710: Ravi Gupta - The Anti-Dabbler's Guide to Mastering One New Skill Every Year, Why Presence Isn't Enough, Bourdain's Masterclass in Humility, and Pairing Reasonable Goals With Delusional Ones

The Learning Leader Show with Ryan Hawk www. LearningLeader.com https://www. LearningLeader.com New Book - The Price of Becoming www. LearningLeader.com/Becoming https://www. LearningLeader.com/Becoming Connect with me on socials Twitter/X - @RyanHawk12 Instagram - @RyanHawk12 Join 10's of thousands of leaders, subscribe to Mindful Monday My guest: Ravi Gupta is the founder of RePublic Schools, whose flagship Nashville schools became the first in Tennessee to rank in the top 5% statewide for both growth and achievement. He co-founded Arena, which trained more than 7,000 political staffers, worked on the first Obama campaign, and wrote speeches for UN Ambassador Susan Rice. Today he runs The Branch, a media company fighting polarization. His new book is The Invisible List: One Passion a Year, Every Year. Key Learnings One new passion a year, every year. When Ravi left his job running schools, he decided to treat every year like a school year with himself as the only student. He's done it for seven years. Surfing, tennis, screenwriting, a novel, Italian cooking. Be an anti-dabbler. The seductive version is a little boxing, a little salsa dancing, a little cooking. You get fifteen years of sampling and none of the skill. Pick the thing, commit to the year, see it through even if you come to regret the pick. The rule that makes it work: no new thing midyear. You can maintain old passions. You cannot start a new one. He broke his own rule and learned why it exists. Bored one day and avoiding his cooking, Ravi walked into a Muay Thai gym on his corner. He loved the class, walked out, and told himself it was off the table until January 1. The pull wasn't interest. It was the rush of early wins, and that rush is the most convincing form of procrastination there is. Trying something and quitting can be worse than never trying. Once you've tasted it, you start seeing it everywhere, and you replay the version of your life where you stuck with it. Pair a reasonable goal with a delusional one. Ravi almost always hits the reasonable one. He almost never hits the unreasonable one right away, but he often gets there eventually. The pairing is the point. Tim Ferriss's observation on why that works: there's less competition for big crazy goals, because so few people think that way anymore. December is the meta-learning month. Thanksgiving to New Year's, Ravi wraps up the current year and pulls together the next one: the books, the experts, the sequence, what it actually means to be great at the thing. Don't start researching it in August. He has next year's candidates in his head by late summer, but he refuses to buy books or line up coaches until December. Planning next year's passion is an elaborate way to avoid this year's. Output goals need a skill set attached. Example: hiking an outrageous number of national parks. Ravi's counter: keep the output goal, but build the skills underneath it. Pitching a tent, starting a fire, navigation, survival prep. Then the year leaves you with something beyond a number. Each year becomes a chapter. 2020: surfing. 2021: tennis. Childhood is memorable because it's divided into grades with names attached. Adult years blur into one undifferentiated stretch, and Ravi thinks that blur is part of why people get depressed looking backward and forward. The reframe on aging: turning 50 in seven years is only grim if those are seven blank years. Seven more passions is a different sentence entirely. Join an accountability group. The Invisible Posse is a group of readers all pursuing their own skills at the same time, at readinvisiblelist.com http://readinvisiblelist.com. New challenge every two weeks, a leaderboard, points for doing the work. The list is a solo project. The accountability isn't. Do the thing publicly in the first two weeks. The group's first challenge was to do your new skill in front of people immediately. The winner was a man learning to sing who sat his cousins down on vacation and performed a whole song. Once you're past being judged, you're doing it instead of planning it. The second challenge is the one most people skip: get feedback from someone who actually knows how to do it, then do it again. Protecting your time is on you. From Neil Strauss, in a writing group Ravi joined during his writing year: "It's nobody's responsibility but your own to protect your time." The complaint that nobody respects your boundaries is a complaint about your own boundaries. Which means the conversation has to be explicit. You take Saturday, I take Sunday. One of us has mornings. I've carved out 45 minutes and you know about it. Writing is especially hard to defend because it doesn't look like work. Treat your session time like a flight. Strauss again, this time on writer's block. Nobody waits to feel motivated before going to the airport. You wake up early, sit in the security line, get wedged next to someone taking up too much room, and you never treat any of it as optional. Put the sessions on your calendar and defend them the same way, whatever your thing is. The question that ended writer's block for good: your mom is a nurse, does she get nurse's block? When Ravi still stalls, he falls back on Hemingway's one true sentence, and since the surgery, he dictates rather than types if that's what it takes to get words out. Teach tools, not answers. The book's dedication is to the teachers who gave Ravi tools instead of answers. He trained his own teachers not to be "the sage on the stage." He can't name a single fact those teachers gave him. He can name what they built in him. A doctor friend gave him a portable framework instead of an opinion. When Ravi tore his bicep, friends told him to take peptides. Rather than answering yes or no, his doctor friend walked him through the questions: what's the theoretical mechanism, what do controlled peer-reviewed trials actually show, what are the downsides? Ravi now uses it on everything. In a disagreement, show your process, not just your conclusion. If you lay out how you arrived at an answer, the other person may not accept the answer but can engage the method, or show you where you went wrong. It lowers the heat. The 10 out of 10 version of humility. Andy Greenwald wrote a piece ripping Anthony Bourdain, comparing him to a lion declawed and put in a zoo. Bourdain read it, told his staff, "This guy got me," then had the team invite Greenwald over for a conversation. Nurturing your own passions is not stealing from your family. The oxygen mask applies. Your kids will be more inspired by you and your spouse, more drawn to you if you're a person who is actually lit up by something. Presence alone is a thin theory of parenting. Ravi would rather have had a father who skipped a game to pursue something real and then talked about it over dinner than one who dragged himself to the bleachers out of obligation. Availability matters. So do wisdom, example, and energy. People are drawn to anyone who is fully activated. The musician playing a Nashville bar at 2:00 PM on a Wednesday who is completely in it, playing like the room is full. Ravi's champagne moment a year from now: settling down. Not flying airplanes, not the bestseller list. He says he needed the seven years of this process to come out a whole person capable of devoting himself to someone else again. A relationship or parenting year is a legitimate list item, but not the first one. Most people have been too selfless already and need the selfish pursuits first. And it only works if you attack it systematically, with real metrics, because that kind of goal gets squishy fast. Action What is your one thing for 2027? Name the reasonable goal you'll hit with consistent effort, and the delusional one that scares you a little. Look at your calendar for next week. Where is the time for that thing, and who in your life needs to know it's protected before Monday? If you enjoyed this episode with Ravi Gupta, check out episode #647 with Tim Ferriss: Chasing Your Curiosity https://learningleader.com/timferriss/ Episode Chapters 00:00 Apply for the Learning Leader Circle 01:36 Meet Ravi Gupta 03:09 Three Injuries, One Arm 05:03 Teachers Who Give Tools, Not Answers 06:58 A Framework Instead of an Opinion 10:36 Why Hosting a Show Changes Your Mind 13:59 Bourdain: "This Guy Got Me" 16:28 His Mom and the Yale Law Tour 20:31 One Delusional Goal, One Reasonable One 23:56 The Anti-Dabbler Rules 29:13 Nobody Protects Your Time But You 33:25 How He Actually Became a Writer 37:06 How He Picks the Year's Skill 38:50 Salsa and the Unfinished Ending 40:35 The Burnout Wake-Up Call 43:09 Your Passions Make You a Better Parent 48:19 The Invisible Posse Challenges 51:09 The Champagne Question 54:05 Make Relationships a Skill 55:55 Skills Underneath the Goal 01:00:19 EOPC

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Ryan Hawk?

  Applications are now open for our next Learning Leader Circle. You can go to learningleaderscircle.com to apply. I thought it would be helpful for you to hear from some current members of my Learning Leader Circle. Here they are.

• 0:17Speaker 01

  I chose Learning Leader Circle because I wanted to be around really winning professionals, people killing at work, but even better people.

• 0:25Speaker 02

  Ryan does such an amazing job of vetting the group. It's all A players. It is all amazing rock star people who want everybody to become their best and just add value to the group.

