RyanHoliday.net - Meditations on strategy and life
  • Home
  • About
  • Newsletter
  • Reading List
  • Blog
  • Best Articles
    • Archive
  • Speaking
  • Books and Courses
  • Contact
Home
About
Newsletter
Reading List
Blog
Best Articles
    Archive
Speaking
Books and Courses
Contact
  • Home
  • About
  • Newsletter
  • Reading List
  • Blog
  • Best Articles
    • Archive
  • Speaking
  • Books and Courses
  • Contact
RyanHoliday.net - Meditations on strategy and life
Blog

It Always Takes Longer Than You Expect (Even When You Take This Into Account)

When I finished my first book, I hired a publicist.

I was 25.

It cost $20,000 and was, to that point, the most money I had ever spent in my life.

As part of the scope of work, they had me put together a list of my top twenty or so media targets—–what I thought I had a reasonable shot of getting and what would be good platforms with the book.

Pretty much none of those opportunities happened. It wasn’t the publicist’s fault–they did a good job. It was that I had been preposterously unrealistic. You have these high hopes, you think this is my shot and of course, it turns out that the world has other plans.

You’re going to get everything you want when you want it?

GTFO.

If you really want something, you better be ready to hurry up and wait.

That was especially true for me then, since I was a kid, already getting to publish my first book far earlier than most people get to dream of.

All of this came back to me as I was flying home from New York from the launch of The Daily Dad. I had just done The Daily Show, CBS This Morning, and a daytime talk show in the span of a week. Which meant that 11 years and 14 books later, I was finally making a serious dent in the list that I had made back then. It had sometimes seemed like slow going, but then in the span of just a few days I had crossed off the best and hardest-to-get outlets.

There is this law called Hofstadter’s Law which says it always takes longer than you think it’s going to take. Even when you think it’s going to take a long time. Even when you take Hofstadter’s Law into account.

I started blogging in 2005. My first book came out in 2012. The Obstacle is the Way came out in 2014…and took six years for it to hit any bestseller list. I didn’t hit the New York Times Bestseller list until 2019, on my 13th book.

If you had told me that’s how long it would have taken, I might have been able to endure it. But Tom Petty was wrong. Waiting is not the hardest part. It’s the not knowing when the waiting is going to end.

But that’s life. That’s how success works.

It takes longer than you want. It takes longer than you expect. It takes longer than you’re willing to wait.

In any case, it takes however long it takes.

Talk to parents who had trouble conceiving. Talk to people waiting for their immigration papers to come through. Talk to scientists taking a drug through clinical trials and regulatory approvals.

This isn’t to say there isn’t good news along the way, that there aren’t trending signs and little hits that keep you going. There will be. I’m not sure I would have kept going if there hadn’t been.

But it’s going to take a while to get what you want.

Interminably longer.

It just will.

I thought opening my bookstore would take a few months…COVID delayed it a full year.

On February 25th, 138AD, the emperor Hadrian adopted a 51-year-old man named Antoninus Pius on the condition that he in turn adopt Marcus Aurelius. Given life-expectancy statistics of the time, Hadrian figured Marcus would be at the helm in three or four years, max. All was well, except Antoninus lived and ruled…for twenty three years.

In 1971, at the age of 26, Ed Catmull defined his dream: to make the first computer-animated feature film. He accomplished it when Toy Story was released…twenty-four years later.

The writer Steven Pressfield published his first novel, The Legend of Bagger Vance, in 1996…after twenty-seven years of trying to get a novel published.

I thought it was a matter of hiring the right publicist and having a good product. How entitled and naive. If that was all it took…there aren’t enough media slots in the world to satisfy all the people who satisfy that criteria.

No, I had to go out and earn my spot many times over. I had to prove that I had great stuff. I had to demonstrate that I had an audience. I had to prove that I wasn’t going away. I had to prove I was good on camera. I probably even had to reassure some skeptics or critics who I pissed off with my first book.

