How to End Bad Boomer Leadership

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welcome to raging moderates i'm just

few years building the bench for the future of the democratic party now she's written a book for those who are ready to step up and lead she's the co-founder and president of run for something and the author of the new book when we're in charge the next generation's guide to leadership amanda littman welcome to the show Thank you for having me.

Thank you for being here.

I want to definitely get into the book, which was was awesome, and talk about some of the run for something candidates who we've been having on the pod recently and just very excited about.

But, you know, the big news is the government shutdown.

We're talking on day one of this.

What are your vibes when it comes to the shutdown?

Who do you think is going to blink first?

How are you feeling?

I don't know how this ends because it doesn't.

Well, here's what I'll say.

I will hope that Democrats don't blink.

I think that showing some fight right now is the right thing to do for the base.

I think Chuck Schumer clearly understands this moment is different than in March.

He cannot back down.

Senate Democrats cannot back down.

I'm a little concerned that already three all voted for the initial spending bill, which is a little alarming.

But I am hopeful that Democrats will stay strong because Republicans control the House, the Senate, and the White House.

It is on them to be able to get things to work.

Like the job of a politician is to get your opponents to agree with you and to vote with you, to build coalitions.

And if they can't do that, they can't do their jobs.

I don't know how this ends because because I don't see either side backing down easily.

I don't know.

What do you think?

I mean, I know that I'm paid to have a good answer to that question, but, you know, I'm unsure.

I've been heartened to see Jillabrand and Gary Peters and Brian Schatz, who all voted for the initial keep the government open in March, basically say like, this is different.

Yeah.

And we didn't know what.

governing under the Trump administration 2.0 was going to look like in the same way in March.

and you could make the argument that they essentially operate as if the government is shut down whether it's open or not you know they're they're uniparty rule at this point i'm watching new hampshire uh what sheen and hasn't do i understand the concerns you know russ vote is scary he's a scary dude

and this is what he wanted.

Like if you read Project 2025, which I wish that we had talked about that more on the campaign trail past August, I'm like, oh, we kind kind of gave up that talking point.

This is a playground, right?

He's gone to, he's at like six flags at this point.

So that concerns me, but it does feel like Chuck Schumer got the message, especially from the base.

And that leads us, you know, directly into the work that you do with Run for Something, you know, making politics more responsive to where Americans are and especially younger Americans.

So how is Run for Something going in Trump 2.0?

And you started right after Trump was first elected.

It feels, I mean, it is technically a long time, but it feels like 50 years.

It feels like

10 lifetimes.

Yeah.

So Run for Something was born of the ashes of the 2016 election.

We launched on Trump's first inauguration day, thinking this would be a small side project.

We'd get 100 people who want to run.

Like I was going to take a real job.

I was campaigned before that.

We had 1,000 people in the first week.

As of today, we're up to nearly 250,000 young people who've raised their hands to say they want to run, nearly 70,000 of of them in the last 11 months.

Amazing.

So we've had more people sign up since Trump won in 2024 than we did in the entirety of his first term.

It has been a huge moment for candidate recruitment, for people looking around both at the Republican Party and the Democratic Party and saying, if these guys aren't going to lead, I'm going to have to get in myself and run.

We've endorsed more than 3,000 campaigns.

We've helped elect more than 1,500 millennials and Gen Z to state and local office all across the country.

We've won elections in 49 49 states.

We're only missing Idaho.

And it's a real building box of power.

It's how you build long-term sustainable power.

And what do you do exactly for your candidates?

So it starts with recruitments.

We ask people to sign up at runforwhat.net to look up where they could run.

Once they do, they get put into an online community that allows them to both interact with each other, with experts.

They go through some curriculum and some trainings on how to prepare to run either now or a couple of years down the road.

They get invited to regular calls where we talk about the basics of running for office.

They also get information about stuff our partners are doing.

And we work with more than 200 groups across the country, both local and national, to help candidates really understand what does it mean to run for office and how to actually execute on it.

Once they're on the ballot, they can apply for our endorsement.