• 0:37Speaker 03

  We have people with agriculture backgrounds. We have people with white collar backgrounds, blue collar backgrounds, people in education.

• 0:43Speaker 04

  The totality of the room is very impressive with the amount of knowledge we have to be gained, but when you sit down and you break out with five, six, seven people, you can have that intimate, that in-depth conversation that allows you to go a little bit deeper.

• 0:55Speaker 05

  We got additional coaches this year. They live their lives according to what they teach. These guys will all jump in and get you back on course.

• 1:05Speaker 06

  Definitely do it. Don't think twice about it. Know that you're going to leave with new relationships, new takeaways to make you better at your job, better as a parent and as a person. So it was just a very intimate, very inclusive environment.

• 1:26Ryan Hawk?

  To apply for our next Learning Leader Circle, go to learningleaderscircle.com.

• 1:36Ryan Hawk?

  Welcome to the Learning Leader Show presented by Insight Global. I am your host, Ryan Hawke. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now on to tonight's featured leader, Ravi Gupta founded Republic Schools, whose flagship Nashville schools became the first in Tennessee to rank in the top 5% statewide for both growth and achievement. He worked on the first Obama campaign and wrote speeches for UN Ambassador Susan Rice at the United Nations.

• 2:20Ryan Hawk?

  Today, he runs the branch, a media company fighting polarization. His new book is called The Invisible List, One Passion a Year Every Year. During our conversation, we discussed why you should choose one new passion to chase each year and commit to it. Ravi has done this for the past seven years and it has changed his life. Then he shares his unique goal-setting philosophy. He likes to set one delusional, huge goal, and then one that's more reasonable. We talk about how this could be potentially helpful for you.

• 3:00Ryan Hawk?

  And then Ravi shares a useful piece of advice he got from Neil Strauss about setting boundaries. Ladies and gentlemen, please enjoy my conversation with Ravi Gupta.

• 3:15Ryan Hawk?

  I'm glad I got you early in the book pub podcast tour because you probably have more energy now than maybe you will a few months from now.

• 3:25Speaker 07

  I'm fresh and idealistic, but I am actually injured because this is relevant to the book. So I tore my bicep tendon a couple of weeks ago surfing. This is not a great sales pitch for my book, but I might as well be honest. In the past two years, I fractured my wrist playing tennis, which is a chapter of the book. I've ruptured my bicep tendon surfing. And then one unrelated to the book is I dislocated my shoulder eight months ago, motorcycling. And that's not part of the book. That was just totally accidental. And those are the only three injuries I've ever had in my life, all on the same arm, all in the past two years.

• 4:02Ryan Hawk?

  Ooh, surgery on the bicep? You have to get surgery?

• 4:05Speaker 07

  Yeah, I was in Costa Rica. I went for two weeks. I was looking at the waves from here in New York and I was like, oh wow, there's two weeks of perfect waves that are down the line. And so I flew to Costa Rica. I had not surfed since I dislocated my shoulder. So I was like, okay, first wave back. I misjudged a wave, hyperextended my arm, tore my bicep on the first wave back and had to fly back and get surgery a couple of weeks ago. I actually couldn't type until like a couple of days ago. So I was without typing, which I'm a writer like you, which is torture. Couldn't work out, couldn't play sports. So I was very much feeling sorry for myself. So I've just emerged from a few weeks of pity partying and now I'm ready to go and I have now restored my self-confidence and energy.

• 4:49Speaker 07

  So had you caught me a couple of weeks ago, I would have been on like painkillers and just totally sad and immobile. So we're in a good place now.

• 5:00Ryan Hawk?

  All right, I'm glad we got you now. Okay. I love studying the people that impact high achievers and you've accomplished a lot already in a short period of time. And you dedicate this book for teachers who gave me tools instead of answers. I appreciated that phrase. What do you mean by the teachers who gave you tools instead of answers?

• 5:27Speaker 07

  Right, because I think there's this sense of, you know, I used to run schools down south. I was a school principal and then a superintendent of a network of schools I started in the deep south for kids in some of the poorest corners of this country. And what I used to tell my teachers when we were training them is you don't want to be what they call the sage on the stage, right? You don't want to be out there and be like, this is the capital T truth. And let me just talk on and on and on about what that is. Instead, what you want to do is help them learn to think, help them build skills, and then help them build the qualities and values that will help them succeed in this world. And when I think about the teachers who've really set me straight in my life, I couldn't

• 6:11Speaker 07

  tell you a piece of knowledge they've imparted on me, but I can tell you so many things in those three domains I just talked about that they gave me and that I carry with me every day.

• 6:22Ryan Hawk?

  Someone who teaches you to learn how to think. So my favorite mentors in life are the ones who, when I go to them with a challenge, a problem, a question, they usually respond with questions, more curiosity, because they understand the importance of me having ownership over the solution. So they help me find my way to the solutions to whatever problems I'm coming to them with. So they approach me with curiosity, which I think is my way I both give and receive love. How do you help someone learn to think?

• 7:01Speaker 07

  There's a domain-specific part of this, and then there's kind of a generalizable way of attacking either problems or debates, right? So I think of it like, let's talk about debating for a second, right? Because I've spent a lot of time in politics and I have such an eclectic series of beliefs that I'm often, if I'm not careful, debating anybody, whether they are in the same political party as me or not. And actually often lately, I've been debating people in my own party more than other people. And for the people in my schools or the people that I've worked with in politics or like to be around, this sort of series of tools and ways of thinking are logic and what's a fallacy and how do you lay out an argument? How do you separate good evidence from bad evidence?

• 7:46Speaker 07

  You know, that can seem domain-specific to politics, but it's really generalizable, right? So you take it into the health and fitness world, right? When I tore my bicep tendon, for example, I had friends in my life who were like peptides, right? So I'm like, all right, what tools can I bring to this peptide discussion? And a doctor friend of mine helpfully laid out to me a framework, which was what the benefits, you know, mechanistically could be, like potentially theoretically, what could they be? What have peer-reviewed studies with controlled trials, et cetera, et cetera, et cetera? What have they laid out? And then what are the potential downsides? That's the tool and framework you should do for anything like this, not just peptides. And I was like, oh yeah. I'm like, okay, I could use that for anything now.

• 8:30Speaker 07

  Like, so the next time, you know, it's like platelet-rich plasma or GLP-1s or something down the line that I may decide statins, I can use this as opposed to, he didn't tell me, do peptides or not, right? He taught me how to think of the question of peptides in a way that could help me later on, which I thought was helpful.

• 8:50Ryan Hawk?

  So it's almost like a portable lesson. So you take it to this specific question, problem that you have or something you're considering doing, and it's almost a decision-making framework tool as opposed to just being like, dude, take peptides or no, don't take those things. They're from China or whatever, right?

• 9:06Speaker 07

  Right, right, right. And it also, I think, helps you cut through the heat. So I think like, you know, a good example to me is like in the world of politics, right? Like, let's come up with an example, like in New York City. Do we have city-run grocery stores, right? Is like a debate. And there's like a way to think about it that's divorced from what your political party is and even what even your economic policies are generally. You could be like, well, okay, do people have access to ready groceries? What would happen if the city ran a grocery store and decreased prices? How would that affect the customers, but also the grocery stores around that? Who are the people who own those grocery stores? And does the city have the money to do this, right?

• 9:49Speaker 07

  And these are like questions I try to ask in any domain that it's like, okay, if I'm sitting across from somebody who believes differently than me, if I like lay out the way I thought about the problem, I'm like, okay, you may not like my answer, but you might like the process and we could at least agree on that. Or you could tell me where I erred in my process. And I think it kind of simmers everything down to an extent. Obviously, the internet being what it is and people being what they are in 2026, you have to be in the right context, like you and I talking right now. Like if you and I were anonymous Twitter bots, we probably wouldn't be speaking in complete sentences and paragraphs and finding common ground if we were on the different side of an issue.

• 10:31Speaker 07

  But I do think like long-form discussions are perfect for this kind of thing.

• 10:36Ryan Hawk?

  Do you think hosting a podcast?

• 10:40Ryan Hawk?

