concrete detail

of like how to think about modeling decision making models, how to think about talking through them and explaining them, you know, the tensions of transparency. But it is not everyone's job to be worried about the things that the boss is worried about. It's the boss's job. And like, that's what the money is for, you know? Yeah. Yep. Exactly. So you interviewed over 100 people for this book. Can you share a few of the most impactful stories you've heard? Oh, I could do this for hours. It's so fun to get to talk to folks. I remember speaking in particular to Marshall Hatch, who's a pastor and faith leader out in Chicago. We were talking

a lot about the challenges of thinking about your work as a calling. Chinno is a resident for a lot of people who do passion work, whether it's in faith or non-profits or public service or like, I think you think of your work as a calling to really educate women about the power that financial literacy can have. And what happens when that consumes you? What happens when you're getting lots of different calls? He, at the time we were talking, was about to have another kid and like, what does it mean to want to be a different kind of dad than he had had and like show up differently for his family and not having great models for that? It was such a fascinating conversation.

And I loved hearing it in particular from someone whose work was so deeply grounded in his faith and also his commitment to his family, both his parents and his kids. I love talking to this woman who ran a summer camp in North Carolina up in the mountains. We were talking about inclusivity and how to create environments that were welcoming. And she was saying that one of the challenges that they had was they wanted to create a camp for boys that was really expansive and how it understood masculinity. Especially if a little boy is just like, if you want to send your kids somewhere, your son somewhere, where they're going to come home with painted nails and that upsets you, then this is not the right summer camp for you. And that's okay. That doesn't mean that we have to be for everyone.

To be welcoming and inclusive does not mean needing to be for everyone. It means being for the people you are for and knowing that to be inclusive, you gotta be a little exclusive. You gotta draw the lines somewhere. I'd say the last person actually I'd say, I loved talking to you for this book, Tori, because I think it was such an illuminating conversation. I'm gonna blow up your spot a little bit

about the way in which you deal with negative feedback online and like the red lipstick and leather jacket that allows you to perform as Tori without giving all your full self away. I think about that a lot. And like, the way that it can feel when there's, you know, 100 comments under a video can feel like 100 people screaming you on the street. It's a drop in the bucket in the grand scheme

of the impact and staying focused on that impact allows you to stay focused through the work. It was really fun talking to you and honestly like a fun little therapy session for me. And yeah, the hundred people thing, I've talked about it on this show before, but I think that what folks might not understand is, and we all have, you know, even if we don't have millions of followers, we all have a version of this, right? Where we get told 95 lovely things, just those five seem really, really heavy. And it's very easy to ignore the other 95. But also the 95 are extremely overwhelming. And I think that's unique for somebody in my position where, yeah, the metaphor I give,

I was walking down the street and 100 people yelled at me and 95 people yelled nice things and five people yelled horrible things. One that five is going to be awful. That's just going to be rough. But it's still an overwhelming thing to have 100 people yelling at you. And I think for somebody, again, running a public facing business or who is a public person, that might be a unique thing that the average person does not experience. But we all experience a version of this where we get a lot of feedback and we have to determine

what feedback is actually valuable, what just feels hurtful and not constructive at all, and how do we parse through that? So that actually leads me to a question I have for you too, which is how do we receive feedback in a way that doesn't devastate us if we care so deeply about the work we're doing? When we come back, we're wrapping up our conversation with Amanda, including how to overcome the need to be liked as a leader and how to advocate for your needs within leadership if you're not a leader yet. Stay tuned. You know, I think about this, I guess, there's a lens of my work in politics, which is like the most effect of most popular politicians in the world would

have a 70% approval rating. Like that doesn't happen anymore. A 70% approval rating. That still means 30% of people don't like them. And like that reminder that if you are doing a good job and you are standing for something and you are staking out a vision, people are going to disagree with you. And some of them are going to disagree with you really loudly. And some of them are going to disagree with you in a way that is personal and pointed and shitty, and sometimes in a way that feels dangerous.

It's worth naming that for a lot of folks that can be very, like, put their physical and emotional health at risk. In the book, I make the case for arming yourself with a suit of your integrity. If you know that you are making decisions with the right goals in mind, that you have a clear values framework that you're using to work through them, especially when you have to make the hard calls, the feedback doesn't get to you because you know you did the right thing. The point when the feedback gets to you is when you know they're right.

I think about the decisions and the things I've messed up over the years, and I write the book a ton about the ways in which I have messed up. It's when I know that I put ego or myself or feelings above the work or above the bottom line. If you are like in service of your integrity and your goals, yeah, feedback is always helpful. A lot of feedback is a gift, but a lot of feedback is not a gift, or it's the gift in the form of like should be left on your doorstep. You can ignore it.

And that I think really helps think about the thick skin that you need to build when you're in charge. Yeah, I think especially for me a couple of years ago, I'll add to what you said that for me, the feedback that hit hardest was sometimes, yeah, I knew I could have done that better, but it was often the thing that I myself was insecure about. So it was, you know, especially a couple years ago, and I always think about this, but any conversation about, you know, I'm not doing enough as a white person was always something that hit really close

to home because that's always what I'm worried about. And I think before I had the tools to manage that feedback in a way that was healthy, it was like, it felt so acute because it was something that I was secretly scared of, that I was secretly nervous about was that I wasn't doing enough or that I wasn't showing up enough in the right way. So I think that that can also, that is also where the feedback feels sometimes really personal is it's because, you know, it's the thing that you're self conscious about too. Yeah, it's like whether or not it's right. It's like that's the thing that I'm beating

myself up about as well. Like, right, you know, did I make that decision? I yap a lot on the internet about politics. And if I say something that might, you know, I might like wish I had said it differently. And oh, if I said it actually this way, it like hurt our relationship with a partner, like hurt a funder, like, ah, that insecurity about it is what makes that feedback so hard to hear. It's us. So when we're thinking about our position, if we're not leaders, how can we mirror this leadership style up or advocate for better leadership

in our current spaces? I love this question. Something I've been thinking about a lot. They are like mid-level, even more junior. I think really being clear about what you can demand of your employer. You could demand clarity. It is totally reasonable to say, hey, you are asking me to do this. Can you define what success looks like?

