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As parents, we worry about having all the right answers. But I think it’s better to focus on asking the right questions. The right question at the right time can change the course of a life, can still a turbulent situation, can provide a totally different perspective. While every situation can generate its own, here are 15 questions that have challenged and helped me the most every day both as a parent and then as a writer, as I researched and wrote what became The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids, (it would mean so much to me if you could preorder it!!!). These 15 questions from some of the wisest philosophers, most incisive thinkers, and greatest parents that ever lived. I’m not saying I know the answer to any of them, but I can say there is value in letting them challenge you. Certainly they have challenged me and continue to challenge me… Start now by asking: Will I Be An Ancestor or A Ghost? In his Broadway show, Bruce Springsteen—whose songs have often focused on the painful legacy of our parents—explained the choice that all of us have as parents. “We are ghosts or we are ancestors in our children’s lives,” he said at the beginning of his broadway show Long Time Comin’. “We either lay our mistakes, our burdens upon them, and we haunt them, or we assist them in laying those old burdens down, and we free them from the chain of our own flawed behavior. And as ancestors, we walk alongside of them, and we assist them in finding their own way, and some transcendence.” Will you be a ghost or an ancestor to your children? Will you be the kind of example they need? Will you leave the kind of legacy that will guide them? That will inspire them to be decent and disciplined, great and good? Or will you haunt them with your mistakes, with the pain you inflicted on them, with the things left unsaid or unresolved? Of course, we all know which of those two we want to be, just as Bruce’s flawed father surely did. But then our demons, our issues, the ghosts of our own parents, get in the way. That’s why we go to therapy and read good books. That’s why we stay up at night before bed talking to our spouse about how hard this parenting thing is, to exorcise those demons by bringing them into the light. It’s why, wordlessly, when we hold our kids, we promise ourselves to do better, to try harder, to not repeat the mistakes we endured growing up. Because we want to be an ancestor—someone who guides them and inspires them. We don’t want to haunt their future selves like a ghost. Am I Cherishing The Garbage Time? We save and plan for elaborate vacations. We anticipate for months and months. And when it inevitably isn’t as special or elaborate or photo-worthy as we’d hoped, we feel awful, like we’re not enough, like we haven’t done enough. Yet the comedian Jerry Seinfeld, who has three kids, questions the “quality time” that so many of us chase. I’m a believer in the ordinary and the mundane. These guys that talk about “quality time”—I always find that a little sad when they say, “We have quality time.” I don’t want quality time. I want the garbage time. That’s what I like. You just see them in their room reading a comic book and you get to kind of watch that for a minute, or [having] a bowl of Cheerios at 11 o’clock at night when they’re not even supposed to be up. The garbage, that’s what I love. Special days? Nah. Every day, every minute, can be special. All time with your kids—all time with anyone you love—is created equal. Eating cereal together can be wonderful. Blowing off school for a fun day together can be wonderful—but so can the twenty-minute drive in traffic to school. So can taking out the garbage or waiting in the McDonald’s drive-through. In my pocket, I carry a medallion that says Tempus Fugit (”time flies”) on the front and “all time is quality time” on the back, so I’m constantly reminding myself to cherish the “garbage time.” Because it’s the best kind of time there is. Am I Doing What I Want Them To Do? The bestselling author and father of two Austin Kleon talks about how this is the hardest part of parenting: You have to be the kind of human being you want your children to be. You have to do the things you want your kids to do. “I find this with parents all the time,” he said. “They want their kids to do things that they don’t do themselves.” He wants his kids to be readers, so he makes sure they see him reading. He wants them to explore different hobbies and interests, so he makes sure they see him practicing an instrument or tinkering in a sketchbook. He wants them to work hard and find work they care about, so he makes sure they see him working in his studio. He wants them to treat others with respect and kindness, so he makes sure they see him giving their mother something he made for her. Who you are forms who they will be. So be who you want them to be. Do what you want them to do. It’s hard, but it’s the only way. Does This Really Matter? Your kid wants to go swimming, but you have to make this phone call. Your kids want to wrestle, but you have to cook dinner. Your kids want you to come tuck them in, but it’s a tie game with forty-two seconds left in regulation. We pick these things because they’re urgent. Because they’ll only take a second. But mostly, we pick them because we can get away with it. If something seemingly more urgent or out-of-control [...]

My top 10 highlights from the book: 1. I may lose once but I never lose twice. 2. He had such an appetite for victory and such a capacity for work that he was bound to succeed. 3. Arnault is an iron fist in an iron glove. 4. He did not stray from his path. Relentlessly he pursued his ascent and seized every passing opportunity. 5. It i...