Once you're endorsed, which we do about half the people who apply, our regional directors will work directly with you.

It's a one-part coach, one-part consultant, one part therapist.

Do you need help getting the state party to answer your emails?

Great.

We know them.

We will shake them down for you.

You need access to the voter file.

We can do that.

You need tools for texting, we can do that.

It is a full-service soup to nuts.

And then we stick with people post-election day.

So our alumni community made up of our endorsed candidates, we help them figure out their next steps.

We stay in relationship with them as they think about running for higher office.

We make sure that the folks doing recruitment for higher offices know these people are there and leading.

We promote them across our network.

We're really part of like long-term talent incubation.

Yeah, you have some very prominent alumni, I would say.

Yeah.

And I want to talk about two candidates in particular that are running this cycle for Senate, Mallory McMorrow in Michigan, James Tallarico in Texas.

We've had both of them on the podcast.

I just saw James Tallarico's fundraising numbers for the first three weeks, $6.2 million.

Can you talk about them and their journey and

how you're working with them and why you think they're, that's like 80 questions, but why you think they're resonating at this level?

So Mallory, we worked with in our first state Senate race back in 2018.

We were her first endorser.

And she often tells, especially when I'm in the room, about how she took our endorsement with her to various other state and local groups who took her seriously because she was endorsed by Run for Something.

She was just a mom wanting to run for office.

She had Googled how to run for office and found us, found a merge, and got in the race, flipped that seat, and is now a very competitive candidate for the United States Senate.

James was a middle school teacher in Texas.

Texas who decided to run for state ledge down there to flip a seat in the Texas State House.

People often don't remember that.

He did flip that seat.

He held it in 2020.

Both of them we've been in conversation with since 2018.

So I often describe my work as like being the person who sees the band at the small club before they go do the arena tours.

Like I know the cool people who are cool before they're cool.

Both of them have a very shared ability to talk like normal people, to so clearly know what they believe, and to be interesting and normal online.

And I think it's actually a uniquely millennial Gen Z thing.

I know we'll get into the generational stuff a little bit, but but I think because both of them have been online their entire lives, they have always had cameras around them, they have always thought about what it means to curate a public presence that is who they are, but with some boundaries, they

understand that you have to be a normal, engaging human being.

You can't be like a robot politician.

Now, they're not fully aligned ideologically.

They're not running the same kind of campaign.

You know, they both do talk about their faith, although for James, it is much more prominent in his work.

They both talk about their family, although Mallory is like a mom of a little four-year-old and James is not a parent, not married, I don't believe.

They both are so in touch with their communities.

I think that's what makes them really powerful, even as they are very different.

Yeah, I'm glad that you brought up their policies or the ideology of this, because I think that there's a big misconception that all young candidates have to be like wild progressives.

And that's not the case at all.

You just need to be the genuine article to look and talk and seem like you come from the community that you are asking to elect you.

Like it wouldn't make sense in Texas if we are to have any pipe dream shot of ever, you know, flipping that seat to blue for you to have the same politics as AOC.

And I think like what they both clearly have is like a set of values that they hold strongly.

Like they really know who they are and what they believe.

And that more so than actually like the specifics is what comes through.

Not that they don't also have like very specific policies they're advocating for.

And, you know, they're both very clearly like equity aligned, justice aligned, like pro-democracy.

But they talk about it very differently.

They're prioritizing different policies.

They are thinking about this as how they can best represent the places they're running.

And if Democrats are going to win in places both like Michigan, Texas, and also New York and California, that's what we need.

Yeah.

I'm a big fan of it.

Obviously, I work in conservative media, so I spend a lot of time with people on the other side of the fence, but I hate

this rush to do ideological purity tests or to jump on someone who's won a super competitive race.

Like you might not love everything Alyssa Slaughtin is saying, but like, could you have won her race?

I don't really know.

So I wish people would just stand back a little bit.

I think it also like the ideological purity testing or the even like the discourse of you must believe this or that, like that misses how people consume information.