Hey, we have a code of conduct that feels pretty vague. It just says don't be an asshole. Can you tell me what your definition of asshole is and what my definition of asshole is so we can make sure we're speaking the same language here? You can do that in a way that is respectful, but you can do that in a way that serves the ultimate team and like makes you, sets everyone up to succeed.

The other thing I would say, especially in your more junior space in your career is you really like start building the muscle now of how you want to show up online, in Slack, on Zooms, like build the persona that you want to have when you're in charge now so that when you are in a position of power, you don't have to make it up as you go. Because if it becomes more of a habit today, it'll serve you better down the road. I will also give advice to anybody who is more junior, that you will have moments where you let yourself down or you let your team down, or you didn't show up the way you wanted to. And sometimes the only way you figure that out is through going through it. Like, oh, that didn't feel good in my body.

I made somebody feel like shit today and that was on me. Or, yeah, I didn't follow up when I was supposed to and the project didn't get done on time. Okay, or I didn't figure out what was, you know, the clear objection of success from my leader. So those moments are sometimes, they're often, all the time, very uncomfortable in the moment, but they're 100% how you learn. And please take those as learning opportunities.

Don't just like sit in a spiral of shame of going like, shit, shit, shit, how could I have done this? And then not learning anything from it. Yeah. You're allowed to be disappointed in yourself. And you're especially, you're allowed to be disappointed in yourself. And you're especially, you're supposed to use that disappointment to make sure that something changes in the future. I think about it like weightlifting, where like if you want to get stronger, if you want to be better, one, you're going to hurt yourself from time to time, but two, there's going to be a little soreness as part of that growth. The muscles are going to hurt. And that's part of the process.

The muscles are going to hurt. And that's part of the process. Growth is uncomfortable. Discomfort is in service of a better ending. And the flip to that is like, much like with weightlifting, you've got to rest. You're not going to rise to power if you're working yourself out around the clock. The other weightlifting metaphor I've heard too, is that weightlifting makes you stronger, but it makes you feel weaker while you're doing it. And like, that's what growth is. Yeah.

It's like, there's so many things in our life that, you know, vulnerability makes you feel weak in the moment, but actually makes you stronger. Like, there's so many versions of this that feel really uncomfortable in the moment, but ultimately make you stronger, better, more empathetic. But you don't get any of those things unless you do the thing. And the only way out is through, unfortunately. My hope and what I think if you read the book and you come away with it is that at the very least, you will only make new mistakes. Don't repeat the mistakes that you and I have already made, that the leaders coming up now should try and only make new ones

because we've already learned from the old mistakes and hopefully you can try and avoid them. Yeah. So, I mean, with that, my last question for you is, how does a world full of Gen Z and millennial leaders look? How does the world change when all of us are in charge? I love this question because I think it looks so beautiful. I think it's so expansive. Like, imagine the kind of person you could be for your friends, your family, your partner,

your team. If you could show up to work, know what is expected of you, know how to engage, and then leave it at the end of the day. Like, imagine a world where millions of business owners were able to pay people well, give them good benefits in healthcare, provide for their mental health as much as reasonable at the workplace, could create an inclusive environment, but also didn't demand them that they burn themselves out. And then your team could go home and like be present.

It could expand and transform our relationships with each other, with our jobs, with our communities, with our government, if every space we were in was more compassionate, more humane and more boundary. I think millennials and Gen Z are gonna save us. One, because we have to, but also because I think we have it in us to do it. We are the hero generations ready to take over and I'm excited for it. Amanda, I said this to you the last time you were on the show, but you continually inspire

me and are one of my favorite people to listen to because I always walk away a more interesting, better person. Plug away. I am so excited for your book. I have a copy downstairs. Please tell people where they can find it. You can get When We're In Charge wherever you get your books. It's in hard copy, ebook and audiobook, which I narrated so you can listen to me yap on for a couple hours. You can find me online at amandalittman.com, as of a sub stack that I'm doing, amandalitman.substack.com and all the other normal social platforms where just yapping and posting away. Thank you.

Thanks, Tori. Thank you to Amanda for joining us. Both of her episodes of Financial Feminist are so helpful. She wowed me the first time we met, which was to record that first episode. I believe it is episode 34, all about how to save democracy, which feels especially relevant right now. So I would really recommend going back and listening to that episode with her if you enjoyed this conversation. You can get her book when we're in charge wherever you get your books. Thank you as always for being here, Financial Feminist. We appreciate you subscribing and sharing the show. Only a small percentage of people do both of those things.

And we love when you're outliers. So thank you for supporting the show. We'll see you back here very soon. Have a good day. Bye. Thank you for listening to Financial Feminist, a Her First 100K podcast. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com.

If you're confused about your personal finances and you're wondering where to start, go to herfirst100k.com slash quiz for a free personalized money plan. Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristin Fields and Tamesha Grant. Research by Sarah Shortino. Audio and video engineering by Elisabeth Midcalf. Marketing and operations by Karina Patel and Amanda Lafue. Special thanks to our team at her first 100k. Kailin Sprinkle, Masha Bakhmakeva, Sasha Bonar, Ray Wong,

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