What If Managing Wasn't Miserable?
Amanda Litman walks us through a different mode of leadership
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I’ve admired Amanda Litman for years. She co-founded Run for Something — one of the few engines in politics making me hopeful right now. She piloted (and then instituted) a four-day work week. She’s tried really hard to figure out how to make passion work — political work, but also just passion work generally — more sustainable.
Litman new book, When We’re In Charge, is the first I’ve encountered that looks honestly at what’s already happening (and what needs to happen) as the next generation of leaders (specifically: millennials and Gen-Zers) grapple with what leadership and management could look like in the decades to come. Amanda is a longtime Culture Study subscriber and very much on board with this whole project, and she’s working earnestly to figure out a way forward that allows us to keep doing the work that we love (or even just the work that we like just fine, that matters too).
I’m eager to hear your thoughts, hopes, and dreams about how a different form of leadership could change your workplace. Read and then let’s hang out (with Amanda) in the comments!!!
You can follow Amanda on Instagram here, find out more about Run for Something here, and buy When We’re in Charge here.
This is one of those questions that we, as authors, get asked in our “Author Questionnaires” while we’re writing our books and it’s always difficult to answer, but: who is this book for? I think a simplistic read would suggest that it’s only for people like you — a relatively young person in charge of their own organization. And it’s for the Yous of the world, of course, because so many of us end up writing the book we wanted most in the world when we were coming into adulthood. But who else is it for?
I wrote When We’re in Charge with a few specific readers in mind (including, as you suggest, myself — both the me of ten years ago who started managing people and had no idea what I was doing, and the me of today, a working mom of two kids under three who does meaningful work and wants to keep doing it, but also wants a life outside of work, too!)
Imagined Reader #1 is the You that is likely a millennial or Gen Z in a position of leadership — probably at work, but maybe outside of it — and wondering why this feels so damn hard.
You want to do things differently than nearly any boss you’ve had before, but you feel like you’re just tripping over landmines on a daily (or hourly) basis. You’re lonely, and tired, and you feel like you’re doing your best but somehow it’s not enough.
What you’re doing is hard because it’s hard — we don’t have a ton of role models or examples for how to lead differently. My hope is that you feel seen by this book, that you finish it with the language to talk about your challenges and also with concrete solutions, and that you can reimagine how you show up for your team and yourself.
Imagined Reader #2 is the You that is someone either just starting out in their career or is about to get promoted into the Big Job, and is looking for advice on how to do it right.
I hope the book gives you the shortcuts through the lessons many of us learned the hard way, so you go into your leadership role eyes wide open, knowing that the challenge before you is immense but that it is absolutely possible to lead without losing your humanity.
Think about ways you can incorporate the advice in this book into your work presence now. For example: Don’t treat your work Slack like your group chat! What you write online can and will be seen by your employer (and, ahem, all your past and future employers)! You will be better off down the road if you start acting now the way you will when you’re in charge.
Fair warning that if this is You, you might read the book and say to yourself: “leadership sounds hard and lonely, why would I want to do this?”
I hope I can convince you that it’s worth it. If you don’t take on the big, sticky leadership roles, someone else will, and they might not come to it with the same eagerness for work-rest integration or the deep urgency to create equitable workplaces. If you’re the kind of person who thinks intentionally about any of this stuff, you’re the kind of person we want and need in positions of power.
Imagined Reader #3 is the You that is a boomer or gen Xer who I probably offend a little bit, and who I preemptively ask for forgiveness.
I hope the book is your field guide to understanding how leadership norms are shifting. Regardless of your age or generation, you can break old habits. In fact, I argue that you need to break old habits in order to succeed because, in all likelihood, your teams are going to be demanding all the things I write about it. We’ll all be better off if you’re able to adapt.
You have full permission and encouragement to try new things, adjust your policies, and show up as your responsibly authentic self. Take what might work for you—the scary-but-exciting freedom next-gen leaders have is available to you, too.
I think we should start with some table-setting about leadership books in general — and leadership advice, at least how it’s generally packaged in mass form. What were the recurring themes, ticks, and strategies — and what did you want to do differently with this book? (And how did you go about doing it?!?)
One of the great challenges in conversations about leadership, work, or really any self-help-type discourse (which my book arguably falls under) is that ultimately we live in a society.
Consider Lean In by Sheryl Sandberg, the urtext of women’s leadership — which, phew, did not age well — and which entirely misses that no amount of ~leaning in~ can get someone over the barriers that American capitalism in particular puts up against women.
There are few individual choices that can make up for problems like no universal paid leave, no national childcare policies, no structural fixes for the gender pay gap, etc. It’s not that individual choices don’t matter; rather, every choice is made within the constraints of reality. And alas, reality can feel pretty bleak.
Beyond that, so many leadership books seem to be written by a heterogenous chorus of mostly older white men, most of whom either ran big companies that had totally different values or problems than my lived experience, or started things while they had financial safety nets, or (ahem) had wives or partners to handle the domestic labor, and/or hadn’t really managed people directly in quite some time.