The way that, you know, James talks about wanting to fight for LGBTQ people versus the way that Mallory does versus the way that like Zora Mamdani does, each of it sounds a little different.

They're talking about different levers that they can pull.

They're talking about it through a very different lens.

But because of who they are and their stories and the places they're running, it seems real.

They believe it.

And that's what matters almost more than anything else.

Totally.

You mentioned social media and I want to talk about that because it's, you know, it's a blessing and a curse, right?

We're all.

overly addicted and it's causing, to my mind, a tremendous amount of damage also in people's lives.

What are you seeing in terms of how social is being used for politics, both in the good and the bad ways?

And what do you see as like the right sweet spot for how you can run a viral campaign and also keep people sane?

Yeah, I think for the campaigns, we've seen candidates use it really well when they come off like normal people.

So they use it the way that they probably would.

Like I think a lot, Chuck Schumer's probably never opened his Instagram account.

Yeah.

And I'm actually, it's one of my favorite things to ask older politicians is like, what social medias do you actually use?

Like what platforms are you on?

What is your algorithm showing you?

And if they don't even understand the question, that's usually my first flag.

Like, I want to know that my candidates and my leaders are the right amount of online.

They need to be like just enough that they understand how they're creating content.

They understand how people consume it.

You need to be enough of a consumer to be a producer, but I don't want them to have the brain rot.

like the worm.

Like I feel like I've got the worms where my brain is like all omelets and toddler content on the internet and it's not good.

Totally.

I think that the candidates who are getting it right, I think Mallory is really good.

I think James is really good.

I also think there's like a New York City Council member, Chi O Say, who's really, really good.

Christian Menavey, who's running for Congress down in Texas, super compelling online.

Zach Walls is running for Senate in Iowa, super compelling.

Musab Ali, who's running for mayor of Jersey City.

Yeah.

Really fun.

Really, really fun.

There's like a bunch of really cool candidates who are each doing it a little differently.

And I think the thing that I really love about them is most of them are not doing like memes.

They're not, you know, pandering to folks.

They're not jumping on trends.

I mean, like occasionally they'll do the sort of like music stuff, but mostly they're just treating their audiences like adults and they're using their social media platforms like any other 30-something.

What do you think about, I mean, you mentioned Chuck Schumer and he's definitely had some of the cringiest moments online, I think, of

anyone, especially being the Senate minority leader.

But then there are other

boomer elected officials like Amark Warner, for instance, who I think has made a very genuine effort to kind of get with the times, right?

And he does his car videos and he's gotten a little more professionalized about it.

And Run for Something is really focused on younger people, though.

So where do you see the gerontocracy battle at this particular moment?

You know, the gerontocracy is a scourge upon the earth, both in government and basically everywhere else.

And I think we are at a tipping point for how it's going to change.

There are record numbers of young people running for office this year and into 2026.

I think we will see more file.

There's also, thank God, quite a few older senators who are retiring and making way for this exciting benches.

There are young leaders jumping into primary, these older Democrats.

I think the challenge is that generally speaking, there are certainly some exceptions here, but generally speaking, the older leaders in the Democratic Party have neither the skills nor the stomach to fight in this moment.

Like it took Chuck Chumer getting basically

dragged for months,

both online and in person and yelled at by donors to get to a point where he was ready to shut down the government to fight for our values.

We've got to get candidates and leaders in there who have a really clear-eyed understanding of who our opponents are, that the Republican Party at this moment is not interested in good faith governance.

They are not good faith partners in negotiating.

This is not George W.

Bush's party or Romney's or John McCain's.

It is Trump all the way down.

And if you came of politics in the last eight years or came up to it, generally speaking, you see that really clearly.

Whereas if you sort of have been in the Senate since the 90s or older, you like have a misconception.

The same way that like we like the music we liked when we were 13, politics is stuck in the moment when you first engaged in it.

Yeah, like going out to the sphere to see the Backstreet Boys, that kind of stuck in my mind.

I absolutely do that in a heartbeat.

Yeah, 100%.

My husband was like, let's go see the dad.

I was like, get out of here.