  I've found it, it has made me a much more reasonable person, as well as someone who lives way more in the gray and less in the black and white. Because it's easy on the internet to say it's either this, or it's that. It's a one or a two. It's A or it's B. It's black or it's white. And then you actually get in the real world and you have conversations with hundreds and hundreds of people from all over the world and different industries and different ages and different jobs. And you realize, it's almost never this or that. It's in the gray. It's in between. It's much more nuanced. We become less judgmental, more reasonable, because it's always kinda messy.

• 11:24Speaker 07

  For sure.

• 11:25Ryan Hawk?

  Do you feel that from doing this type of work?

• 11:27Speaker 07

  I do. I do think podcasting, plus, you know, I grew up in Staten Island, New York, where it's an eclectic place. You know, my family is split, both politically, but also in every possible way, like just very different types of people. We come from a family where debate is sports. And I think having the podcast, and I treat the podcast like you do. I don't treat my interviews like gotcha moments. So when I'm interviewing people, my goal is to let them tell their story and lay out the way they think about the world. And I trust my audience to make heads or tails of it, right? So, and if somebody says something I think I wanna push on, I do it respectfully. And what I've found is, you're totally right. Like, if I think of just the past few months, I've had people who've served in every potential

• 12:12Speaker 07

  political administration over the past few years. I've had people on health debates, economic debates, even like investment debates. You know, I've had different investment experts have wildly different theories. And my goal often in interviewing people, and I say this to my audience often, is, had you not known who I was, I would want you to be able to listen to the interview and not be able to tell what I think. And so, maybe it's somebody who I would generally agree with, I'm giving them a harder time, even. It's also fun that way, because you get to stress test your own beliefs. And I imagine, Ryan, and I'm wondering, you know, maybe this is your experience, I find that just having a show means I change my mind a lot.

• 12:55Ryan Hawk?

  Oh my god.

• 12:56Speaker 07

  Because you're talking to tons of people who have spent more time thinking about issues than you have, and you're like, oh yeah, I hadn't seen this. Like, I did this once with a, I was ripping on hospice care providers, of all things, in Arizona once. This was a couple of years ago. And I was like, these are like grifters and blah, blah, blah, blah, blah, because there was some study that ProPublica came out. And then one of my audience members was like, hey, I run hospice care in Arizona. And we started emailing, and I was like, oh yeah, sorry, man. Like, you made a good point.

• 13:22Ryan Hawk?

  I think it's a great quality in a person. It shows a lot of confidence and security in oneself, in that, an open mind, a curiosity about the world, about people, about their stories, being interested more than trying to be interesting, like, all of that, I think, leads to great conversations, learning, which is, I think, an attractive quality in a person to be a part of any type of group or in any sort of leadership role of, yeah, we can go, we need to go, but I'm also open to changing my mind when better evidence presents itself.

• 13:59Speaker 07

  You wanna hear a great example of this?

• 14:01Ryan Hawk?

  Yeah.

• 14:01Speaker 07

  So, Anthony Bourdain, you know, I have him on my mind, because I just watched that Tony movie that just came out. I just saw the screener for that, and it was surprisingly great.

• 14:09Ryan Hawk?

  There's a new one about him?

• 14:10Speaker 07

  Yeah, it's like, it's like, basically about one summer he spent in Providence Town. It's not out en masse yet, but in New York, they filmed the screener over the weekend. I think for you guys, it'll be out in the next week or two. And then, by the time this is posted, people will, it'll be familiar with people. But, I was listening to an interview with Andy Greenwald. I think he was a writer at Rolling Stone or something, before he was at The Ringer. And he once wrote a piece about Anthony Bourdain, where he ripped Bourdain, and I think compared him to a lion who had then been captured and brought to a zoo and declawed it and defanged. And basically, he was like, because Bourdain, whatever period of time Bourdain was in, I think he had, he was now doing some kind of like kitschy cooking show on one of the cooking networks.

• 14:55Speaker 07

  And Bourdain ripped him for it in this column, and was like, hey, this is like, not who the true Bourdain is, blah, blah, blah. And Greenwald recently did an interview where he talked about how Bourdain didn't react the way you'd think. Bourdain read this, apparently told the people on staff, this guy got me, meaning he captured me perfectly. And then they called up Greenwald and invited him over to have a conversation with Bourdain. And they had this wide-ranging conversation. What you were saying, Ryan, it's like, that's the A plus, 10 out of 10 version of humility, because, you know, when people come at you, it's really hard to keep your sanity. You know, you wanna be like, no, you know, like, this is who I am. But sometimes people get you, you know? And you gotta be like, you know what, you got me.

• 15:39Ryan Hawk?

  Yeah. Well, again, I love Bourdain's stuff. Man, his writing, his shows, I wish he was still with us, but I think it's, as you said, 10 out of 10 humility, a willingness not to get defensive, even if it stings or it hurts, you get this feedback. But, like, if you wanna get better, we talk about excellence a lot here. If you wanna get better, if you wanna sustain excellence over time, I think that's a necessary quality in a person, is to have an openness to, wait a second, maybe they're right, even though if I don't want them to be.

• 16:11Speaker 07

  Right.

• 16:11Ryan Hawk?

  That's a cool story. I'm looking forward to read that. Okay. None of this was what I'd planned, but I love that. That's, these are my favorite kinda conversations.

• 16:18Speaker 07

  I know, this is where the publisher kills me, where they're listening to this interview, and they're like, wait a minute, you wrote a book. What are you talking about?

• 16:23Ryan Hawk?

  Let's get to some of that stuff. It's always happens when it's like, the most interesting people. Okay. The first person you talk about in your acknowledgements is your mom, master's degree in her 50s, single mom, she's a professor, I mean, multiple degrees. I can't even imagine, it's an inspiring story to read more about her. What are some of the things you've learned from your mom and all of the work she's done?

• 16:44Speaker 07

  My mom, you know, I grew up in Staten Island, New York, in a working-class neighborhood. And I had an Indian dad, who's an immigrant, and a mom, who's a Polish-American mom. And they met, because my dad's a doctor and my mom's a nurse, they met in a hospital in Brooklyn. And then my dad basically took off. He came and went when I was a kid, but he was, he was gone for good by the time I was in middle school. So my mom raised us, worked two jobs, and had an associate's degree in nursing, and took on tough jobs. I mean, like, AIDS, she worked on one of the city's first HIV/AIDS wards, worked in geriatric wards. And my common experience with her was, she would just leave $5 on the table, and that would be my money that I would use to get dinner when I got home from school, from Burger King or wherever.

• 17:28Speaker 07

  I have a brother, and then I have a sister. By the time we all went to college, my mom was like, she always was fascinated with history. She wanted to be a history professor. So she went back to school when we left, and got her bachelor's degree, and then got her master's degree, and now teaches at the College of Staten Island, history, has been doing it for years. And I mention her because I am a, I am an imperfect mascot. You know, when people read the book, they'll be like, okay, bachelor with no kids, and like Ivy League degree, and all this kinda stuff. So I try to, and do, every step of the way, remind people that there are tons of folks who have obstacles that are probably greater than most readers, that have done more amazing things than I have.

• 18:11Speaker 07

  So my mom is one of them, but throughout the book, people with cancer, woman with lupus who takes up painting, people whose spouses died, and they're in their 70s, 80s or 90s, and take up cooking, a friend of mine who learned to do pull-ups while she was diagnosed with breast cancer. So I try to take my own very 11 out of 10, kind of like, I'm gonna go to Costa Rica and learn to surf type of examples, and always pepper it with somebody like Amy, who is battling lupus, and watching Bob Ross YouTube videos in her cottage.

• 18:43Ryan Hawk?

  Hmm. But your early years, though, you may have made some poor choices, right?

• 18:50Speaker 07

  Yes.

• 18:51Ryan Hawk?

  As a 14-year-old, you're getting your stomach pumped. 16, you're getting arrested.

• 18:55Speaker 07

  Yep.

• 18:55Ryan Hawk?

  But then you go to Yale.

• 18:57Speaker 07

  It is crazy, man.

• 18:58Ryan Hawk?

  For law school. And you get hired to work in the Obama White House. It's like, dude, walk me through 14-year-old.