That took time, a lot of time. A decade!

We conceived and raised a six year old in less time than it took me to earn my spot.

Intersecting with Hofstadter’s Law. is Murphy’s Law. Things go wrong. There are delays. There are mistakes. Communication breaks down. The market shifts. Lucy yanks the football away right as you’re about to make contact. The outfielder robs you of a home run. They sell out right before your turn in line.

Are there exceptions to these rules? Are there people who get it all faster, quicker? Are there times when all the greenlights line up?

Maybe.

Sure.

OK.

But you are probably not that person. You are probably not on that path, and that will not be your fate.

Which means you’re going to have to buckle up.

You’re going to have to learn patience, humility, perseverance.

You’re going to have to find other ways to measure your progress and your success.

You’re going to have to put that energy into getting better, into understanding the game better.

You’re going to have to wait, and then wait some more…and then wait more after that.

 

Tweet
July 11, 2023by Ryan Holiday
Blog

36 Lessons on the Way to 36 Years Old

The amount of times I had to do the math to see how old I was this year was alarming. Even as I wrote this piece, I had to check, 36, right? Wait, did I accidentally do 36 last year? I don’t know why, because this is definitely not old enough for senior moments, but I’d like to think that this is a sign that I’m living my life the right way. 

Seneca had a great line. At the end of your life, he said, you should have more to show for it than just a number. My view is that if you love what you do, you lose track of time. That’s how I know I’m really in the zone on a book—the hours fly by, the days follow. 36 isn’t a big enough number that I should lose track of it, but then again, if I have packed a lot of living into those years, if they’ve all blurred together, maybe it is. 

Anyway, today on my birthday, which also happens to be the 16th or 17th year I have written one of these birthday posts, I thought I would put together some lessons (or in some case, observations) I have picked up on the way to 36. Doing my best to pack a lot of living into these years, I’ve learned a lot—through both mistakes and experiences, successes and failures, by original discovery as well as by the experiences of others. (You can also check out/track the evolution of these lessons from my collections at 35, 34, 33, 32, 31, 30, 29, 28, 27, and 26).

–The word of the year for my wife Samatha and I has been LESS. Less stuff. Less distractions. Less screentime. Less commitments. Less so we can have more—more presence, more peace.

–As part of that, I made the difficult decision to call my publisher to push my next book a year or so. This was a massive clearance on my schedule—several hours a day did not have to be spent researching and writing on a project. Yet it was remarkable how little my life changed. Because tasks expand to fill the space, because it is so easy to say yes to other things. Less demands vigilance and discipline, perhaps even more effort than actually doing stuff. 

–Which is to say that less is actually harder to do than more.

–I’ve caught myself several times, after getting out of the cold plunge, waiting for the shower to warm up before I jump in. I just got out of 38 degree water…and I’m waiting for the shower to be the perfect temp? It’s like when I take the elevator three floors down at the hotel…to go outside and go for a run. Challenging yourself is great. Exercise, cold plunges, whatever—but don’t be so focused on them that you miss yourself of the ordinary, always accessible challenges of life that are right there. They might be small, but they add up too. 

–I was talking to a financial advisor a couple years ago and I was talking about how, you know, I have a very unpredictable career, that I didn’t know how much longer it would keep going as well as it has been—you know, typical artistic insecurity. He stopped me and said, “But have you put any thought into what happens if it gets even better?” He was right. I was only planning/worrying about the wheels coming off. I wasn’t thinking, “What if I keep getting better? What if my hard work keeps paying off?”

–Related to that…My business has grown year over year for many years. My book sales have grown year over year for many years. This is wonderful, but I’ve also taken to telling myself: It doesn’t have to be this way. You don’t always have to top what you did before. You can be happy with what you have.

–It isn’t that assholes never succeed—just look around. It’s that if you look closer, you see all the ways that being an asshole holds them back. The way it moves what they really want just a little bit outside their grasp, the way it prevents them from ever really enjoying or appreciating what they’ve done. 