I mean, he's a weird Gen Xer.

but um,

it seems as though there's this emergent theme.

And, you know, hats off to Bernie Sanders and AOC, who I feel like have really been pounding us with it.

But you're seeing, I think, some of the most powerful communication around the us versus them, not Democrats versus Republicans, right?

Like the rich and the poor, the big guy and the little guy.

I just had Dan Osborne on from Nebraska.

He's running against Pete Ricketts this time.

John Osoff has been really compelling and impressing me with his ability to constantly bring the conversation back to corruption.

And that's Democratic corruption and Republican corruption.

And that we have to be the antidote to that.

And, you know, he's a millennial as well.

I think he's 39 now.

Is that what you see as like the winning through line for these races and your candidates?

It's definitely something that's coming up a lot with them and like really articulating the system isn't working.

Or I've heard some even put it like the system is is working.

It's just working for them.

It's not working for you.

The system is working as it's intended for the rich, for the wealthy, for the elite, for the people who are buying their way in.

It is not working for normal people.

And I think, especially for younger voters who feel like, what is the American dream anymore?

How am I ever going to buy a home?

How am I ever going to afford kids?

How am I ever going to get out of the student loan debt?

You told me I had to go to college and now I'm graduating from college.

I don't have job prospects and I have hundreds of thousands of dollars I owe.

Like, it feels hopeless.

And it feels like every system has been set up to burn us, not support us.

So I think candidates who can really speak to that sense of suffocation,

I think Mom Donnie, one of the things that he really spoke to very powerfully was, you know, his thing was like, afford to live, afford to dream.

And I think that second half of the sentence is really meaningful for younger people because it's like, God, what could you do with your life if you didn't feel so crushed by finances or by the systems that have failed us?

Yeah, I particularly loved, I think he was talking to Erin Burnett and she asked about like, do you want billionaires to exist anymore?

And he said, the real question is, is do you think that working people should be allowed to exist anymore?

Yeah.

And, you know, we both live in New York City and understand that for a majority of people here, that's kind of what's pulsating through their lives and their conversations on a daily basis.

I mean, my husband and I talk about it.

almost every day of like, yeah, if we could afford another kid, we'd have one.

We can't.

You would have a third?

I'm a maybe.

Okay, no, I'm just like, because I'm scared.

Yeah.

Like, we do it too, because we're like, oh, but we're not going to have a baby again.

And it's

cute.

They're so cute.

And then I'm like, oh my God, it's also so much work.

And three in the city is a lot.

Well, that's two Ubers.

That's anywhere you go, that's two Ubers.

I know.

And I don't have two Uber money.

That's what it is.

We're going to take one quick break.

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Welcome back.

I want to make sure that we talk about your book, which is very different from a traditional leadership book, right?

That's kind of focused on people who are C-suite or C-suite adjacent.

You know, yours is really focused on young people, new people stepping into power.

Tell us about it.

So When Orange Charge just came out in May, and it's not about politics at all.

It's about power.

It's about work.

It's about the future of work and about what it it means to lead differently in this moment.

You know, I am 35 years old.

I've been running this organization for almost a decade, and I've had to do things very differently from thinking about how we create an environment that has work-life balance and sustainable work culture to how to take family leave as the boss, which when I googled how to do it, I got a lot of how to ask your boss for maternity leave and nothing about how to take it if you actually are the boss.

How to run a diverse, equitable, and inclusive environment that is both productive and also psychologically safe for folks.

How to post on Instagram if you're the boss.

Like my employees, follow me on social media.

What does that mean about how I think about posting and engaging and like faving their comments, that kind of stuff?

It is such a different challenge.

And for the book, you know, I interviewed more than 130 leaders across a bunch of different sectors.

I talked to lawyers and doctors and faith leaders and teachers and of course politicians.

I talked to people who, you know, Evan Spiegel, the CEO of Snapchat, Hercia Sharma, the editor-in-chief of Teen Vogue, and Maxwell Frost and a number of members of Congress.

And the themes themes that I heard echoed across those conversations were all so similar.