• 19:04Speaker 07

  It all goes back to my mom. You know, you nailed it with my mom, right? So, so much of this book comes from my mom. Because my mom was incredibly aspirational. So even as I was screwing up, so I got my stomach pumped for alcohol poisoning when I was in middle school, caught cutting school every step of the way, got arrested when I was in high school for a fight that I got into. So, and I had these kids in my neighborhood who I loved, they're still some of my best friends to this day. But by the time I left my neighborhood, and I was able to go to SUNY, you know, State University of New York, I just was a monk. I was like, oh my god, I can learn. And I also had my mom in my ear, who was like, you are better than this. And I remember one time, when I was in Binghamton, I must've been like a sophomore or something, my mom was like, hey, meet me in New Haven.

• 19:49Speaker 07

  This is how crazy my mom is, in a good way. We go meet for a night in New Haven, and she's like, I wanna take you somewhere. She takes me to Yale Law School.

• 19:59Speaker 07

  And gives me a tour of Yale Law School, tells the security guard at the front of Yale Law School, "My son is gonna go here one day." I wasn't even pre-law. I was pre-med. And it's crazy, because Binghamton at that time, I don't know if it was 15, 20 years, they hadn't sent somebody to Yale Law School before. Because Binghamton, great school, is not Princeton, it's not Harvard, it's not like these elite feeder schools, it's working class, you know? But within two years, I'd gotten into Yale, first person in 15, 20 years, because my mom put it in my head. That's my mom. You know, she's an incredible person.

• 20:31Ryan Hawk?

  What do you think of this idea, because now you're, you can be this person for others, this book will help be that for others, of, "I am jacked up to be around people who have sometimes like delusional confidence or belief that they can go to Yale Law School and be the first person in 20 years from that undergrad place to go," or other crazy ideas? Like, I think the world needs delusional confidence and big thinking. Certainly, the work needs to follow that, like it sounded like you did. But this idea of people like your mom and other leaders that you've been around that

• 21:11Ryan Hawk?

  think almost delusionally big, and how that is a good attribute to have, that we all could potentially have, we just need to work on developing it and then doing the work.

• 21:24Speaker 07

  You know, it's something interesting Tim Ferriss wrote recently. He was like, "If you have big, crazy goals, in some weird way, there's less competition for them, because so many people don't think like that anymore." I've been thinking about that a lot ever since, because I think it's, it's hard to maintain ambitious goals, especially in the face of people in your life who are just gonna be like, "What? That's crazy." You know, so I viewed that as a challenge. I read that not too long, maybe a couple of weeks ago, and I've been thinking, as I've, as I've been sitting around, unable to do anything with my injury, I've been thinking about that a lot, like, "Oh, yeah." And I actually think that gets to some of the book stuff, because, you know, the listeners might not know this, but the book is about how, following my mom's example and my own

• 22:07Speaker 07

  example of being a school leader, when I left my school, it's running schools in the South, I decided that I would treat every year like a school year, and myself as my only student, and I would learn one new passion or hobby every single year. And the book is really a record of that journey, but really a how-to. And I often pair a reasonable goal every year with an unreasonable goal, and often, I almost always achieve the reasonable goal, and then almost never achieve right away the unreasonable goal, but then, a lot of times, I get to it eventually. And that pairing, I think, is a beautiful pairing.

• 22:45Ryan Hawk?

  The Anti-Dabbler Handbook. It's crazy, the phrasing, when I was reading this. So, I had this event in Scottsdale where I hosted a guy named Ed Lattimore. Do you by chance know Ed?

• 22:58Speaker 07

  No, I don't think so.

• 23:00Ryan Hawk?

  Okay. So Ed is like a Renaissance man, he's a physics major, a heavyweight boxer, chess master, I mean, truly, like crazy. So it sounds like, what I'm about to say, like, might not make sense, but he told me, like, one of his goals in life was to beef up his obituary. And I'm like, what a cool, like, meta, like, cool phrase, like, beef up your obituary, like, you know, pack in like a lot of cool moments of life. And I feel like you're kind of doing that right now, too, and you have with this book, certainly. But I go, "How do you, how do you beef up your obituary? Like, what do you do?" And he goes, "I'm not gonna dabble. If I'm gonna go do something, I'm gonna go do it. If I'm gonna play chess, like, I'm gonna play chess, right? If I'm gonna be a boxer, I'm gonna be a boxer." And like, he fought and won a bunch, whatever.

• 23:45Ryan Hawk?

  And so, he said, "I'm just not gonna dabble." And so when I saw this, like, dude, this is too much coming together here with like, anti-dabbling.

• 23:52Speaker 07

  I need to meet this guy.

• 23:53Ryan Hawk?

  I'll introduce you guys. You both, you love each other, like, you're both awesome. So, yeah, just, I'd love to hear more about like, your overall ethos when it comes to not dabbling.

• 24:01Speaker 07

  This is counterintuitive in some ways. And, and the word I used before my publisher helpfully told me, it was too fancy of a word, was dilettantes, anti-dilettante. You know, dilettante, I guess, is like a kind of person who kind of just does a little this, a little that, you know? Dabbler is the kind of same thing. And it's seductive to be like, "You know what? I'll try a little boxing, I'll try a little bit of salsa dancing, and I'll do this and that." But we're adults. Even as kids, you kind of, you need focus, right? And you need to stick with it. A lot of good parents, like, a good parenting thing is, like, "Look, I'm not gonna tell you what to do, but if you're gonna do it, I want you to commit to a certain amount of time in that thing." I think that's a good thing for a parent to say to a kid, to be like, "Look, pick anything, but if you're gonna pick it, this year, we're gonna see it through. That's how I would parent.

• 24:46Speaker 07

  I'm not a parent, yep." And I do that to myself, it's like self-parenting. So every year, it's like, "I'm doing this thing." And it could suck, you could regret picking it, but you do it that year, and you see it through. And that also means that you don't pick up any other new thing that year. If you have time, you can continue to maintain other previous passions, right? So, I'm doing Italian cooking this year, but obviously, I try, I still was surfing, up until I ruptured my arm again, or I was, I played tennis also, until I hurt myself, and I still will find time for those things. But when in doubt, the first thing has to be the first thing, and the main goal of the year always comes back to, if you only have 30 minutes to spare, an hour to spare,

• 25:30Speaker 07

  you devote it to that thing that you're pursuing for the first time that year. And that also means that you have to be careful about going to a random salsa class or boxing class, right? So I had this happen to me earlier in the summer, where I live in the Lower East Side of Manhattan, there's like a great Muay Thai boxing place on my corner, I've always known I would love that kind of stuff. And I made the mistake of going in for one class, I was bored one day. And bored slash, and actually, this is relevant, bored slash, didn't want to do my main thing, cooking. So I was like, "You know what? Let me just procrastinate by trying something new, which is totally against my rule." I went in, I loved the class, I walked out, and I said to myself, "Good to know, but

• 26:15Speaker 07

  I can't do this thing anymore this year. If I want to do it, January 1st." Right? It would be my new thing. Because in my head, I use it as an excuse to not do my own thing. Because also, there's this rush of starting a new thing, right? If you're in the middle dog days of your year, and you're like, "Damn it, the wins aren't coming easy anymore," you'll be like, "You know what? Let me get that high, if you've done this enough times." You're like, "Let me get that high of walking into this new class and getting all those benefits of the rush of early wins, right? And the excitement of learning something new." But that will pull you off course.

• 26:49Ryan Hawk?

  Why does it have to only be like, one new thing a year? Why couldn't you have been the boxing workout class with Italian cooking? Why not both?

• 26:59Speaker 07

  It's more of like a multitasking thing, like, I think of like a long-term multitasking, it's like, why, when you sit down to write or to work on something hard, can you only do one thing at a time? I think of that in a year. Unless you are in exceptional territory where you have no job, no kids, and you kind of, you could structure your year like a college semester, where you're like, "I can take four classes." Unless you're in that rare territory, most of us have to make trade-offs. And so, there's this simplicity in saying one thing per year, but there's also a story benefit to it, which is, every year becomes a theme in your life. So, you get to say, "2020 was the year I learned to surf, 2021 was the year I learned tennis."