–Literally from the first doctor’s visit with your newborn, they are telling you how your kid stacks up against other kids—their height and weight percentile, etc etc. It never stops…unless you stop it. You are not raising the average child, you are raising YOUR child. How many of the things you’re worried about as a parent would worry you if you didn’t know or didn’t look at what other families were doing? 

–I’d like to think I am more open minded, more caring, more patient, more aware than I was a year ago. If that’s not the direction you’re going, where are you headed? 

–There is a quote from the physicist John Wheeler about how as your island of knowledge grows, so does the shoreline of ignorance. To me, that’s not only about being a perpetual student but also realizing, as you go, just how limited your experience of the world is. One of the beautiful things about reading is that it opens you up. I was reading this memoir of the high school experience of the musicians Tegan and Sara this year—what the hell did I know about being a gay Canadian teenager in the early 90s before that? But like I said, my heart and mind are more open now than it was before. 

–As a public speaker, your agent has as your “fee” which they “quote” to people who inquire about hiring you. These numbers can get preposterously large, especially when you consider how not that long ago you’d have gladly done it for free (as many other people still would). There is another important term though, it’s called “fee integrity” and it has to do with whether you actually mean that quote, or if you regularly accept much less. Fee integrity is important in life. You have to know what you’re worth (both to yourself and according to the market) and you should not accept less. It’s not just bad business, it’s also sort of shady. 

–We had to put our 16-year-old dog  down in May. The last few years had involved a lot of clean up and ruined carpets/floors etc. Of course, the second she was gone this all felt very unimportant. I try to remember this with my kids: Paint is cheap. Even sheetrock itself is easy to replaced. Where is the car my own parents were so worried about getting dirty when I was a kid? It’s in a junkyard somewhere…which by the way, is where all your stuff will end up someday. 

–People like to say that facts aren’t feelings, which is true BUT one thing I have come to understand is that other people’s feelings are facts to them. The irony of the ‘facts aren’t feelings’ crowd is that they spend all this time trying to argue other people out of their feelings… as if that has ever worked. As if that’s not a super emotional and irrational thing in and of itself. The sooner you accept that a person feels a certain way and meet them there (or just let it go), the sooner you can come to a resolution and an understanding (or just move on with your life). 

–I heard of a great rule from many writers that pertains to this: When someone tells you something is wrong (with your writing), they’re right. It’s not working for them. Does that mean they know how to fix it? No. Or even that you should fix it? No, it may well be that they’re not the audience you’re aiming for. But you cannot—with your writing, with your kids, with anyone—tell them actually their reaction is incorrect. Hear what they are saying, respect it, then decide what you’re going to do about it (which may well just be letting them know that you heard them and you appreciate the time they took to say it).

–All success is a lagging indicator…all the good stuff (and bad stuff) is downstream from choices made long before. 

–I have trouble wrapping my head around the fact that Free Fallin’ by Tom Petty came out in 1989. Like it’s only a couple years older than Smells Like Teen Spirit? I remember hearing someone play it by a campfire at a Boy Scout camp when I was in elementary school and thinking that it was from the 60s or something…in fact, it was still new! Great art is like that, timeless and timeless—really, it’s out of time, apart from time (If you told me that The Night They Drove Old Dixie Down was actually from the the Civil War, I’d believe you…and to many people Kate Bush’s Running Up That Hill felt like a new release)

–There’s a funny clip of Theo Von on Rogan recently, where he says something like, “There’s nothing better than peeing in the pool while you’re having a conversation with someone.” Rogan laughed but says, “what are you talking about?—that doesn’t even make the top one thousand great things”. The smell of fresh baked bread is better, he says, even if you don’t get to eat it. Anyway, I think the point is that there is a list of a thousand tiny, absurd, weird things that really are great (Neil Pasricha has a whole book of awesome stuff like that). Most of it is cheap. Most of it is accessible to you in an instant. If you want to be happier and live a richer life, seek these things out, appreciate them as much as the big things. 