People were struggling to figure out how to manage both their feelings and their staff's feelings.

They were trying to do things differently, but didn't really know what that looked like.

In the same way that I think, you know, I have to take it back to parenting, but the same way that in particular, millennial parents are trying to do it differently than our boomer parents did for us.

Millennial and Gen Z bosses are trying to do it differently, but without a playbook, that's so, so hard.

So when we're in charge is the playbook for how to do it.

One of the key lessons, and I see that it's also in your swag, is the we don't dream of labor.

Back there.

Yeah.

Yeah, right there.

It's a good placement.

I think a good.

My husband got my book cover framed.

But can you talk about that and how it relates to how young people can lead and run these organizations?

You know, not just in politics, obviously, but across the board.

Yeah, we do not dream of labor.

Sort of my, people say it's James Baldwin quote.

I can find no proof of that on the internet.

But this idea that we don't have dream jobs, we have dream lives.

I think it's one of the biggest challenges that we are experiencing.

Honestly, right now with the gerontocracy, actually,

I submitted, I was the expert question for Kara Swisher's interview with Tina Smith last weekend.

And my question for her was, why is it so hard for so many of your colleagues to retire?

And her answer was, first thing she said, I think for so many of them, their jobs are their identities, and they can't figure out what to do beyond that.

Millennials in Gen Z have seen that our work will not love us back, that we will get laid off, that that our institutions will crumble, that our companies are not going to be our homes.

We cannot count on staying somewhere for 20 or 30 years and retiring in our same job we started.

So, how do we build identities beyond our profession?

Hard for anyone, really hard when you're the boss, really, really hard when you are the entrepreneur or the founder, or your job is for many young people, influencer or content creator.

How do you create systems and structures such that allow both you and your team to enjoy your work, find dignity in your work, get fairly compensated and good benefits for your work, but also have a life outside of it so that your identity isn't totally wrapped up in your career?

So I get into all of that in the book and really try to answer the question: you know, what does a dream life look like?

And how can you build a workplace that makes that possible?

Yeah, I just, I love it.

It's aspirational, obviously.

I think in a lot of ways, you know, I have a dream, like I married the right guy and I have beautiful kids and I can afford to to live here.

Yeah.

Um, though I still complain about it.

But I think that the kind of natural feeling is

you hear something like that and you think it's all well and good, but that feels like a pipe dream to me.

This idea that I don't need to be working all the time.

You know, it's a fantasy work-life balance, especially with phones and connectivity, especially when you are the boss and especially when so many people have some form of content creator or messenger as part of their job description.

I don't think it means don't work hard.

Like, I work my ass off.

I wrote a book while pregnant, while running an organization.

I don't know how you do it.

And think about a third.

Don't let my mom hear that.

I don't think that means don't work hard.

I think that means have an identity that is beyond your work, whether that's your relationship to others, as a parent, as a partner, as a friend, as a community member, and then create the systems and structures such that you can do that.

So, like, part of the way that I have done this is that Run for Something has a four-day work week.

That means me and all of my staff work Monday through Thursday, 32 hours a week, plus or minus, Fridays or weekends.

I wrote the book on Fridays through 2024.

I now have fellowships and I see friends and I go to a yoga class and I spend time with my partner on Fridays.

It is what has allowed me to have both the balance that can make more things possible, but it also has not touched the organizational efficacy or impact in any way.

Again, we've had our biggest year yet.

You can do both if, and this is why I think it's both aspirational, but also quite practical.

Imagine what happens if thousands or hundreds of thousands of business owners, of community leaders, of company executives decide to make their businesses prioritize work-life balance and build that in from the top on down and staff in such a way and structure schedules in such a way that people could not have to answer emails after five or six o'clock, that people could leave in the middle of the day to go pick up their kid and then come back later, that really could be well compensated for their work and also have lives outside of it.

The addition here is like, what could be possible for you as an individual, both you specifically, but also your listener, if your job didn't suck you dry at the end of the day?

Like, how could you show up differently for yourself, for your partner, for your family, for your community?