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Before we dive in to this week’s newsletter: New pod episode is live with Jackson Fall. We talk about his viral “HustleGPT” AI tweet that got 20M+ impressions, 100k+ followers in 7 days and changed his life. It’s a must listen. Listen on Spotify and

It is only from doing hard things, the Stoics said, that we learn what we’re capable of. A little over three years ago, my wife and I had the craziest idea we’ve ever had in our lives: to open a bookstore in Bastrop, Texas. Opening a small business is always hard. But opening a small business during a pandemic in a small town in rural Texas? To call it a challenge would be an understatement. We’ve learned a lot…about business, about books, and about what we’re capable of. Last year, I wrote a piece on the lessons we’d learned in our first year of business at The Painted Porch. Now, another year has passed and we have learned a few more…and re-learned some of the ones we thought we’d gotten the first time. I share them here so you can perhaps learn a little from my experiences and hopefully go create something cool of your own out of it. [1] Anything can be a good business if you treat it like a business. Too many indie bookstores are started because people think they’ll be fun…or because they love books. No, you have to be serious. I learned this as a writer: treat it like a job. [2] The bookstore of course is not just a bookstore. It is my office. It is my employee’s office. It is where I record podcasts and film YouTube videos. I rent part of the building to another business (a really cool record store called Astro Records). When you are thinking about taking a big risk, look for little ways to take some risk off the table. Find multiple uses, multiple options so that if one fails, you can still succeed. [3] On the Daily Stoic podcast, Matthew McConaughey gave me a better framework for making big decisions. He told me he’s known in Hollywood as a Quick No, Long Yes. His No’s are quick. But before he says Yes to something, “I give myself about 2 weeks in each frame of mind—Yes I’m in, No I’m out—and then I measure what keeps me up at night.” [4] Keep your eye on the prize. What is success to you? What metrics actually matter to you? Remembering why you did something and how you measure success helps you calibrate your decisions properly. I’m happy enough to be putting books out in the world, making this community better, having a physical space, challenging myself, etc…as long as I don’t lose lots of money, that’s a win. [5] Forget the politics. It’s been interesting to watch people in our small town care a lot about what other people in the small town think. Except this small town isn’t big enough to support a bookstore. When you’re starting out doing things, you get strong opinions from people in your local scene etc. But that’s not who you should be trying to impress, or who matters in the long run. Look outward, onwards. Don’t be stuck thinking small, don’t let the scene you chanced into constrain you. [6] Don’t be afraid to be political though. We delayed opening during the worst days of COVID. We kept up safety protocols even after the state of Texas washed its hands of its responsibilities last year. We did it even though people got mad at us for it, even though it probably cost us business. My conscience is clean and that’s what counts. Keeping your community and your staff safe is good for business in the long run anyway. [7] Beware of mission creep. Our original plan was that we’d have only a couple hundred books, only my absolute favorite books, only the books I put in my Reading List Email. It would only be those books. But the problem is, I’m always reading and discovering new favorite books. So the temptation to add and add and add is always there. In the military, they call this mission creep. It’s hard to predict exactly how things are going to unfold, so there tends to be a gradual broadening of objectives as a mission or battle progresses. If you are setting out on a project, just something to be aware of. [8] For everything you add, take something away. There’s a great story of Mark Parker who, just after he became CEO of Nike, called Steve Jobs for advice. “Just one thing,” Jobs said. “Nike makes some of the best products in the world. Products that you lust after. But you also make a lot of crap. Just get rid of the crappy stuff and focus on the good stuff.” “He was absolutely right,” Parker said. “We had to edit.” Because we’ve always done it this way, is not a good reason. Or in our case, because we’ve always carried this book or because it sold well in the past, is not a good reason. We have to edit. [9] Whenever I am at the store, people are excited to see me and ask a bunch of questions. Whenever my wife is there people ask her, “Where are your kids?” No one has EVER asked me that. It’s just a reminder that entrepreneurship is easier for some than others and the whole idea of just pulling yourselves up by your bootstraps is nonsense. Be aware of your advantages and privileges. [10] Speaking of which…something that’s been hard to navigate is all the people who come to the bookstore to see me. On the one hand, it is awesome. But on the other hand, if I give everyone twenty minutes, my day is gone. This means I sometimes have to be rude…but if I am not, then I am rude to my writing, to my family, to myself. [11] If you’re successful, your people should be successful. Nothing feels better than distributing profits or raises to the team. If you don’t take pleasure in that, you’re doing it wrong, prioritizing the wrong things. [12] A few weeks ago, an employee made a bad call [...]

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