–You look back at the things you took very seriously earlier in your life—the things you fretted about, fought about, took personally, held onto—and now you laugh. Chances are, most of the things you’re fretting, fighting, taking personally, holding onto today will fall into the same category in the future. 

–Several years ago, a business partner and I had a falling out and went in different directions. They were very public about all their successes as time went on, and even though I believed what they were doing was largely a hustle and something I wanted nothing to do with it, it was hard not to feel insecure, not to compare myself against it. Then more recently, it was revealed that the whole thing was basically a house of cards and it all came crashing down (harming quite a few people in the process). It’s just another reminder, first off, not to compare yourself to other people, because they are often lying or exaggerating. Second, it’s Seneca’s reminder to stay on the path you’ve chosen for yourself and to not be distracted by those that criss cross yours, especially when those people are hopelessly lost. 

–A decade and a half ago, Tyler Cowen first told me about the idea of “quake books”—books that shake your whole view of the world. At the time, I asked him if he’d read any recently and he said, “There just aren’t books like that left for me anymore. So I read many more, to learn bits, but haven’t in years experienced a ‘view quake.’ That is sad, to me at least, but I don’t know how to avoid how that has turned out.” At 20, I could not relate. At 36, I understand more. 

–In fact, I noticed a version of that as I wrote this very post. After I finished, I went back and looked at last year’s and noticed I had written many of the same lessons! Maybe my rate of new ideas/breakthroughs is slowing down…Or a more positive way to think about it is that I am still chewing on and working my way through bigger insights, and that as I get older and wiser, it’s not such a fast or instantaneous process. There’s more to integrate now, more to integrate into now. 

–I’m not saying going for a walk will solve all your problems, I’m just saying there’s no problem that’s going to be made worse by going for a walk. (I put that on an Instagram reel this year…and somehow like 15,000 people have made their own versions of it. Insane).

–The thing I’ve learned about leveling up in your career, or breaking through different ceilings, is that you really only realize that it happened in retrospect. Just like you don’t notice your hair growing or your face aging, you can’t really feel it as it’s happening. Be patient—evaluate later. Don’t kick yourself now because you think you’re stuck. You might be the opposite of stuck and just not know it. 

–My wife and I have been going back and forth a lot about how we want to educate our kids. Home school? Private school? Public schools, like we did? Some combination of all three? Should we move somewhere with better schools? Anyway, my editor Adrian Zackheim said something to us that was quite helpful: Everyone who cares about their kids’ education has these same issues…and always have. I took from this that there is no perfect solution and that we shouldn’t fool ourselves (or feel guilty) thinking that other parents have it all figured out. 

–Sometimes just as I am about to fall asleep, some bit of current events will slip into my mind and make me so angry I can’t sleep—book bannings, groups that smear gay people with the word ‘groomer,’ cowards who have enabled Trump, anti-vaxxers, etc. Then I try to remember the arc of American history—there were the oligarchs who controlled the levers of power to until the Civil War, then fought social reformers of the Gilded Age, then resisted the social safety net during the Great Depression, that fought tooth and nail to preserve segregation…it’s a dark energy that forms in opposite of the progress or justice of the day, that attacks or persecutes, that becomes reactionary and obstinate often in regards to issues that neither picks one’s pocket nor breaks their legs. The big test on any issue is what does the dark energy think about it? Start forming your own views at the opposite. Don’t let them suck you in.

–Even more than not just getting infected by their toxic beliefs though, you can’t let them make you bitter either. You have to find a way to process the anger and the frustration and the disappointment before it curdles into cynicism. Basically, you can’t let the sonsofbitches turn you into a sonuvabitch. 