Would you have more time to volunteer?

Would you be a better friend?

Would you host dinners more?

Like, what would be possible if you weren't so tired?

That's what I'm trying to implore folks to not settle for the way things have been done yesterday as the way we have to do them tomorrow.

How are you finding kind of, I guess, I mean, we talked about gerontocracy and politics, but even the generational reaction to your book, because I think that a lot of boomers, old Xers kind of nod and smile about this stuff.

And they're like, we want to lift you up, right?

Like, we know that the way that we did it doesn't necessarily work for this generation.

And there have been a lot of negative consequences, but like in reality you're gonna have to do it exactly the same way have you found like doors opening or minds opening i guess to a new way of thinking about this or is it more that if you're 42 and under we're just gonna be building a totally different america I have loved hearing from so many of the older folks who've read or listened to the book and told me it really helped give them empathy for what their kids or their grandkids or their colleagues are working through.

Like it really opened their eyes, especially, you know, I write in depth about the internet and online communication and virtual workplaces and the emotional labor of leadership in this moment.

And they're like, oh, I didn't really think about that.

Like it just like really gives them a language to understand the challenges.

I gave a talk a couple of weeks ago at the University of Albany and there was an older community member there, one of the oldest people in the room, who came up to me after and said, you know, when you said work won't love you back, that hit me right in the gut.

Because you're right, it didn't.

And if I had known that earlier, I would have made some different choices.

Like that's, that's the whole point point here.

I mean, because what is Gen X?

I will say the final thing is that I

love hearing from Gen Xers who get very mad that I don't really talk about Gen X in the book because being mad that you're left out, it's so classic Gen X to be mad that you're not talked about, which I just live up to the stereotype, my dude.

Yeah, it's funny.

They get to be invisible when they want to be, and then they throw a fit

when they feel like they have something to contribute or to talk about their music.

Well, and it's not, it's not my fault, and it's not Millennials' fault.

Blame the boomers.

I've seen this.

There's a wall street journal story from about a month or two ago that said that even in fortune 500 companies you know these boards are deciding to go from boomer ceo to millennial ceo like they are looking for the they're skipping gen x entirely and i'm sorry that's not my fault but i am sorry because that sucks for you it does um

i don't want to be snarky because i i'm married to a gen xer but yeah i think we feel the same things about this um so I always ask folks who come on, what's one thing that makes you rage and one thing you think we should all calm down about?

Um,

one thing that makes me rage, uh, I am deeply irritated by the, you know, we talked about this a little bit earlier, by the discourse about the ideological purity of the Democratic Party.

Like, recruit a candidate, get him to run for office, then tell me how it works out.

Unless you are actively recruiting candidates, shut the fuck up.

Is that productive?

No, but that's how I feel.

Um, one thing that makes me happy or calm down about, but happy's good too.

My toddler is obsessed with Daniel Tiger, as all toddlers are, and really likes to sing the when you feel so mad that you want to roar, take a deep breath and count to four song.

And I find myself singing that in work meetings and after donor meetings quite a bit lately.

And, you know,

in politics as in parenting, I find that very resonant thematically.

Yeah, it's also, I mean, if we want to put it in the like calm down about thing, I think it links very well to writing about what professional environments are now that like people are so appreciative of humanity, actually,

when, you know, don't bring all your home stuff to work.

But a fair dose of it to remind us that like I'm a pet owner, I'm a parent, you know, if someone would say a pet mom, I feel like I don't actually have a pet and all my dog friends would be like, you're not an owner, you're like part of a family.

Yeah, I'm a dog owner.

It's fine.

Okay, but totally.

And our Tony box gets a lot of play with the Daniel Tiger orbit over here as well.

Well, and I just find it very helpful to remember that when all of this is over, my kids and yours and everyone else's, they'll still be little kids.

Time is long, and we've got a long ways to go, but also

things can change fast, and that's very comforting to me.

Awesome.

Well, Amanda, thank you so much for your time.

It was great to have you.

Same, thank you for having me.

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