These Are Leadership Ideas I Try To Apply Every Day
Coach Pete Carroll has said that another disappointing season with the New England Patriots—some 15 years into his career—it struck him that he didn’t actually have a coaching philosophy. He was mostly winging it.
Inspired by John Wooden’s “Pyramid of Success” philosophy, Carroll got to work filing binders with notes, compiling, defining, and codifying what would become known as his “Win Forever” philosophy—the winning actions and mindsets he aims to instill in his staff and players. It was a transformative decision: he went on to win two national championships and then a Super Bowl with the Seattle Seahawks.
Now, when Carroll gives talks, he often opens with a simple question: What’s your philosophy? I once asked him about it, and he told me it’s shocking how many people don’t have an answer. There are many CEOs and generals and investors and coaches at the highest levels who reveal, accidentally, that they have just been winging it.
Although I always saw myself as a writer and wanted that to be my life, I found myself running the marketing department of a publicly traded company by 21. I started my own company in 2012, and given how the world works now, few writers can just be writers. We now have a team of roughly 20 employees across Daily Stoic and The Painted Porch. Which means I’ve had to develop a leadership philosophy to try to get the best out of the people who are part of it. You can’t make every decision for people, so it’s essential to establish the principles and rules by which others make decisions and operate on a day-to-day basis.
While this post isn’t a totally comprehensive breakdown of my philosophy (if you want that, check out The Daily Stoic Leadership Challenge), these are the core tenets—the maxims, rules, and reminders the people who work for me hear most often.
Sense of urgency. At The Daily Stoic offices above The Painted Porch, I hung up a sign that says, “A Sense of Urgency.” It’s something I cribbed from the kitchens of Thomas Keller, the creator of Per Se, one of the best restaurants in the world. A sense of urgency—that’s what a great chef, a great service staff, a great organization has. While in my personal life I may need to work on slowing down a bit—I’m a ‘sense of urgency’ guy, always have been—I’d say most people could use a little speeding up. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, “We’ll unpack those tomorrow.” I’m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer’s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That’s why it’s important—whether you’re packing boxes, replying to emails, or making big strategic calls—to think a step or two ahead. Don’t procrastinate. Do it now. Do it with urgency.
Slow down…to go faster. Yes, it’s important to have a sense of urgency. But there’s a difference between urgency and rushing, hurrying, going quickly for the sole sake of speed. There is an old Latin expression that I think captures the balance here nicely: Festina Lente, which means, Make haste slowly. A sense of urgency…with a purpose. Energy plus moderation. Measured exertion. Eagerness, with control. It is about getting things done, properly and consistently. They like to say in the military that slow is smooth and smooth is fast.
Start the clock. One of the things I say all the time is “Have we started the clock on this?” When someone tells me that it’s going to take six weeks for our bindery to make another run of the leatherbound Daily Stoic, I want to “start the clock” as soon as possible. I don’t want to add days or weeks to that process by being indecisive about how many to order or by procrastinating on finalizing the order or by being slow in processing an invoice. We don’t control how long it takes other people to do stuff, but we control whether we waste time, whether we are inefficient on our end…The project is going to take six months? Start the clock. You’re going to need a reply from someone else? Start the clock (by sending the email). It will likely take a while for the bid to come back? Start the clock (by requesting it). It’s going to take 40 years for your retirement accounts to compound with enough interest to retire? Start the clock (by making the deposits). It’s going to take 10,000 hours to master something? Start the clock (by doing the work and the study).
Don’t touch paper twice. That’s a great rule from the productivity guru David Allen. If you look at an email, begin to edit a piece of content, open a text, whatever—complete the task then and there. This has been driving me nuts on a home remodel we’re doing. The amount of decisions that have come to us more than once is insane. Because the contractor forgets things, because it turns out they didn’t give us the right parameters the first time, because they were asking before we were ready. But people do this all the time! They have bad processes that make them do more work than they need to.
What’s taking up a lot of your time? One question I regularly ask my employees—and myself—is: What’s eating your time? Sometimes this is just life but sometimes, it’s unnecessary. On one of our weekly calls not too long ago, I could tell my video producer was feeling overwhelmed. I asked, what’s taking up a lot of your time? Animations. He said it was taking hours to produce just two minutes of animated content for our Daily Stoic videos (which a previous editor had often included in our videos and become part of the style). I like animations…but not that much! So we cut way back on them and everything got better. Unless you want your boss to micromanage you, you can help them by flagging things that if they knew about they would help you fix. (And by the way, AI has now helped us do these animations faster).