–Another constant: Being able to adapt and make use of new tools. I have no idea what the long term implications of artificial technology will be, all I know is that the best approach as an individual is to find a way to use it to get better at what you do. 

–Having now been in pro locker rooms and board rooms and briefing rooms with special forces operators and the Senate dining room etc etc—all very different worlds, I have come to believe that elite performance is elite performance is elite performance. That while these folks all do very different jobs at very different levels of fame or fortune, they’re all basically thinking about the same handful of things, accessing the same core mental skills: Resilience. Creativity. Focus. Collaboration. 

–Oh, related to that: I’ve had the privilege of doing a fellowship for the Stockdale Center at the U.S Naval Academy this last year and have done a series of lectures (you can see some of them here). Some right wing critics have tried to claim that the armed forces are becoming ‘woke,’ but when I look out into the audience, I see what it is: The cream of the crop of American talent is incredibly diverse. And as your population gets diverse, particularly a diverse population of talent that can choose to be or do anything they want, an elite organization has to figure out how to meet the needs of that talent. If you want to know why they’re taking the names of Confederate generals off of bases, or doing really anything that pisses off old white dudes, it’s because they—the military, Wall Street, etc etc—is for the first time seriously having to cater to constituency that is not old white dudes. [For the Navy, you can plug in a bunch of industries/companies here]

–Funny thing related to that too: I talked about Stockdale the last time I was there, particularly in regards to these attempts to ban certain books (like where I live in Texas). When Stockdale was in the Hanoi Hilton, he would get in long debates with his captors about Marxism…and he would win. Why? Because he had actually read Marx. While he was at Stanford (where the Navy sent him), he had done a whole course on the original communist texts. Most of his captors had only been given propaganda, sometimes second or third hand. You build strong, resilient people by exposing them to information, not hiding it from them. 

–And then finally, a couple weeks ago, I interviewed Dave Carey, a POW who went to the Academy and was locked up with Stockdale. He told me the secret to parenting/life/negotiation is to remember that the main goal in every conversation is to have the next conversation. He was saying that you never want to behave in a way that shuts the door for good, never want to say things that end things. I love that. 

–When we were getting off a plane the other day, my oldest son was sort of misbehaving and causing trouble. I asked what was up. My youngest looked up and said, “Clarkie is tired and he’s having trouble making good decisions.” Then a couple days later, we were in the car and my youngest was upset and yelling. I asked what was going on and my oldest said, “I think Jonesie is overstimulated right now.” I say this not to celebrate our parenting but to say that I wish I could get better at having that kind of awareness—of myself and of what/why other people are doing. 

–I looked out into my garage at some point this year and had this feeling that I was looking out into a graveyard. Strollers we don’t use anymore, a crib we won’t use again, toys they’ve outgrown. But this only has to be a sad scene if you didn’t use the shit out of the stuff when you had it, if the stroller doesn’t remind you all the wonderful time (and walks) you spent together, if you regret how not present you were for the periods the stuff all represents. 

–I don’t know many smart people who watch cable television news. Just as I would get up and move away from someone who was smoking, when I see it on at the airport or a waiting room or whatever, I go wait somewhere else.

–Speaking of waiting rooms, sometimes something as jarring as a pandemic helps you see differently, but the idea that all the sick people wait in the same windowless room at the doctor’s office or urgent care or whatever is completely insane. Yet when I politely told the receptionist as urgent care earlier this year I was going to go sit on the bench outside (where the weather was wonderful), she—the person getting breathed on by sick people 40 hours a week—looked at me like I was the weird one. 

–We did this course for Daily Stoic about money and as I built out the marketing/messaging, I was very sensitive about not wanting to have anything in it that seemed scammy or hustle culture-esque, I certainly didn’t want to present Stoicism has being a get-rich-quick kind of a thing. And the nine week course we wrote is very much the opposite of any of that vibe too. But you know what happened? People still accused me of doing exactly that…meanwhile, because I bent over backwards to not offend, we found that the marketing didn’t land with some people who otherwise would have bought it. Every time I pull my punches because I am worried somebody who already doesn’t like me won’t like me, I regret it. 