• 27:42Speaker 07

  And you could think of all the friends you made, the places you went, the ups and downs, and that time dilation, I think is what they call it, is a beautiful way to ensure that the passage of time is not scary, but that it's a kind of this beautiful book that you're writing for yourself, which, to your friend Ed, is it right? Ed Lattimore, you mentioned? So to Ed, that's probably how he's thinking about his obituary, right? It's like, it's these chapters, because once you leave school, because school is like first grade, you get the teacher, the classroom, sometimes a different building, new friends, new subjects, you remember it all, right? You probably still remember to this day, certain things that happened in each grade, books you read, people you met, field trips you went on, sports teams you played on, because it's first grade.

• 28:27Speaker 07

  It's Mrs. So-and-so, or Mr. So-and-so. But when you become an adult, it all kind of becomes this homogeneous gray goo, and I actually think that can make people depressed. And also, you could be depressed looking ahead, where if you're like me, and you're getting older, I'm in my early 40s, you look ahead and you're like, "Shit, I'm gonna be 50 in a couple of years, and I never thought I would be 50. I never pictured myself as a 50-year-old. 50-year-olds are fucking old." But you'd be like, "Wait a minute." Instead, I could be like, That's seven years. I could be having Tom Cruise. I could fly airplanes and helicopters, and I can speak Spanish and Italian. You know what I'm saying? Like, you could rewrite your own stories. You could be like, instead of being like, oh, my God, I'm gonna be 50, you'd be like, holy shit, I could be a badass if I do seven more years of this process.

• 29:13Ryan Hawk?

  One of the stories you talk about is the Lin-Manuel Miranda. He's one of my favorites to study, too. Can you tell that story about him? You know, just like, I gotta go, sorry.

• 29:22Speaker 07

  Yeah, I mean, this could be apocryphal, but he apparently was writing one of the songs for Hamilton, and he was like on his way to go see a friend's birthday or something like that. And he was like on the subway or something, and like, it was coming to him, like this song, which, if you're that talented as him, I imagine is something that happens quite often, but you have to capture that lightning when it happens. So he basically knocks on the friend's door and is like, hey, I love you, happy birthday, or whatever the occasion was. I have to go. And then he left. And that protecting your time is critical for anybody who's, especially in creative work, but any work where you want to take it seriously. And this is a somewhat controversial point that I should probably spend some time on here with you, is that Neil Strauss,

• 30:06Speaker 07

  who had joined his writing group while I was in my writing year, you know, Neil, who's written so many books, and most recently co-wrote The Creative Act with Rick Rubin. And Neil is an incredible writer, but also somebody who thinks really deeply about the process of writing and creativity, said to me in this writing class, it's nobody's responsibility but your own to protect your time. So you will often get into this phase where you'll be like, woe is me, nobody respects my boundaries. But those are your boundaries. You have to protect them against all comers. And what that means is you have to take stock of what your obligations are. So obviously, if you have an infant, or a daughter, or a family and all that, the book isn't about abandoning those responsibilities.

• 30:48Speaker 07

  It's about sitting down with the people in your life and saying, hey, like, let's do some give and take. If you have a spouse, one of us is on morning duty, one of us is on, you know, whatever duty, and, okay, I've carved out 45 minutes to an hour in the morning, and you respect that, we're now talking about it, I'm gonna write during that time, or vice versa. Or, I know some spouses are really good at this, you take Saturday, I take Sunday. You can leave the house, do whatever you want. I'll leave the house, do whatever I want. Like, you come up with these things, right? Or if you're dating somebody, like, if you're writing, you know this, writing is so hard to protect because it doesn't look like work. Sometimes you're staring off into space, you're going to Starbucks, and if you're with us, I've had this with significant others before, where you're like,

• 31:34Speaker 07

  okay, I gotta go somewhere and write. And it seems like an unreasonable ask. But you have to protect that time if you care about it, you know, and you want to get something done.

• 31:43Ryan Hawk?

  The airport analogy. Was that from Neil Strauss, too?

• 31:45Speaker 07

  That was also Neil. Yeah, he was like, this is about writer's block, which I get a lot of questions about writer's block. Somebody else said to me, your mom is a nurse, right? He was like, did your mom get nurse's block? I was like, no. I was like, well, then you're a writer, it's easier. Write, don't make excuses. I was like, I think about that all the time. But what Neil said was, look, you gotta treat it like a thing, like, there are tons of things you don't want to do. If you gotta make a flight, you wake up early, you go to the airport, you wait in line, you go through security, you sit wedged in the seat next to somebody who's taken up too much room, and you get to where you're going. And you don't treat it like it's optional. And that's how you have to treat your writing. And I think about that all the time. Just get the words on the page, you know, what did Hemingway say, one true sentence?

• 32:30Speaker 07

  I was thinking about this yesterday. I'm writing this article now about adult camps and like the importance of adult immersive experiences, going away somewhere on vacation to learn something. And I'm just, for one reason or another, having a very hard time organizing my thoughts for this piece. And I was just thinking about the Hemingway line, one true sentence. I was literally just being like, one true sentence. And actually, with, one interesting thing that happened with my injury was that I started using Whisperflow, which is a dictation tool. And so sometimes, now with my quote-unquote writer's block instinct, I'm like, I can't get up. Worst-case scenario, I will talk into the machine and talk my words onto the page if I don't feel like typing, but I'm getting the words out, one way or the other.

• 33:16Speaker 07

  I credit Neil for that, because he, and he's got all kinds of tricks, like turning your internet off, using Freedom, all this kind of stuff.

• 33:22Ryan Hawk?

  You wrote speeches in your earlier life. How do you write speeches for somebody else?

• 33:27Speaker 07

  It's weird, and I, and I, in my book, I definitely tempered people's expectations around this, because I never really became a writer until I started this process, the invisible list process, which, by the way, the book is called The Invisible List. You should get it, wherever you get your books. But I never called myself a writer until a couple of years ago, when I wrote my first novel in screenplay. Because when I was writing speeches, you know, I had worked on the Obama campaign, I then got a job with Susan Rice as her special assistant while she was the ambassador of the UN. But if people have seen Veep before, I was like her Gary. Like, I was carrying her purse and all this, but she was very good about giving you work to test how good you were. And she realized, okay, this kid can handle Security Council remarks

• 34:11Speaker 07

  when they come through, which sounds like this hugely substantive thing. But in reality, what it was is, the national security apparatus, it has to go through defense, state, USAID, the National Security Advisor, on and on and on and on, until it gets cleared to go in front of the Security Council, and your instructions are not to get cute with it. So it's a perfect writing assignment for somebody who doesn't really know how to write that well. So for me, I would get in there, and then, actually, I was not allowed to write well. So I was like, all right, like, it's not here for any flourishes. You really need to take this and just put it into intelligible language,

• 34:51Speaker 07

  and don't add anything else. And that was my first writing job. And it sounds awesome. I wrote Security Council remarks. But really, what it was, was a copy paste with a little bit of grammatical copywriting. And so it goes. I mean, she gave me other responsibilities, like if she were like speaking at a reception, or the remarks she'd give to the entire embassy and all that. So she gave me reps, and I got a little bit better each time, but I wasn't confident in my writing. It was only until I became a school principal, and I had to teach my own students and build the curriculum for writing and reading for my kids, that I, like, started reading a lot and writing, learning like the basics of grammar and all that,

• 35:35Speaker 07

  you know, because of my upbringing as a child, that had huge gaps in my knowledge of writing and grammar and all that kind of basic stuff that really ate away at my confidence. So then I had that background by the time I then started my invisible list process. I come out of running schools, and I'm like, okay, I can take this one piece at a time. And one of my first years, it was my second year, I decided to do screenwriting, which is like, adept screenwriters will hate this description, but at least to me, I treated it like training wheels writing. Now, Craig Mazin, or whoever's listening, Aaron Sorkin, I'm sorry. I know you guys are, what you do is not training wheels writing. But for me, as somebody who had spent a lot of time watching TV,

• 36:17Speaker 07

  a lot of time watching movies as a kid, and had a more natural sense and talent for dialogue and pacing on the screen, that was a way easier assignment than what came a few years later when I decided to do novel writing, which only could have happened after screenwriting, because I needed to work out some of the screenwriting skills.

• 36:37Ryan Hawk?