(FWIW, whenever I check the online lists of best sellers of “leadership” books, it usually takes scrolling down to #20 or later to find something written by a woman, and even longer to find an author under the age of 50 or who runs their own Instagram account)
And when it comes to generational divides, it was jarring how most work culture books treat millennials and Gen-Z like nuisances to manage around, as if those of us in our 30s and early 40s are still the pesky young whippersnappers. That’s not to say there weren’t useful frameworks and tips among the 60-ish books I read for research or my own professional development over the years — I listed a bunch of them here — but so much of it didn’t translate to 2025, and fewer still had practical tips.
I wanted When We’re in Charge to be specific and useful for people who are living in this reality — for example, we can’t “manage by walking around” because (1) LOL that’s not really management and (2) more practically, we don’t go into offices consistently anymore.
We have to think about little things, like which emojis we use or what and when we post on social media, and also big things, like what we want our career trajectories to be when the ladders we thought we could climb don’t meaningfully exist anymore, or what it means to balancing being a caregiver of either young kids or aging parents (or both) and also be a boss.
Finally, I really wanted my book to be honest about how hard leadership is and how much of a psychological toll it takes to be in charge of other people’s livelihoods. The book is definitely not a memoir, but I felt it was necessary to be candid about my personal experiences and the challenging days/months/years I’ve had, in no small part because “even though we’re succeeding by all possible metrics, this is really fucking hard and sometimes I wonder why I do this” was a theme in so many of the conversations I had with other millennial and gen Z leaders.
You interviewed a ton of people for this book from so many different industries doing so many different types of work. From those conversations, what would you say is the most essential part of being a leader right now — but also the hardest to implement? What do people know they should be doing, say they should be doing, but struggle to actually do?
Sorry but I have three answers for this (well, I have 272 pages worth of answers for this, but you know what I mean!). Thematically, they all come back to setting clear boundaries and saying no more.
Specifically:
(1) Building diverse, equitable, inclusive teams is both the right thing to do (perhaps a hot take in 2025 but: I think segregation is wrong!) and also it’s good for business. Diverse teams get better outcomes.
In order to do that well and create inclusive environments, you need to be a little bit exclusive. You have to keep out assholes, bigots, sexists, racists, and other -ists: leaders need to draw firm boundaries around what kind of behavior is and is not appropriate, then hold those boundaries with appropriate consequences.
And: So many of the leaders I spoke to named that sometimes it feels like there is more of a penalty for trying to build an equitable space and falling short than for simply not trying at all. I argue it’s worth doing anyway, especially in this environment. Don’t get scared out of doing the right thing.
(2) I know the Culture Study community will get what I mean with this: Work cannot be everything to everyone. I mean that both emotionally (as in: work cannot be the place where people find all their meaning) but also quite practically (work cannot be the only place to care for or provide for your physical health, mental health, social life, civic engagement, etc.; Maurice Mitchell’s excellent article about Building Resilient Organizations is a must-read here.)
Work is an economic relationship, first and foremost. And: the boss/company should try to be as generous and compassionate as it can be within the container of that relationship. Your job as the leader is to establish what you can and can’t provide to your team, be clear and upfront about those boundaries, and hold the line accordingly. Frustration comes when expectations do not meet reality — don’t overpromise and under deliver.
(3) The biggest one, and I am my own worst enemy when it comes to this one: In order to work better, you have to rest better. Take time off! Working around the clock serves no one (especially you) and models shitty behavior for your team. Life is hard right now and the more we can give people control of their time back, the better. That might mean saying no to good ideas or being extra-rigorous around prioritization and mission- or scope-creep. That’s okay! The trade-off is worth it.
Your organization, Run for Something, implemented a four-day workweek in January 2022. We here at Culture Study are big proselytizers for the four-day workweek (which doesn’t work for every situation, but works for a lot more than people think!) so I’m going to give you the pulpit to talk a bit about how you made it happen at Run for Something…..and what that has to do with next-gen leadership.
I’m obsessed with our four-day workweek (4DWW) and think it is absolutely possible in more places than you might expect. Here’s the backstory…
As you note, Run for Something implemented a four-day workweek after a pilot period in 2022. We got there slowly but intentionally.
First, in summer 2019, we tested out summer Fridays -- there were no major issues with us ending work around 2pm on Fridays, so we decided we’d continue the schedule the following year. In 2020, when COVID hit, things shut down, and people started feeling crispy fast, we decided to start summer Fridays early, kicking them off in April with no official end date. Again, no issues arose, so we kept the shortened Friday hours into the fall, winter, and into 2021.
At that point, my co-founder, Ross Morales Rocketto and I started wondering: What if instead of no work on Friday afternoons, we did no work on Fridays at all? We were tired, our team was tired, and shit still felt bleak. So we asked our incredible chief operating officer, Cassandra Gaddo, to look into the research and come up with a plan for testing this out. She ultimately found us a pilot to enroll in, where we’d test out the new schedule along with a bunch of global companies and a team of academics would regularly do surveys of our staff as to whether it was improving key metrics, like productivity, engagement, burnout, and anxiety.