Don’t punish people for improvements. Sometimes people are afraid to tell you about inefficiencies or even potential improvements because they are worried it will turn out badly for them. That you’ll get mad. Or you’ll take away responsibilities or find someone else to do it cheaper. I try to reiterate all the time: I not only won’t punish you for this, I will reward you. If you help save us money–by reducing an unnecessary vendor or service–I’ll give you a piece of it. If you find out that something in your role no longer has a positive ROI or isn’t worth doing, we’ll get rid of it and find something different and better for you to do. If you find a way to work faster with AI, I’ll celebrate that. Your job is to make the company better, not to do your ‘job’ as it was originally defined.
Make a positive contribution every day. Compound interest is one of the most powerful forces on earth. And you can apply that to your own work. People sometimes ask how I write the Daily Stoic email every morning, which of course, I don’t. I write one or two every day, constantly making small deposits to the bank of emails. Over time, that compounds—we have a Google Doc we call “UNSENT,” which, as I type this, is 217 pages long with emails ready to go. Little things add up. The line from Zeno was that big things are realized by small steps. That’s what I try to instill in my team: every day, make a positive contribution. Most of all, I try to show this with my own writing habits.
Be there when they’re losing, not when they’re winning. When we were working on What You’re Made For, George Raveling told me that when he got the head coaching job at Washington State, the athletic director told him, “I’ll always be there when you’re losing,” he said. “I’ll never be there when you’re winning.” I loved that. I find that I talk to my team the most when they’re struggling—when something’s broken, off-track, or unclear—not when everything’s going well. That’s the job: to help people solve problems, to help them get unstuck. If someone needs constant reassurance or regular praise to stay motivated, they usually don’t last long here. I’m reminded of a time I called Dov Charney, founder of American Apparel, about some little success I’d had on some project. He was very busy and frustrated that I’d interrupted, but politely, he said, “Ryan, you are calling me to tell me that you did your job.”
Don’t repeat the same mistake. On the one hand, I’ve always loved the story of IBM CEO Tom Watson supposedly calling an executive into his office after his venture lost $10 million. The man assumed he was being fired. “Fired?” Watson told him, “Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.” But on the other hand, the thing that frustrates me the most—and the only reason I’ve ever fired someone—is when they keep repeating the same mistakes. If you learn from your failures, great. But if you’re just stuck in a loop, not applying the lessons, it’s not going to work.
Why is it being done that way? One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That’s how so-and-so showed me when I started. No one had questioned it since. This happens all the time—in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this? This is especially important to ask of tasks that eat away at time better spent on something else.
Steal like an artist. (This is also a great book we carry at The Painted Porch.) At some point, I realized many of our best ideas were inspired by others. The book tower—as I’ve written, one of the single best marketing and business decisions we made in the whole store—was partly inspired by a cool floor-to-ceiling tower of books about Abraham Lincoln in the museum attached to Ford’s Theater in DC. Some of our top-performing reels on Instagram were inspired by other creators. So now, at the end of every weekly staff meeting, we go around and share one idea we’ve seen out in the world—on social media, on podcasts, on YouTube, in movies and documentaries, at other small businesses—and talk about how we might do our own version of it. Not copying, but adapting. Remixing. Borrowing what works and making it ours.
I’m leaving this with you. Like a lot of men of my generation, I’ve learned about this concept of “mental load” in relationships (the way, unthinkingly, a lot of responsibilities, emotional obligations and tasks are placed on women). My leadership philosophy is that when I give you a task, that’s your task. Your job is to handle it and be in charge of it. If I have to follow up with you, if I have to push you to get started, if I have to check your work, then I may as well have done it myself. If you are coming to me with problems (as opposed to solutions) or, when you are explaining something to me, not explaining your assumptions, you are putting it back on my plate. In a successful working relationship, I should be able to have an idea, go to the right person with it, and after I explain it say, “I’m leaving it with you.”
Respect boundaries. As a leader, you have to understand that your decisions and actions have consequences for people, not all of which are immediately obvious. But you have to think about that. For example, I sometimes have to reiterate that just because I am emailing late at night or on the weekend doesn’t mean I expect a response right then. And for this reason, I’ve gotten better at scheduling emails. But the broader point is that as a boss you have to realize your actions, however seemingly small, carry weight. You have the power to blow up someone’s day or evening or weekend. Try not to do that. Try to be mindful of other people’s time and headspace.
Kids are not a distraction from your work. They are your work. I bring my kids to the office. I talk about them in meetings. When they’re a fan of the guest, I let them pop into podcast recordings and ask questions. And I encourage others to do the same. If you need to take paternity or maternity leave—take it. If you want to bring your kid to work—bring them. If you have to duck out for a school pickup—go. Especially as a father, I’ve tried to model this. I don’t want to treat my kids like a separate life I live outside of work, and I don’t want the people who work for me to feel like they have to either. Being a parent is not a liability or a distraction—it’s one of the most meaningful things a person can do. Our policies, our expectations, and our culture should reflect that.