  What's your process to decide what that year is going to be? How do you think, futuristically, have you ever made a mistake and said, ah, why did I pick this? I should not, let's change it? What's the process? Because I, this is something I would love, I want to do, I want to implement, I want other people to implement this, to say, it's gonna be the year of that. Or maybe they're wrestling between two things, that's this year, then the other one's the next year. What's the overall process to pick your thing for the year?

• 37:06Speaker 07

  Generally speaking, what I do is around now, so I'm speaking to you in August. Around now, I start thinking about it, and this is the fun part. I have my running list, but I kind of just sit down and I'll journal, and I'll observe things. And, and I'll even check things out a little bit, especially, and I really carve out the month of December for this. Basically, from Thanksgiving to the end of the year is what I call my meta-learning period, where I kind of finish the thing I've worked on the previous year. And there might be a little overlap, right? But generally speaking, I'm wrapping up the thing I did the previous year. And what I allow myself to do is read the books, watch the podcasts, visit the experts.

• 37:47Speaker 07

  For, I give myself a couple of weeks where I can do this, up to a month, to kind of pull together the body of work, the skills, the sequence, the experts of what it means to be great at that thing. But I tend to go into that month of December with a fairly good idea of what that thing is going to be. And I stress test it the month of December. And it's really now around August that I'm like, okay, what about next year? Do I, like, and I have it in my head now. Like, I have these things on my list. Salsa dancing, flying airplanes. You know, I have this crazy idea of fire jumping. There's this fire academy in Alabama where you can go and learn to fight wildfires. So I'm like, I have all these things in my head and I'm kind of, in my own head, I'm

• 38:29Speaker 07

  just like, okay, I'm having fun thinking about next year. But I try not to do anything serious about any of that until December because it can become its own form of procrastination. So if I'm starting to like Google websites, to go to this school or that school, or buy books, or line up coaching, or read books about that other thing, it's an elaborate form of procrastination against the thing you're doing.

• 38:50Ryan Hawk?

  Was the salsa dancing one, though, you want to do it with your wife?

• 38:53Speaker 07

  Yeah, wife or significant other that will be my wife, you know? And so there was a lot of pressure as I was going, you know, because this was a many years process where I, at a certain point, I, maybe midway through all these years, I kind of got a sense, oh, maybe I want to write a book about this one day. So you start to have this observational experience where you're now like, almost like in your own documentary. You're like, oh, this is for other people now, too. So you want to be as cool and interesting as possible sometimes, which can be helpful or harmful, depending on how you think about it. But I wanted to tie a bow at the end of the book because I opened the book saying salsa was the thing that gave me the realization that I'd been deferring these skills. And I had this experience where I was just watching people dancing on a dance floor.

• 39:35Speaker 07

  And I was like, damn it, if I just started doing this even a year ago, I wouldn't have this pang of guilt and disappointment. And that's really the beginning of this book. But I don't end the book saying, I conquered salsa dancing, because I'm not ready for it yet. Like, the whole problem I had with salsa dancing, among many others, is that I would change relationships or partners and things like that, and I would use that as an excuse not to finish. So I was like, okay, when I do get around to getting married and I know who that person is, I will do it with them and that will be a beautiful experience. And reader, I don't need to falsely tackle this thing so I can give you a neat ending. Actually, I think the whole point is that it doesn't have to be super neat.

• 40:19Speaker 07

  And you can have years where you fall flat on your face. You can have a year, like my tennis year, where I play my buddy in tennis and he beats me. Like, you know, my whole goal was to beat him in tennis and I didn't beat him in tennis, right? So it's like, you can have those years. That's totally fine. As long as you try, you put your all into it.

• 40:35Ryan Hawk?

  I know we didn't go in proper order, but I was going to open with the wedding in Napa, as you do. What happened? What happened in that moment? And why did it, it seems like it was an inflection point?

• 40:45Speaker 07

  Yeah, there are a couple weddings that kind of blend together in my life, but there were, I think there were three of them that all had the same, and they were all around the same time, where people would say things to me like, are you on drugs? And I wasn't. And essentially what was going on was I was burnt out. You know, I was running schools. I wasn't present. I was thinking about people I was responsible for. I was gaining weight. I wasn't taking care of myself. Like, I look at myself now as a 43-year-old and I look at myself when I was in my late twenties and early thirties, and I look older then than I do now.

• 41:20Ryan Hawk?

  Hmm.

• 41:20Speaker 07

  And not because I'm on some kind of Brian Johnson-esque quest to reverse aging, but because back then, I was so stressed all the time. And every wedding I showed up to, because weddings have a way of revealing you, right? Like, you haven't seen somebody in a while, these are people who care about you, and they'll be like, whoa, you don't look right, you don't seem right, and all that. So I had a bunch of experiences like that. And I had one experience where I was like, a groomsmen, and I said to my buddy Zach, we were talking, and I was like, hey, man, I think I either said, and I have the exact language in the book, but I was either like, oh, man, when are you getting married? Or, oh, you got married or something? And he was like, yeah, man, I invited you.

• 42:05Speaker 07

  And you never replied. And I had a couple of those things happen. Like, I even ran into somebody recently in Nashville, you know, because I lived in Nashville for a while, who's like a good buddy, was a good buddy of mine. And he was like, not acting as a good buddy would. Guy, I hadn't seen him in a few years. He was almost acting like we didn't know each other that well. And I was like, what is, what's happened to this guy? It's a super jovial guy. I realized, like, a couple of days later, as I sat down, I was like, you know what? I think he got married. And I vaguely remember an invite that I, and maybe I didn't respond to it because I didn't go to a wedding. So like, I have these things in my head where I'm like, it was such a blur, you know? And so I was just, needless to say, not in a good place during these periods of time. You know, I was neglecting other people that weren't my sole responsibility in my job,

• 42:49Speaker 07

  and I was neglecting myself. What I was really good at was taking care of those people. But in the long term, I failed everybody because I wasn't doing it sustainably. I wasn't doing it so I could stick with a, like, a job at that pace for the rest of my life. You know, so it was a false sense of duty, you know? And I think people were listening. If you're a surgeon, you're a nurse, you're a teacher, you're a police officer, whatever it is that you do, there's that well-worn metaphor of the oxygen mask. You have to put that mask on first. And I think one of the most important things you could do is continue to nurture your passions. It may seem selfish to take up salsa dancing, Spanish, surfing, whatever your dream is. It may seem selfish. People might even tell you it's selfish.

• 43:34Speaker 07

  First of all, it's okay to be a little selfish. Everybody's a little selfish, if not a lot selfish. But number two is, your kids will respect you more and be more inspired by you. Your wife will be more attracted to you, your husband will be more attracted to you, if you are fulfilled and passionate about things that you do.

• 43:51Ryan Hawk?

  I was gonna say, I'm glad you actually, you kind of answered it, but someone could say, well, dude, it's easy for you to say, you're not married, you don't have kids. I have married kids and a very demanding job with stretch goals that my company dumps on me, right? This is kind of the avatar of the show, like a SVP of whatever at a Fortune 500 company, for example.

• 44:11Speaker 07

  Right.

• 44:12Ryan Hawk?

  And say, dude, I'm literally just kind of getting to each kid's practice and then going to those national sales meeting and then, you know, trying to have a date night here and there, like, where am I going to squeeze in, learning to play guitar or whatever?

• 44:23Speaker 07

  Right.

• 44:23Ryan Hawk?

  What do you say to that person?

• 44:24Speaker 07

  Well, I think about it like myself. You know, when my dad was around, my dad was lost all throughout my childhood, and that's why he left. Now, my dad would show up to some of my games, right? And he thought that's what a good idea of parenting was. Now, if my dad had just not shown up to my games and instead went to a taekwondo class or whatever the heck people were doing back then, and had a sense of purpose about himself, and then we would have dinner that night and he would tell me what he learned and I'd tell him how my game was, I would prefer that to him dragging himself to my game, that that is some idea of parenting. Or, if, you know, modern day, my dad goes to the bleachers and he's typing away his

• 45:05Speaker 07

  novel while he's half paying attention to my game, I'd be like, my dad's a badass. You know, that's my dad over there. I think there are many ways to be a good parent. You know, I know people love hearing from non-parents about parenting, but the one thing I have is like, look, you don't have to have a heart attack to be a heart surgeon, right? And what I did was spend a lot of time with kids. There are many ways to be a great parent, and one of them can be leading by example, right? So if your kids are struggling through learning, you could struggle with them and alongside them and often in different things, right? You could still drop them off at practice. You could still go to some of their practices. But I think modern parenting, I think, is falsely premised on this idea that just presences everything. But you don't want to be an empty shell.