We started the new schedule on January 31, 2022, with the plan of trying it for six months to see how it would go. Our team would be fully off on Friday — no emails, no Slack, no Zooms, just a three-day weekend every single weekend. (And when holidays rolled around, sometimes that’d mean a four-day weekend.)
We put out a Medium post explaining our decision, tying it back to our organization’s values. I expected some pushback from donors or partners—our work is urgent and (I believe) necessary to save democracy. But it is not an emergency room, and we are not first responders; we’re not literally saving lives.
While our mission is urgent, not every task in service of that mission is urgent—a 4DWW forces us to be ruthless in prioritization, rigorous about our time management, and able to discern the distinction between work that was useful and work that made us feel useful.
By the end of the pilot, our staff survey results were indisputable. Every metric you’d want to see go up (engagement, sense of balance, productivity, job satisfaction, etc.) went up, and all the bad things, like anxiety, burnout, and exhaustion, went down. Our overall output did not change (in fact, 2022 was one of our most impactful years to date), and our team was happier.
Now, two years in, we’re still doing it and we all (myself included!) take it seriously! We treat Fridays like weekends. And just like in most jobs, most of the time, the expectation is that weekends are yours — you can plan to be free, and the time is to do with what you’d like. It’s been magical and has made this work sustainable over the long haul. One of my employees who was most wary about kicking it off said after the pilot: “The things I have to say no to at work are balanced by the things I get to say yes to outside of it.”
Zooming out, I really think it’s possible for more people and more industries than you might think — we’ve seen autoworkers fight for it in new union negotiations! — but it requires leadership to have a little imagination. Consider that the 40 hour work week is older than the boomers themselves. It is traditional, sure, but that doesn’t mean it still works for us. A better way is possible!
That’s really what next-gen leadership is about, and is why I think this book is about work, but also so much more than work. Imagine if over the next fifteen years, the four-day workweek became the norm, not the exception, because of the decisions individual leaders collectively made.
Imagine what day-to-day life might be like for millions of people if a vast majority of business leaders operated with an eye toward compassion and profit, instead of treating those like mutually exclusive options.
Picture how much better things might be if your job didn’t make you miserable, even if you don’t love it, because at the very least you knew exactly what to expect from your workplace, how to succeed, and what kind of resources it could and could not provide for you.
If all that was true: What kind of time and space could it open up for you to be a better member of your community? What kind of civic engagement would be possible for you? What kind of parent or partner or friend can you be?
We’ve been focused on your book, but there are a LOT of fans and supporters of Run for Something in the audience here and I’d love to have you do something I’ve seen you do very effectively on social media the last few months: talk about what’s making you hopeful about the next few years — and the sort of leaders you see coming down the pipeline.
First, a quick TLDR on what Run for Something is: We recruit and support young diverse leaders running for local office. I started the organization on Trump’s first inauguration day in 2017, expecting maybe 100 people to sign up to run. Instead, in the first week, more than 1000 people signed up to consider a run for office.
Today, we’re up to over 200,000 people who’ve ever raised their hands to run for local office — more than 45,000 of whom have signed up just since the November election. That’s more people in six months than in the first three years of Trump’s first term!!
We’ve also helped elect more than 1,500 millennials and gen Z across 49 states — just missing Idaho! — and have seen them do incredible things like lower the cost of insulin in Texas, bring free lunch to kids in Virginia, transforming zoning policies in Cambridge, MA, and stand up for trans kids in Montana.
I’m hopeful right now, in spite of everything, because every single day, our team engages with totally ordinary people who are willing to do the extraordinary thing of running for office and serving their community.
Just last week we talked to: a young medical professional who got fired from the CDC in Atlanta and is now considering a run for local office to bring their health care experience into city government; a professor and openly LGBTQ man who became a citizen a few years ago and now wants to run for office in Florida; and a mom who wants to run for school board in the Tennessee community she grew up in because as a neurodivergent kid, the school system failed her and now she wants to fix it.
I am genuinely so moved by their bravery and commitment to public service, even and especially when it’ll be hard to make change.
People keep asking where the opposition leadership is — it’s in the Run for Something community! We don’t need one leader fighting back (if we could even agree on one person in the first place). We want and need thousands of leaders, all across the country, doing whatever they can to remind people that when good people are elected, government can do good things.
I’m not going to say don’t feel bad, because things are horrible and scary and Trump is going to do so much harm. But there are people rebuilding from the ground up, fortifying local governments, mitigating harm, and advancing progress. The only way out of this period in our history is through it -- the leaders stepping up now to get us to the other side are going to make what comes next absolutely transformative (in a good way.) ●
You can follow Amanda on Instagram here, find out more about Run for Something here, and buy When We’re in Charge here.
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