I mentioned Seneca above, and I’ll close with my favorite insight of his. “This is our big mistake,” he wrote, “to think we look forward to death. Most of death is already gone. Whatever time has passed is owned by death.” He’s right—we are dying every day. No day, once dead, can be revived. So the question, I try to round out each of my birthdays with is a quick thought of the fact that I’ve just lived/died XX years. Did I spend them well? Did I live it while I was in it?

I wish you the same.

Tweet
June 16, 2023by Ryan Holiday
Blog

31 Lessons I’ve Learned About Money

I remember learning how to play the recorder in elementary school. I remember square dancing. I remember cursive. I built a model of a Spanish mission out of sugar cubes.

Some of this was fun. Some of it wasn’t. Some of it probably contributed, in some indirect way, to my general ability to learn and function in the world. Most of it, I think it’s safe to say, did not.

Something I don’t remember learning about at all? Money. Even our math problems were mostly about potatoes and trains, not how to calculate the interest rate on credit cards or the return on an investment. There was the occasional—and now very politically incorrect—remark from teachers about how if you didn’t do well in school, you’d end up working at McDonalds. But even with all the pressure to go to college, school provided very little in the way of discussion about what kind of careers paid what, how to live within one’s means whatever that career was, let alone how one might create their own business and work for themselves.

This is sad and strange and hardly rare. We leave it to kids who become adults who then have kids to just figure it out for themselves. Not everyone does. I’ve since met high income earners who were terrible with money. I’ve met people who were quite rich by every financial metric but whose relationship with that money was quite terrible, (you’d never want to trade places with them). I’ve met people who have been the victims of scams and frauds because they lacked the basic knowledge needed to protect themselves.

To the Stoics, the solution to these timeless problems—the way to be better with money, to improve your relationship with money, to not fall for every smooth talker, Marcus Aurelius said—is the same: get smarter. Become better educated on the topic of money. “Wisdom,” as Seneca said, “offers wealth in ready money.” It’s something I’ve been thinking a lot about in my own journey—growing up with two civil servant parents, dropping out of college, succeeding in the corporate world until I dropped out of that as well to work for myself. I’ve been thinking about it a lot now that I have kids.

And I’ve been thinking about it a lot in researching and writing what is the most in-depth course ever built over at Daily Stoic: The Wealthy Stoic. It’s a 9-week course packed with the best wisdom from the Stoics, as well as today’s leading money experts, on how to be rich, free, and happy. Along with ~30,000 words of exclusive content, there will be 3 live video sessions where I’ll be joined by bestselling authors, pioneering businesswomen, and investing and finance experts. I’m really excited about this course. I think it’s going to be one of our best, and I would love to have you join us—you can learn more at thewealthystoic.com.

Here are 31 lessons I’ve learned about money…

–I’ve never met a person who ever reached ‘their number.’ You know, people say, ‘When I hit $Xm, I’ll be good.’ They say, ‘Once I have X years salary in the bank, I’ll be good.’ No one ever seems to get to that number. We’re never ‘good’ because we move the goalposts…(or because we set a preposterous and unrealistic number to begin with).

–It’s important to remember what once seemed like a lot of money to you. When I dropped out of college to work as an assistant in Hollywood, I took a salary of $30,000. I remember saying to myself–no joke–”What am I going to do with all this money?” It was enough for an apartment and all the books I wanted to read. Remembering that as an anchor point has not only kept me humble, it’s kept me grateful. Think about what your parents made, think about what you used to get paid per hour to make smoothies or mow a lawn. People manage to live on that–you yourself once did.

–Seneca said that poverty wasn’t having too little, it was wanting more. He wasn’t talking about poor people. He was talking about rich people. He was talking about people who are insatiable. ‘Rich’ is having enough–as this story illustrates.