• 45:47Speaker 07

  You don't want to wake up and then you send your kids to college and then you're kind of empty, right? Where you're like, okay, what am I? I'm this vessel who maybe built a great company selling widgets and I was at all my kids' practices, but I don't have any definition in my life beyond what I've been doing for other people. And am I really doing it for them? What did I accomplish in just merely making myself available all the time, right? Like, there's more to parenting than that. Availability is so important, but there's a lot more to parenting than that. There's wisdom, there's the example you set, there's the energy you bring. And I also think it feeds into the relationship you have with your spouse, if you happen

• 46:31Speaker 07

  to still be married to the mother or father of your children, right? It's like, showing your kids that you're still sexy people who are in love with each other and have all this energy. And like, although you care about them, you also aren't pining for their attention all the time. You have your own things, right? That's actually good for kids, right? They shouldn't think you're constantly just watching them and living vicariously through them.

• 46:56Ryan Hawk?

  I think humans, I know I am, but humans in general are deeply attracted to people who are fully activated.

• 47:06Speaker 07

  Yes.

• 47:07Ryan Hawk?

  So you lived in Nashville for a bit. I was there recently and it was like a... Wednesday afternoon, you know, not the great slot where you're playing music, you know, but they're playing music 24/7 essentially there. But anyways, like 2 o'clock in the afternoon, Wednesday, right? There are a billion better slots. It's not Thursday night or Friday night or Saturday night. Like it's during the day, it's a weekday. And what I love seeing though, is you go into one of those bars, there's tons of them, and you watch the musician who's performing at 2 o'clock on a Wednesday afternoon and they are just in it. You know, like just in it, doing it. They're not just mailing it in, but they are like, I'm playing and I'm singing and I don't care how many people are here, I am in it.

• 47:52Ryan Hawk?

  And I'm like, I love that guy, I love that girl, like just watching them do their thing. I think what you're saying is that version of that, like what is the thing that activates you so that you look like that person who's Tuesday, 2 o'clock in the afternoon, just playing, like as hard as you can go? I think your spouse will be attracted to that, your kids will be like, let's go, that's my dad, you know? That's a version of what you're talking about.

• 48:18Speaker 07

  For sure. And actually, it's funny, I have this group, you know, the book's called The Invisible List, and I created this thing called The Invisible Posse, which if you're listening to this, if you go to readinvisiblelist.com, you could see this, you could fill this out, you could join the posse. It's this group I started of people who want to go the extra step, not just read the book, but start to just attack their own list. I have this group now of people who've just pre-ordered the book, who all are pursuing their own skills, and actually every two weeks I give them a challenge, and we have a leaderboard where you earn quote unquote points for doing certain things in pursuit of your challenge. And challenge one was go out and do whatever the thing you're learning is publicly, even though it's the first two weeks you're learning it.

• 49:01Speaker 07

  And this one guy in my group, everybody did some amazing stuff, went to the skate park and, you know, just messed around in front of people, or shared their writing with somebody. But the gold medal goes to this gentleman who's learning to sing and who's on vacation with his cousins and made them all sit down as he sang an entire song in front of them. And I was like, that's what it's about. Cause now, and that's why I made that the first challenge, it's like, once you get over that feeling of, oh, people are gonna judge me, all that, and you just get into the experience of doing it, as opposed to thinking about doing it, or planning doing it, you're off. Like you've ripped that Band-Aid off, to use another well-worn metaphor. And so our next challenge, which is the one we're now in, is get feedback doing your

• 49:43Speaker 07

  thing from somebody who knows how to do it, and then redo it. So that's, and so that's what people are doing these two weeks. So if you want to join that posse, people who are listening, and if you want to go beyond the book, you could just sign up on our website.

• 49:55Ryan Hawk?

  That's awesome. I think of like the comedians in my life who have not got on stage yet, like I'll drag you to the open mic night and be there and laugh extra loud in the crowd for you, you know, the people who are, cause like there's some funny people I know that, I'm like, they're just a little scared, it's like this would be the perfect thing for people like that.

• 50:13Speaker 07

  Yeah, actually funny, stand-up comedy is like, it's, I wouldn't say it's at the top of my list, but it's definitely been something I've thought about.

• 50:19Ryan Hawk?

  I feel like you have a knack for, I don't know, because you're witty and smart and a good writer, so it seems like, and you seem like, well, you're obviously willing to try stuff, and then go forward and do it for a year.

• 50:31Speaker 07

  I've thought about it.

• 50:31Ryan Hawk?

  Commit to it.

• 50:32Speaker 07

  First of all, thank you. My friends like to joke about how not funny I am, but I actually think, people can judge by my book, I think in the written form, I'm funnier than I am in person. I have friends who'll be like, oh, that actually was funny when I say something, which is to tell that I'm not that funny. But I almost view it as a challenge, just like I wasn't a good cook, and I couldn't play tennis. If I can become a half decent stand-up comedian, and I live in New York, the best place to do it, and I could walk to Comedy Cellar, not that they're gonna let me in today, but like you could walk to these open mics everywhere, I do think, you know what, it's funny, I'll follow up with you if I decide to do it, it's not a bad idea. And it's like helpful in general, cause it's like, you know, my big dream is to make a movie one day, right? That's my big one.

• 51:16Speaker 07

  Everybody's got a big one, that's the biggest one I have, is I want to make a movie. Comedy's kind of a tool in the toolkit. A lot of actors become actors because they were comedians first, you know? So it is a tool, you know? And improv and these types of things are all elements of the same thing.

• 51:33Ryan Hawk?

  It's funny you mentioned a big dream, so I love asking the champagne questions. Comes from my friend Jason Gainard. The champagne question is this, Robbie, and I'd love for you to answer it, is it's one year from today, you are surrounded by loved ones, friends, family, all the people that love you, and you guys are popping bottles, you're spraying it all over each other, you're celebrating like crazy. My question is, what are you celebrating?

• 52:00Speaker 07

  This is gonna be a cop out, not a cop out, but it's gonna be a surprising answer, given the choices I've made in my life. And a year might be too soon, but it's possible, is like celebrating, I think for me, it's celebrating that I've finally settled down, I've found somebody that's that person. And that could be surprising to people, because they'll be like, you're 43 and you've probably dated a lot of people. I needed to go through the process in this book, in order to come out as a whole person who could devote myself to other people again, in a healthy way. And so now, whether it's a year, or two years, or whatever, I never, I'm like, not, obviously

• 52:39Speaker 07

  not a fan of forcing the timeline, but to me, the thing that's now left, it's not flying airplanes, all those things are amazing, and I want to do those things, it would be cool to be a New York Times bestseller, awesome, all these things, great. But the thing that's left is like the unsexy wake up, and you're like, this is the place I'm in, this is the people I'm with, and I'm ready to attack this next phase in my life. That's what I think, that's on my list.

• 53:04Ryan Hawk?

  Do you have that person?

• 53:06Speaker 07

  I'll put it this way, I told my mom, cause I went through a particularly bad breakup a couple of years ago, I told my mom, I would never tell her about anybody else in my life until I'm walking down the aisle, which I know is an exaggeration, but she gets so attached to some of these people, so now I'm like not, I'm very careful about not going there, because I had to, I had to go through two breakups the last time I broke up. One was with the person, and then I had to facilitate the people in my life who were mad at me for breaking up with that person. And so I was like, and they're mourning over it. So now I'm like, okay, I'm more careful.

• 53:39Ryan Hawk?

  Would that make you more hesitant though? Cause like, part of this stuff is you gotta kind of go for it, knowing that there's a lot of uncertainty.

• 53:47Speaker 07

  Yeah.

• 53:48Ryan Hawk?

  You know what I mean?

• 53:48Speaker 07

  For sure.

• 53:49Ryan Hawk?

  I feel like that could paralyze you a bit, cause you're worried, like, I don't want to hurt all the people I love by going through another breakup, but you know, like, every relationship has the potential to break up. That's, that's unfortunately part of the deal, right? That's life.