Do things only we can do. Something that’s happened with Daily Stoic over the years is as it has grown, so has the number of copycats. And so we’re constantly asking, what can only we do? With the bookstore, for example, we’re lucky to have authors constantly passing through to record the podcast. While they’re here, they sign books. Sometimes we do live events with them. Those books, those experiences—you can’t get them anywhere else. This has always been good advice, but with these AI tools making it easier and easier to copy and replicate and reproduce, it’s more important than ever to find and focus on the things only you can do.
Do the hard things first. The novelist Philipp Meyer (whose book The Son is an incredible read) told me on the Daily Stoic podcast, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.” A corollary to this: the poet and pacifist William Stafford had a great daily rule: “Do the hard things first.” Well-intentioned plans fall apart as the day progresses. Our willpower evaporates. The world makes its demands. My assistant knows not to schedule anything before mid-morning because early calls and meetings don’t just take time—they sap the energy I need to do the hard work. I want to give my best self to my most difficult things. And I encourage my team to do the same: protect the early part of the day, guard your energy, and use it on what matters most.
It’s not a principle until it costs you something. There are lots of ways to make money—many of them easier and more lucrative than writing about an obscure school of ancient philosophy or opening a small-town bookstore in the middle of a pandemic. Of course, it still has to make money, but not being motivated solely by profit gives me a certain freedom: the ability to act with a heart and conscience, to take stands, to say what I think needs to be said. Every time I write something even mildly political in a Daily Stoic email, we lose a disproportionate number of subscribers. I get lots of angry emails. People accuse me of having changed or they say the Stoics would be disappointed. I sometimes remind them–if not something about how all of the Stoics were active in politics and explicitly said the philosopher is obligated to participate in politics–that I didn’t build an audience to not write or say what I think. Or when the team alerts me to the number of followers we lost after I said something political on social media, I tell them the same. And besides, how successful are you really if you censor yourself because you’re afraid it will cost you?
Help people get to where they want to go. It’s very unlikely that anyone you hire is being hired for their dream job. They are not signing up for lifetime employment. No, this job is a waystation. I don’t think we should pretend otherwise. In fact, we should embrace it. When Tim Ferriss was looking for someone to run his podcast and email a few years ago, he asked me if he could hire Hristo Vassilev, who was then my research assistant. You know what I said? I said “Of course.” And he’s been Tim’s right hand ever since. Brent Underwood, who started as my intern more than a decade ago at the marketing company I was building, has gone on to write a bestselling book and build a hugely popular YouTube channelabout the ghost town he owns. My last assistant currently runs a large nonprofit. To be clear, I’ve had some assistants and employees that didn’t work out. But I think I’ve got a pretty good “coaching tree” so far. In sports, a coach’s success isn’t just defined by wins and losses, but by their “coaching tree”—the players, coaches, and executives that they discovered and mentored who’ve gone on to do great things in their own careers. It’s a concept I think about a lot and ended up doing a chapter on it in Right Thing, Right Now because it deserves to be recognized outside of sports. It’s just a wonderful way to measure a life. Your job as a leader is to have a large coaching tree. Almost no one you hire is going to be a lifer. Chances are, you are not offering them their dream job, but you could be the one who helps them get closer to that dream job.
Don’t try to map out the whole game. Along these lines, a few years ago, during our year-end one-on-one, I asked my current researcher, Billy Oppenheimer, where he wanted to go. If you’re still working for me in this capacity in five years, I said, we both screwed up. The way to get the most out of this kind of relationship is if I have some idea of where you want to go. Then I can try to help you get there. He told me he wanted to be a writer but was just waiting to know for certain what I wanted to write about. After he described some complicated way in which he was privately writing stuff and looking for patterns to determine what to write about publicly, I told him, Just start. You’re trying to map out the whole 9 innings. Just throw the first pitch. Soon after, he started a great newsletter I read every Sunday, which led to him now also working for Rick Rubin and signing his first book deal last year.
So yes, it’s critical to define the principles and rules you live and lead by. It’s critical to have an answer to that question, What’s your philosophy?
But as you get to work figuring out yours, keep in mind, you’re better off starting imperfectly than being paralyzed by the delusion of perfection. As they say, another way to spell “perfectionism” is p-a-r-a-l-y-s-i-s.
Don’t try to map out the whole game.
Just throw the first pitch.
Just start.