–My work is unpredictable, and even success comes in the form of lump payments. So when it comes to savings and investing, I have always favored things that are dependable. My wife and I invested quite a bit in different real estate things over the years, with the idea being to eventually create enough annual income that we could be independent from my creative/entrepreneurial/artistic decisions. This strategy is not for everyone, but it worked for us. I could stop writing tomorrow and know the spigot isn’t going to be turned off.

-My parents did a good job modeling how to be responsible with money. They also taught me how to be savvy at investing and growing one’s money. I wish they had done a better job modeling generosity and the proper value of money (that is to say, that most things are more important than money). There have been lots of other opportunities since to learn the skills I got from them, the others much less so…

-Pick the low hanging fruit. I’ve had to remind the Daily Stoic employees several times to be sure to sign up for their 401k/matching we offer. I’ve left money for too long in checking accounts when the easiest of transfers would have significantly increased the interest I was earning. Don’t get overwhelmed by the whole of life, the Stoics would say, do easy things first.

–If you don’t take the money, they can’t tell you what to do. That’s what Bill Cunningham said: If they pay you, they get to tell you what to do. Remember his words: “Money’s the cheapest thing. Liberty, freedom is the most expensive.”

–The trope that a day job takes away from your art or your hustle is stupid. There’s a great exhibition at the Blanton Museum right now about artists who had day jobs. I wrote 3.5 books while I was the Director of Marketing at American Apparel. I started my own marketing company while I was a writer. I have my bookstore. A job for someone coming up is like a trust fund you’ve earned. It helps.

–Learning is priceless. Robert Greene used to have to nag me to submit my hours when I worked for him. To me, the money was an afterthought, I knew the real return was my access to him, that he would answer my questions, that I could see how a real pro did the job.

–That doesn’t mean internships should be free. When you make it, you have an obligation to try to support the people coming up (which is why Robert insisted on paying me even though I didn’t care). It just means sometimes you have to accept a bad deal to learn what you know you need to learn…and also to walk away if you stop learning.

–I’ve had the privilege of talking to many, many extremely wealthy people. They are not that rare. Rarer is the one who actually likes what they do for a living (for instance, half the ones I meet all seem like they’d rather be writing books for some crazy reason). Rarest is the one you’d want to trade places with.

–When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.

–I had this idea that I wanted to be a millionaire by 25. Where this number came from, I don’t know. I made it up, it was ego, and I didn’t hit it. But you know what the difference of getting there a little later was? Nothing. No one throws you a party. Accomplishments don’t change who you are.

–I talked with Tim Ferriss when I was starting my marketing company. He asked me what I was working on and what I was trying to accomplish, and I gave your typical answer: I wanted to be financially successful. Then he asked me something I’ve never been asked. “Ryan,” he said, “What do you do with your money?” Basically, I just put it in the bank, I told him. “Then why are you doing so many things you dislike to earn more of it?” he replied. This insight changed the course of my business as well as my life. Making money is easier than most people think—knowing why and what for, and not being driven in the wrong direction to get it? Much harder.

–You work really hard to get money…and then once you have it you spend time worrying whether you’re putting it to work right. James Altucher once pointed out that you don’t have to make your money grow. You can just have it. It can just sit there. You can spend it. Whatever. You don’t have to whip yourself for not investing and carefully managing every penny. The reward for success should not be that you’re constantly stressed that you’re not doing enough to “capitalize” on that success.

–At the same time, I love Charlamagne’s “Frugal Vandross.” The less expensive stuff you have, the less there is to worry about.

–Be responsible. I have a life insurance policy. I have money saved. If something happens to me, people I care about will be taken care of.