• 54:05Speaker 07

  Well, you can count on me not writing a relationship book anytime soon, because you can read this book, everybody, and you will know I'm very good at a lot of things. I'm clearly not good at this yet. People have honestly come up with good ideas, like if you devoted one year to being a good friend, or being a good boyfriend or husband, I think that's totally in the cards. I don't think you should start that way, because I think like, most people have to be a little selfish first, cause you've probably been too selfless. But I think as you round out this process, like I have, and you've done so many quote unquote selfish pursuits, I do think spending a year being like, what would it mean to be an awesome boyfriend? What would it mean to be an awesome girlfriend, or husband, or wife, or parent? But you have to tackle it systematically, right? You could get squishy about it.

• 54:49Speaker 07

  So you have to be like, let me read every book about, parenting is a good example, let me read every book about parenting, let me really dive into it, maybe I'll even start a parenting podcast, or I'll write articles about it. So you have to come up with metrics, because you could otherwise get squishy about it, you know? I don't think it's crazy to think about, like a couple of years from now, a year even, where that would be my year, where I'm like, I'm gonna be awesome. You know, I'm gonna buy flowers and use, you know, my cooking skills, and think about my communication, and my mood, and their mood, you know, like, I do think you can be, people can look at that and be like, that's creepy, but to me, it's like, it's just intentional, if you do it the right way, you know? I think like, a lot of things are a skill, and I think like, a lot of this is a series

• 55:32Speaker 07

  of skills to be good at anything, and there's nothing more high stakes than some of these relationships.

• 55:37Ryan Hawk?

  I could go all day, man. Uh, this is great. The book's called The Invisible List, one passion a year, every year, this is like something I feel like I want to do with my community too, of, when I feel like I'm hesitating, that usually means, that's because I'm a little bit scared, which means I should do it.

• 55:54Speaker 07

  Yes. What's on your list? Tell me your list right now, like off the top of your head, like if you were just like, what are the things you want to do?

• 56:00Ryan Hawk?

  A musical instrument.

• 56:01Speaker 07

  What would it be?

• 56:03Ryan Hawk?

  I mean, I just love guitar. It's not something I have any innate talent or skill for, I mean, my background's in sports, so I can do that stuff, right?

• 56:12Speaker 07

  And you said you do have kids, or no?

• 56:14Ryan Hawk?

  Yes, we have kids, so.

• 56:16Speaker 07

  So you could play guitar around the campfire, you know, it'd be like, oh yeah.

• 56:19Ryan Hawk?

  The other thing, and I was gonna ask you this too, is like, one of the things my wife and I love to do is hike, and I was like, what's an ambitious, crazy, stupid goal of the number of mountains and/or national parks, or like, put an outrageous number out there? Does that count? Like, would that count for this invisible list? Like, like a year of hiking all of the most beautiful places in America, or something?

• 56:42Speaker 07

  I view output goals, like if it's a strict output, I will generally try to steer somebody towards a body of skills alongside it, right? So if you're like, I want to this year, write a certain amount of words, I'd be like, okay, but let's like build into that the skill of novel writing. From what I understand. Whether it's hiking or mountaineering, there are skills involved and it could be out to preparation and survival.

• 57:07Ryan Hawk?

  Like I never camped before, so that would probably be a part of like, you actually sleep and get a tent and do all that stuff like.

• 57:12Speaker 07

  So yeah, what I would do is I would, I would have the goal of like, okay, the, the sheer output, right? But the real goals I would put in there, and this is what you would achieve in your meta learning year are, okay, what are all these skills pitching a tent, starting a fire, tracking, whatever, you know, I, I don't know shit about this. So it's like hard for me to go over the spot.

• 57:31Ryan Hawk?

  That's pretty good.

• 57:32Speaker 07

  But you know, it's like, and, and then, and then I would put that in your, what we call a scope and sequence in the book and say, okay, I'm going to attack these systematically and then you could find places to go. Like here's this survival course, here's a survival expert, here's a place where I could test that. Here's a moment in time, I will take my kids camping in blank place and I will pitch the tent myself, I will start the fire myself. That's how I would marry these things. So you could take the achievement of going to all these places and alongside it, say, I checked a new skill off of my list.

• 58:03Ryan Hawk?

  The skills along, not just like I hiked this place, but here are the skills you develop along the way.

• 58:08Speaker 07

  I don't get mad at people who have like, the Japanese, I think, call it misog, where you just do one big thing a year and it could just be a weekend or something like, I don't get mad at people who do that, but I, I generally, my book's approach is a little bit more, not little, significantly more in depth in the sense of like, it's a process that plays out throughout the entire year. And it generally speaking is an accumulation of skills. That's a body of work each year is kind of like a domain of work. Italian cooking, surfing, like it's a domain. It's a lot of skills built into one thing that we call it something. It's like saying that you've entered this sort of sacred space of people who've been thinking about this for a long time.

• 58:50Ryan Hawk?

  Yeah. Well, I, I love it too, because you've, when you dedicate and commit a year of your life to the thing, then you've got that, then you go to the next one, but you still got that one too. And you, you just stack so many years. That's the cool part about as opposed to just kind of dabbling around for 15 years and you don't have any of it, right? Like I can't cook, I can't surf, right? I've tried, you know, like it's a lot of dabbling, a lot of people trying stuff, not necessarily actually getting anywhere close to mastery of the thing.

• 59:19Speaker 07

  Yeah. And I'll leave people with this. Trying and giving up the thing sometimes can be worse than never trying it at all. And the reason why I say this is because once you get a taste of it, you then will start seeing it everywhere and you will replay in your head, the alternate universe that would have existed had you followed through on it. And that is a bad feeling. So that's why I'm a little careful of not trying too many things like, and if I do, if you follow my process, let's say you do what I did, which is walk into a Muay Thai place, but then you stop. It doesn't eat at me now because I'm like, okay, now it's on my list. I, I probably shouldn't have walked in, but now that I've done it, I've now know a little bit to know that I could see myself doing that. And now it's on my list and I could picture myself maybe when I'm 45 doing it.

• 1:00:01Ryan Hawk?

  Love it. Well, thank you for being here, man. Again, love the book, love your work, love learning more about you through the process of preparing for this and would love to continue our dialogue as we both progress, man.

• 1:00:12Speaker 07

  Let's do it, man.

• 1:00:13Ryan Hawk?

  Love it. Thank you so much, man.

• 1:00:15Speaker 07

  Thank you, Sarah.

• 1:00:19Ryan Hawk?

  It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, [email protected]. Let me know what you learned from this great conversation with Robbie Gupta. You takeaways from my notes, pick one thing for 2027 and set two goals for it, one reasonable goal you can realistically hit with consistent effort and one delusionally big goal that scares you a little bit. Robbie always seems to hit the reasonable one. And every so often he hits the crazy, delusional one. Spend December researching and planning so that you are ready to go on January 1. Next, treat your practice time like a flight.

• 1:01:02Ryan Hawk?

  Nobody waits to feel motivated before going to the airport. You book a flight and you go to the airport. So put your sessions on the calendar, whatever the thing is that you're choosing, and defend them the same way. Remember the Neil Strauss line, it's nobody's responsibility but your own to enforce your boundaries. Your friends might not understand why you're leaving the party early, but we got to be at peace with that like Lin Manuel Miranda was when he was writing, hey, happy birthday, gives him a hug and turns around and goes home to finish the writing. And then I love the story of Robbie's mom taking him to visit Yale Law School and telling them that her son was going to go there.

• 1:01:46Ryan Hawk?

  Super delusional and the best possible way as leaders, we can use the weight of our words to instill belief in others. He didn't think that was even possible, but she said it and he did the work to make it a reality. Think about how we as leaders can do that for someone else. That's one of the coolest parts about being a leader. Once again, I would say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of the Learning Leader Show with Robbie Gupta. I think it'll help you become a more effective leader because you continue to do that. And you also go to Spotify, Apple Podcasts, you subscribe to the show, you rate it, hopefully five stars and you write a thoughtful review. By doing all of that, you are giving me the opportunity

• 1:02:31Ryan Hawk?

  to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Bye.