–But not too responsible. The reason they will be taken care of and that I feel creatively and professionally satisfied, is that I have taken a lot of big risks. I dropped out of college (this gave me a two year head start on a lot of people). I left a good job. I bit off more than I could chew many times. Why could I take those risks? Because I had been responsible. I had money saved. I knew what was important to me. I had built a support network. I eliminated the tiny risks so I could take the right ones. If you cover your bases, then you can afford to bet on yourself.

–The best decision I ever made was taking a pay cut to write The Obstacle is The Way (less than half what I got for my first book). I knew it was what I wanted to write. I thought it could sell. I had my day job. It still seemed like a TON of money to me. Sometimes you have to take a step back to go forward,

–If you can, pick up the check. If you can, tip amply. It feels good, it’s nice, it also normalizes not sweating small amounts of money.

–As I wrote recently, a couple years ago, I made the decision to stop basically all the advertising that my business does. I decided to put that money into making content instead—videos, articles, etc. I did this because it occurred to me that the money I was spending on ads made basically no positive impact on the world (if any impact at all), but articles and videos could at least be enjoyed by people (for free no less), even if they didn’t drive the same amount of ROI. In the long run, this content will be around forever and have a bigger and more meaningful reach. This is a small-scale decision given the size of my business, but if people spend more time trying to maximize the positive externalities of what they did instead of optimizing for short-term profits, I think they’d be happier…and ultimately do better…and the world would be better.

–But if I am content with what I have, won’t I stop getting better? No. We play better with house money. Feel better too.

–A wise person once told me…if it’s a problem that can be solved by money, you don’t have a problem.

–If you never hear no from clients, if the other side in a negotiation has never balked to something you’ve asked for, then you are not pricing yourself high enough, you are not being aggressive enough.

–Anticipate the fact that maintaining discipline is hard. Automate. I’m always amazed when I check the balances of accounts where we’ve set up automatic transfers for investing, for our kids’ college, for our emergency reserves–things I set up a long time ago have been doing their job, a far better job that I would have done had I put it on my monthly to do list.

–Don’t compare yourself to other people. Caesar famously wept at the feet of a statue of Alexander the Great. “Do you not think it is matter for sorrow that while Alexander, at my age, was already king of so many peoples, I have as yet achieved no brilliant success?” he said. Um, you were both fucking terrible. And now you’re both gone. Who cares whether so-and-so did this or that earlier than you? Who cares that so-and-so had more?

–Acceptance is a difficult thing, but it’s an important skill as you become successful. Accepting that there will be a certain amount of your investments that fail, accepting that mistakes will cost you, there will be fees and other costs of doing business. Taxes are another thing you have to come to terms with. We must pay all this stuff gladly, the Stoics say, otherwise success will be a form of misery.

–If you live somewhere cheap, you’ve got a head start. Moving to an expensive, popular city ‘to make your start’ is a tough gamble. There is more opportunity…but less runway. I’m grateful to New Orleans in 2011 for giving me plenty of runway as well as friendships and inspiration.

–Yes, it’s true that money is better spent on experiences than material possessions. But, I will say that just because an experience presents itself doesn’t mean you have to feel obligated to do it. Remember, there is a cost to saying yes. And not just a monetary one, but it will take your most precious, non-renewable resource–your time.

–They say that if you think professionals are expensive, try hiring an amateur. This is true in the sense that being cheap or looking for a bargain on services has come back to bite me many times. HOWEVER, I have also been disappointed with how many professionals are actually amateurs. Sometimes, if you want a thing done well, you have to do it yourself. It’s very rare that you’ll just be able to hand stuff off–and don’t be fooled by high priced experts and consultants. You may end up still doing the job yourself in the end…after having shelled out for their fee.

–If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success. If starting a business makes you a worse person—if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives. It’s not successful.

Tweet
May 15, 2023by Ryan Holiday
Page 3 of 280« First...«2345»102030...Last »

“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” - Murakami

© 2018 copyright Ryan Holiday // All rights reserved // Privacy Policy
This site directs people to Amazon and is an Amazon Associate member.